Chicago, Illinois · City Break
Skyscrapers, deep-dish & the great American lakefront
The world's best architecture cruise, Millennium Park, the Art Institute, blues clubs in the South Loop, deep-dish pizza and a 26-mile lakefront trail along Lake Michigan — Chicago is the most under-rated short break in the USA.
Why Chicago
The Best Big City in America
Voted the Best Big City in the U.S. for nine years running by Condé Nast Traveler readers, Chicago combines world-class architecture, museums and food with proper Midwestern friendliness — and a lakefront that feels like a coastline. Pair a few nights downtown with a Route 66 fly-drive, a Great Lakes loop or onward to Nashville and the Deep South.
Explore More · Top Tips
Top things to do in Chicago
Highlights drawn from Choose Chicago, the city's official destination organisation — tell us which appeal and we'll fold them into your itinerary.
Take the Chicago Architecture Center river cruise
The single best thing to do in the city — a 90-minute cruise along all three branches of the Chicago River with a trained CAC docent telling the story of more than 50 landmark buildings. Book the morning departure for the clearest skyline light.
Millennium Park & Cloud Gate (The Bean)
Anish Kapoor's mirrored sculpture is Chicago's most photographed spot — go at sunrise to have it almost to yourself. Stay for the Crown Fountain, the Frank Gehry-designed Pritzker Pavilion and free summer concerts.
Up the Willis Tower & 360 CHICAGO
Step out onto The Ledge — glass boxes cantilevered 1,353 feet above the street at Willis Tower's Skydeck. For a different angle, head to 360 CHICAGO on the 94th floor of 875 N Michigan Avenue and ride 'TILT' out over the Magnificent Mile.
The Art Institute of Chicago
One of the great museums of the world — Hopper's 'Nighthawks', Grant Wood's 'American Gothic', Seurat's 'A Sunday on La Grande Jatte' and a knockout Impressionist collection. Allow at least half a day.
Eat your way through Chicago
Deep-dish at Lou Malnati's or Pequod's; Italian beef at Al's #1; a Chicago-style hot dog at Portillo's (no ketchup, ever); pizza puffs and tacos in Pilsen; fine dining at Alinea, Smyth or Kasama (Filipino, Michelin-starred breakfast).
The Museum Campus — Field, Shedd & Adler
Three giants on the lakefront in one walkable park: the Field Museum (Sue the T-Rex), the Shedd Aquarium (beluga whales and a coral reef) and the Adler Planetarium for the city's best skyline view from the lakeshore.
Navy Pier & a lakefront stroll
The 150-foot Centennial Wheel, free fireworks on Wednesday and Saturday nights in summer, the Chicago Children's Museum and lake cruises from the pier. Walk or cycle the Lakefront Trail south to Museum Campus.
Catch the blues, jazz or a comedy show
Chicago invented urban blues — Buddy Guy's Legends in the South Loop and Kingston Mines in Lincoln Park run nightly sets. For jazz try the Green Mill (Al Capone's old haunt in Uptown), and for comedy The Second City in Old Town launched Belushi, Murray, Fey and Carell.
Shop the Magnificent Mile & Gold Coast
The half-mile stretch of N Michigan Avenue between the river and Oak Street is Chicago's flagship shopping strip — anchor stores, the historic Water Tower and side-street boutiques in the Gold Coast just beyond.
Catch a Cubs game at Wrigley Field
Built in 1914, Wrigley is the second-oldest ballpark in baseball — ivy-covered outfield walls, the hand-turned scoreboard and the legendary rooftop seats across Waveland and Sheffield Avenues. Go for the atmosphere as much as the game.
Explore the neighbourhoods
Wicker Park & Bucktown for indie shops, vintage and the '606' elevated trail; Pilsen for Mexican food and the National Museum of Mexican Art; Logan Square for craft cocktails; Andersonville and Boystown for brunch and bookshops.
Day trip ideas
Frank Lloyd Wright's Home & Studio in Oak Park (30 min by L-train); the Indiana Dunes National Park lakefront (75 min); Milwaukee for beer and the Calatrava-designed Art Museum (90 min); or pick up the start of historic Route 66 on Adams Street and head south.
Source: choosechicago.com, the official Chicago destination marketing organisation.
Ready for Chicago?
Pair a few nights in the Loop with a Route 66 fly-drive, a Great Lakes circuit or onward to Nashville and the Deep South — we'll build the hotel, the architecture cruise, the show tickets and the day trips around you.