You may be on a trip, but that doesn't mean you take days off. Chicago is a great destination for those who are always on the go, and these ideas make up an active three-day itinerary. 

Start in Humboldt Park and finish in Lincoln Park

The 606 4Start your morning in Humboldt Park, a west side neighborhood that's known for its Puerto Rican heritage. Fill up on doughnuts and a strong brew at CC Ferns or pick up a sandwich and expresso at Cafe Colao for some energy to start the day.

Hang out around the Humboldt Park Boathouse and make your way to the National Museum of Puerto Rican Arts and Culture. Explore the neighborhood's namesake park and the lagoons and trails inside it.

From there, jump on to The 606, Chicago's 2.7-mile elevated trail. Run, jog, walk or bike the path east toward Logan Square and Wicker Park/Bucktown, two neighborhoods with a laid back vibe and brimming with local coffee shops, small bars and boutique shopping. 

If you keep heading east, you'll find yourself in Lincoln Park, another expansive city green space. Wander around the free Lincoln Park Zoo, start a game of baseball or stroll around the Alfred Caldwell Lily Pond. 

Spend a day on the Lakefront Trail

Chicago bike ride

Pack a towel, bring some snacks and spend all day at a beach. For family-friendly beaches, go north to Loyola Beach or south to 57th Street. Montrose Beach is a dog-friendly escape and great kayaking location. Everyone is welcome at LGBTQ+ hangout Hollywood Beach, and there's always a big party happening at North Avenue Beach. Chicago beaches are popular with the locals all summer, and you'll often find paddleboaders, boaters and beach volleyball players at any beach. 

The Lakefront Trail connects all of Chicago's waterfront and is entirely public, and you'll share the path with the bikers, jogging and bladers who regularly exercise here. Peel off the trail to explore spots likes Northerly Island or the Montrose Point Bird Sanctuary for natural beauty and great skyline views. 

Explore all day downtown

Maggie Daley Park-3

The Chicago Riverwalk is a must-see for all visitors, but explorers will want to get on the water. Kayak your way through the canyons of the city (you can also let a captain do the work for you) or join a walking tour of the Loop. 

Make your way to Maggie Daley Park on the Millennium Park campus, where you can rent scooters and roller blades to ride around a skating ribbon. At the park's center, two rock climbing structures jut 40 foot into the air and can hold up to 100 climbers at a time. 

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Related Listings

Maggie Daley Park
337 E. Randolph St.
Chicago, IL 60601
(312) 742-3918

Chicago's Lakefront Trail
300 S. Lake Shore Dr.
Chicago, IL 60605

Chicago Water Sport Rentals at 31st Street Harbor
3155 S. Lake Shore Dr.
Chicago, IL 60653
(312) 924-7994

Chicago Riverwalk
376 N. Michigan Ave.
Chicago, IL 60601

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