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12-Day Road Trip from Orlando to Chicago via Washington, DC

We had a doctors appointment in Chicago and currently live in Orlando. Instead of flying in for a quick trip, we decided to pack up the car and our toddler for a 12-day cross-country adventure. In this trip report, we’re sharing everywhere we went and everything we did in our journey across the country.

Deciding to Drive from Orlando to Chicago with a Toddler

When we booked a doctor’s appointment three months ago, we knew we’d be living in Florida by then. We kept it though because we figured it would be a great chance to get back to the city.

However, per usual, COVID had other plans. When Omicron hit, we were so cautious, stayed at home, and managed to get by without getting sick. We didn’t want to throw all that away just to catch it on a plane as it was on the decline.

We couldn’t cancel the appointment, so driving was our next best option. The drive from Orlando to Chicago is about 18 hours. That’s a long time in the car for a kid, so making the trip in one or even two days was out of the question.

We decided that if we couldn’t get there as fast as possible, we’d get there with as much adventure as possible.

Road Trip Baby

Planning Our Route

We took a similar road trip from Rochester, IL to Orlando, FL after Christmas. It was the same situation where we planned to fly, but COVID changed our plans last minute.

That trip was shorter and we broke it up with stops at two National Parks in two days. We didn’t want to do the same thing again, so we were looking for new destinations this time around.

We kept our route to Chicago pretty direct with stops along the way at Reed Bingham State Park (Georgia), Atlanta, and Rochester, IL.

Coming back though, there weren’t any good different stops that made sense with our travel schedule, so we decided to really commit to going out of our way. Instead of coming straight southeast, we decided to go all the way east and then south.

After Chicago, we added stops in Ohio, West Virginia and Washington, DC. Here’s a peek at our route. We’ll break down everything we did at each stop below.

Getting Ready for Our Road Trip

We thought this trip would be pretty smooth because we had the luxury of preparing for it, which we didn’t have before our last road trip. That wasn’t completely true, but it did help.

Our first priority was food. Kenny and I are vegetarians, so we planned on eating a lot of Subway and Burger King Impossible Whoppers along the way. It’s a bit tougher to rely on fast food for our toddler, Zoe.

There aren’t a ton of good, healthy fast food options for a vegetarian toddler. They also eat on a set schedule and we preferred to keep them out of restaurants anyway for COVID safety reasons. To avoid constantly scrambling for their meals, we packed four bento box meals and planned to restock along the way.

Bento boxes + travel highchair harness and Zoe can eat just about anywhere, anytime!

We also stocked up on snacks for us, canned coffee drinks for emergencies, and sparkling water. We didn’t have a cooler, so we picked up this picnic basket cooler for the trip. The cooler itself worked well, but we have a lot to learn about cooler best practices.

Beyond food, there were a few things we had to plan for. First, was the fact that Zoe would be sleeping in 6 different beds over 12 days. We needed a mobile, packable bedtime station that helped Zoe feel consistency even with locations changing. We’ve got this down to an art now!

Lastly, we needed to account for a huge weather shift. It was 82°F when we left Orlando and was down to 26°F by the time we got to Illinois. We needed to pack a full winter wardrobe for all of us.

Bears Hat from Scheels | Winter Coat from Patagonia (so warm!) | Snow Pants from Columbia but bought second hand on eBay | Boots from Walmart | Mittens from Target | Leg Warmers (not visible but clutch in the carrier) from Amazon

Once we thought we had everything packed up, we hit the road!

Day 1: Orlando, FL to Atlanta, GA

It is a 6.5 hour drive from our apartment to the SpringHill Suites near the Atlanta, Airport. We headed out just after breakfast, around 8:30, and arrived at our first stop, Reed Bingham State Park, just before noon.

Why Reed Bingham State Park? A few reasons! First, it was a convenient location, right in between Orlando and Atlanta. Second, it was lovely! But mostly, it was for Zoe’s state count.

