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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.

Top chillin spots in and near Chicago

  • Chicago, Illinois

    Explore Chicago's Luire Garden

    Visiting Chicago I was on a mission to find a great outdoors spot to be in. This definitely fulfilled my goal of finding a beautiful garden to hangout in! There are plenty of different paths and areas to explore just within the city! Location Located in Millennium Park it will be easy to find, t...
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  • Willow Springs, Illinois

    Black Oak Trail at Little Red Schoolhouse Nature Center

    4.5
    1.67 mi
    The trails traverse a rolling glacial highland of oak woods and prairie. The hiking trails connect to miles of multi-use trails where you can hike, mountain bike, cross country ski and snowshoe. Lastly, there is an interpretive center with exhibits about local nature and history.The trailhead s...
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  • Des Plaines, Illinois

    Watch the Sunset at Axehead Lake

    In a large city, it's nice to be able to find pockets of nature oasis amidst the chaos. It's great to come here with a journal or sketchbook and pass the time while watching the sunset. Fishing is available at this lake and there is a forest preserve that has a couple small trails. 
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  • Lemont, Illinois

    Hike the Waterfall Glen Trail

    4.5
    9.5 mi / 961 ft gain
    This trail is recommended for use from March - November, but is great for cross country skiing in the winter. The trail is covered with packed down gravel, and is sometimes used by equestrians. 
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  • Evanston, Illinois

    Catch a Sunrise at The Lakefill

    5.0
    From the Northwestern University campus, head to the Ryan Center for the Musical Arts to access the southern-most section of The Lakefill. If driving, parking is usually available nearby on Sheridan Road, to the southwest of The Lakefill. Once at the Ryan Center, take the pedestrian bridge on the...
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  • Gary, Indiana

    Hike the Dune Succession Trail, Indiana Dunes National Lakeshore

    4.5
    1 mi / 150 ft gain
    This hike provides a great opportunity to explore the variable landscape and terrain in Indiana Dunes National Park. From the parking lot head north on a paved walkway toward Lake Michigan's shoreline. Next, walk down the boardwalk to the beach. Once you reach the coast, you'll have amazing view...
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  • 41.662199,-87.062991

    Hike the Indiana Dunes State Park Loop

    1.6 mi / 410 ft gain
    The Indiana Dunes State Park Loop is a 1.6 mile trail that offers scenic dune landscapes and a view of Lake Michigan. The trail is used for hiking, and is open year-round. Dogs are allowed on the trail if kept on leash. Visitors to Indiana Dunes State Park also use the trails for birding. The Ind...
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  • Chesterton, Indiana

    Photograph the Chicago Skyline from the Indiana Dunes

    Indiana Dunes State Park and Beach is a family friendly beach perfect for a day out in the sun. However, it has something to offer most beaches don't - a view of Chicago over the water!  It's a great shot to try to capture on your camera, especially at sunset when colorful clouds fill the sky ove...
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  • Chesterton, Indiana

    Hike the 3 Dune Challenge

    5.0
    1.5 mi / 552 ft gain
    Start at the Indiana Dunes State Park Nature Center (the first exit off the roundabout in the park after the toll), after receiving your park map, and follow the 3 dune challenge. This challenge, looping trails 8 and 4, involves climbing to the top of Mt. Jackson (176 feet), Mt. Holden (184 feet)...
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  • Chesterton, Indiana

    Stroll along the Beach at Beverly Shores

    This is a great neighborhood to stop and walk the beach in for as long as you'd like. Enjoy views of the Chicago skyline across Lake Michigan as you splash in the waves and climb the small dunes. There is a parking lot for Kemil Beach, which is a short walk down to the shoreline. Be sure to check...
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  • Grant Park, Illinois

    Take a Stroll through Grant Park

    4.5
    Grant Park is located on the east side of Chicago. It is a great place to spend the day and explore. From the famous "Bean", which is actually named "the cloud", to Buckingham Fountain there is plenty to see in this park. It is also a great place to see the Chicago skyline, as well as have a picn...
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