Chicago!
Willis Tower is one of Chicago!.

1. Willis Tower

8.5
233 S Wacker Dr (btwn W Adams St & W Jackson Blvd), Chicago, IL
Structure · The Loop · 311 tips and reviews

BingBing: Incredible views of Chicago from the top of the nation’s tallest building.

900 North Michigan Shops is one of Chicago!.

2. 900 North Michigan Shops

7.5
900 N Michigan Ave, Chicago, IL
Shopping Mall · Streeterville · 42 tips and reviews

Chicago TribuneChicago Tribune: Tthe building is 871 feet tall. The exterior of the tower is clad in limestone and green glass which reflects the light. Interesting story about shopping on the Mag Mile: http://bit.ly/mVJkUl

Water Tower Place is one of Chicago!.

3. Water Tower Place

8.3
835 N Michigan Ave (E Pearson St), Chicago, IL
Shopping Mall · Streeterville · 158 tips and reviews

Chicago TribuneChicago Tribune: 859 feet tall, 74 stories. Floor after floor of shopping - and don't stop until you get to 7 ... lots of places to eat and snack up there. More stories on Water Tower Place: http://trib.in/oVOobe

Trump International Hotel & Tower® Chicago is one of Chicago!.

4. Trump International Hotel & Tower® Chicago

7.7
401 N Wabash Ave, Chicago, IL
Hotel · Near North Side · 105 tips and reviews

Chicago TribuneChicago Tribune: 1,389 feet tall, not counting the hair. Great story from the Tribune's Blair Kamin on Trump Tower. http://trib.in/oCe3oR

Willis Tower is one of Chicago!.

5. Willis Tower

8.5
233 S Wacker Dr (btwn W Adams St & W Jackson Blvd), Chicago, IL
Structure · The Loop · 311 tips and reviews

Chicago TribuneChicago Tribune: 1,451 feet tall. If you're brave enough, the skydeck is amazing. You literally feel like you're floating on top of the world. For more stories mentioning the Willis Tower, go to http://trib.in/ogoEOZ

CTA - Damen is one of Chicago!.

6. CTA - Damen

1588 N Damen Ave (btwn Milwaukee & Pierce), Chicago, IL
Metro Station · Wicker Park · 37 tips and reviews

Chicago TribuneChicago Tribune: When the sun is rising in the east, this is a great vantage point to snap a photo of the skyline. Just don't make too big of a deal about it - security keeps a close eye on shutterbugs. Read more.

Bongo Room is one of Chicago!.

7. Bongo Room

8.0
1470 N Milwaukee Ave (at Honore St), Chicago, IL
Breakfast Spot · Wicker Park · 153 tips and reviews

Chicago TribuneChicago Tribune: Look for options like three-apple brioche French toast and Black Forest pancakes. Egg dishes--in massive portions--are also popular choices. Read more.

The Boring Store is one of Chicago!.

8. The Boring Store

1331 N Milwaukee Ave (btwn Hermitage & Paulina), Chicago, IL
Office Supply Store · Wicker Park · 13 tips and reviews

Chicago TribuneChicago Tribune: Before you go to the store, go to the Website. It's awesome. Seriously fun. Read more.

Polish Museum of America is one of Chicago!.

9. Polish Museum of America

7.2
984 N Milwaukee Ave (Milwaukee/Augusta), Chicago, IL
History Museum · Noble Square · 10 tips and reviews

Chicago TribuneChicago Tribune: Hours are 11 a.m. to 4 p.m. Friday–Wednesday. Closed Thursdays and major holidays. Read more.

Chicago Velo Campus is one of Chicago!.

10. Chicago Velo Campus

8615 S Burley Ave, Chicago, IL
Race Track · South Chicago · 11 tips and reviews
Ping Tom Memorial Park is one of Chicago!.

11. Ping Tom Memorial Park

9.3
300 W 19th St (btwn Lumber St & Wentworth Ave), Chicago, IL
Park · South Loop · 24 tips and reviews
Garfield Park Conservatory is one of Chicago!.

12. Garfield Park Conservatory

9.4
300 N Central Park Ave (at Lake St), Chicago, IL
Garden · East Garfield Park · 75 tips and reviews
Oak Street Beach is one of Chicago!.

