The Best Chillin in Chicago

Looking for the best chillin in Chicago? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Chicago. The detailed guides, photos, and reviews are all submitted by the Outbound community.

  • Explore Chicago's Luire Garden

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  • Black Oak Trail at Little Red Schoolhouse Nature Center

    4.5
    1.67 mi
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  • Watch the Sunset at Axehead Lake

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  • Hike the Waterfall Glen Trail

    4.5
    9.5 mi / 961 ft gain
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  • Catch a Sunrise at The Lakefill

    5.0
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  • Hike Herrick Lake Trail

    4.0
    8 mi
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  • Hike the Dune Succession Trail, Indiana Dunes National Lakeshore

    4.5
    1 mi / 150 ft gain
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  • Hike the Indiana Dunes State Park Loop

    1.6 mi / 410 ft gain
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  • Photograph the Chicago Skyline from the Indiana Dunes

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  • Hike the 3 Dune Challenge

    5.0
    1.5 mi / 552 ft gain
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  • Stroll along the Beach at Beverly Shores

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  • Take a Stroll through Grant Park

    4.5
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