7 days in Chicago Itinerary

7 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

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Route & dates

7 days in Chicago Itinerary

Start: Brampton
Drive:  11​h 30​min
1
Chicago
— 5 nights
Fly + Drive:  10​h 30​min
End: Brampton

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get in touch with nature at Deer Grove Forest Preserve and Swallow Cliff Stairs. Your cultural itinerary includes sights like The Magnificent Mile and Chicago Cultural Center. Explore the numerous day-trip ideas around Chicago: Hawthorn Hollow - Nature Sanctuary and Arboretum (in Kenosha), Volo Bog State Natural Area (in Ingleside) and Prairie Wolf Slough (in Highland Park). There's much more to do: see what you can catch with a fishing tour, stroll through Little Red Schoolhouse, try to win big at Horseshoe Hammond, and make a trip to Buckingham Fountain.

For more things to do, photos, and more tourist information, you can read our Chicago route builder app .

Brampton, Canada to Chicago is an approximately 8-hour car ride. You can also fly. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In May, daytime highs in Chicago are 25°C, while nighttime lows are 13°C. Finish your sightseeing early on the 16th (Thu) to allow enough time to travel back home.

Things to do in Chicago

Wildlife Parks Outdoors

Side Trips

Fishing Charters & Tours, Swallow Cliff Stairs, Little Red Schoolhouse, Hawthorn Hollow - Nature Sanctuary and Arboretum, Prairie Wolf Slough
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Horseshoe Hammond ©
Horseshoe Hammond
Fourth Presbyterian Church ©
Fourth Presbyterian Church

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