Christmas in Chicago Planning Guide — Best things to do + Sample Itinerary

Maybe it’s because I grew up in a small town, but I’ve romanticized Christmas in a big city. There’s something about the twinkle of skyscrapers in the early evening and the sidewalks bustling as the shoppers rush home with their treasures, if you will. Christmas in any city seems magical, but Christmas in Chicago specifically truly brings this scene to life. This post is dedicated to all things holiday in the Windy City. We’ll start by setting the scene before we dip into some travel planning logistics. Then we’ll get into the fun stuff, like all the very best things to do and how we recently spent a perfect 3-days in Chicago at Christmas. Whether you’re visiting Chicago for the first time or you live a few Metra stops away, spending a few days celebrating the season in Chicago is always worth it.

In this post

• Why we love Chicago at Christmas
• Best Christmas things to do in Chicago
• Plan your stay in Chicago
• How to get around Chicago
• What to pack for Chicago in the winter
• Sample 3-day Chicago itinerary in December

Why we love Chicago at Christmas

Ah, Chicago. The Windy City. The Second City. My kind of town. The city known for its pizza, Italian beef sandwiches and unwavering stance that ketchup has no place on a hot dog. After spending the past 10 years living in Chicago (and even longer for my husband who grew up there), we learned to love the city during all seasons. But if we had to pick a favorite time to be there, Christmas just might be it. While Chicago winters get a bad rap, we’d argue that December is actually a perfect time to visit. Winter officially starts in December, but the weather in Chicago usually isn’t that bad around then. Temperatures average in the low 30s °F. It’s cold enough to break out your winter coat, but warm enough that you still want to go outside. The chance of snow is small, but even the grinchiest among us can admit that snow isn’t so bad when it falls on Christmas lights, right? And if there’s one thing people from Chicago love most about the cold, it’s finding a cozy place to escape it. The city is filled with festively decorated restaurants, cafes and bars serving up seasonally inspired sips and bites. Nothing beats a seat by the fireplace at the Starbucks Reserve Roastery on a cold day, watching the lights on Michigan Avenue twinkle and sipping a hot mocha or espresso martini. There’s a ton of stuff to do in Chicago at Christmastime, too. There are special seasonal events and shows, like Christkindlmarkt and The Nutcracker, but there’s also Christmas overlays on traditional Chicago attractions, like ZooLights at Lincoln Park Zoo and Light up the Lake at Navy Pier. Even a simple stroll up State Street or through Gold Coast feels like walking through a winter wonderland. December is a magical time in Chicago. Yes, it’s chilly, but I’d argue that makes it even better. And since the chance of snow is actually quite small in the December, your risk of flight delays shouldn’t be as bad as you may think. Have I convinced you? Let’s start planning!

Best Christmas things to do in Chicago

There are a ton of Christmas activities in Chicago. The festivities usually kick off the weekend before Thanksgiving and carry on through the new year. You could see a different show, visit a different holiday-themed bar or attend a different seasonal event every day and the holiday season would be over before you ran out of things to do. But if you don’t have time to see and do everything, here is a list of our favorites.

Classic Chicago Christmas activities

• ZooLights at Lincoln Park Zoo — The entire zoo is lit up with Christmas lights and decorations, plus other holiday touches like strolling carolers, a Christmas-themed bar where you can make your own s’mores and a photo op with Santa. The event takes place on select nights from November 19–January 1. Tickets are required and cost $5, but are free on Mondays. Get more info here.
• Christmas Around the World at the Museum of Science & Industry — At this annual holiday event, you can see over 50 Christmas trees decorated to represent countries from around the world. You can learn more about global holiday traditions, dine on seasonal fare and even watch ‘snow’ fall over the Grand Tree. The event runs from November 16 through January 4, 2022. This special experience is included with general museum admission, which costs $22 for adults and $13 for children 3-11. Get more info here.
• Christkindlmarket — I would say this is hands-down the most popular Christmas thing to do in Chicago. It’s your classic German Christmas market complete with hot Glühwein in little boot mugs, potato pancakes and booths selling beautifully decorated ornaments. There’s three locations, but the best/main one is at Daley Plaza. It’s fun in theory, but it is always crowded and usually cold. Be sure to plan ahead. It’s open daily from November 18 through Christmas Eve. Get more info here.
• Ice Skating at Millennium Park or Maggie Daley Park — Ice skating in front of Cloud Gate (the bean) is quintessential Chicago Christmas. Skating at the Millennium Park rink is free, but reservations are required. Skate rental is an additional fee. At nearby Maggie Daley Park, there is an ice skating ribbon (think lazy river but frozen), which is a fun twist on traditional ice skating. Prices vary by day and range from free (with your own skates) to $22 (with skate rental). Get more info here.
• Light up the Lake at Navy Pier — This is a relatively new event that replaced Winter WonderFest starting in 2021. It’s an indoor lights festival complete with a train ride, indoor ice skating, photos with Santa and a ride on the Centennial Wheel. The event runs from November 25 through January 7. Get more info here.

