The Best Things to Do in Chicago

Create a fully customized
day-by-day itinerary for free

Itinerary Planner
+ Add destination
2 adults
Adults
- +
Teens
- +
Kids
- +
Close

Plan your trip to Chicago

  • Get a personalized plan

    A complete day-by-day itinerary
    based on your preferences
  • Customize it

    Refine your plan. We'll find the
    best routes and schedules
  • Book it

    Choose from the best hotels
    and activities. Up to 50% off
  • Manage it

    Everything in one place.
    Everyone on the same page.

Where to stay in Chicago

The Midwest's major center for business conventions, Chicago boasts many affordable places to stay, with most hotels located around the airport and the city's central business district. To discover the city from a comfortable base within walking distance of most tourist attractions, aim for one of the big chain hotels in the downtown area. If you're traveling on a limited budget and wish to get a deeper sense of Chicago's many diverse neighborhoods, consider staying away from the pricey city center and explore suburbs on a commuter train line for easy city access.
Millions of travel reviews on TripAdvisor
2 adults
Adults (12 +)
- +
Children (2-11)
- +
Infants (Under 2)
- +
Close
Live like a local, find unique places to stay
2 adults
Adults (12 +)
- +
Children (2-11)
- +
Infants (Under 2)
- +
Close

Recently planned trips to Chicago

37 days in United States BY A USER FROM PAKISTAN June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 25 days in United States BY A USER FROM UNITED KINGDOM June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 8 days in United States BY A USER FROM CANADA August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium 5 days in Chicago and Beyond BY A USER FROM UNITED STATES July, teens, popular PREFERENCES: July, teens ATTRACTION STYLE: Popular PACE: Medium 11 days in United States BY A USER FROM INDIA October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium 40 days in United States BY A USER FROM ALGERIA June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 26 days in United States BY A USER FROM INDIA June, fast-paced, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Fast-paced 3 days in Chicago BY A USER FROM UNITED STATES June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 1 day in Chicago BY A USER FROM UNITED STATES June, outdoors, popular PREFERENCES: June, outdoors ATTRACTION STYLE: Popular PACE: Medium 35 days in United States BY A USER FROM VIETNAM June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 45 days in United States BY A USER FROM THAILAND March, popular PREFERENCES: March ATTRACTION STYLE: Popular PACE: Medium 20 days in Chicago & Yellowstone National Park BY A USER FROM FRANCE August, culture, outdoors, wildlife, popular PREFERENCES: August, culture, outdoors, wildlife ATTRACTION STYLE: Popular PACE: Medium
View more plans