45 Cheap Things to Do in Chicago

Published On 11/03/2015 Published On 11/03/2015
Turtle racing
Turtle racing | Sean Cooley/Thrillist

If you’re digging through your George Costanza-sized wallet only to discover there’s nothing left except a scrap of paper for guitar lessons and your last $20, do not panic. There’s plenty of fun to be had in Chicago on the cheap. Enjoy exploring the big city without big price tags by trying out these 45 things to do in Chicago for $20 or under.

The Art Institute | Flickr/JanetandPhil

1. Toast to Hollywood at Brew and View

Brew & View has been doing the whole “drinking and a movie” thing likely since before you had your first taste of either. Most movies are still only $5 screened at The Vic, still one of Chicago’s finest live music venues. And you’re gonna need the extra laugh potion to make it all the way through The Nice Guys.

2. Reenact the scene from Ferris Bueller's Day Off at the Art Institute

You’re gonna get your money’s worth at pretty much any museum in town, so even if you miss the free days, the $14 general admission ain't bad.

3. Hit up Chicago’s year-round film festival at the Music Box

Sundance has been called many things, but it’s never been called cheap. The Music Box, on the other hand, offers similar vibes for about one-billionth of the price.

4. See a show at the Hideout

From Empty Bottle to Burlington, cheap live music is not exactly scarce in Chicago. But we doubt you’ll have more fun seeing cheap music than you will have seeing cheap music at the Hideout.

5. Get naughty at a burlesque show

A lap dance at a strip club is not exactly the most economical use of $20. Vaudezilla, on the other hand, offers $20 admission to burlesque shows -- which, yes, you can probably pay for in singles.

6. Dial up a PB&J Special at Boiler Room

Long known as one of the finest deals in all of Chicagoland, a slice of pizza, PBR tall boy, and shot of Jameson can be yours for a measly $8.50 at Boiler Room. All day. Every day.

Furious Spoon

7. Grab a $1 beer with a side of ramen

For a killer bowl of ramen, you know to stop by Furious Spoon. Also stop by for one the cheapest drinks in the city: $1 Hamm’s. Yes, ramen and Hamm’s. It’s a thing. All day every Wednesday.

8. Stare & stumble during a Chicago architecture tour

From tours of the Chicago Athletic Association Hotel and Board of Trade Building to historic skyscrapers and neighborhood tours, the Chicago Architecture Foundation offers tours of pretty much anyplace worth touring in Chicago -- mostly for $20 or less.

9. Grab Chicago’s Best Burger at Au Cheval

There are literally (okay maybe not literally) billions of places to enjoy great cheap burgers in the Chicago, but with a $20 budget why not go with the best? The single cheeseburger (which is actually a double burger) at Brendan Sodikoff's greasy spoon is pretty much the best in town, pretty much everyone in town agrees.

10. Enjoy one of the city’s best lunches under $10 at Sultan’s Market

For $7, the lamb shawarma dinner at Sultan’s Market is one of the best deals to be had in Chicago. Go crazy and splurge for the extra falafel on the side for an additional 50 cents.

Kailley Lindman/Thrillist

11. Get messy devouring the world’s largest sundae

It’s a half-gallon of ice cream with six scoops and two toppings. It’s at Margie’s Candies. It’s $14.95. Your move.

12. Thumb through some vinyl at Reckless Records

CDs? Cheap vinyl? Free in-store shows? We get it, it’s not a 99-cent download. That’s what makes it cool.

13. Learn how to dance to hip-hop

No, you spilling beers as you make awkward circles on the dance floor as Eminem plays does not qualify as dancing. There is an art to dancing to hip-hop. An art you can learn in an actual class. For $20.

14. Check out a leather museum

It’s only $8 for admission to this 10,000sqft, two-story palace of kink, which comes complete with more than 25,000 books and magazines, a climate-controlled archival storage space housing art and records of notable BDSM activists, and its own 164-seat auditorium. Not to mention its own dungeon, screening room, and Leather Bar. Naturally.


15. Watch the Mud Queens of Chicago do their thing

Admission to their regular mud-covered battles around town are probably cheaper than your cleaning bill if you get too close.

16. Tour Chicago’s best brewery

There are many Chicago breweries you could tour on the cheap. But for a measly $10, including pint glass and sampling, why not tour the best

17. See a movie in a badass renovated theatre

They don’t get much nicer than the recently renovated Logan Theatre, where you can see movies on the cheap AND drink booze in your seat, which is always a good combo.

18. Get weird behind the wheel at Whirlyball

It’s a $15 per person walk-in rate for a half hour of the most fun you’ve had in a moving cart since that time you drove that golf cart into the pond at your uncle’s country club. 

Madeline Northway

19. Get a beer & pizza for $10 at Nellcote

A beer and a 10in pizza for $10 Mon-Fri, 5-7pm; Sat-Sun, 11am-7pm at one of Chicago’s most beautiful bars? What’s not to love?

20. Bowl $1 games at Diversey River Bowl

Bowling isn’t exactly known as an expensive sport, but $1 games on Monday really stretch the value of a $20. If you can’t handle 20 games of bowling (and what human can?), spend the leftovers on karaoke. Yes, karaoke.