13. Oak Street Beach

9.1
1000 N Lake Shore Dr (at Oak St), Chicago, IL
Beach · Gold Coast · 58 tips and reviews
Ohio Street Beach is one of Chicago!.

14. Ohio Street Beach

8.6
Ohio St (at Lake Shore Dr), Chicago, IL
Beach · Streeterville · 34 tips and reviews
South Shore Cultural Center is one of Chicago!.

15. South Shore Cultural Center

8.9
7059 S South Shore Dr, Chicago, IL
Cultural Center · South Shore · 20 tips and reviews
Green Mill Cocktail Lounge is one of Chicago!.

16. Green Mill Cocktail Lounge

8.8
4802 N Broadway St (at W Lawrence Ave), Chicago, IL
Jazz and Blues Venue · Uptown · 135 tips and reviews

Explore ChicagoExplore Chicago: This Chicago landmark presents jazz nightly, from traditional to experimental, amid a "speakeasyesque" décor. Read more.

Jane Addams Hull-House Museum is one of Chicago!.

17. Jane Addams Hull-House Museum

8.3
800 S Halsted St (at UIC), Chicago, IL
History Museum · University Village - Little Italy · 20 tips and reviews

Explore ChicagoExplore Chicago: Today, visitors can explore historic exhibitions, borrow seeds from an heirloom seed library, learn about urban horticulture, eat soup and debate politics, and see contemporary art exhibitions. Read more.

Ping Tom Memorial Park is one of Chicago!.

18. Ping Tom Memorial Park

9.3
300 W 19th St (btwn Lumber St & Wentworth Ave), Chicago, IL
Park · South Loop · 24 tips and reviews

Explore ChicagoExplore Chicago: Among the Park’s cool features are a pagoda-shaped pavilion, where you can catch a water taxi to downtown Chicago, and a unique railroad drawbridge. Read more.

Chicago Velo Campus is one of Chicago!.

19. Chicago Velo Campus

8615 S Burley Ave, Chicago, IL
Race Track · South Chicago · 11 tips and reviews

Explore ChicagoExplore Chicago: The Chicago Velo Campus is a large, banked track for bicycle racing, and is the first velodrome built in Chicago in a generation.

20. iO Chicago

8.8
1501 N Kingsbury St (Blackhawk), Chicago, IL
Comedy Club · 88 tips and reviews

Explore ChicagoExplore Chicago: Famous for training some of the sharpest minds in comedy today, iO Theater is a leader in improv comedy and hosts shows 7 nights a week. Plan on a fun–and surprising!–night out in Wrigleyville.

iO Chicago is one of Chicago!.

21. iO Chicago

8.8
1501 N Kingsbury St (Blackhawk), Chicago, IL
Comedy Club · 88 tips and reviews

Time Out ChicagoTime Out Chicago: Not only has iO churned out legendary folk like Mike Meyers and Amy Poehler, but it consistently puts the art of improv first. The shows are cheap and the classes a must for budding improvisers.

Landmark Century Centre Cinema is one of Chicago!.

22. Landmark Century Centre Cinema

8.3
2828 N Clark St (at Diversey Pkwy), Chicago, IL
Indie Movie Theater · Lake View East · 75 tips and reviews

Time Out ChicagoTime Out Chicago: Along with a great selection of hard-to-find and independent films, the theatre's concessions counter is one of the best in the city, with vegan cookies and a popcorn seasoning bar on offer.

Green Mill Cocktail Lounge is one of Chicago!.

23. Green Mill Cocktail Lounge

8.8
4802 N Broadway St (at W Lawrence Ave), Chicago, IL
Jazz and Blues Venue · Uptown · 135 tips and reviews

Time Out ChicagoTime Out Chicago: This jazz institution is legendary for three things: it was once a Capone hangout, it’s haunted, and the no-nonsense staff will shush you and the friends who dragged you in during jazz sets.

The Doughnut Vault is one of Chicago!.

24. The Doughnut Vault

8.6
401 1/2 N Franklin St (at W Kinzie St), Chicago, IL
Donut Shop · River North · 145 tips and reviews

Time Out ChicagoTime Out Chicago: Download a podcast. Bring a long-lost friend. Get there at 8:30am. This is the doughnut we’ve been waiting for.

Water Taxi of Chicago is one of Chicago!.