Date-specific Chicago Christmas events

• City of Chicago Christmas Tree Lighting on November 18 — The city’s official tree is lit at 6 PM, usually surrounded by speakers, carolers and other festivities. Official details are released by the city as the date nears.
• Chicago Christmas Parade on November 19 — The parade is part of the Magnificent Mile Lights Festival which starts the day before (November 18) with a small festival in the plaza above the Apple store and the lighting of the tree at the Wrigley Building. On Saturday (November 19), the parade heads down Michigan Ave and lights the trees along the way. Mickey and Minnie Mouse and Santa Clause are featured in the parade. Get more info here.
• Brewlights at Lincoln Park Zoo on December 1 — The classic Lincoln Park Zoo ZooLights becomes a craft beer festival for one night a year. This adults only, ticketed event includes access to all the holiday lights, rides on the carousel, photos with Santa and samples of craft and seasonal beers. Get more info here.
• TBOX on December 10, 2022 — The Twelve Bars Of X-mas (aka TBOX) is a massive holiday bar crawl that takes place in Wrigleyville every year. People wear their ugliest sweaters, drink a bunch of booze starting early in the morning and raise money for charity while they’re at it. Get more info here.
• Renegade Winter Craft Fair on December 17-18 — Shop local for gifts this year at this famed artisan market. A slew of vendors fill Morgan Manufacturing in the West Loop for the annual holiday makers market.

Best Christmas trees downtown Chicago

A Christmas Tree Crawl is always a good idea if you’re downtown Chicago. Here is where you can find some of the best and biggest Christmas trees in Chicago.

• City of Chicago Tree — This tree is located in Millennium Park near Michigan Avenue and Washington Street.  The tree is lit from November 18, 2022 till January 8, 2023.
• Macy’s Great Tree — This indoor tree is located on the 7th floor of the State Street Macy‘s department store. The tree is lit from November 5, 2022 till January 8, 2023.
• Wrigley Building Christmas Tree — This tree is located in front of the Wrigley Building on Michigan Avenue just north of the river. The tree is officially lit on November 18, 2022 and usually stays till mid January.
• Pioneer Court Tree (Apple Store) — This tree is located in the plaza just above the Apple Store on the northeast corner of Michigan Ave and the River.
• Hancock Building Tree — This tree is located in the plaza in front of the John Hancock building on Michigan Avenue between Pearson and Chestnut.
• 900 North Michigan Shops Tree — There are larger-than-life trees inside most malls, and this is one of them. I’m noting it here because it’s a good indoor tree to warm up by if you’re embarking on an otherwise cold, outdoor Michigan Avenue Christmas Tree Crawl.

Honorable Mention

• The Lions at the Art Institute — Every year on the day after Thanksgiving, the Lions that guard the Art Institute of Chicago on Michigan Ave receive their holiday wreaths. While not a tree, it’s some iconic greenery to feast your eyes upon.

Christmas bars, restaurants & cafes in Chicago

• Butch McGuires — The otherwise basic Division Street bar gets a Christmas makeover that rivals some of the best holiday pop-up bars in the city, and it’s been doing it long before those were a thing. It’s a super fun and festive place to grab a drink. Be sure to come around 4 or 5 to beat the crowds.
• The Berghoff — Nothing says cozy like a hot mulled wine and oversized pretzel. The traditional German decor at this iconic Chicago restaurant is accented with lights and greenery for the holidays. If you’re not due for a meal, stop by the attached Adams Street Brewery for a seasonal drink.
• Lou Malnati’s Gold Coast — If you’re visiting Chicago, pizza is always required eating. The Gold Coast location of Lou Malnati’s always has just the right splash of holiday decor. It’s a great place to hole up after a day of Christmas shopping. Get the deep dish Lou, well done, and thank me later.
• Intelligentsia — You’ve probably heard of Intelligentsia, but did you know they were founded in Chicago? They have a few coffee bars in the city, including one near Millennium Park. For something seasonal, try the Avena latte and ask for a dash of cayenne.
• The Gage — This gastropub on Michigan Ave across from Millennium Park is famous for its upscale takes on pub classics. During the holiday season, it’s a great spot for hot and cold seasonal cocktails.
• The Walnut Room — Enjoy a meal at the base of the Macy’s Great Tree. It’s a holiday tradition for some and bucket list item for others. Walk-up seating is sometimes available, but reservations are recommended. Get more info here.
• Christmas Pop-up Bars — Chicago has a ton of kitschy Christmas pop-up bars, particularly in Wrigleyville. They’re great for the ‘gram and can be a super fun night out with friends (and sometimes even with kids). Frosty’s Bar and Elf’d Up are two popular picks.
• Starbucks Reserve Roastery — The five-story Starbucks Reserve Roastery on the corner of Michigan Ave and Erie Street is not like your traditional Starbucks. Each floor has a different unique menu that includes things like a nitro gelato cold brew float and an espresso martini. At Christmastime, enjoy your coffee by a cozy fireplace overlooking the holiday lights on Michigan Avenue.

Holiday shopping in Chicago

• Macy’s State Street — The State Street Macy’s is a great place to start a day of Christmas shopping in Chicago. See the famous window display and of course the Great Tree, but also be sure to check out the massive toy floor and Holiday Lane.
• Christkindlmarket and Winterland at Gallagher Way — The park outside of Wrigley Field is home to the city’s second Christkindlmarket. It’s more spacious and usually less crowded than the one downtown. Inside the stadium is Winterland, which requires a paid ticket to enter and includes ice skating, games and rides.
• Malls & Shopping Streets — For general Christmas shopping, be sure to explore Michigan Avenue north of the river and State Street south of the river. For indoor shopping, visit Water Tower Place, The Shops at North Bridge and Block 37. For higher end shopping, hit up Oak Street between Michigan Avenue and State Street or pop into the 900 North Michigan Shops.