21. Play golf. Indoors. For $5 a game.

No, it’s not Golden Tee. It’s Top Golf, where you can drive the tee while practicing your Bill Murray Caddyshack impression without having to deal with the outdoor elements (or wear stupid pants). A guest playing card is just $5 a game, and lasts 30 days.

22. Play video games at Logan Arcade

Cheap booze, cheap games, even the occasional magician. This you gotta see.

Flickr/myk Jordan

23. Eat food from a truck

Did you hear the news? Food trucks are now legal in the city of Chicago. Use Chicago Food Truck Finder to help you choose. Or this

24. Track down the Tamale Guy

There are plenty of imitators, but only one true Tamale Guy. Track him on Twitter and have your George Washingtons ready when he storms into the bar.

25. Get a classic Chicago dog at a classic Chicago drive-in

Not only is Chicago institution Superdawg one of the last places you can do this in Chicago, it’s also something you need to do before you die. 

26. Escape to Puerto Rico by way of the steak jibarito

It simply has to be done. 

Mike Gebert/Thrillist

27. Go under the radar for your Italian beef

Sure, you could make your own, but that could end up costing you. And while a beef sandwich won’t break the bank, there are deals to be had. Especially when you go under the radar

28. Order a Mother-In-Law for your mother-in-law

Not only is the unholy creation known as the Mother-In-Law something you need to eat before you die, it’s less than $3.

29. Spend the day climbing rocks

If you want to climb rocks on the cheap, get a $13 day pass to Climb On and… well, climb on (ching!). 

30. Scour Hot Tix for cheap theatre tickets

Second City is great, but not cheap. There are, however, MANY cheap theatre options out there… which you may handily peruse all in one place thanks to Hot Tix.

31. Get a $5 haircut

While $5 haircuts are not as prominent as they once were, there are still plenty of places to get a decent cut on the cheap. And while there are usually risks involved, Betty & Nick’s Family Haircare are among the best.

32. Shoot to thrill at Archery Bow Range Chicago

Just $10 per hour. Apples not included.

Sean Cooley/Thrillist

33. Turtle racing 

Hey, better than cock fighting.

34. Peep the Uptown Poetry Slam at Green Mill

There are many reasons to visit Green Mill. Uptown Poetry Slam might be one of the cheapest and most overlooked.

35. Take a class at Second City

Don’t want to commit to a full course? Drop in for one two-hour $20 class and cross this one off your Chicago bucket list.

36. Explore Chinatown by water taxi

The Chinatown water taxi might be the most overlooked mode of transport in the city. $8 gets you an all-day pass to explore the area, starting with the beautiful Ping Tom Memorial Park. Hop off to explore a wonderful world of cheap eats.

37. Plan a nature escape to Morton Arboretum

While nature is usually free, you need to shell out a few bucks for entry to Chicago’s living tree museum ($14 per day/$9 on Wednesdays), which is actually well worth it.

Courtesy of Longman & Eagle

38. Dine at a Michelin-starred restaurant

Not only is Longman & Eagle Chicago’s number one hipster restaurant, the one-starred resto is also the only Michelin-starred restaurant in the city where you can score an entrée for under $20. Which you should totally do.

39. Shuck it up at oyster happy hour

Every Thursday starting at 5:30pm, The Bedford offers $1 oysters and half-off bubbly -- yours to be consumed in a renovated bank vault lounge. Date night done.

40. Plan a boozy brunch with the folks

The best way to make it through brunch with the parents? Plan a boozy brunch at a place like Chief O’Neill’s, where $19.95 gets you gets you access to the brunch buffet (with omelette station, seafood, and build-your-own sundaes), which includes a Bloody Mary bar, Sat-Sun 10am-2pm.

Flickr/Jeff Gunn

41. Tour a Frank Lloyd Wright home

There are many to choose from thanks to the fine folks at Frank Lloyd Wright Trust, but The Rookery is one of the coolest. And it’s only $7. Bonus: shady local pols history.

42. See up-and-coming comedy Downtown

The Comedy Bar is the city’s only Downtown comedy club. Which means it’s the perfect place to stumble in after your work happy hour closes and you’re looking for some cheap laughs, with most shows priced at a cool $20.

43. Have horrible fun at an improv Show

For $15 you'll get three cards that, if they match the cards pulled by the judge at Under the Gun Theater, get you on stage where they act out whatever is on your card. This could get weird.

44. Do your best Paul Newman impression at a pool hall

Practice your pool sharking skills amidst 13 professional Brunswick tables and eight LCD TVs at Pressure Billiards, where you can shoot unlimited stick for $7.50 an hour.

45. Go on a Pokémon tour

Like bumping into things as your stare at your phone? Then you’ll love this $5 Pokémon Go tour, where you’ll scour the city looking to capture those little bastards.

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Jay Gentile is a Thrillist contributor and world-renowned cheapskate whose Costanza wallet could explode at any minute. Follow @innerviewmag



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