Comedians You Should Know

You’ll always find fun and people at Tim O’Toole’s, regardless of the day of the week. I like Wednesdays when Comedians You Should Know takes up shop at 9pm in a back room/​bar that seats about 45. It’s a series of 4 or 5 stand-​up comedians plying their trade and coupled with specials like $ 5 Absolut mixed drinks.
I couldn’t tell you any names but the comedians seem to range from fairly established traveling types who may have even been on late night TV shows like Conan to more up-​and-​coming aspring types. That’s part of the fun of it — you may really laugh at someone truly funny or kind of cringe inside and try to laugh for support at someone who’s not but giving it their best shot. And I give mad props to anyone who gets up there in front of the mic and puts themselves out there like that!
Drink specials are pretty good and service is okay though your cocktail server may not come by often enough given how many tables they’re covering and the tight confines.
Buy tickets online in advance for $ 5 but do so at least a few hours ahead or else you’ll unwittingly buy a ticket for the following week’s show. $ 10 at the door.
Sometimes they’ll feature one comedian the whole night who’s recording their CD or a video. I didn’t like this night as much because one comedian who wasn’t that great for 1+ hours wasn’t fun. I prefer the variety of 4 – 5 10 – 15 minute spots!

Baloney Sandwich! We got advance tickets through Brown Paper Ticket and then were refused entrance due to capacity overflow. No refund available, but a suggestion from the snarky door girl to «come back Wednesday.»

CYSK is the best comedy showcase I’ve seen in a long time, and my best friend is a comedian so I go to a lot of shows. One of my pet peeves at shows are when the host and comics completely drag it out. Not here. CYSK are boom, boom, boom — no crickets here. The producers are legit, paid their dues, are all making names for themselves and they book quality comics. Atmosphere is nice, good location, drink specials and they serve food throughout the entire show. CYSK is great for girls/​boys night out, date night, birthdays… highly recommended. You won’t be disappointed.

What a great experience! Timothy O’Toole’s is a huge place, but there’s a cozy atmosphere in the basement lounge where the show was. The service was great and I LOL’d constantly– every comedian’s act was hilarious and fresh.

Went here on a whim and was so glad we did. It was very entertaining and such a value at $ 5. If you live in or visit Chicago you need to check this out! A great night.

I went last minute 15 minutes before showtime to secure a good seat. It’s $ 10 at the door but $ 5 if you plan ahead.
The acts were absolutely hilarious. It’s without a doubt a great 1^st date scenario with simple bar bites & drink specials. I’ll never stop coming back. Great for groups of friends.

Best independent comedy show in the Midwest. CYSK is a showcase, meaning you will see 6 – 8 comedians do shorter sets in ranging from 6 – 15 minutes in length. This is great cause you get more bang for your buck and there will be something for everyone. On top of that they regularly get surprise guests that are national touring acts. There’s no drink minimum and if you get your tickets online (which you should, they regularly sell out) its only 5 bucks. The only way you won’t enjoy this is if you are a real asshole.

I’ve seen these comedians perform several times and they are consistently funny. For $ 5, you get to see a 2-​hour show consisting of local and visiting comedians. I highly recommend the show.

This is hands down one of the best run showcases in Chicago. Each comic comes with years of experience and its a great model for how other shows should be run. Perfect intimate space, an affordable cover and comedians that are solid. They really have the system down and the comedians are all different and likeable each with a unique voice. Picking one is difficult as they all have a different style that somehow compliments the other from dark, to witty, to really absurd and funny and some that are masters of crowd work. They are all committed to making this the best show in Chicago and it blows my mind that it doesn’t get the National attention it deserves. Every show is different and they also bring in nationally touring Comedians, and local up and coming comics. The food at Timoth O’tooles is outstanding as well and not marked up downtown prices. If you’re looking for solid stand up but don’t feel like a two drink minimum at Zanies or another club check it out. There’s even a promo code if you buy ahead of time online.

Great show for the price! Very small and intimate setting, expect to sit with some strangers unless you’re with a group of 4 or more. Drinks average about $ 7 each I’d say, so they make up for the cheap show there. Worst part is that the chairs are uncomfortable as all hell and the since the show is about 2 hours long you’ll be feeling it afterwards. That said, I would definitely go again!

