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Comedians You Should Know (Chicago) Review

Comedians You Should Know is a stand-up comedy show that takes place weekly in Chicago’s Streeterville neighborhood. In this post, we review the show, along with providing tips for getting buying tickets, getting there, and finding nearby activities.

Showtimes, Location, and Getting There

Comedians You Should Know performs weekly at Timothy O’Toole’s Pub, at 622 N Fairbanks Ct, Chicago, IL 60611 in Streeterville. As of publication, shows are on Wednesdays at 9:30PM with doors opening at 8:30PM.

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Timothy O’Toole’s is about 11 minutes walking from the Grand and State Red Line stop. You’ll do best to exit the northeast exit from the Red Line stop, head north one block to Ohio, and then walk east across Michigan and into Streeterville. Check out our guide to riding Chicago’s L train system

There are also a variety of buses that service the area, primarily those that run down Michigan or to Navy Pier. We recommend using Google Maps to plan your route. We have a guide to riding the CTA bus system.

Buying Tickets

Tickets can be purchased at the door for $12, but it’s recommended you purchase them online in advance for $9.27 (includes service fee) in case the show sells out.

Online tickets are sold through Brown Paper Tickets. Just make sure to select the proper showtime, as multiple weeks are sometimes sold at once.

You’ll be prompted to create an account as part of your purchase. Major credit cards are accepted. This is a 21-and-over event only. You will need to show your ID at the door.

Arrival and Check In

Doors to the show open at 8:30PM. As it’s in the back of a bar, you can arrive as early as you please and hang out waiting for the doors to open.

We arrived at 9PM after dinner at nearby Beatrix. We’d been to Timothy O’Toole’s before but never to its event space. The doorman directed us straight back through the bar, to a small room with a bar, stage, and room for about 100 people.

Since we pre-purchased tickets, my name was on a list. Tickets were also available for purchase for $12.

We had pretty good choice of seats when we arrived. We chose a table in the second row against the wall. As you can see, it was a pretty small space. Not pictured are the bar and additional standing room.

Like the rest of Timothy O’Toole’s the venue is at basement level. This isn’t a lounge or a huge theater—it’s exactly the kind of space you expect heading to the backroom of an underground bar. That’s not to imply anything negative, it was clean and well kept.

Food and Drink at Comedians You Should Know

I’d saved room to try some food, and we ordered the Warm Pretzel Trio. I don’t think I’ve ever had deep fried pretzels before. They were very heavy and the dips were okay.

You can see (below) the menu doesn’t really offer full meals, so you’ll probably want to eat dinner beforehand. Timothy O’Toole’s has a more extensive pub menu. If you’re looking for something a little more modern American, we recommend Beatrix.

The drink specials included $4 select cans and bottles, $16 Miller Lite pitcher, and $6 Absolut mixed drinks. I went through three or four drinks.

Service was great throughout the sets. The server made a mistake and brought me the wrong can at some point, but comped it in an unnecessarily gracious move.

The Sets

At 9:32PM we were given the five minute warning: checks will come after the show, no flash pictures, no recording, keep the table talk to a minimum, no heckling, and please turn off your cell phones.

Comedians You Should Know changes its setlist on a weekly basis. The comedians are mostly local Chicago comedians (you can read about many of them on the Laugh Factory website), with a few out-of-towners mixed in.

There were sets from eight comedians. Marty DeRosa opened and emceed the evening. Lael O’Shaughnessy, Cleveland Anderson, Carly Kane, and Joe Kilgallon were the Chicago-based comedians. There was a fifth, but I unfortunately didn’t get his name and he wasn’t on the set list.

Drew Michael, whose HBO special received praise for its bold experimentation, made a surprise appearance with an awesome set. And Brendon Burns headlined, bringing energy and his in-your-face style.

Overall we were really impressed with the quality of the lineup. It’s not like we had reason to doubt CYSK, but it isn’t among the more famous comedy venues in Chicago. (Here’s our review of the UP Comedy Club’s She The People show, part of The Second City.)

We both considered this evening better than some we had spent at some of those other venues in the past. We’ll be reviewing those as well down the road. Comedy is tricky, as comedians and sets change from show to show. We’ll be returning to Comedians You Should Know in the future to see how a different group does.

Because the venue is so small, table talking was a potentially big problem. The comedians kept it under control by shutting down table talkers real quick, which always leads to some enjoyable improv.

The show ended sometime around 11:20PM, about 100 minutes after it started. The local comedians stuck with sets around 5 to 10 minutes, with Drew Michael and Brendon Burns going a bit longer.


Checks were handed out immediately after the show ended. This was fine, but it meant we had to go open a new tab at the bar to keep drinking, a minor inconvenience. We wound up spending $48 (pre-tip) for five drinks and the pretzels.

Comedians You Should Know has the space until 12:30AM, but about half the people in the room cleared out right after the show ended and another quarter were gone within 15 minutes. A few comedians stuck around. We had one more round and chatted about the show.

Unless you’re talking with the comedians, I’d suggest just starting your second tab at the regular Timothy O’Toole’s bar. The show space is fine before and during the show, but afterwards you’re mostly surrounded by everyone’s half-consumed food and beverage.

What’s Nearby

We’ve already mentioned Beatrix and Timothy O’Toole’s as good options. For some traditional tourist activities before the show, consider shopping on the Magnificent Mile. Just under a mile south, you’ll find Millennium Park.

River North, the neighborhood on the other side of Michigan Avenue, is packed with dining and drinking options.


We highly recommend Comedians You Should Know. For $9 to $12, you’re getting a great value.

Having a nearby dinner and arriving at 9PM was perfect timing, as it allowed us a good choice of seat and to get a round in before the show.

As with all things comedy, shows and individual sets are going to be hit or miss. The audience has a lot to do with this, so do your part and laugh. Particularly at jokes where you might be the only one who finds it funny.

If you’re a resident of downtown Chicago, Comedians You Should Know is a great option for a weeknight out. If you’re in town on vacation, the venue definitely offers you more of a local vibe—and a more reasonable price—than some of the more famous comedy acts in town.