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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
CDs? Cheap vinyl? Free in-store shows? We get it, it’s not a 99-cent download. That’s what makes it cool.
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.
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.
Admission to their regular mud-covered battles around town are probably cheaper than your cleaning bill if you get too close.
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?
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.
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.
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?
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.
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.
Cheap booze, cheap games, even the occasional magician. This you gotta see.
23. Eat food from a truck
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.
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.
It simply has to be done.
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.
If you want to climb rocks on the cheap, get a $13 day pass to Climb On and… well, climb on (ching!).
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.
Just $10 per hour. Apples not included.
33. Turtle racing
Hey, better than cock fighting.
There are many reasons to visit Green Mill. Uptown Poetry Slam might be one of the cheapest and most overlooked.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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