9 days in Chicago Itinerary

9 days in Chicago Itinerary

Created using Inspirock Chicago trip planner

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Route & dates

9 days in Chicago Itinerary

Start: Fairfield
Drive:  5​h 30​min
— 8 nights
Drive:  5​h 30​min
End: Fairfield


Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Take a break from the city and head to Silver Beach County Park and Swallow Cliff Stairs. Get some cultural insight at Museum of Science and Industry and The Field Museum. Change things up with these side-trips from Chicago: Matt's Produce (in Racine), Hawthorn Hollow - Nature Sanctuary and Arboretum (in Kenosha) and Weko Park (in Bridgman). Next up on the itinerary: take a stroll through The Magnificent Mile, delve into the lush surroundings at Deer Grove Forest Preserve, stroll through Lincoln Park Zoo, and enjoy the sand and surf at Bender Park Waterfront.

Plan trip to Chicago with our itinerary maker to find out where to go and what to do.

Fairfield to Chicago is an approximately 5-hour car ride. You can also fly. In July, daytime highs in Chicago are 83°F, while nighttime lows are 67°F. Finish your sightseeing early on the 14th (Sun) to allow enough time to travel back home.

Things to do in Chicago

Parks Outdoors Wildlife

Side Trips

Highland Park, Weko Park, Matt's Produce, Bender Park Waterfront, Silver Beach County Park
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Museum of Science and Industry ©
Museum of Science and Industry
Field Museum ©
Field Museum