Chicago
Chicago Travel Guide 2026: Things to Do, Attractions & Itinerary | Trip.com
About Chicago
Recommended trip: 2–5 day(s)
Recommended trip: 2–5 day(s)Current weather conditions
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Things to do in Chicago
What to do
Looking for things to do in Chicago? We provide up-to-date info on everything from must-see scenic spots to local hangouts.
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Where to stay
Discover the most popular places to stay in Chicago, complete with recommendations from fellow travelers and special hotel offers
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What to eat
Want to eat like a local? Don't miss out on these top Chicago dishes and foodie spots.
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Chicago Moments: Through Travelers' Eyes
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Chicago in 1 Day: An Itinerary from The Bean to the 94th Floor.
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Embrace the Sunshine and Embark on an Extraordinary Island Luxury Journey
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Pick High Altitude Roaming, Chicago’s Soul in the Clouds
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Chicago | Sitting Gently Across from the City in the World's Largest Starbucks
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The Chicago Athletic Association Hotel: A Vintage Luxury Steeped in Rich History and Culture
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The St. Regis Chicago: An Architectural Marvel Born from the Heritage and Innovation of Eastern and Western Cultures
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Four Seasons Hotel Chicago: A Luxurious Dream Above the Clouds
LOUIS MANNING
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Best of Chicago
Top 20 Instagrammable Hotels in Chicago
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Top 10 Gourmet Hotels in Chicago
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Top 20 4-Star Select Hotels in Chicago
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Popular Best Things to Do Near Chicago
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Popular 4-Star Select Hotels Near Chicago
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Popular Types of Attractions in Chicago
Nature and wildlife | Natural scenery | Beaches and shores | Exhibitions & events | Performances | Concerts | Exhibitions | Historical attractions | Sightseeing tours | Night view | Boat tour | Cultural institutions | Themed exhibition halls | Museums | Science & technology museums | Leisure activities | Farms and pastures | Camping and campsites | Spa/massage | Parks | Outdoor activities | Shooting | Cycling
Popular Ranked Lists
Top 20 Global Traveller-Picked Attractions in Dalian | Top 20 Global Traveller-Picked Restaurants in Shangrao | Top 20 Global Traveller-Picked Attractions in Foshan | Top 50 Global Traveller-Picked Hotels in Chengdu | Top 10 Global Traveller-Picked Attractions in Kaifeng | Top 50 Global Traveller-Picked Restaurants in Guangzhou | Top 20 Global Traveller-Picked Hotels in Kunming | Top 50 Global Traveller-Picked Restaurants in Jiuzhaigou | Top 50 Global Traveller-Picked Restaurants in Tongxiang | Top 50 Global Traveller-Picked Restaurants in Xi'an | Top 10 Global Traveller-Picked Attractions in Yulong | Top 20 Global Traveller-Picked Hotels in Shangri-La | Top 50 Global Traveller-Picked Restaurants in Hangzhou | Top 10 Global Traveller-Picked Attractions in Anji | Top 20 Premium Hotels in Huizhou | Top 50 Global Traveller-Picked Restaurants in Huangshan City | Top 20 Premium Hotels in Shijiazhuang | Top 50 Global Traveller-Picked Hotels in Xi'an | Top 20 Global Traveller-Picked Hotels in Dali City | Top 50 Global Traveller-Picked Restaurants in Huizhou | Popular Global Traveller-Picked Attractions in Songpan | Top 20 Premium Hotels in Zhengzhou | Top 50 Global Traveller-Picked Hotels in Shenzhen | Top 20 Premium Hotels in Yinchuan | Top 10 Global Traveller-Picked Attractions in Leshan | Top 20 Premium Hotels in Fuzhou | Top 50 Global Traveller-Picked Attractions in Chengdu | Top 20 Premium Hotels in Hefei | Top 50 Global Traveller-Picked Attractions in Xi'an | Top 50 Global Traveller-Picked Restaurants in Changsha
Popular Restaurants in Chicago
