Chicago trip planner
Create a fully customized
day by day itinerary for free
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. Use our United States trip itinerary tool to plan your trip to Chicago and other destinations in United States.
Create a full itinerary — for free!
Plan your trip to Chicago
Get a personalized trip
A complete day by day itinerary
based on your preferencesCustomize it
Refine your trip. 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
Popular things to do in Chicago
Kid-friendly things to do in Chicago
Museums in Chicago
Hidden gems in Chicago
Side trips from Chicago
Historic Sites in Chicago
Places to visit with Chicago
Springfield
Trip planner
BEST FOR: History Museum, Historic Site, Landmark
Galena
Trip planner
BEST FOR: Historic Site, Distillery, Nightlife
Oak Park
Trip planner
BEST FOR: Architectural Building, Historic Site, Religious Site
Ottawa
Trip planner
BEST FOR: Spa, State Park, Specialty Museum
Evanston
Trip planner
BEST FOR: Room Escape Game, Theater, History Museum
Recently planned trips to Chicago
7 days in New York City & Chicago
BY A USER FROM PHILIPPINES
New York City
·
Chicago
60 days in United States
BY A USER FROM SOUTH AFRICA
New York City
·
Chicago
·
Yellowstone National Park
4 days in United States
BY A USER FROM THE NETHERLANDS
Washington DC
·
Baltimore
·
Philadelphia
18 days in United States
BY A USER FROM PORTUGAL
San Francisco
·
Los Angeles
·
Las Vegas
60 days in United States
BY A USER FROM HONG KONG SAR CHINA
New York City
·
Washington DC
·
Orlando
20 days in Midwest
BY A USER FROM UNITED STATES
Branson
·
Saint Louis
·
Custer