23 Hidden Gems You Must Visit In Chicago

1. Sweet Mandy B’s Old-Fashioned Desserts

1208 W. Webster Avenue, Lincoln Park

“Perfect for a sweet-tooth craving!”

2. Chicago Cultural Center

78 E. Washington Street, The Loop

“It’s an amazing building, completely free, and always has really interesting art exhibits.”

3. Kuma’s Corner

2900 W. Belmont Avenue, Avondale

“Where all the items on the menu are named after metal bands, and the two-hour wait is worth it.”

4. Baby Wants Candy Improv Show

The Apollo Theater, 2540 N. Lincoln Avenue, Lincoln Park

“They perform improv musical shows at 10:30 p.m. every Friday. I’ve never laughed and cried so hard in my life.”

5. Ferrara Original Bakery

2210 W. Taylor Street, University Village

“You can stop in and have a delicious lunch at a reasonable price! If you go on a weekday, you can expect to dine next to Chicago’s finest boys in blue or lawyers from the court building a few blocks away. A few scenes from the Chicago Fire TV show were also filmed here!”

6. Myopic Books

1564 N. Milwaukee Avenue, Wicker Park

One of Chicago’s largest and oldest used bookstores, Myopic Books buys and sells over 80,000 editions of books. And they have a strict no–cell phone policy.

7. Original Rainbow Cone

9233 S. Western Avenue, Beverly

The shop has been around since 1926 and serves a signature layered cone that includes chocolate, strawberry, Palmer House, pistachio, and orange sherbet flavors.

8. Harold Washington Library

400 S. State Street, The Loop

“The ninth floor has a winter garden, which is basically a big, beautiful atrium with free Wi-Fi. It’s the best place to kill a few hours.”

9. Rub BBQ

6954 N. Western Avenue, West Rogers Park

This homestyle BBQ restaurant serves HOME-SMOKED kettle chips and coleslaw with almost every meal, and has some really genius, unique items on its menu — including custard-filled cornbread, pictured above. Wipe up your drool.

10. Maggie Daley Park

407-461 S. Columbus Drive, The Loop

The park has slowly been opening, and currently the ice skating ribbon and playground are open to the public. The ice skating ribbon has been noted for its breathtaking views of the skyline.

11. Pequod’s Pizzeria

2207 N. Clybourn Avenue, DePaul

“Best deep-dish pizza I’ve ever had!”

12. Big Monster Toys

21 S. Racine Avenue, West Loop

Visitors have described entering Big Monster Toys as feeling like you’re entering Oz.

13. Pizano’s Pizzeria

864 N. State Street, Near North Side

“This place is truly a family restaurant. The pizza is Mama Malnati’s (of Lou Malnati’s restaurant fame) original famous recipe, and the wings are out-of-this-world amazing.”

14. Too Much Light Makes The Baby Go Blind

5153 N. Ashland Avenue, Andersonville

“The theater troupe, The Neo-Futurists, are the longest-running troupe in Illinois, and this show is comprised of 30 plays in 60 minutes. The cast throws an after-party pizza show if they sell out, and you roll a die for what you pay.”

15. Superdawg Drive-In Restaurant

6363 N. Milwaukee, Norwood Park

“Best hot dog and fries anywhere, served in a box. Car hop service by the best hops ever. The place is living history.”

16. 57th Street Books

1301 E. 57th Street, Hyde Park

“Fantastic little indie bookshop.”

17. Ann Sather Restaurant

3411 N Broadway Street, Lakeview

“If you are in Chicago and haven’t had a cinnamon bun here, all I have to say is…for shame!”

Submitted by Lauren Pfeifer, Facebook

18. The Pedway Downtown Pedestrian Walkway System

Central Business District

This underground walking system is used by tens of thousands of pedestrians each day and connects to CTA trains and buildings over roughtly 40 blocks in the Central Business District.

Submitted by William Zambole, Facebook

19. Headquarters Beercade

2833 N. Sheffield, Lakeview

This incredible bar’s most unique trait is its wide selection of FREE arcade games. From classic games to pinball, this place has it all. And the drinks are priced well, too.

20. Mario’s Italian Ice

1068 W. Taylor Street, University Village

“If you have a sweet tooth and want something cool and refreshing, go there because they make homemade Italian ice and it’s to die for.”

21. Chicago Pizza And Oven Grinder Co.

2121 N Clark Street, Lincoln Park

“Rumor has it, the house above the now-restaurant served as a lookout post for Al Capone’s henchmen. The atmosphere is gorgeous and homey and warm and gorgeous. For dessert, DO NOT SKIP THE TORTONI. A local Chicago Italian ice cream shop makes this special just for for CPOGC.”

22. Puppet Bike

Various places in The Loop

Puppet Bike is a traveling puppet show where puppets dance under a disco ball to oldies songs. It has a perfect five stars on Yelp.

23. Promontory Point at Burnham Park

5491 S. Shore Drive, South Side

“This place has the most underrated view of the skyline! The South Side never gets enough love.”

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