21 days in Chicago Itinerary

21 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
— 20 nights

21
days
Chicago

Chicago
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Do some cultural sightseeing at The Magnificent Mile and Millennium Park. Let the collections at The Art Institute of Chicago and Museum of Science and Industry, Chicago capture your imagination. Get out of town with these interesting Chicago side-trips: Gayety's Chocolates & Ice Cream (in Lansing), Utica (Starved Rock State Park, Matthiessen State Park, & more) and Jasper-Pulaski Fish and Wildlife Area (in Medaryville). There's lots more to do: stroll through Silver Beach County Park, pause for some serene contemplation at Basilica of the Sacred Heart, admire the majestic nature at Grand Mere State Park, and look for all kinds of wild species at Sarett Nature Center.

To find ratings, reviews, other places to visit, and tourist information, you can read our Chicago travel planner.

If you are flying in from Italy, the closest major airports are Chicago Midway International Airport, Chicago O'Hare International Airport and South Bend Regional Airport. November in Chicago sees daily highs of 11°C and lows of 1°C at night. Wrap up your sightseeing on the 30th (Thu) to allow time to travel back home.

Things to do in Chicago

Parks Outdoors Wildlife

Side Trips

Lake Geneva, Utica, Michigan City, Coloma, Saint Joseph
Highlights from your plan
Starved Rock State Park
Starved Rock State Park
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park

Similar Plans

22 days in Chicago BY A USER FROM GREECE April, popular & hidden gems PREFERENCES: April ATTRACTION STYLE: Popular & hidden gems PACE: Medium 23 days in United States BY A USER FROM UNITED KINGDOM November, culture, outdoors, romantic, beaches, historic sites, museums, wildlife, fast-paced, hidden gems PREFERENCES: November, culture, outdoors, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Hidden gems PACE: Fast-paced 23 days in Chicago, Rhode Island & New York City BY A USER FROM UNITED KINGDOM August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium 25 days in United States BY A USER FROM NETHERLANDS August, culture, outdoors, historic sites, wildlife, slow & easy, popular & hidden gems PREFERENCES: August, culture, outdoors, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 23 days in United States BY A USER FROM BELGIUM August, outdoors, historic sites, wildlife, slow & easy, popular & hidden gems PREFERENCES: August, outdoors, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 22 days in United States BY A USER FROM SAUDI ARABIA October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium 22 days in United States BY A USER FROM SWEDEN October, popular PREFERENCES: October ATTRACTION STYLE: Popular PACE: Medium 24 days in United States BY A USER FROM LEBANON December, popular PREFERENCES: December ATTRACTION STYLE: Popular PACE: Medium 24 days in United States BY A USER FROM THAILAND December, popular PREFERENCES: December ATTRACTION STYLE: Popular PACE: Medium 32 days in Chicago BY A USER FROM UNITED STATES November, shopping, popular PREFERENCES: November, shopping ATTRACTION STYLE: Popular PACE: Medium
View more plans