City guide · USA
Chicago
Skyscraper birthplace with deep-dish swagger and lakefront blues
April–June & September–October
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English
North America
The guides
The best of Chicago, by category
Chicago invented the skyscraper, perfected the blues, and still argues about whose deep-dish is best. Stretched along 26 miles of Lake Michigan shoreline, the city pairs world-class museums and architecture with neighborhood institutions that have barely changed in decades.
The shortlist
If you only have time for the best
The single highest-rated picks across every category in Chicago.
Hotels
See all 6- 1
The Langham, Chicago
River North
4.8★3,000+ reviews - 2
The Peninsula Chicago
Magnificent Mile
4.7★2,000+ reviews
- 3
Four Seasons Hotel Chicago
Gold Coast
4.6★2,000+ reviews
Restaurants
See all 6- 1
Alinea
Lincoln Park
4.7★3,000+ reviews
- 2
Girl & the Goat
West Loop
4.6★10,000+ reviews - 3
Lou Malnati's Pizzeria
River North
4.5★10,000+ reviews
Bars
See all 6- 1
The Aviary
West Loop
4.6★2,000+ reviews - 2
The Violet Hour
Wicker Park
4.6★2,000+ reviews - 3
Green Mill Cocktail Lounge
Uptown
4.6★3,000+ reviews
Attractions
See all 6- 1
Millennium Park
The Loop
4.8★100,000+ reviews - 2
The Art Institute of Chicago
The Loop
4.8★25,000+ reviews
- 3
Skydeck Chicago (Willis Tower)
The Loop
4.6★25,000+ reviews
Where to base yourself
Chicago neighborhoods, decoded
Pick your area first — it shapes everything else about the trip.
West Loop / Fulton Market
Meatpacking-turned-restaurant rowFormer meat-market warehouses now hold the city's densest stretch of acclaimed restaurants along Randolph Street's Restaurant Row. Tech offices and boutique hotels keep it humming day and night.
Wicker Park & Bucktown
Indie shops and bar crawlsThe city's longtime creative quarter, stacked with vintage stores, record shops, and cocktail dens around the Damen Blue Line stop. The 606 elevated trail runs through on an old rail line.
Lincoln Park
Leafy lakefront family territoryBrownstone-lined streets between a free zoo and the lakefront beaches, with a lively student strip along Lincoln Avenue. It is also home to Alinea and a Victorian glass conservatory.
Pilsen
Murals, taquerias, and galleriesA historically Mexican-American neighborhood where 16th Street's murals lead to the National Museum of Mexican Art and generations-old taquerias. Galleries open late on the second Friday of each month.
Beyond the city
Day trips worth the ride
Oak Park
25 min by Green LineFrank Lloyd Wright's home, studio, and the world's largest concentration of his Prairie-style houses, plus Ernest Hemingway's birthplace.
Milwaukee, Wisconsin
89 min by Amtrak HiawathaA lakefront art museum with Calatrava's winged sunscreen, historic breweries, and the Harley-Davidson Museum.
Starved Rock State Park
1 hr 45 min by carEighteen sandstone canyons with seasonal waterfalls and winter bald-eagle watching along the Illinois River.
Eat like a local
What to order in Chicago
Deep-Dish Pizza
Buttery, high-walled crust holding inverted layers of mozzarella, sausage, and chunky tomato—a knife-and-fork pizza invented in 1943.
Try it at: Lou Malnati's Pizzeria, River North
Italian Beef
Thin-sliced roast beef soaked in jus on a chewy roll, ordered 'dipped' with spicy giardiniera.
Try it at: Al's #1 Italian Beef, Little Italy
Chicago-Style Hot Dog
An all-beef frank 'dragged through the garden' with mustard, neon relish, sport peppers, and celery salt—never ketchup.
Try it at: Portillo's, River North
Garrett Mix Popcorn
Cheddar and caramel popcorn mixed in one bag, a sweet-salty habit Chicagoans have queued for since 1949.
Try it at: Garrett Popcorn Shops, Michigan Avenue
Good to know
Chicago essentials, answered
Three to four days covers the Loop's architecture and museums, a ballgame or blues club, and a neighborhood day in Wicker Park or Pilsen. Add a summer day for the lakefront beaches and an architecture river cruise.
Keep exploring