Eleven City Diner | Cafe Jumping Bean | Irazu Costa Rican Restaurant & Catering | Cafe Marbella Tapas | Enoteca Roma Ristorante | Mercat a la Planxa | Trattoria Gianni | Rollapalooza | STRETCH BAR/GRILL | Do-Rite Donuts & Chicken | Maple & Ash | Proxi | Gino's East | Honey Butter Fried Chicken | Anteprima | Macello | Nia Restaurant & Wine Bar | NoMI | RL Restaurant | Shanghai Terrace | Sofi Restaurant | Untitled Supper Club | Aurelio's Pizza of Chicago South Loop | Petterinos | Dining Room At Kendall College | Agami | Mrs. Murphy & Sons Irish Bistro | Park Tavern | The Palm - Chicago | Duck Duck Goat
Recommended attractions at popular destinations
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Popular Trip Moments
5-Day US Trip Guide for Mid-Autumn Festival: The Ultimate Itinerary | Save this 5-day US travel guide for later | First time in the US? You must try these 15 classic foods 🇺🇸 | The Langham, Chicago is truly something special! It features the most incredible floor-to-ceiling picture windows in the entire Windy City. | 8-day mini-vacation guide to the US with a super comprehensive checklist | What I ate in Chicago at the tail end of summer: | A short vacation to the US is totally worth it | Luxurious Stay with Exceptional Service | This guide totally gets me for a summer trip to the US | Mackinac Island — The American Town Where Cars Are Banned and the Ferry Is the Only Way In | Holland — The American Town Where Tulips Bloom by the Million and Dutch Heritage Lives on the Lake | Galena — The American Town Where Brick Streets Climb Above the Galena River and History Lives in Eve | One of America’s Big Four Art Museums! Step into Monet’s Water Lilies and the Golden Halls of Pharaohs for Boston’s Most Profound Artistic Journey. | 6-day US mini-vacation guide: super practical | If You Love Dinosaurs, The Field Museum is a Chicago Must-Visit! | 🌆 Chicago, A Day Between City & Nature | Welcome to Chicago on a Budget: Free Museums & Cheap Things To Do | Top-Tier Service and Elegance | Cloud Gate | Fourth Presbyterian Church ⛪️, greenery tranquil hidden place in Chicago | An Extraordinary Luxury Stay with Thoughtful Service | 8-day US summer vacation guide: A stress-free, comprehensive itinerary | 🏡 Frank Lloyd Wright Home & Studio — An Architecture Lover’s Chicago Hidden Gem | 🦋🦊 One of Chicago’s Most Unique Hidden Gems — The Insect Asylum 🪲🐢 | 🌈🌿 Chicago Day 4 Itinerary — Lincoln Park, Lakeview & LGBTQ+ Chicago | 🏡🌮 Chicago Day 3 Itinerary — Oak Park, Pilsen & Chinatown! | 🦖🍜 Chicago Day 2 Itinerary — Hidden Gems, Amazing Food & Weird Chicago | What to Buy in China? A Guide to Popular Souvenirs. | 🇺🇸 Chicago Day 1 Itinerary 🌭🏙️ The Perfect First Day in the Windy City
More Things To Do in Chicago
Chicago Architecture River Cruise | Flyover Experience in Chicago | Chicago first lady sightseeing river and lake cruise | Go City: Chicago Explorer Pass (Discover over 30 top attractions | 360 CHICAGO, Skydeck Chicago & more) | Chicago CityPASS | Chicago River 90-Minute Architecture Tour | BIG BUS Chicago hop-on hop-off bus tour | The Art Institute of Chicago: Fast Pass | 360 Chicago Observation Deck: Entry Ticket | Chicago Lake and River Architecture Tour | Go City Chicago Explorer Pass - Go City Chicago Explorer Pass | Chicago CityPASS: 5 attraction admission tickets | The Art Institute of Chicago: Skip The Line Ticket + Exclusive Guided Tour | Lake Michigan & Chicago River: 1.5-Hr Sightseeing Cruise | Chicago: Architecture Foundation Center River Cruise aboard Chicago's First Lady | Chicago Architecture Boat Tour & Hop-on Hop-off Bus Tour | Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA | Chicago: Riverwalk Self-Guided Walking Tour | United States Tourist / Visiting Relatives and Friends / Business Visa (Hong Kong Application) | City Cruises Chicago: Premier Lunch or Dinner Cruise | Chicago Explorer Pass: 2 to 7 Attractions including SkyDeck | Chicago: Small Group ICONIC Landmarks & Skyline City Tour | Chicago: Historical Lake and River Fireboat Cruise | Skyline Lake boat tour from Navy Pier | Chicago in a Day: Food & Walk Tour+Free Bike or Kayak Rental | Chicago: Best of Attractions Walking Tour +Bike/Kayak Rental | Chicago: BYOB Spray Paint and Sip Workshop | Chicago: 90-Minute Architecture Tour on the Lake & River | Chicago: Architecture Cruise | Chicago: Gangsters and Food Tasting Walking Tour