32 days in Chicago Itinerary

32 days in Chicago Itinerary

Created using Inspirock United States Trip Planner

You are viewing a shared plan.  Customize plan

Route & dates

View / edit route

Chicago
— 31 nights

32
days
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get a sense of the local culture at The Art Institute of Chicago and The Field Museum. Get some historical perspective at Millennium Park and Basilica of the Sacred Heart. Venture out of the city with trips to Michigan City (Shady Creek Winery, Barker Mansion, & more), LaPorte (La Porte County Historical Society & Hesston Steam Museum) and Middle East Conflicts Wall Memorial (in Marseilles). Plan for a day of cool, family-friendly fun on the 29th (Sun) at Six Flags Great America. Next up on the itinerary: immerse yourself in nature at Starved Rock State Park, explore and take pictures at Wrigley Field, engage your brain at Museum of Science and Industry, Chicago, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

To see reviews, more things to do, where to stay, and more tourist information, read our Chicago travel planner.

If you are flying in from Taiwan, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. In October, plan for daily highs up to 20°C, and evening lows to 10°C. Wrap up your sightseeing on the 10th (Fri) to allow time to travel back home.

Things to do in Chicago

Parks Museums Historic Sites

Side Trips

South Bend, Utica, Rockford, Saint Joseph, Michigan City
Highlights from your plan
Millennium Park ©
Millennium Park
The Art Institute of Chicago ©
The Art Institute of Chicago
The Field Museum
The Field Museum

Similar Plans

36 days in United States BY A USER FROM UNITED STATES December, culture, outdoors, relaxing, shopping, wildlife, popular PREFERENCES: December, culture, outdoors, relaxing, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium 60 days in United States BY A USER FROM INDIA October, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife, slow & easy, hidden gems PREFERENCES: October, culture, outdoors, relaxing, romantic, beaches, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 56 days in United States BY A USER FROM CROATIA April, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife, popular PREFERENCES: April, culture, outdoors, relaxing, romantic, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium 33 days in Chicago BY A USER FROM UNITED STATES September, popular PREFERENCES: September ATTRACTION STYLE: Popular PACE: Medium 41 days in Chicago BY A USER FROM UNITED STATES September, outdoors, relaxing, beaches, popular PREFERENCES: September, outdoors, relaxing, beaches ATTRACTION STYLE: Popular PACE: Medium 7 days in Chicago BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, fast-paced, popular PREFERENCES: September, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular PACE: Fast-paced 35 days in United States BY A USER FROM AUSTRALIA January, culture, outdoors, romantic, historic sites, museums, shopping, popular PREFERENCES: January, culture, outdoors, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular PACE: Medium 37 days in United States BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular PREFERENCES: May, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular PACE: Medium 40 days in Chicago BY A USER FROM UNITED STATES September, outdoors, slow & easy, popular PREFERENCES: September, outdoors ATTRACTION STYLE: Popular PACE: Slow & easy 48 days in Seligman & Chicago BY A USER FROM IRAQ October, culture, outdoors, historic sites, wildlife, slow & easy, hidden gems PREFERENCES: October, culture, outdoors, historic sites, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 44 days in Chicago BY A USER FROM UNITED STATES September, outdoors, beaches, popular PREFERENCES: September, outdoors, beaches ATTRACTION STYLE: Popular PACE: Medium 31 days in United States BY A USER FROM SINGAPORE December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: December, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium
View more plans