We decided that in order for Zoe to get “credit” for a state, they needed to have at least one meal and do at least one actual activity. The bottom bar for an activity needed to be at least a state park, and Reed Bingham State Park was a perfect one!

We had a lovely picnic lunch at the gazebo. Kenny and I had PBJs and Zoe ate one of the meal boxes we prepared. Then we spent some time running around the park, checking out the lake and kicking pine cones.

As we headed out, I spotted a playground in the distance that I couldn’t pass up. Zoe went down all the slides and even got some impressive climbing practice in! They were zonked by the time we left fell asleep in the car pretty much immediately.

It was a 3 hour drive from the state park to our hotel near the Atlanta Airport. Kenny had stayed in the area before, so it was an easy pick. We stayed at SpringHill Suites, which is our preferred hotel for stays with a toddler.

We picked up Subway for dinner for us and Zoe had another prepared meal box, which we all ate at the hotel.

Day 2: Atlanta, GA to Rochester, IL

After Zoe’s breakfast, we picked up coffee from the hotel lobby and hit the road. Our plan was to drive to Nashville, Tennessee. Kenny recently spent one night in Nashville and we thought we’d do something similar.

As the day went on and we made quick progress, we started second guessing things. We thought could push the drive a bit and make it all the way to St. Louis, MO. Neither Kenny nor Zoe have been to the Gateway Arch, and that seemed like a fun thing to do the next morning.

St. Louis is only 1.5 hours from Rochester, IL, which is where my parents live and where we’d be staying for a few days. At first, the short drive in the morning sounded tempting, but then started to feel silly. We got the idea in our heads that if we could make it to St. Louis, we could just make it all the way to Rochester. So we did!

It was a 10 hour drive between at Atlanta and Rochester. We broke it up with three great play breaks along the way!

Our first stop was the Chattanooga Welcome Center to run around. We stopped for gas around Nashville just at lunch time and found Antioch Park just up the road. It was a bit too cold outside for a picnic, so we ate in the car, but played for a while at the playground.

Zoe napped in the car as we made our way to Illinois. Our final stop was the Rend Lake rest area near Wayne Fitzgerrell State Park in southern Illinois. We had passed into snow territory so we had ourselves a little snowball fight.

Those last 2.5 hours to Rochester were among the toughest of the trip, but we made it! Arriving at my parent’s house just in time to eat dinner and go to bed.

Days 3 – 5: Rochester, IL

We arrived in Rochester shortly after a winter storm barreled through the midwest. That meant that there was a good six inches of snow outside when we got there.

Our Florida baby was a little unsure about the snow at first, especially after their first encounter involved falling in the snow before they had boots or socks, but they came around.

Once we busted out the full snow-proof outfit, they were good to go. We had so much fun taking winter walks and sledding, but their favorite part was definitely eating the snow.

Our timing in Rochester could not have been better. We had two full days in town, and one of those happened to be my dad’s birthday! This was already great, but made even better when I found out my brother and his girlfriend would be coming to visit, too! It was such a fun family get together.

Days 6 – 7: Chicago, IL

We left Rochester after lunch so Zoe could nap in the car on the way to Chicago. We thought this 3.5 hour drive would be a breeze after our previous 10 hour drive day but we were wrong. Zoe screamed more on this leg than the rest of the trip combined.

Even a screaming toddler, though, can’t take away the magic of seeing the Chicago skyline for the first time in a while. She is a beauty and it was so nice to be back for the first time after moving in November.

If you’ll recall, we were actually only taking this trip because we had a doctors appointment. We got that out of the way on our first morning and it went well. Zoe got rewarded with a cake pop and I got rewarded with a new phone (which I was very long overdue for).

It was pretty cold, but we bundled up and took a few walks through our old stomping grounds. We spent one afternoon visiting our favorite bookshop (after-words bookstore) and one of our favorite coffee shops (Dollop Coffee Co) and it was such a delight.

