Explore iconic attractions, hidden gems, and travel guides. Plan the perfect Chicago trip!

Save this place to a Trip, where you can track your faves and get personalized picks as you plan. Chicago’s got the big-city vibes you want, but friendly locals and a walkable layout make it …

Dec 6, 2025 · Discover accommodations in downtown Chicago, offering access to top-tier dining, cultural hotspots, and captivating entertainment. From Millennium Park to the Art Institute of …

Jul 28, 2025 · Must-visit attractions in Chicago include the Navy Pier, Wrigley Field, Second City, Skydeck Chicago, and of course, "The Bean." Find more fun things to do in Chicago.

Planning a trip to Chicago? This ultimate guide covers how to get here (Amtrak, O’Hare, Midway, Greyhound), the best neighborhoods to explore, and hotel recommendations for every budget.

Ready to explore Chicago? Discover must-see sights, fun things to do, and where to stay. Find exclusive deals on hotels, tours, and attraction tickets. Plan it all on Trip.com!

Aug 16, 2025 · A comprehensive travel guide to Chicago with tips on things to do, costs, accommodation, ways to save, transportation, and more.

May 2, 2025 · I’m a local, and I love showing friends and family everything Chicago has to offer when they come to town. I have the inside scoop and, in this itinerary, I’m going to detail …

3 days ago · Chicago, perched on the shores of Lake Michigan, is one of the largest and most dynamic cities in the U.S. Known for its world-class art, iconic museums, rich history, and …

5 days ago · Here are Chicago's hidden gems that you won't find anywhere else. These are prime reasons to visit Chicago over other cities in North America. Even if you're a first time visitor to …