Chicago trip planner

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

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

Chicago

Trip Planner USA  /  Illinois  /  Chicago

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. Plan your vacation with our United States tourist route planner and discover the best things to do in Chicago.
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.

Extend your holiday

Springfield Best for: Museums, Historic Sites, Parks Glencoe Best for: Parks, Nightlife Galena Best for: Historic Sites, Breweries, Nightlife Schaumburg Best for: Fun & Games, Nightlife, Shopping Naperville Best for: Historic Sites, Nightlife, Fun & Games

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.
Live like a local, find unique places to stay
Millions of travel reviews on TripAdvisor

Recently planned trips to Chicago

13 days in Chicago, Alabama & New Orleans BY A USER FROM UNITED STATES October, kids, culture, beaches, museums, wildlife, hidden gems PREFERENCES: October, kids, culture, beaches, museums, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 3 days in Chicago BY A USER FROM NETHERLANDS November, culture, outdoors, relaxing, romantic, beaches, museums, popular PREFERENCES: November, culture, outdoors, relaxing, romantic, beaches, museums ATTRACTION STYLE: Popular PACE: Medium 8 days in Chicago BY A USER FROM UNITED STATES October, culture, outdoors, relaxing, historic sites, museums, slow & easy, popular PREFERENCES: October, culture, outdoors, relaxing, historic sites, museums ATTRACTION STYLE: Popular PACE: Slow & easy 2 days in Chicago BY A USER FROM UNITED STATES September, popular PREFERENCES: September ATTRACTION STYLE: Popular PACE: Medium 18 days in Los Angeles & Chicago BY A USER FROM NORWAY May, popular PREFERENCES: May ATTRACTION STYLE: Popular PACE: Medium 12 days in United States BY A USER FROM BRAZIL November, outdoors, historic sites, wildlife, popular & hidden gems PREFERENCES: November, outdoors, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 3 days in Chicago BY A USER FROM UNITED STATES November, popular PREFERENCES: November ATTRACTION STYLE: Popular PACE: Medium 5 days in Chicago BY A USER FROM UNITED STATES September, popular PREFERENCES: September ATTRACTION STYLE: Popular PACE: Medium 4 days in Chicago BY A USER FROM UNITED STATES October, culture, historic sites, museums, popular PREFERENCES: October, culture, historic sites, museums ATTRACTION STYLE: Popular PACE: Medium 18 days in United States BY A USER FROM ISRAEL September, kids, popular PREFERENCES: September, kids ATTRACTION STYLE: Popular PACE: Medium 49 days in United States & Europe BY A USER FROM NEW ZEALAND November, culture, relaxing, historic sites, museums, shopping, popular PREFERENCES: November, culture, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular PACE: Medium 30 days in United States BY A USER FROM AUSTRALIA October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium
View more plans