Christmas shows & performances in Chicago

There are so many holiday shows and performances in Chicago! Here are a handful of my annual favorites, but be sure to check local theatre schedules for new and changing events happening each year.

• The Nutcracker performed by Joffrey Ballet — Chicago’s premier ballet company puts on an excellent rendition of the The Nutcracker set against the backdrop of the 1893 World’s Fair. Get tickets here.
• Millennium Park Holiday Sing-Along — The best way to spread Christmas cheer is singing loud for all to hear. Community singing groups lead the crowd through holiday tunes in front of Cloud Gate (The Bean) every Friday November 25 through December 16.
• A Christmas Carol at the Goodman Theatre — The show runs from November 19 through December 31. Get tickets here.
• Holiday Comedy at Second City — I’ve seen a few shows at Second City and they’re all so good. During Christmastime, they always do a few different seasonal sketch shows. Check for this season’s line-up and get tickets here.
• Chicago Symphony Orchestra Christmas Performances — Their Christmas lineup varies each year. In 2021 they played the score to a screening of Home Alone and in 2022 they are performing a collection of Christmas carols in Merry, Merry Chicago. Get more info here.

Things to do on Christmas Day in Chicago

Visiting Chicago on Christmas Day can be tough because so many places are closed, but don’t rule it out entirely. Here are a few things to do on Christmas Day in Chicago.

• Go out for a Christmas Meal. A handful of Chicago restaurants are always open on Christmas Day, just be sure to do your research first. There’s always a round-up of open restaurants posted online a few days before the holiday. Here’s a sample of which Chicago restaurants were open on Christmas Day in 2021. Tip generously if you can.
• Stroll through Gold Coast. The residential streets in Gold Coast are always decorated to the 9s for the holidays. It’s my favorite place to walk to see Christmas decorations and lights. Explore State Street and Dearborn Street between Division Street and North Ave.
• Go a movie. My family would often see a movie in the afternoon on Christmas day. Most theaters, including all AMC Theaters in Chicago, are open on Christmas day.
• Jack Frost Winter Walk. This festive Christmas pop-up has historically been open on Christmas Day. You can enjoy seasonal beverages, holiday photo-ops, bumper cars, ice skating and more. Get more info here.
• Visit the Lincoln Park Zoo. There is no ZooLights on Christmas Day, but the free public zoo is open during the day. The Zoo usually opens at 10, but be sure to confirm the official hours as they usually close early on Christmas Day.
• Go ice skating. The ice rink at Millennium Park is open on Christmas Day, but be sure to make a reservation in advance.

Where to stay in Chicago at Christmas

If you’re in Chicago during Christmastime, we recommend staying in the Loop. We wouldn’t typically suggest staying in the Loop at any other time of the year, but it’s a great location for a holiday trip. There are a few reasons for this. First, is the location. For those unfamiliar with Chicago, the Loop is the central business district. The neighborhood is actually called the Loop because several of the train lines make an actual loop around the neighborhood. Many bus lines pass through or end in the Loop as well. All of the nearby transportation options make it easy and quick to get to many of the best holiday destinations scattered across the city. Second is price. As we mentioned, the Loop is the business district. Prices at Loop hotels tend to be higher during business days, and can actually be lower on weekends and over the holidays. For example, a king studio room at the Residence Inn Chicago Downtown/Loop is listed at $264 on a Tuesday night in December, but then drops to $162 the following Friday and Saturday. There are lots of great hotel options in the Loop at varying price points. Good hotel options include the Palmer House, Hilton Garden Inn Chicago Downtown Riverwalk and  Hyatt Centric The Loop. My brother and sister-in-law stayed at the later during this same trip and enjoyed it. We personally chose to stay at one of our favorite hotel brands, the JW Marriott Chicago. In 2021, we paid about $220 a night the week before Christmas. We booked a King Bed, Interior View room, and it was perfect for two adults and one toddler. The one downside to staying in the Loop is that it tends to be quite desolate after 6 PM and on the weekend. Don’t be surprised if you walk outside on a Saturday to an empty sidewalk and a few closed coffee shops. Don’t worry. Just walk a few blocks though, and you’ll find plenty of festive fun (and coffee).

How long should you stay in Chicago during Christmastime

If you’re planning a Chicago trip in December with the goal of doing Christmas activities, we’d suggest staying for three days. Depending on how far you’re traveling from, that can mean three or four nights. Three days gives you the chance to see all of the best Christmas activities that Chicago has to offer, but it won’t leave you feeling like you’re doing things just to do them. It’s the perfect holiday weekend destination.

How to get around Chicago

The easiest way to get around Chicago — all the time not just at Christmas — is by public transportation. The Chicago Transit Authority (CTA) operates trains and buses that connect the entire city. There are 8 train lines in Chicago, each named by color, and over 100 bus routes each named by number and street name or destination. Chicago’s train lines are often elevated, earning them the nickname the ‘L.’ To pay for the train or bus in Chicago, simply tap any contactless credit card when you board the bus or train. It costs $2.50 to take the train and $2.25 to take the bus. The full fare includes up to two transfers within two hours. If you plan to take more than two trips throughout the day, you can benefit from an unlimited travel card. You can buy an unlimited transit card for 1, 3, 7 or 30 days from the ticket kiosk located in all stations. If you’re arriving in Chicago by air, you can take the train from either major airport (Midway or O’hare) to downtown Chicago. There is a $5 fare premium to take the train from O’hare. Depending on when you arrive, the train is often faster than taking a taxi or rideshare. It is not necessary to rent a car in Chicago. If you are local to the Midwest, I’d recommend taking a train into the city instead of driving. The Metra connects many nearby suburbs and the Amtrak connects cities and states further away. Both Metra and Amtrak will get you to the Loop at either Union Station or Ogilvie Station. If you have to drive, be prepared to deal with traffic, hard-to-find street parking and/or expensive parking lots. If you’re staying at a hotel, make sure to check if they have parking available — not all do. Parking is also usually not included in hotel prices downtown Chicago.

