From kayaking to biking, Chicago visitors can always find something active to do in the city.

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Photo: acuestareig

From kayaking the Chicago River to biking their way through Chicago's famous foods and brews, your groups can always find a unique outdoor adventure in the city.


As a city perched at the mouth of a river, where it meets enormous Lake Michigan, some of Chicago's best views can be found from the cockpit of a kayak. Kayaking the Chicago River is as active as it is scenic — and even beginners can maneuver these easy-to-operate boats.

Make It Happen

  • Classic Chicago Kayak Tour (Wateriders): This 2.5-hour tour leads groups down the Chicago River, under articulated ironwork bridges, past the beautifully landscaped river-edge promenade and beneath some of the greatest American architecture of the 20th and 21st centuries. Details.
  • Kayak Rentals (Wateriders): Let groups cruise at their own pace and on their own schedules with a kayak rental. Wateriders rents both doubles (suggested for novices) and singles, ensuring that paddlers of every skill level find their ideal vessel. Details.


Did you know that Chicago is one of the most bike-friendly cities in the country? It's true — Chicago is home to 19 miles of lakefront bike paths, more than 100 miles of on-street bike lanes, countless off-street paths and more than 10,000 bike racks. So, encourage groups to push the pedal to the pavement on a guided bike tour.

Make It Happen

  • Bikes, Bites and Brews (Bobby's Bike Hike): On this four-hour, 13-mile tour, groups bike through some of the city's most popular neighborhoods while sampling foods from each of Chicago's four favorite food groups: pizza, hot dogs, cupcakes and beer. (Vegetarian options available.) Details.
  • Lincoln Park Bike Adventure (Bike and Roll): Here, groups cruise the car-free Lakefront Trail for two to three hours, enjoying a mix of nature and attractions peppered throughout Lincoln Park. Think: beaches, lagoons, parks, the Lincoln Park Zoo and Conservatory. Great for kid-friendly groups and families. Details.


Safe and simple to use, Segways are a great way for groups to whirl around the city without exerting the same energy they would on a bike or kayak.

Make It Happen

  • Holiday Lights Tour (Segway Experience of Chicago): In November and December, the city literally sparkles for the holidays. On this two-hour evening tour, groups zip around Millennium Park and the theater district before hopping off to wander around Christkindlmarket, the open-air German market with holiday shopping, music and more. Details.
  • Lakefront/Museum Campus Tour (Absolutely Chicago Segway): This eight-mile tour glides along Millennium Park, travels down the rose gardens of Grant Park and weaves around the Museum Campus, offering insights about The Field Museum, Shedd Aquarium, Adler Planetarium and Soldier Field. Details.
  • Design Your Own Tour (#1 Chicago Segways): Looking for something super flexible? All year long, #1 Chicago Segways allows groups to customize their tours with stops, duration and add-ons like a scenic stop for lunch. Details.


Your groups haven't seen golf courses like these before. Set in the heart of the city, they feature fantastic views and gorgeous greens to make for a memorable golf outing.

Make It Happen

  • Sydney R. Marovitz Golf Course: It ranks among one of the most challenging golf courses of the Chicago Park District, with tight greens, numerous bunkers and championship length. Plus, it has dramatic views from the very first hole, which runs parallel to Lake Michigan. Details.
  • South Shore Golf Course: A former private club, South Shore is a par 33 course with panoramic views of Lake Michigan, along with tree-lined fairways and small greens. Details.

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#1 Chicago Tours
155 N. Harbor Dr.
Chicago, IL 60601
(312) 946-9467
Absolutely Chicago Segway Tours
238 E. Monroe
Chicago, IL 60603
(312) 552-5100
Bobby’s Bike Hike Chicago – Bike, Walking, Food Tours & Rentals
540 N. Lake Shore Dr.
Chicago, IL 60611
(312) 245-9300
Jackson Park Golf Course
63rd Street and Lake Shore Dr.
Chicago, IL 60637
(773) 667-0524
South Shore Golf Course
7059 E. S. Shore Ave.
Chicago, IL 60649
(773) 256-0986
Sydney R. Marovitz Golf Course
3600 N. Recreation Dr.
Chicago, IL 60613
(312) 742-7930
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