Chicago
Chicago Travel Guide 2026: Top Attractions, Things to do & Itinerary | Trip.com | August, 2026
About Chicago
Recommended trip: 2–5 day(s)
Recommended trip: 2–5 day(s)Current weather conditions
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Trip.Best: Chicago
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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
Mason Turner
Chicago | Sitting Gently Across from the City in the World's Largest Starbucks
Mason Turner
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 4-Star Select Hotels in Chicago
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Popular 4-Star Select Hotels Near Chicago
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Other recommended cities
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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 Attractions in Chicago
Annunciation Greek Orthodox Cathedral | South Side Community Art Center | Shoreline Sightseeing | Martyrs' | Ukrainian National Museum | Aqua at Lakeshore East Apartments | Sullivan Center | Auditorium Theatre | Balzekas Museum Of Lithuanian Culture | Assumption Catholic Church | Newberry Library | Pullman National Historical Park | Magnificent Mile | Soldier Field | Frederick C. Robie House | St. Therese Chinese Catholic Church | The Last Defender | Goodman Theatre | Huntington Bank Pavilion at Northerly Island | Harborside International Golf Center | New Mt Pilgrim MB Church | Chicago Seventh-Day Adventist Church - Hrišćanska Adventistička Crkva Čikago | St. Monica's Roman Catholic Church | Johnny Twist Blues Museum | Ford Calumet Environmental Center | Apostolic Church Of God | Jefferson Park Branch, Chicago Public Library | Grand Park | The Grid Church | Begyle Brewing
Popular Ranked Lists
Popular Premium Hotels Near Wallan | Top 50 Global Traveller-Picked Restaurants in Chengdu | Popular Premium Hotels in Al Khor Al Sharqi | Popular Best Things to Do in Panzhihua | Popular Best Things to Do in Lichuan | Popular Premium Hotels Near Sepaku | Top 50 Global Traveller-Picked Restaurants in Guangzhou | Top 20 Must-Visit Restaurants in Dongyang | Top 20 Must-Visit Restaurants in Wutai County | Popular Premium Hotels in Ogijima | Popular Premium Hotels in Lasbela | Popular Best Things to Do in Linxia Prefecture | Popular Premium Hotels Near Shymkent | Top 50 Global Traveller-Picked Restaurants in Suzhou | Top 50 Global Traveller-Picked Attractions in Xi'an | Popular Premium Hotels in Sestroretsk | Popular Premium Hotels in Cernobbio | Top 20 Must-Visit Restaurants in Saint Petersburg | Top 20 Must-Visit Restaurants in Krabi Town | Top 20 Must-Visit Restaurants in Chicago | Popular Premium Hotels Near Sindh | Top 20 Must-Visit Restaurants in Oslo | Top 50 Global Traveller-Picked Attractions in Guangzhou | Top 50 Global Traveller-Picked Restaurants in Chongqing | Top 20 Must-Visit Restaurants in Chengde | Top 20 Must-Visit Restaurants in Lushan City | Popular Best Things to Do in Ziyuan | Top 20 Must-Visit Restaurants in Pingyao County | Popular Premium Hotels Near Overland Park | Popular Premium Hotels in Bumi Harapan
Popular Restaurants in Chicago
Eleven City Diner | Alinea | NoMI | Shanghai Terrace | Untitled Supper Club | Dining Room At Kendall College | Boka | Au Cheval | EL ideas | Oriole | Elske | Miru | Tufano's Vernon Park Tap | The Purple Pig Restaurant | Firecakes Donuts | The J. Parker | Portillo's & Barnelli's Chicago | River Roast | Sepia | Tanta | Gibsons Bar & Steakhouse | Yolk - Marina City | The Dearborn | Terrace 16 | Mako | Galit | Wildberry Pancakes & Cafe | The Cheesecake Factory | Pequod's Pizza | m.henry
Popular Destinations
Muskogee County Travel | Nanaimo G Travel | Tacna Travel | Hastings District Travel | Cumberland County Travel | Purbeck District Travel | Wuhu Travel | Ashland Travel | Zanzibar South Region Travel | Koh Tao Travel | Bo'ai Travel | Nanyuki Travel | Ningxia Travel | English Harbour Travel | Yiyang Travel | Hilvarenbeek Travel | Conway Travel | Morristown Travel | Soufriere Travel | Yla-Pirkanmaa Travel | Parnu Travel | Lodi Travel | Robina Travel | Bridgewater Travel | Lower Mount Bethel Township Travel | Suihua Travel | Kings County Travel | Shimian Travel
