29 days in Chicago Itinerary

29 days in Chicago Itinerary

Created using Inspirock Chicago itinerary builder

This plan was created by another user. Make it your plan

Route & dates

View / edit route

— 28 nights


Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your cultural itinerary includes sights like The Magnificent Mile and The Field Museum. Get in touch with nature at Lincoln Park Zoo and Swallow Cliff Stairs. Get out of town with these interesting Chicago side-trips: Little Red Schoolhouse (in Willow Springs), Chesterton (Coffee Creek Watershed Preserve & Cowles Bog) and Whihala Beach (in Whiting). There's lots more to do: don't miss a visit to Millennium Park, grab your bike and head to Grant Park, explore the world behind art at The Art Institute of Chicago, and get curious at Museum of Science and Industry.

For other places to visit, reviews, where to stay, and other tourist information, refer to the Chicago trip website .

In April, daily temperatures in Chicago can reach 59°F, while at night they dip to 40°F. Cap off your sightseeing on the 18th (Sat) early enough to travel back home.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Oak Park, Skokie, South Bend, Chesterton, Highland Park
Highlights from your plan
Chicago Greeter ©
Chicago Greeter
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum