312
trips planned in the last hour
8.7
out of 10
Trustscore rating

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

23 days in United States BY A USER FROM UNITED STATES May, slow & easy, popular PREFERENCES: May ATTRACTION STYLE: Popular PACE: Slow & easy 4 days in Chicago BY A USER FROM SOUTH AFRICA September, outdoors, relaxing, historic sites, shopping, fast-paced, popular PREFERENCES: September, outdoors, relaxing, historic sites, shopping ATTRACTION STYLE: Popular PACE: Fast-paced 5 days in Chicago BY A USER FROM SOUTH AFRICA September, fast-paced, popular PREFERENCES: September ATTRACTION STYLE: Popular PACE: Fast-paced 11 days in United States BY A USER FROM UKRAINE September, culture, outdoors, relaxing, shopping, wildlife, popular PREFERENCES: September, culture, outdoors, relaxing, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium 29 days in Chicago BY A USER FROM ISRAEL October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium 45 days in United States BY A USER FROM PAKISTAN October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium 34 days in United States BY A USER FROM VIETNAM September, popular PREFERENCES: September ATTRACTION STYLE: Popular PACE: Medium 15 days in United States BY A USER FROM UNITED STATES May, popular PREFERENCES: May ATTRACTION STYLE: Popular PACE: Medium 15 days in United States BY A USER FROM UNITED STATES March, slow & easy, popular PREFERENCES: March ATTRACTION STYLE: Popular PACE: Slow & easy 22 days in United States BY A USER FROM UNITED STATES September, popular & hidden gems PREFERENCES: September ATTRACTION STYLE: Popular & hidden gems PACE: Medium 27 days in United States BY A USER FROM UNITED STATES October, popular & hidden gems PREFERENCES: October ATTRACTION STYLE: Popular & hidden gems PACE: Medium 33 days in United States BY A USER FROM UNITED KINGDOM June, culture, outdoors, relaxing, beaches, historic sites, wildlife, popular PREFERENCES: June, culture, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular PACE: Medium
View more plans