Holiday Transit Tip!

Keep your eyes and ears peeled for the holiday train! Ever year, select trains get a full Christmas makeover. The holiday train is covered top to bottom in lights, they hand out candy canes, and Santa’s sleigh even gets a personal escort on the train. You can check the holiday train schedule here. In 2021, they stopped providing the exact times for the holiday trains to prevent over crowding, but they do provide a time range and day.

What to pack for Chicago in the winter

• Warm outerwear: Chicago is cold in the winter and many of the Christmas activities are outdoors. Be sure to have a warm coat, hat, touchscreen gloves, the works.
• Small tote bag: You’ll want to bundle up while you’re outdoors, but you’ll need to shed those layers when you’re inside. My favorite hack is to carry a small tote bag with me in the winter so I can easily carry my layers while I’m inside.
• Rechargeable hand warmers. Honestly, what will they think of next? If you have lots of outdoor activities planned, pick up a few of these electric hand warmers. They’re just like the disposable ones, but they last longer and are reusable.
• Waterproof shoes: There’s a good chance it rains or snows and nothing ruins a day out like having cold, soggy toes. Be sure to have a comfortable pair of waterproof boats that will survive slushy walks through city sidewalks. My husband and I both have and love the Nike waterproof Pegasus sneakers.
• Contactless credit card: It’s easy to tap-to-pay on public transportation if you have a contactless credit card.
• Portable charger. Looking up directions and restaurant reviews can drain your battery quick, so we always like to keep a portable charger on us when we’re out.
• Leg warmers for babies. If you have a baby in a carrier, you might be familiar with the struggle of their pants getting pulled up and their little legs being exposed. I was buying pants two years too big to cover this gap before I discovered the magic of leg warmers.

Our 3-day Chicago itinerary in December

As we covered above, there is a lot to see and do in Chicago at Christmastime. In this section, we’ll share how we plucked the best things from that list and built out a delightful 3-day Christmas Chicago itinerary. Our trip includes a 3-night hotel stay in the Loop with a midday arrival on day one. We then had 2.5 days of Christmas fun in Chicago followed by an early departure on our last day. FYI, this section is detailed. If you just want the summary, jump down to this section.

Day 1 – Arrival, Macy’s & Christmas Tree Crawl

We landed at O’Hare shortly after 11 AM and went straight to the Blue Line train. We were downtown in about 45 minutes for $5 per person.

Coffee & Lunch

It was nap time, so our toddler (Zoe) slept in the carrier the whole train ride. We got off the train at Washington, which has indoor Pedway access to Block 37 (an indoor mall). We got off there so that the cold outside wouldn’t wake up Zoe. It was a perfect excuse to get our first Starbucks holiday coffee of the trip. When Zoe woke up, it was lunchtime. We didn’t have a plan but passed Urbanspace food hall on our walk toward our hotel. Chicago has a few of these food hall concepts, which offer several restaurants in one place. We split up and Kenny went to Bhoomi to get paneer phulka (wraps) and I went to Spanglish for pepper & cheese gorditas and a quesadilla for Zoe. The food was delicious and Zoe ate really well. Urbanspace does not have high chairs so we used our travel highchair harness.

Checking in at the JW Marriott Chicago

After lunch, we braved the cold and headed to the JW Marriott. It was a short walk, but walking into the cozy, decorated lobby got us right into the Christmas spirit. Our room was ready and we went right up. We took a few minutes to get organized. We also called front desk for a Pack ‘n Play, which was promptly delivered to our room. We unpacked a bit and let Zoe play with the remote for as long as they wanted (a favorite hotel pastime).

Chicago Macy’s at Christmastime

We left around 3:30 for our first Christmas activity of the trip. We picked up another round of warm holiday beverages from Starbucks and headed for the State Street Macy’s windows. This was a quick 10 minute walk from our hotel. Every year, Macy’s on State Street in Chicago decorates their windows with elaborate, often moving, always sparkly displays. The windows tell a story, which you can read as you walk along. To read the story in order, start at the north end, across from Walgreens. This year, the windows didn’t seem quite as elaborate as I remembered, but it was still cute and we had a nice time. It takes about 20 minutes to see the windows and read the story. After the windows, we went inside with the intentions of seeing the Macy’s Christmas Tree. The tree is in the middle of the Walnut Room restaurant on the 7th floor of Macy’s. Typically, you can see the tree from a viewing area a floor above, but that was closed in 2021. There was a small selfie spot with the tree near the restaurant check-in for non-patrons. While the tree was a bit of a bust, we did find the toy floor, and I have never seen a happier baby. Our 16-month-old spent almost an hour looking at and trying out all of the toys. We’re at that perfect age where they don’t yet ask us to buy any of the toys, so we spent zero dollars and had the absolute best time. This was probably Z’s favorite part of the entire trip.

