234
trips planned in the last hour
8.9
out of 10
Trustscore rating

Chicago trip planner

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

Itinerary Planner
+ Add destination
2 adults
Adults
- +
Teens
- +
Kids
- +
Close
Trip Planner USA  /  Illinois  /  Chicago

Chicago

4.4

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants. Renowned for its distinct architecture that provides countless sightseeing opportunities, the city attracts tourists with its cosmopolitan atmosphere and genuine friendliness, charming visitors with a sense of hospitality rarely found in other urban centers its size. The hub of the Midwest, Chicago features a picturesque skyline set against the waters of Lake Michigan, resembling more an inland sea than a freshwater lake. You have plenty to choose from for a diverse itinerary, including visits to the city's lakefront, huge parks, public squares, and world-class museums of art and science. Chicago is in Illinois (IL). Use our United States trip planner to arrange your visit to Chicago and other destinations in United States.Read the Chicago Holiday Planning Guide
Create a full itinerary — for free!

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.
View more tours

Popular things to do in Chicago

View all >
4.8
Duration: 2​h
4.7
Duration: 1​h
4.6
Duration: 3​h
4.6
Duration: 2​h 30​min

Kid-friendly things to do in Chicago

View all >
4.0
Duration: 2​h
4.5
Duration: 3​h
4.4
Duration: 3​h
3.8
Duration: 3​h

Side trips from Chicago

3.5
Duration: 2​h 30​min
4.8
Duration: 4​h
4.7
Duration: 1​h 30​min

Hidden gems in Chicago

4.8
Duration: 3​h
4.7
Duration: 1​h
4.7
Duration: 1​h 30​min
4.8
Duration: 2​h 30​min

Museums in Chicago

View all >
4.8
Duration: 1​h 30​min
4.4
Duration: 2​h 30​min
4.6
Duration: 30​min
4.8
Duration: 1​h 30​min

Historic Sites in Chicago

View all >
4.6
Duration: 30​min
4.7
Duration: 1​h 30​min
4.7
Duration: 1​h
4.2
Duration: 1​h
4.4
Duration: 3​h
4.5
Duration: 1​h 30​min

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

17 days in United States & Cancun BY A USER FROM HUNGARY August, hidden gems PREFERENCES: August ATTRACTION STYLE: Hidden gems PACE: Medium 4 days in Chicago BY A USER FROM UNITED STATES March, culture, romantic, museums, shopping, popular & hidden gems PREFERENCES: March, culture, romantic, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 26 days in United States BY A USER FROM SAUDI ARABIA August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 47 days in United States BY A USER FROM SAUDI ARABIA August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 27 days in Continental USA BY A USER FROM CANADA April, fast-paced, popular & hidden gems PREFERENCES: April ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 28 days in Santa Monica & Chicago BY A USER FROM BELGIUM July, culture, outdoors, historic sites, hidden gems PREFERENCES: July, culture, outdoors, historic sites ATTRACTION STYLE: Hidden gems PACE: Medium 26 days in United States BY A USER FROM UNITED KINGDOM July, popular sights PREFERENCES: July ATTRACTION STYLE: Popular sights PACE: Medium 1 day in Chicago BY A USER FROM INDIA May, popular sights PREFERENCES: May ATTRACTION STYLE: Popular sights PACE: Medium 22 days in United States BY A USER FROM SOUTH AFRICA June, popular & hidden gems PREFERENCES: June ATTRACTION STYLE: Popular & hidden gems PACE: Medium 27 days in United States BY A USER FROM POLAND August, slow & easy, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Slow & easy 6 days in Chicago BY A USER FROM UNITED STATES June, popular sights PREFERENCES: June ATTRACTION STYLE: Popular sights PACE: Medium 14 days in Chicago BY A USER FROM AUSTRALIA April, popular sights PREFERENCES: April ATTRACTION STYLE: Popular sights PACE: Medium
View more plans