25. Water Taxi of Chicago

Chicago, IL
Boat or Ferry · River North · 3 tips and reviews

Time Out ChicagoTime Out Chicago: Take a ride on the river for as little as $4 (b/w Michigan and Union Station). If you use them to commute during rush hour, they're even cheaper, but we prefer a lazy-day vibe.

Cascade Drive-In is one of Chicago!.

26. Cascade Drive-In

1100 E North Ave (at Prince Crossing Rd), West Chicago, IL
Drive-in Theater · 43 tips and reviews

Time Out ChicagoTime Out Chicago: Catch a double feature under the stars while you still have a chance.

Green Mill Cocktail Lounge is one of Chicago!.

27. Green Mill Cocktail Lounge

8.8
4802 N Broadway St (at W Lawrence Ave), Chicago, IL
Jazz and Blues Venue · Uptown · 135 tips and reviews

Explore ChicagoExplore Chicago: In the movie "High Fidelity" (2000) Rob (John Cusack) reminisces about his ex-girlfriend Laura over drinks at the Green Mill Cocktail Lounge. Read more.

Lincoln Park Zoo is one of Chicago!.

28. Lincoln Park Zoo

9.1
2001 N Clark St (btwn Fullerton Pkwy & LaSalle Dr), Chicago, IL
Zoo · Lincoln Park · 283 tips and reviews

Explore ChicagoExplore Chicago: The Lincoln Park Zoo is free and open 365 days a year. http://bit.ly/alwaysfree Read more.

Skydeck Chicago is one of Chicago!.

29. Skydeck Chicago

8.3
233 S Wacker Dr (btwn Adams St & Jackson Blvd), Chicago, IL
Scenic Lookout · The Loop · 393 tips and reviews

Explore ChicagoExplore Chicago: Despite having a fear of heights, Christian Bale donned his batsuit, looking 110 stories down from a ledge on the Willis (Sears) Tower for a scene in "The Dark Knight" (2008). Read more.

Lake Point Tower is one of Chicago!.

30. Lake Point Tower

505 N Lake Shore Dr (at Grand Ave.), Chicago, IL
Structure · Streeterville · 7 tips and reviews

Explore ChicagoExplore Chicago: In the film "While You Were Sleeping" (1995), Lucy (Sandra Bullock) gets to know Jack (Bill Pullman) in scenes shot outside of Lake Point Tower. Read more.

Historic Site of Illinois Central Depot, The Black Ellis Island is one of Chicago!.

31. Historic Site of Illinois Central Depot, The Black Ellis Island

7.2
200 E Roosevelt Rd (at S Indiana Ave), Chicago, IL
Historic and Protected Site · Grant Park · 4 tips and reviews

Explore ChicagoExplore Chicago: 2 granite blocks mark the former spot of the Illinois Central Depot, or the Black Ellis Island, where thousands of southern African Americans arrived to start new lives in Chicago - the Promised Land. Read more.

Cone Gourmet Ice Cream is one of Chicago!.

32. Cone Gourmet Ice Cream

8.4
1047 W Madison St (btwn Morgan St & Aberdeen St), Chicago, IL
Ice Cream Parlor · Near West Side · 34 tips and reviews
Jeni's Splendid Ice Creams is one of Chicago!.

33. Jeni's Splendid Ice Creams

9.3
3404 N Southport Ave (at W Roscoe St), Chicago, IL
Ice Cream Parlor · Lakeview · 78 tips and reviews
Firecakes Donuts is one of Chicago!.

34. Firecakes Donuts

9.1
68 W Hubbard St (at N Clark St), Chicago, IL
Donut Shop · Near North Side · 165 tips and reviews
Margie's Candies is one of Chicago!.

35. Margie's Candies

8.9
1960 N Western Ave (at W Armitage Ave), Chicago, IL
Ice Cream Parlor · Logan Square · 93 tips and reviews
Eataly is one of Chicago!.

36. Eataly

9.1
43 E Ohio St (at N Wabash Ave), Chicago, IL
Gourmet Store · Near North Side · 409 tips and reviews

EaterEater: It doesn't get much hotter than Mario Batali and Joe Bastianich's land of magic and pasta. With eight restaurants and a world of retail, Chicago's food scene has been greatly expanded.

iCream is one of Chicago!.

37. iCream

1537 N Milwaukee Ave (btwn N Damen Ave & N Honroe St), Chicago, IL
Ice Cream Parlor · Wicker Park · 47 tips and reviews