You’re a fool if you don’t go check this out. Amazing local comedians in an intimate setting without the drink minimum for super cheap! Who doesn’t want to laugh on a Wednesday night?

Great spot! You just cannot beat the entertainment value. $ 5 in advance and $ 10 at the door. Went last night for the first time and enjoyed the comedians… except the last one. Things got a little out of control with 4 obnoxious ladies in the front row who were distrupting the show. It went down hill from there and there were even mentions of the Conn shooting victims.
All that said, I will be a regular here.
Food at the pub was pretty good too and WOW do they have a great beer selection!
All in all a great spot for your entertainment dollar on a Wednesday.

CYSK is a great group of dedicated, hilarious dudes who are totally worth the 5 or 10 dollars you spend on them!
It’s a quiet room off the side of Timothy O’Tooles, with no overlap of noise. Cozy setup with candles on tables and full bar with easy access and also waitresses serving tables as well, good beers with no drink minimum… that’s right no drink minimum! But you’ll end up getting drunk anyway with $ 3 beers in the city.
The comedians are fantastic and hilarious, with guests and regulars taking the stage!
A lot of fun with a date or with a group of friends, highly recommend checking it out!

Went on a recent Wednesday night and really enjoyed the show. The comics were all really funny (some more than others) and they put on a really solid show. There’s nothing wrong with belly laughing on a Wednesday night all for the fair price of $ 5! I’ll be back again soon and will bring some more friends with me next time!

$ 5 with flyer from Timothy o’Tooles. Best $ 5 spent in ages! Hilarious comics and fun crowd. Will be back next time I’m in town.

This is pants down the best stand up in Chicago. It’s a group of very talented, relatively fledgling, and somewhat rotating cast of local comedians. I went for the first time last night by myself and laughed so hard I almost forgot how terribly alone I was. The performers were Joe Kilgallon, Liza Treyger, Dan Ronan, Marty De Rosa, and Mike Lebovitz. Each had their own style, were well-​polished, and should be more goddamn famous, but thankfully for me I could see them all perform their balls off for $ 5. Plus, they all hung out after the show, and were generally affable, though they may have just been looking for a ride.

I will tell you this much, where else can you take a date for ten bucks (two people) unless you go for ice cream or go to redbox… ice cream melts in five minutes and a movie rental can’t be played outside… anyway…the show was great, funny, included five comedians and lasted over two hours. It is first come, first serve, sit anywhere you want. If you’re a couple you’ll sit with another twosome. If you don’t enjoy sitting with strangers come in a group of four. There is no drink minimum which is great but the down fall is paying six bucks for a draft beer. You can park on the corner after six for ten bucks.
I brought a first date here! What a great idea, she laughed her ass off, I didn’t even need to talk… she just remembered having a great time and it won me a second date… just sayn!

Pretty much the best way to beat the mid week blues: drinks & cheap comedy
I’ve been here twice and have laughed hysterically both times. It’s casual, a younger crowd, kind of small, the comedians are really funny, and the drink service is usually quick.
PS. Extra points for not being obnoxious with their email list and constantly sending annoying emails. Plus, it’s actually worthwhile — I won four free tickets by being on the list!

We went on a Wednesday night. The house was packed. Very cool for a Wednesday.
Good News: Very nice space– audience and comic friendly. The folks working the service end were awesome.
The Line Up: Five comics and an emcee. They clearly capped the weak and inexperienced comics with the stronger ones.
The Bad News: The middle comics were pathetic, immature and inexperienced– cripplingly horrible. The end cap comics (emcee included) were obviously more experienced but primarily appealed to a young, immature male audience that wants to hear about getting drunk and having cheap sex. There was a lot of «my dick» humor. IMO these topics get old really fast.
Good Material: I didn’t catch his name, but one comic did a bit on Roe v. Wade and sandwiches that was really great. Too bad his stage persona was not credible and cheapened the POV of his material.
Good luck to anyone who goes there. Hopefully you’ll hit a better night than we did.

Talented, funny comedians for $ 5 at a place with no drink minimum?
They’ve just beat Zanies on three fronts.