Downtown Chicago Christmas Tree Crawl

Now we were off to find all of Chicago’s best Christmas trees … or at least the ones we could walk to. From Macy’s, we headed north on State Street to Wacker Drive and then east to Michigan Avenue. Our first tree was at the Wrigley Building, which is my favorite tree in the city. It’s framed perfectly by the intricate building and there’s often a street performer nearby playing Christmas music on a saxophone. In 2020 during peak COVID, I could see this tree from my apartment balcony. It was always such a beacon of hope and cheer, and it will forever hold a special place in my heart. Across Michigan Avenue is another massive tree in Pioneer Court, between the Apple Store and Tribune Tower. This one has more of a blue ice theme. We continued south on Michigan Ave toward Millennium Park. Here you’ll find a magical, multi-colored Christmas tree-scape which sparkles as much as the city itself.

Dinner at the Hotel Room

We were in the market for a quick dinner and opted for pick up from P.F. Chang’s. It’s tough for us to find restaurant meals for Zoe at this age, so we honestly just went for the easiest and closest option. We’re not foodies over here, so if you’re looking for nicer dinner recommendations check out Goats on the Road. We ate in our room and then put Zoe to bed. Our room was not a suite, so when Zoe went to bed, we had to keep it mostly dark and quiet. We put a Christmas movie on the tablet and soon fell asleep ourselves.

Honorable Mentions

If you have more time, I’d recommend walking all the way north up Michigan Ave to Oak Street and back. The decorations along the way are a treat and you’ll find more beautiful Christmas trees at the 900 North Shops, Water Tower Place and the Hancock building. If you have even more time, cozy up on the 3rd floor of the Starbucks Reserve Roastery with a seat by the window overlooking Michigan Ave. Or if you’re in the mood for ice skating, you can find a rink in front of Cloud Gate (aka the Bean) or an ice skating ribbon at Maggie Daley Park. If you’re looking for a cozy cocktail, I’d recommend The Gage. I went there with my girlfriends after seeing The Nutcracker and it was so perfect. They offer different seasonal cocktails every year, but there’s usually at least one warm option. They also have great food, though not the best for vegetarians like us.

Day 2 – Museum of Science & Industry, ZooLights

Our schedule today would be split between a warm indoor activity during the day and a cold outdoor activity at night. These are two of our absolute favorite things to do in Chicago at Christmas. We know these are two very popular attractions. We’re in the camp that popular things are popular for a reason, so we don’t feel bad liking them.

Coffee & Transit

We tried to work in city walks as much as we could during this trip. We like holding a warm holiday drink and walking through the city, so we started our day doing just that. Saturdays in the Loop are quiet, but the calm actually added to the holiday vibe. It felt like even the city was taking a break. With a peppermint mocha in tow, we walked east from our hotel toward Michigan Ave, then went north a few blocks. Before Wacker, we turned back south and then went west on Monroe over to State to catch our bus. To get to the Museum of Science & Industry, we took the 6 Jackson Park Express bus. We got on at State & Monroe and rode south to Hyde Park & 56th. It took about 30 minutes.

Museum of Science & Industry, Christmas Around the World and Holidays of Light

The Christmas Around the World exhibit at the Museum of Science & Industry is one of our absolute favorite holiday traditions. The seasonal exhibit includes 50+ trees decorated to represent the culture and customs from different countries around the world. Timed entry tickets were required in 2021. Our ticket was for 9:30 AM, which was also the time the museum opened. We arrived shortly before 9:30 and there was already a pretty long line to enter. The ticket scanning process was very efficient, and we moved through the line quickly. We were exploring the museum by 9:40. Zoe (16 months old) usually loves Christmas trees so we thought for sure they would love this. We made it through about 2 trees before we realized it was not going to go as we planned. Our visions of nicely reading about each tree were quickly shattered as we restrained our toddler from constantly running into the Extreme Ice exhibit. We were immediately suckered into purchasing a Mold-O-Rama Christmas tree. While our toddler didn’t love hearing us read about Christmas customs at this age, they did have a ton of fun doing everything else at the museum. They absolutely adored the modeled trains, loved running around Yesterday’s Main Street and they danced up a storm to the silly song that plays in the element exhibit. Other highlights included the Farm Tech area, the 727 plane exhibit and everything in the Science Storms section (except the Tesla Coil which scared the poo out of this baby). Pro tip: In the instance that your toddler pees through their onesie like ours did, the museum gift shop does sell baby & kids clothes!

Lunch & Nap at MSI

The main cafeteria was closed for refurbishment and there was a pop-up Holiday Kitchen available instead. It wasn’t great, but it had enough options for us. We ordered a kids Mac & Cheese, yogurt and fruit for Zoe, and Kenny and I split a PB&J sandwich and veggie hummus wrap. There was one other restaurant open, Finnigan’s Sandwich Shoppe, and then two smaller snack shops. We prefer the cafeteria, and look forward to it opening up again. It was approaching 12:30, which is Zoe’s nap time. We don’t have a stroller, so carrier naps are SOP for us. We could have headed out and done the nap on the bus, but we thought Zoe could still have more fun at the museum after so we decided to stay and do the nap in the carrier there. If you’re looking for a quiet-ish place to start a nap at MSI, we recommend the area behind Finnigan’s by the back doors (which are locked so no one is coming and going) or the second floor near the elements section. After Zoe woke up, we stayed and played at the museum until about 2:30. I would recommend spending at least 4 hours at MSI with a toddler and up to 6 if you plan to eat and nap there.

