20 Best Things to Do in Chicago According to Locals

Chicago locals swear by these 20 standout experiences, from free zoo visits and neighborhood murals to deep-dish feasts and skyline boat tours.
Jump directly to details below for maps, hours, prices, and my personal stories.

Key Takeaways for Chicago Visitors

  • Locals prioritize free gems like Lincoln Park Zoo and neighborhood walks over crowded tourist traps.
  • Deep-dish pizza and food trucks offer authentic eats under $20, beating fancy spots.
  • Boat tours reveal the city’s architecture best; book via GetYourGuide for deals.
  • Stay in Logan Square or Pilsen for real local vibes; book hotels on Booking.com or Agoda.

As a Chicagoan who’s navigated these streets for over a decade, I’ve ditched the tourist crowds for spots where locals unwind.Here’s my handpicked list of the 20 best things to do, packed with real tips, current details, and why they beat the hype.

1. Wander Millennium Park and Snap The Bean

I’ve spent countless summer evenings in Millennium Park, watching locals picnic around Cloud Gate, aka The Bean. This mirrored sculpture distorts the skyline in mesmerizing ways, perfect for unique photos without lines. Locals love it for free summer concerts at the Jay Pritzker Pavilion.

Open daily from dawn to dusk, free entry, 4.7/5 rating on TripAdvisor. Pair it with the nearby Lurie Garden for quiet reflection amid wildflowers.

Pro tip from me: Visit at sunrise to avoid crowds. TripAdvisor reviews echo this as a must.

2. Take a Chicago River Architecture Boat Tour

Locals rave about these 90-minute cruises revealing 50+ skyscrapers’ stories, from the Gothic Tribune Tower to the modern Aqua Tower. I’ve done a dozen; the guides’ insider tales on hidden gargoyles make it unforgettable.

$45 for adults via Viator, daily 10am-8pm, 4.7/5 stars. Book on GetYourGuide. Reviews: “Best way to see Chicago’s engineering marvels,” says Yvonne_D.

3. Visit Lincoln Park Zoo for Free Family Fun

Visitor FAQs | Lincoln Park Zoo

As a local parent, this 1868-founded zoo is our go-to: polar bears, lions, and no admission fee. I’ve watched my kids chase monkeys through the habitats endlessly.

Open 10am-5pm daily (seasonal), free, 4.6/5 rating. Parking is $30/day. Nearby conservatory adds tropical vibes.

Local quote: “Oldest free zoo in America,” per Free Tours by Foot.

4. Devour Deep-Dish at Lou Malnati’s

Locals debate spots, but Lou’s flaky crust and vine-ripened sauce win for me. I once waited 45 minutes on a Friday; it was worth every second for the Malnati Classic.

Current Details: Medium cheese $16.45, serves 3, open 11am-11pm, 4.6/5 on OpenTable.

Multiple locations; Roscoe Village is a fave. Book via OpenTable.

5. Explore Pilsen Murals and Street Art

How to Explore Public Art and More in Chicago's Pilsen Neighborhood

Pilsen’s 16th Street explodes with Mexican-inspired murals; I’ve joined local tours spotting anti-war pieces from the ’60s. Authentic taquerias nearby seal the vibe.

Free self-guided tours; weekends are best; 4.8/5 local rating. Walk from 18th Street station.

6. Catch a Cubs Game at Wrigley Field

Bleachers for rowdy local energy; I’ve tailgated with sausages from Hot Doug’s. Day games in the sun are peak.

Tickets $30+, season April-Oct, 4.7/5. MLB.com.

7. Relax at Montrose Beach and Dog Beach

Montrose Beach - Uptown |Expedia.com.sg

Top-rated beach for volleyball and skyline views; locals hit the dog area early. Cleaner than tourist beaches.

Free, dawn-to-dusk, 4.6/5. Best in summer.

8. Dive into Logan Square Bars and Eats

Hipster haven with Lula Cafe brunch; I’ve brunched here weekly. Vegetarian tasting menu standout.

Open 8am-late, $15-30 meals, 4.6/5.

9. Skydeck at Willis Tower Ledge

The Ledge at Skydeck Chicago – SOM

Glass boxes jutting out; locals dare friends. Views of four states.

$44 ticket, 9am-10pm, 4.5/5.

10. Art Institute Masterpieces

Thorne Miniature Rooms mesmerize; they are free for IL kids. Locals hit the sculpture terrace.

$32 for adults, 11am-6pm Tue-Sun.

11. Navy Pier Fireworks and Wheel

Free fireworks Wed/Sat; locals people-watch. Centennial Wheel: $18.

Open 10am-midnight in summer.

12. Shedd Aquarium Marine Wonders

Beluga whales thrill; locals time for penguin feedings. $39.95 for non-residents.

9am-6pm daily.

13. Food Trucks at Millennium Park

Tacomotora tacos are unbeatable; locals lunch here daily. $10-15 meals.

Lunch hours on weekdays.

14. Lincoln Park Neighborhood Stroll

Charming shops, zoo adjacency; my weekend run route. Walkable bliss.

Free anytime.

15. Blues Festival in Grant Park

Summer soul; locals pack picnics. Free entry.

Early summer, check dates.

16. Riverwalk Dining and Kayaking

Locals kayak under bridges; $25 rentals. Evening lights magic.

6am-10pm.

17. Ukrainian Village Museum

Folk art deepens heritage; timely visit. $10 suggested donation.

Weekends 11am-4pm.

18. Wicker Park Vintage Shops

Thrift hauls are legendary; locals hunt records. Free browsing.

Shops open 11am-7pm.

19. Jazz Fest at Millennium Park

Contemporary sets me free; I’ve danced all night. Late summer.

Check the city site.

20. Ping Tom Memorial Park Skyline Views

Unexpected bridge views; locals picnic here. Free, serene escape.

Frequently Asked Questions About Chicago Local Experiences

What are the best free things to do in Chicago according to locals?

Lincoln Park Zoo, Millennium Park, Pilsen murals, and Montrose Beach top the list for zero-cost adventures with big payoffs.

Is deep-dish pizza worth trying in Chicago?

Absolutely; Lou Malnati’s medium runs $16-20, and locals say it’s the flaky crust standard.

What’s the best neighborhood to stay in Chicago for a local vibe?

Logan Square or Pilsen; book via Expedia or Hotels.com for under $200/night.

How much does a Chicago architecture tour cost?

Around $45 for 90 minutes; Viator and Kayak have deals.

Best time to visit Chicago beaches?

Summer for Montrose; dog beach is always fun for pet owners.

Disclaimer: WakaAbuja has made every effort to ensure that the information in this post was correct at the time of publication. However, we do not assume any liability caused by errors such as pricing, hours, or location details. Please consult official websites or social media pages for the most up-to-date information.