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T+L's Guide to Chicago's Greatest Hits
The Peninsula is one of T+L's Guide to Chicago's Greatest Hits.

1. The Peninsula

8.5
108 E Superior St, Chicago (at N Michigan Ave.), Chicago, IL
Hotel · Streeterville · 68 tips and reviews

Travel + LeisureTravel + Leisure: The Peninsula Spa by ESPA on the 20th floor has an indoor pool, sundeck, eucalyptus steam room, and fireplace-equipped lounge—not to mention fabulous views of the Windy City. Read more.

Ambassador Chicago is one of T+L's Guide to Chicago's Greatest Hits.

2. Ambassador Chicago

8.4
1301 N State Pkwy (at E Goethe St), Chicago, IL
Hotel · Gold Coast · 55 tips and reviews

Travel + LeisureTravel + Leisure: Head to Jean-Georges Vongerichten’s Pump Room for reasonably priced farm-to table fare. For dessert, get the salted-caramel ice cream sundae—it’s unbelievably delicious. Read more.

Gibsons Bar & Steakhouse is one of T+L's Guide to Chicago's Greatest Hits.

3. Gibsons Bar & Steakhouse

8.7
1028 N Rush St (at E Bellevue Pl), Chicago, IL
Steakhouse · Gold Coast · 281 tips and reviews

Travel + LeisureTravel + Leisure: The portions are huge, so plan to share every course, including sides (the two-pound double baked potato is a signature) and desserts. Read more.

House of Blues is one of T+L's Guide to Chicago's Greatest Hits.

4. House of Blues

8.8
329 N Dearborn St (btwn Kinzie St & Wacker Dr), Chicago, IL
Music Venue · Near North Side · 197 tips and reviews

Travel + LeisureTravel + Leisure: Lines for Music Hall performances can be very long; avoid the wait by dining at the restaurant, where you can enjoy Southern favorites like buttermilk fried chicken and bourbon bread pudding. Read more.

RL Restaurant is one of T+L's Guide to Chicago's Greatest Hits.

5. RL Restaurant

9.1
115 E Chicago Ave (at Michigan Ave), Chicago, IL
American Restaurant · Streeterville · 115 tips and reviews

Travel + LeisureTravel + Leisure: Dine at the Chicago flagship, where you can enjoy the signature Steak Diane or the classic RL Burger.

The Art Institute of Chicago is one of T+L's Guide to Chicago's Greatest Hits.

6. The Art Institute of Chicago

9.4
111 S Michigan Ave (btwn Monroe St & Jackson Dr), Chicago, IL
Art Museum · Grant Park · 674 tips and reviews

Travel + LeisureTravel + Leisure: The spectacular Modern Wing, designed by Renzo Piano in limestone, glass, and steel was voted by T+L readers as one of the world’s top new landmarks in 2011. Read more.

7. Millennium Park Chiropractic

155 N Michigan Ave (Randolph and Michigan), Chicago, IL
Chiropractor · The Loop · No tips or reviews

Travel + LeisureTravel + Leisure: Don’t miss The Gage, a popular gastropub just steps away from the park, for hearty menu items such as caramelized lobster and dry-aged Manhattan steak. Read more.

Grant Park is one of T+L's Guide to Chicago's Greatest Hits.

8. Grant Park

9.2
337 E Randolph Dr (at Michigan Ave), Chicago, IL
Park · Grant Park · 130 tips and reviews

Travel + LeisureTravel + Leisure: Head to the lakefront park during the summer, when it hosts two major events: Taste of Chicago, the world’s largest outdoor food festival, and Lollapalooza, the annual music festival. Read more.

Willis Tower is one of T+L's Guide to Chicago's Greatest Hits.

9. Willis Tower

8.6
233 S Wacker Dr (btwn W Adams St & W Jackson Blvd), Chicago, IL
Building · The Loop · 312 tips and reviews

Travel + LeisureTravel + Leisure: A series of magnificently scary glass boxes, collectively known as the Ledge, is attached to the venerable Skydeck, where you’ll feel like you’re standing unsupported 103 stories above the ground. Read more.

Intelligentsia Coffee is one of T+L's Guide to Chicago's Greatest Hits.

10. Intelligentsia Coffee

8.8
3123 N Broadway St (at W Barry Ave), Chicago, IL
Coffee Shop · Lake View East · 113 tips and reviews

Travel + LeisureTravel + Leisure: At the North Broadway flagship, enjoy free Wi-Fi and glam-rock tunes with your signature syrupy and sweet Black Cat Classic espresso. Read more.

The Second City is one of T+L's Guide to Chicago's Greatest Hits.

11. The Second City

9.1
1616 N Wells St (btwn Concord Ln & North Ave), Chicago, IL
Comedy Club · Old Town Triangle · 151 tips and reviews

Travel + LeisureTravel + Leisure: Shows are general admission, so arrive early and grab a seat at one of the tables in front of the stage or by the railing on the second level. Read more.

Lincoln Park Zoo is one of T+L's Guide to Chicago's Greatest Hits.

12. Lincoln Park Zoo

9.0
2001 N Clark St (btwn Fullerton Pkwy & LaSalle Dr), Chicago, IL
Zoo · Lincoln Park · 283 tips and reviews

Travel + LeisureTravel + Leisure: Hop astride a Siberian tiger or giant panda on the Endangered Species Carousel, or paddle around the lagoon on a swan-shaped boat. Read more.

Smith Museum of Stained Glass Windows is one of T+L's Guide to Chicago's Greatest Hits.

13. Smith Museum of Stained Glass Windows

600 E Grand Ave (at Navy Pier), Chicago, IL
Art Museum · Streeterville · 16 tips and reviews

Travel + LeisureTravel + Leisure: Most Thursday afternoons, visitors can take a free tour led by the museum curator, Rolf Achilles. Read more.

Chicago Riverwalk is one of T+L's Guide to Chicago's Greatest Hits.

14. Chicago Riverwalk

9.5
Chicago River, Chicago, IL
Waterfront · The Loop · 137 tips and reviews

Travel + LeisureTravel + Leisure: For the first 10 minutes of each hour during the day, Centennial Fountain at the east end shoots water in a great arc across the river. Read more.

Chicago O'Hare International Airport (ORD) is one of T+L's Guide to Chicago's Greatest Hits.

15. Chicago O'Hare International Airport (ORD)

6.5
10000 W O’Hare Ave, Chicago, IL
Airport · 3917 tips and reviews

Travel + LeisureTravel + Leisure: Tortas Frontera, in Terminals 1 and 3, is an outpost of Chicago’s best Mexican restaurant, Frontera Grill. Order a fresh-shaken margarita and one of chef Rick Bayless’s griddle-baked tortas. Read more.

T+L Tech Awards Pop Up at Thompson Chicago is one of T+L's Guide to Chicago's Greatest Hits.

16. T+L Tech Awards Pop Up at Thompson Chicago

21 E Bellevue Pl, Chicago, IL
Miscellaneous Shop · Near North Side · No tips or reviews