6 days in Chicago Itinerary

6 days in Chicago Itinerary

Created using Inspirock Chicago journey planner

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1
Chicago
— 5 nights

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Escape the urban bustle at Lakefront Trail and Bender Park Waterfront. Change things up with these side-trips from Chicago: Oak Savannah Trail (in Griffith), Hawthorn Hollow - Nature Sanctuary and Arboretum (in Kenosha) and Little Red Schoolhouse (in Willow Springs). And it doesn't end there: take a stroll through The Magnificent Mile, hike along Swallow Cliff Stairs, take in panoramic vistas at Skydeck Chicago - Willis Tower, and pause for some photo ops at Cloud Gate.

To see reviews, where to stay, traveler tips, and more tourist information, read our Chicago trip itinerary planner .

In September, plan for daily highs up to 78°F, and evening lows to 61°F. Wrap up your sightseeing on the 19th (Thu) early enough to travel back home.

Things to do in Chicago

Parks Outdoors Trails

Side Trips

Little Red Schoolhouse, Oak Savannah Trail, Rosewood Beach, Block Museum of Art, Swallow Cliff Stairs
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Cowles Bog ©
Cowles Bog
Lakefront Trail ©
Lakefront Trail

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