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Chicago's Best Deals Under $10

Posted on September 24, 2025   |   Updated on September 30, 2025
Simone Alicea

Simone Alicea

Superdawg

A classic Superdawg on the way home from O'Hare. (Emmi Mack / Hey Chicago)

We’re all hunting for bargains these days. So, we’re rounding up the best food, activities, and gifts in Chicago for under $10.

City Cast

How to Have Fun in Chicago for Under $10

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Food

Tacos: La Chaparrita in Little Village

Recently named the City Cast Chicago podcast team’s favorite taco, La Chaparrita offers several types for $3 each. That’s a three-taco meal!

Hot Dog: Superdawg in Norwood Park

The titular Superdawg comes with classic Chicago dog toppings, fries, and a pickled green tomato for $9.15. But that Supershake’s gonna be extra.

Dessert: Legend Tasty House in Chinatown

Unless you go wild with toppings, you can pick up rolled ice cream, milk tea, and smoothies for under $10. Plus, they’re open late.

Drinks: Fat Cat in Uptown

Skip happy hour well drinks. Fat Cat’s Whiskey Wednesdays and Thursday martinis offer $7 classic cocktails plus unique ones like The Riviera and Uptown Royale.

  • 🥈Honorable mention: Little Victories features $10 cocktails, like Moscow mules and daiquiris, daily.
Douglass Park mini golf

Mini golf in Douglass Park in 2022. Thanks to reader Kyle E. for the shot! (Courtesy of Kyle E.)

Activities

Day Date: Mini golf in Douglass Park

For $5 per person per game, play 18 holes on a course inspired by the park’s migratory birds. Beware: The competitive beast inside you may come out.

Live Show: The Drifter in River North

A burlesque performance in a speakeasy behind a hidden door in the basement of one of the city’s oldest taverns? For an $8 cover? Sure, you might make up for it in cocktails, but that’s a bargain for the vibe.

  • 🥈Honorable mention: Lemon frequently features live music and performance in their intimate space for $5-10.

For Tourists: Chicago Greeter Tour

If you’re entertaining visitors and don’t want to splurge, Choose Chicago’s Greeters offer free walking tours across the city’s neighborhoods. Up to six people can join — but book early.

Gifts

Something Shiny: Wintime & Co. in Chinatown

No expensive jewelry here. It’s difficult to find items over $10 at this Wentworth Avenue spot. In fact, they’ve got a three for $10 sale going now.

For Collectors: Hyde Park Records

If you’re willing to dig through the crates outside, you can find some diamonds in the rough. Or at least something to amuse your vinyl-collecting friend.

‼️ More free stuff to do ‼️

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