Transit from MSI to the Loop

We took the 6 Jackson Park Express bus from Hyde Park & 56th and got off at Michigan & Monroe. In the Loop, the bus runs south on State but north on Michigan. The return trip took about 25 minutes. We then walked quickly back to our hotel for a snack and to gather our warmest layers for our next activity.

Transit from the Loop to Lincoln Park Zoo

Today’s schedule is a great example of why we opted to stay in the Loop. It was easy for us to go all the way south to Hyde Park for MSI, and it was just as easy for us to go north to Lincoln Park. The fastest way to get to Lincoln Park Zoo from downtown is to take either the 156 LaSalle bus or the 151 Sheridan bus north. It’s a quick 20 minute journey and they both stop right at Lincoln Park Zoo. Instead, we chose to walk. It takes about an hour, but it’s a walk we used to make all time and one we love. It’s a straight shot up LaSalle through River North, Gold Coast, and into Lincoln Park. We left our hotel at 3:30 and arrived right at 4:30.

Lincoln Park Zoo ZooLights

ZooLights is an annual event at Lincoln Park Zoo that runs on select nights from late November through New Years. The highlight is of course seeing the entire zoo covered in lights. There’s also carolers, holiday treats, ice sculptures, Santa and more at this must-visit holiday experience. The event historically has been free and open to the public, but like many things, that changed with COVID. In 2021, reservations and $5 tickets are required for ZooLights at Lincoln Park Zoo. In 2022, Mondays are free, but a ticket is still required.

Lincoln Park Zoo ZooLights with a Toddler

The lights are primarily outside, but there are plenty of spots to grab warm drinks or pop inside for a bit. Here’s how we balanced the weather, pandemic safety and holiday fun during our visit with a toddler. We entered from the south gate, so we started with the dancing lights on the Winter Wonderlawn. This is always the highlight and it runs every two minutes. Then we warmed up at the new Pepper Family Wildlife Center, formerly the Kovler Lion House, which was pretty empty. It was time for Zoe’s first hot cocoa at Snowy’s Spirits & S’more, located above the gift shop. They sell festive drinks (boozy & not), s’more kits (with little fires to roast your ‘mallows over) and snacks. Zoe absolutely loved the hot cocoa, the light-up snowmen and looking out at all the lights. It was cold and you could tell Zoe wanted to have fun but was also freezing so we kept moving. Next, we tackled the north loop of the zoo starting with a warm-up inside the African Journey. This attraction was a bit too crowded for us, so we moved through it quickly. We finished the loop outside past the polar bears and rhinos, ending by the ice sculptures in the Main Mall. We saw the seals from outside and then headed toward the south portion of the Zoo. The Small Mammal-Reptile house was crowded, but had a great little empty corner where they were playing A Charlie Brown Christmas. After that, we went past the Winter Wonderlawn again and did the loop past the apes (we did not go inside), zebras and camels. We’d recommend spending about two hours at ZooLights, which includes a meal and a snack/beverage. NOTE: ZooLights has a few additional ticketed attractions, including an enchanted forest, mirror maze, carousel, train and s’more station. Each attraction costs between $4 – $8. We didn’t do any of these attractions this time.

Dinner at ZooLights

There are a few places for food at Lincoln Park Zoo, but we opted for the main cafeteria, Park Place Café. The food isn’t great, but it’s easy, quick and there’s ample indoor seating. We got two slices of cheese pizza for us and a cheese quesadilla and fruit for Zoe. The seating area on the upper level was empty, so we found a table there. We even had a view of the Winter Wonderlawn from our table. Park Place Café at Lincoln Park Zoo does have highchairs, but I didn’t immediately see them. Instead, I again used our portable highchair harness and attached it to a regular chair. It worked great, as always. There are strolling holiday carolers throughout the event and they make a stop at Park Place Café. We got lucky and they performed right next to us at the end of our meal. They don’t have a schedule, but they are a delightful surprise when you find them.

Transit from ZooLights to the Loop

If it was just Kenny and me, we’d have taken the hour to walk from Lincoln Park Zoo back to the Loop. But since we were coming up on bed time and our kid was cold, we took the bus. The156 LaSalle and the 151 Sheridan buses both stop right outside the Lincoln Park Zoo west entrance and go to the Loop. The 156 goes straight down LaSalle and the 151 goes down Michigan before cutting west on Adams. We got home just in time to put Zoe to bed and watch another Christmas movie on our tablet. Oh, the wild nightlife of parents.

Honorable mentions

If you didn’t have to put a toddler to bed at 7 PM, we would recommend building out this evening a bit. Second City is a famous comedy club in Chicago. They have several shows, including a few different Christmas shows every year. This is a great place to go before or after ZooLights, depending on the schedule. Be sure to get tickets in advance as they often sell out. If you walk down Wells from North Ave, you’ll have your pick of bars. Woodie’s Flat is a festive pick. It’s got a younger vibe, especially at night, but it’s a great stop off for a casual drink in the afternoon and early evening. When it comes to Christmas bars though, Butch McGuire’s wrote the book on it. This place is literally dripping with holiday spirit. It does get extremely crowded, but if you’re passing by early and it looks tolerable, it’s absolutely worth a stop.

Day 3 – Christkindlmarket, Light Up the Lake at Navy Pier

Our next full day takes us to a Chicago Christmas institution and a (mostly) indoor event that’s great for kids. We met family in town on our third day, which meant one of us got to sneak in an adult afternoon.