We stayed at the Marriott on Michigan Ave. Our room was on the 33rd floor and had a west-facing view. It was so beautiful.

Day 8: Chicago, IL to Canton, OH

An early exit from Chicago got us to Canton, OH in the late afternoon. There’s not much to say about the drive, but the service stations along the Ohio Turnpike were amazing!

The service stations were spacious, clean and mostly empty. It was an unexpected treat to have a warm and COVID-safe place to stop and let Zoe eat and run around a bit. Having a Starbucks and vegetarian fast food option available was just the icing on the cake.

We stayed the night at the SpringHill Suites in Canton.

The service stations also had these toddle chairs in some stalls and it was amazing and I’m officially starting a lobby to have these installed in every bathroom ever.

Day 9: Canton, OH to Morgantown, WV

Why Canton, Ohio? Because it was the site of our first big, new adventure of the trip: the Pro Football Hall of Fame!

When we were planning our route and started looking at going east, we were really excited about how well the Hall of Fame fit into our schedule.

It was the perfect distance from Chicago for a day’s drive (6 hours). And since the museum is actually pretty small, we were able to see it in a morning and then drive in the afternoon.

We had the absolute best time at the Hall of Fame! It’s such a cool museum with lots of history, memorabilia, and interactive exhibits (which Zoe was terrified of but would be fun for most kids). The actual Hall of Fame enshrinement with the busts of all of the game’s greatest was so inspiring.

All of 2020’s greatest

After a fun morning, we headed out toward West Virginia. We stayed the night at SpringHill Suites in Morgantown, WV.

We picked Morgantown, WV because of its location between Canton and DC. Unfortunately we didn’t have time to see or do anything in town, which is why we can’t give Zoe “credit” for visiting WV just yet.

Day 10: Morgantown, WV to Washington, DC

We left Morgantown early and arrived in DC in the middle of Zoe’s nap. We decided to drive around Alexandria instead of going straight to our hotel which would have definitely woken Zoe up. It was a lovely diversion. If I’m back in DC for a longer time during a warmer month, I’d like to explore more of Alexandria.

Our favorite thing to do when we arrive in a new city is go for a walk, get coffee, and explore. So we did! Unfortunately almost every great coffee shop in DC is closed by 4 PM on a Sunday, but we went to Soho Tea & Coffee near Dupont Circle. It was … fine.

We watched the planes fly over, walked through some lovely little parks, passed the White House and Washington Monument and then Zoe promptly shut down. Poor thing was not having it with the cold so we headed back to the room.

It was Super Bowl Sunday, so we ordered Potbelly delivery and let Zoe watch the first 30 minutes of the game before bedtime. We then proceeded to watch most of the rest of the game without sound. (It was going well until the light finally woke Zoe up at the end and most exciting part of the game, and we had to turn it off.)

We stayed at the JW Marriott Washington, DC. We earned Platinum Elite status with Marriott Bonvoy, which includes free upgrades when available. There were no larger rooms available, which was a bummer, but we got upgraded to a room with a view. This turned out to be such a blessing.

It was so cold and we spent more time than we would have liked in the room, so at least it was a nice room. We had a gorgeous view of the Washington Monument and the planes taking off from DCA. There was even a ledge a few stories below our window where the pigeons hung out, which Zoe absolutely loved.

Day 11: Washington, DC

The days before we arrived in DC, the highs were in the 60s. The days after we left DC, the highs were in the 50s. Unfortunately, we perfectly caught a small but mighty cold front and the highs when we were in DC were in the 20s.

After everyone was bundled up, we headed out for coffee. The coffee shop we had originally picked was located on a block that was closed for a film set. So we pivoted and went to Dua Coffee DC, which could not have been a better pick!

Dua is an Indonesian coffee shop, that features beans only from that area. The coffee was amazing, the handmade mugs were beautiful, and the whole space was cozy and pleasant. Even Zoe had some semblance of chill hanging out there, which is honestly rare!

