116
trips planned by users
trips planned by users
Chicago trip planner
Create a fully customized
day-by-day itinerary for free
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.
Create a full itinerary — for free!
Plan your trip to Chicago
Get a personalized plan
A complete day-by-day itinerary
based on your preferencesCustomize it
Refine your plan. We'll find the
best routes and schedulesBook it
Choose from the best hotels
and activities. Up to 50% offManage it
Everything in one place.
Everyone on the same page.
Top Chicago tours
Hidden gems in Chicago
Side trips from Chicago
Parks in Chicago
Featured attractions
Places to visit with Chicago
Recently planned trips to Chicago
33 days in United States, Toronto & Niagara Falls
BY A USER FROM AUSTRALIA
September, teens, kids, popular sights
PREFERENCES: September, teens, kids
ATTRACTION STYLE: Popular sights
PACE: Medium
5 days in Chicago
BY A USER FROM AUSTRALIA
March, popular sights
PREFERENCES: March
ATTRACTION STYLE: Popular sights
PACE: Medium
4 days in Chicago
BY A USER FROM UNITED STATES
November, teens, popular sights
PREFERENCES: November, teens
ATTRACTION STYLE: Popular sights
PACE: Medium
3 days in Chicago
BY A USER FROM UNITED STATES
November, teens, popular sights
PREFERENCES: November, teens
ATTRACTION STYLE: Popular sights
PACE: Medium
3 days in Chicago
BY A USER FROM UNITED STATES
September, popular sights
PREFERENCES: September
ATTRACTION STYLE: Popular sights
PACE: Medium
15 days in Chicago
BY A USER FROM SINGAPORE
December, popular sights
PREFERENCES: December
ATTRACTION STYLE: Popular sights
PACE: Medium
View more plans