About Christkindlmarket Chicago

First, let’s talk Christkindlmarket. It’s a European-style outdoor Christmas market with traditional German food, hot Gluhwein and unique shops. The Chicago market was recently named the Best Christmas Market in the US. The main Christkindlmarket is in the Loop at Daley Plaza, which is what we’ll cover here. Christkindlmarket opens in mid-November and runs through Christmas Eve. Hours vary, but it’s generally open from 11AM to 8 or 10 PM. General admission to Christkindlmarket is free and does not require a reservation. All food and drinks are an additional cost. Generally speaking, we love Christkindlmarket. I’ll be honest though, it can be amazing but it can also be absolutely awful. It’s always crowded and can be really cold. Even the warmest of gluhwein can’t keep your hands functioning well enough to eat a potato pancake with a plastic fork. I always include it on my itinerary though, because I love it more than I hate it. NOTE: There’s also a newer Christkindlmarket location at Gallagher Way by Wrigley Field. I’ve been to both, but prefer the original Daley Plaza location. The downtown location is more lively and feels more spirited, but the Wrigley location is great for families interested in more activities like ice skating and rides.

Visiting Christkindlmarket Chicago (Daley Plaza)

We walked from our hotel and arrived at Christkindlmarket 15 minutes before it opened on a weekday, thinking that would be our best shot at low crowds. Plenty of other people had the same idea and we arrived to a line around the entire block. While we waited, we met up with my siblings. The doors opened on time and the line moved quickly. Our main priorities at Christkindlmarket were potato pancakes and gluhwein. The waits for both of these things were pretty short when we arrived, so we got those first. There’s no seating or highchairs at Christkindlmarket. Instead, there are several shared standing tables around the food booths. We found a standing table pretty quickly with our early arrival. We left Zoe forward-facing in the carrier for lunch and they were able to eat their potato pancakes just fine. After that, we walked around the shops, but that area was already quite crowded. The waits to get into the sweet shop and the ornament shop were quite long, so we skipped those, too.

Nap time & The Berghoff

It was just about nap time. Since we were near the hotel, Kenny took Zoe back there to nap while I stayed out with my siblings. We were looking for somewhere festive to warm up. We decided to keep the German thing going and headed to The Berghoff. The Berghoff is another Chicago icon, dating as far back as the Chicago World’s Fair. We sat on the bar side which goes by the name Adam’s Street Brewery. The bar area of Adam’s Street Brewery is open seating, and we found a great spot by the window. The bar’s decorated for the holidays and just felt so warm and festive! They had gluhwein on the menu, so my siblings kept that rolling. They have a deep beer menu, so I went that route. For the full Oktoberfest vibe, you can buy any beer in a liter stein. As much as I wanted to indulge, I settled for a boring old pint knowing I’d have to parent the rest of the day. I’d never been to The Berghoff before, but we loved it. I’d definitely plan to go back at Christmastime in the future.

Coffee Break at Intelligentsia

Zoe was still asleep and we couldn’t drink the day away, so we headed out for a little pick-me-up. We picked one of our favorite Chicago coffee bars, Intelligentsia. We’ve been to their Loop location (53 W Jackson Blvd) a few times and it’s always delightful. They had two seasonal offerings, a Peppermint Mocha and the Avena Latte. The latter was described as an oat milk latte spiced with ginger, cinnamon, vanilla, and orange peel. Oat milk is too sweet for me, so I got the Avena Latte made with dairy. The barista recommended a sprinkle of cayenne, and he was right. I got two, one for me and one to bring to Kenny as Zoe had just woken up. I loved it and thought it was really spicy and unique. Kenny found the cayenne to be a bit overwhelming, and thought it was just okay.

Transit from the Loop to Navy Pier

We met up with Zoe and Kenny and headed to Navy Pier. We were jazzed on caffeine and decided to make the 40 minute walk instead of taking the bus. The walk from the Loop to Navy Pier is nice and takes you up to Wacker Dr, over the Chicago River (great views!) and through Streeterville (where we used to live). We’d definitely recommend this walk.

Light Up the Lake at Navy Pier

Light Up the Lake at Navy Pier is a ticketed event that takes place primarily in the large event space at the far east end of Navy Pier. It’s an indoor, semi-interactive light display with some added holiday offerings. The event is an adjusted version of the Pier’s usual holiday offering, Winter Wonderfest. Ticket prices vary by date and range from $15 – $26 per person. Children under 3 are free. Included in the price of the ticket is a small train ride, ice skating at the indoor rink, and a ride on the Centennial Wheel, the large Ferris Wheel outside on Navy Pier (an $18 value alone). There are also a few holiday shops, food vendors, and a beer garden with seasonal spirits at the event. Photos with Santa are available for purchase during certain hours.

