Chicago Visitors Guide - 2026
OUTDOOR ADVENTURES
Lisa Shames 2026-01-21 11:11:39
During warm-weather months, the entire city turns into a playground, offering everything from lakefront bike rides to kayaking on the Chicago River.
ON LAND
Some of the city’s most stunning Lake Michigan views can be seen along the 18.5-mile Lakefront Trail. Make the most of the scenery and rent wheels from Bike and Roll Chicago or Bobby’s Bike Hike and cycle the trail solo or on a guided ride. Or join a tour with Absolutely Chicago Segway Tours, which also rents e-bikes.
Kids of all ages will get a kick out of Maggie Daley Park, a sprawling green space that includes the Play Garden and Chicago-themed City Mini Golf. Up the adventure ante and tackle the 40-foot-tall Climbing Wall or rent rollerblades and whoosh along the Skating Ribbon, which morphs into a lovely ice rink in the winter.
Enjoy 91 acres of skyline views, hiking trails, birdwatching and more at Northerly Island Park. Located on the lakefront, this manmade peninsula on the former site of a small airport now provides a beautiful, nature-filled escape from the hustle and bustle of the city.
Located at the southern edge of Grant Park, the Grant Skate Park is a skateboarder’s dream, featuring thoughtfully designed ramps, ledges, banks, and rails that challenge both beginner and advanced skaters. Nonskaters can watch all the gravity-defying moves from a neighboring elevated walkway.
Once a railroad line, The 606 has been beautifully transformed into a landscaped parkland for walking and bicycling, with convenient on-and-off points. The elevated trail spans 2.7 miles and runs through some of Chicago’s hippest neighborhoods, including Logan Square and Wicker Park. Scenic lookout points, art installations, and lush greenery are your reward for making the journey.
Located on the Southeast Side of Chicago, Big Marsh Bike Park features 40 acres designed for two-wheeled adventures like mountain bike courses, pump tracks, and paved bike trails. Cool down with a leisurely walk, taking in the many birds and flora that call this area home.
ON WATER
There is much to see along the Chicago Riverwalk beyond its stellar water views. Learn about the city’s magnificent moveable bridges, shop for locally made goods, view public art, and eat and drink at numerous riverside restaurants. Get a unique perspective of the Chicago River and the city’s iconic landmarks with a tour on the water from Urban Kayaks, with a location on the Chicago Riverwalk.
Another action-packed Chicago spot is Navy Pier, which features 50 acres of restaurants, shops, theatres, seasonal festivals, and the soaring Centennial Wheel, along with Instagram-worthy views. Visit on Wednesday and Saturday nights during the summer for dazzling free fireworks shows. Adrenaline junkies will want to check out the Chicago Seadog Extreme Thrill Ride, which offers high speeds and 360-degree spins on its exciting lake excursions. For a more leisurely experience, hop aboard the 148-foot Tall Ship Windy, a four-masted schooner that allows riders to hoist the sails.
Summer in Chicago must include a day spent at one of its beautiful beaches — and with 26 miles of lakefront, there are plenty to choose from. For terrific people watching and views of the cityscape, head to Oak Street Beach. Nearby, North Avenue Beach features lively sand volleyball games. Looking to pair your beach day with live music? Head to South Shore Beach, which is part of the South Shore Cultural Center. Kick back with food, drinks, and live tunes at the neighboring South Shore Social Beach Club. Or check out Rainbow Beach, a South Side gem with one of the city’s oldest community gardens, in addition to stunning skyline vistas.
Want to add water sports to your beach itinerary? At North Avenue Beach’s Chicago SUP, you can give stand-up paddleboarding a try. For something different, head to Neon Paddle in Chinatown’s Ping Tom Park for motorized paddleboarding lit by glowing neon lights. Kayaking is a fun way to experience Chicago’s waterways. The experts from Chicago Water Sport Rentals at 31st Street Harbor and Bobby’s Kayak Company at Ohio Street Beach can help with rentals, tours, and more. Or rent a jet ski from North Avenue Beach’s Jet Ski Chicago and zoom along the lakefront.
The world’s first floating eco-park, The Wild Mile is located along the North Branch Canal of the Chicago River and is accessible by foot on its boardwalk or via water. Rent a kayak from Urban Kayaks to fully explore this North Side treasure.
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