Recommended attractions at popular destinations
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Popular Trip Moments
Guangdong is not just about the sea! Step into Kaiping, Jiangmen, and discover the century-old watchtowers among the rice fields | An Art Tour in Hong Kong. | Review: Qantas Business Lounge Hong Kong. | Summer vacation 4-day ultimate US trip guide | 7 World Marathon Majors. | Just returned from a trip to the US, and I have some honest truths to share! But don't worry, with this guide, you can still have a blast. | Polishing the Bean: A Photographer’s Courtesy at Chicago’s Millennium Park | 8-day summer travel guide for the US that’s super practical | See Monet's "Water Lilies" in Person for Free! The Hong Kong Museum of Art's Blockbuster Grand Exhibition "Blooming: The Art of Gardens in East and West" Enters the Final Countdown! . | Chicago Winters: Cold, Beautiful, and Unforgettable ❄️ | 6-day itinerary for unique and healing experiences in the US | A 4-day US trip guide you’ll want to save | 8-day USA travel guide to help you explore America with ease | [Last Chance] See Original Monet Masterpieces for Free! 3 Major Exhibitions at the Hong Kong Museum of Art. | Stayed at a vintage hotel in Chicago’s Old Town—absolutely stunning | First time in the US? This guide quickly explains how to choose between the East Coast and West Coast | Chicago legendary window view hotel on Michigan Avenue prime location! Lie back and enjoy the dazzling city and river views | Chicago skyline | 10-Day Road Trip: Discovering the Hidden Gems of the Midwest | Snapshot | This American train station embodies the beauty of economic prosperity. | From "Moonlight Stroll" to "Lion Grove Garden," an ultimate clash of Chinese and Western garden art | Canvas of Legacy | Engines of Imagination | I've found the most authentic Western restaurant in Kunming! It's been run by an American couple for 12 years. | The largest Starbucks in the world is located in Chicago ☕️✨ | Chicago for the First Time: 7 Must-See Places. | The Bean in Chicago: 5 Nearby Places to See in One Walk.
More Things To Do in Chicago
Chicago Architecture River Cruise | Chicago: Fireworks Cruise with Lake or River Viewing Options | BIG BUS Chicago hop-on hop-off bus tour | Chicago CityPASS | Chicago: Navy Pier Centennial Wheel Ticket | Chicago: Willis Tower Skydeck and The Ledge Ticket | Chicago River 90-Minute Architecture Tour | Chicago CityPASS: 5 attraction admission tickets | U.S. airport|Chicago O'Hare international airport/Midway international airport VIP lounge pass|ORD/MDW airport VIP lounge for transit/waiting/rest | Chicago CityPASS City Pass | The Art Institute of Chicago: Fast Pass | Chicago: 90 Minute Architecture Sightseeing Cruise | Chicago by Night River and Lake Cruise | Lake Michigan Skyline Cruise in Chicago | Chicago Crime and Mob Bus Tour | Big Bus Chicago: Hop-on Hop-off Bus Tour | Chicago: Premier Dinner Cruise on the Chicago River | Lake Michigan: Premier Brunch or Lunch Cruise | U.S. Chicago Midway Airport VIP lounge pass/MDW airport VIP lounge transit/rest | Original Chicago Prohibition Tour | US airport|VIP lounge pass at Chicago O'Hare International Airport/Midway International Airport|ORD/MDW airport VIP lounge transfer/flight waiting/rest | Chicago: Craft Brewery Barrel Bus Tour | Lake Michigan & Chicago River: 1.5-Hr Night Sightseeing Cruise | Chicago: Guided Food Tour + Bike or Kayak Rental | Chinese children applying for 10-year multiple-entry Q2 family visit visas are eligible for visa processing across the United States. | Lake Michigan & Chicago River: 75 Minute Speedboat Cruise | Chicago: Canine Cruise | Architecture of the Magnificent Mile | Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA | 360 Chicago Observation Deck: Entry Ticket