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. 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.

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
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 PORTUGAL May, popular PREFERENCES: May ATTRACTION STYLE: Popular PACE: Medium 3 days in Chicago BY A USER FROM UNITED STATES February, popular PREFERENCES: February ATTRACTION STYLE: Popular PACE: Medium 7 days in Chicago BY A USER FROM MEXICO August, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, hidden gems PREFERENCES: August, culture, outdoors, relaxing, romantic, historic sites, museums, shopping ATTRACTION STYLE: Hidden gems PACE: Medium 7 days in Chicago BY A USER FROM MEXICO August, culture, outdoors, romantic, historic sites, museums, shopping, popular PREFERENCES: August, culture, outdoors, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular PACE: Medium 60 days in United States, Colombia & Nakhon Ratchasima Province BY A USER FROM NETHERLANDS January, culture, historic sites, museums, wildlife, popular PREFERENCES: January, culture, historic sites, museums, wildlife ATTRACTION STYLE: Popular PACE: Medium 11 days in Chicago, Boston & New York City BY A USER FROM ARGENTINA October, culture, historic sites, museums, wildlife, popular PREFERENCES: October, culture, historic sites, museums, wildlife ATTRACTION STYLE: Popular PACE: Medium 33 days in United States & Niagara Falls BY A USER FROM AUSTRALIA June, teens, popular PREFERENCES: June, teens ATTRACTION STYLE: Popular PACE: Medium 4 days in Chicago BY A USER FROM BRAZIL August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium 30 days in United States BY A USER FROM TOGO September, popular PREFERENCES: September ATTRACTION STYLE: Popular PACE: Medium 29 days in United States BY A USER FROM AUSTRALIA August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium 47 days in United States BY A USER FROM MOROCCO August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium 20 days in Orlando, Chicago & New York City BY A USER FROM INDIA September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium
View more plans