Chicago trip planner

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

Holiday 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. Use our United States trip itinerary tool to plan your trip 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.

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.
Best Deals Guaranteed

Recently planned trips to Chicago

23 days in United States & Niagara Falls BY A USER FROM ISRAEL September, outdoors, relaxing, romantic, shopping, wildlife, popular PREFERENCES: September, outdoors, relaxing, romantic, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium 2 days in Chicago BY A USER FROM UNITED STATES June, popular PREFERENCES: June ATTRACTION STYLE: Popular PACE: Medium 8 days in Chicago BY A USER FROM DOMINICAN REPUBLIC May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 11 days in United States BY A USER FROM CANADA March, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular & hidden gems PREFERENCES: March, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 14 days in United States BY A USER FROM SINGAPORE July, relaxing, romantic, shopping, popular PREFERENCES: July, relaxing, romantic, shopping ATTRACTION STYLE: Popular PACE: Medium 17 days in United States BY A USER FROM UNITED KINGDOM November, culture, historic sites, museums, wildlife, popular PREFERENCES: November, culture, historic sites, museums, wildlife ATTRACTION STYLE: Popular PACE: Medium 25 days in United States BY A USER FROM CANADA May, hidden gems PREFERENCES: May ATTRACTION STYLE: Hidden gems PACE: Medium 5 days in Illinois BY A USER FROM UNITED STATES April, popular PREFERENCES: April ATTRACTION STYLE: Popular PACE: Medium 60 days in Canada & United States BY A USER FROM AUSTRALIA October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium 39 days in Chicago BY A USER FROM UNITED STATES April, culture, outdoors, popular PREFERENCES: April, culture, outdoors ATTRACTION STYLE: Popular PACE: Medium 3 days in Chicago BY A USER FROM DOMINICAN REPUBLIC May, culture, outdoors, relaxing, historic sites, museums, shopping, popular PREFERENCES: May, culture, outdoors, relaxing, historic sites, museums, shopping ATTRACTION STYLE: Popular PACE: Medium 3 days in Chicago BY A USER FROM DOMINICAN REPUBLIC April, popular PREFERENCES: April ATTRACTION STYLE: Popular PACE: Medium
View more plans