Our Experience at Light Up the Lake at Navy Pier

We arrived at Navy Pier around 5 PM, but it took another 15 minutes to walk the long pier to the actual event. We didn’t see signs until quite a ways down the pier and had to ask for help. The entrance is past the food court, past the funhouse, and just up the stairs on the second floor. The train was our top priority for our little one, so we went there first. The line wasn’t short, but it was no Disney World and took about 10 minutes. The train is billed as all ages, but it is quite small. Each car would fit 2 smaller adults, but multiple taller/larger adults would be cramped. It’s a short ride, but our 16-month-old LOVED it. Meanwhile, Kenny checked out the holiday bar, Alpine Pub. He got a hot chocolate with Baileys which he thought was delicious. After the train, we ran around the lights for a while. Zoe loved chasing people through the oversized lit-up presents and seeing the giant teddy bear. It was certainly fun, but it didn’t keep us busy for too long. The ice rink is only open during certain hours which are posted on the website. It wasn’t open when we were there, but we weren’t interested anyway and skipped that. We spent about 1 hour inside at Light Up the Lake. If you were planning on getting snacks, ice skating or meeting Santa, you should budget 2 – 3 hours inside at Light Up the Lake. The best park of the event is that it includes a ride on Centennial Wheel, which costs $18 on its own. It sounds lame and touristy and what not, but I freaking love the Ferris wheel. The views are great and it’s just really pleasant. Unfortunately the line for the Ferris Wheel was long and we were pushed against bed time. Kenny and I opted to skip it and take Zoe home for dinner and bed. My siblings stayed for the ride and loved it! They’ve been on it before, but still enjoyed riding it again. The event isn’t cheap, and I’d say overall I was disappointed. I think if you were already planning to ride the Ferris Wheel, it’s worth the extra $8 to get the Light Up the Lake ticket which includes the Ferris Wheel. Without the ride on the Ferris Wheel, I did not get $26 worth of value at the event.

Transit from Navy Pier to the Loop, Dinner & Bed Time

After the event, we booked it home. We chose to make the 40 minute walk again because we just like it. For dinner we ate cold leftover P.F. Chang’s in our room. We also started packing and getting our things together, as we had an early train the next day.

Honorable Mentions

One major hole in this itinerary is Christmas shows. Based on our schedule, tonight would have been a great night to see a holiday performance because there are so many great ones in Chicago. One of my classic favorites is The Nutcracker. The Joffrey Ballet puts on an incredible rendition at the Lyric Opera House. The Chicago Theatre often has holiday-themed acts, and in 2021 had Barry Manilow for A Very Barry Christmas. The Chicago Symphony Orchestra always has something festive, and in 2021 played Home Alone in Concert. The list goes on. These are just a few from this year. Be sure to check schedules and ticket availability for your specific trip. I’d be remiss not to mention adding a live show to your Chicago Christmas itinerary.

Day 4 – Departure

We had no plans on our final day as our train out of the city departed at 7:15 AM. The JW Marriott is a 10 minute walk to Union Station, so we left our hotel room at 6:45 and arrived with plenty of time. We boarded immediately and were on our way as scheduled. Our Christmas in Chicago trip had come to an end.

Summary of our 3-day Chicago itinerary in December

Here’s an overview of our 3-day Chicago Christmas itinerary. The times included here are estimates and are intended to show how long we spent on different activities. Costs are rounded to the nearest $5 and include the total price for two adults and one child for each line item. Not listed below is the hotel, which cost $660 total for three nights.

Day 1 – Arrival, Macy’s & Christmas Tree Crawl

Day 3 – Christkindlmarket, Light Up the Lake at Navy Pier

Time	Activity	Cost
8:00 AM	Coffee & slow morning a the hotel	$10
10:45 AM	Arrive at Christkindlmarket Transit: Walk from JW Marriott to Christkindlmarket, 9 mins
11:00 AM	Lunch, gluhwein & shopping at Christkindlmarket	$35
1:00 PM	Arrive at The Berghoff bar, Adams Street Brewery Transit: Walk from Christkindlmarket to Adams Street Brewery, 8 mins	$40
3:30 PM	Coffee at Intelligentsia Transit: Walk from Adams Street Brewery to Intelligentsia (53 W Jackson), 3 mins	$15
5:00 PM	Arrive at Navy Pier for Light Up the Lake Transit: Walk from Intelligentsia to Navy Pier, 40 mins	$55
6:45 PM	Arrive back at hotel Transit: Walk from Navy Pier to JW Marriott, 45 mins
7:00 PM	Dinner at the hotel (leftovers)

Honorable Mentions

There were several things we’ve done in the past but we didn’t end up doing during this trip. Most of those things were evening activities, like bars and shows, or were longer walks that we couldn’t swing with a toddler. If you’re traveling without a toddler (or have a baby sitter), you may consider adding these items to a similar itinerary.

Additions to Day 1:

• Extended Christmas Tree Crawl north on Michigan to Oak Street
• Warm coffee and a window seat on the 3rd floor of the Starbucks Reserve Roastery
• Ice Skating at Millennium Park rink or Maggie Daley Park ribbon
• Festive cocktails at The Gage

Additions to Day 2:

• Holiday comedy show at Second City
• Drinks at Woodies Flat or Butch McGuires (festive bars that are done up for the holidays – go early)

Additions to Day 3:

• Joffrey Ballet’s The Nutcracker
• One of many different holiday performances around town such as by the Chicago Symphony Orchestra or at the Chicago Theater

Closing Thoughts on Chicago at Christmastime

We had an absolute blast during our 3-day trip to Chicago at Christmastime. We thought that three days was just the right amount of time. If we were traveling without a toddler, we would have added even more to our schedule, but we were happy with what we managed to fit in. This itinerary is pretty heavy on popular activities. There are certainly more Christmas activities throughout the city that are less popular and maybe need more attention. We might try to dig for those in the future. Until then, we’ll keep cherishing our favorite holiday traditions and sharing them with our little one. We hope you enjoy your visit to Chicago at Christmas time! What are some of your favorite things to do in Chicago at Christmas time? Please let us know in the comments.