We tried to head to the National Mall after that, but Zoe completely lost it. As it turned out, it was a rightful meltdown because we had a real diaper crisis. We settled for the rest of the morning and nap in the room.

After Zoe woke up again, we tried for a third time to get a Mall walk in and finally succeeded! We walked past the Washington Monument, WWII Memorial, and Lincoln Memorial. Zoe had the best time at the Lincoln Memorial and one specific perfect bench along the way that they simply refused to leave.

It was Valentine’s Day so we ordered Chipotle and had a family dinner together. I also brought heart shaped chocolate chip cookies for everyone, which I’d baked in Rochester (a family tradition).

Day 12: Washington, DC to Orlando, FL

After DC, we had planned to stop at Disney’s Hilton Head Island Resort, but it was booked. Then we considered adding a Civil War site or Savannah, GA, but decided against it.

By this point, everyone was pretty much tapped. The cold really got the best of us in DC, which kind of brought down our vibe. It also seemed pretty clear that Zoe was about over it.

Even though it was surely going to suck, we decided to drive the full 12.5 hours from DC to Orlando in a single day. The drive was long, but honestly Zoe held it together pretty well. We stopped at a few places for gas and food along the way and that seemed to keep everyone content.

Zoe was just happy to be outside without a winter coat when we finally got into Georgia.

The biggest challenge was going to be doing bedtime in the car and then hoping Zoe stayed asleep for 3 hours. Fortunately it went surprisingly well. They woke up a few times screaming, which was sad, but we made it home. Zoe seemed really happy to be put in their own bed just before midnight.

It was a hard day, but honestly the best thing. We were so glad Zoe could wake up in the morning and get to play with their own toys and ride their bike again.

Zoe was pretty amped to get back to our apartment’s playground

Trip Summary

  • Days: 12
  • Cities: 6
  • States: 4 (plus DC)
  • Beds: 6
  • Miles: 2,886

Immediate Takeaways

This trip was exhausting in more ways than one. It was a lot of driving, a lot of entertaining Zoe with a limited set of toys and books, and a lot of cold weather. But at the end of the day, we had more fun times than hard ones and I’m glad we did.

This space sticker book saved the day more than once

We like the idea of roadtrips and would like to do more in the future, but there are some things we have to figure out first.

First is the cooler situation. We really value preparing our own meals for Zoe, but we need a better strategy. Changing the ice constantly was such a chore and we had multiple instances of food getting ruined because the melting ice flooded the container. There’s got to be a better way.

Eventually we learned to only buy foods that were individually sealed. For example, this lunch in the back seat at a gas station was a pre-packaged fruit and cheese snack plate and an Uncrustables PBJ.

The second thing we have to figure out is our stuff! We are backpackers at heart so having to take multiple trips to the car to bring in all of our stuff to every new hotel is just so outrageous. Some things are nonnegotiable, like Zoe’s mobile bedtime station (Pack N Play plus a tote bag), but we need to streamline the rest.

While we certainly struggled in some areas, we do have some things figured out.

The most convenient is Zoe’s sleep situation. We can set up bedtime in any hotel in just a few minutes, and Zoe can sleep pretty much anywhere. The timezone got us on this trip, but other than waking up a bit early, the kid did great.

I also think we settled into a road trip driving schedule that works well. Drive for 3 hours in the morning. Stop for lunch and playtime. Drive for 3 hours in the afternoon, with a 2 hour nap in there.

We try to limit screen time, so we brought all of Zoe’s favorite books. This occupied a lot of our time, but the tablet was definitely utilized more than once.

Closing Thoughts

This trip was a whirlwind, but like I said, I’m overall glad we did it. Our trip this time was out of necessity with a fixed destination, but we dream of another adventure with even more time and even more flexibility. We’d love to explore the US west one day, and I think this was a good peek at what that will look like.

Are you a road trip person? What’s your favorite route or a dream route? If you’ve road tripped with a toddler, hit us up with all your tips in the comments!