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Looking for Fun Group Outings in Chicago?

Looking for something fun to do with a bunch of friends? Need to find a good team-building activity for your employees? Simply check out some of these great group outing ideas in Chicago.

Enjoy These Fun Group Outings for Adults in Chicago

  • Indoor Skydiving at iFly: You can ride the air yourself or pair up with someone else in your group to share the exhilaration.
  • Whirlyball: Whirlyball is much like jai alai played from a bumper, which should be enough to pique your interest. The Chicago location has three courts. For something more traditional, there are 12 bowling lanes and a laser tag arena. Larger groups can book the private VIP space and relax on the rooftop terrace.
  • Chicago Dine-Around: Teams take on a culinary team-building experience where they learn and cook recipes, competing in teams to do the best. Past and current themes include Authentic Italian, Latin-American, and Mixology.
  • Axe Throwing: Embrace your inner Viking with some competitive axe throwing. Backyard Axe Throwing League describe themselves as “a cross between a battle cage and a bowling alley”. Great stress relief and an utterly unique day out.
  • Chicago Tours: America’s Second City is home to a wide range of tours perfect for group visits. You can take walking tours, bus tours, food tours, drink tours, art tours, and history tours. You can even charter a private yacht for a Chicago architectural boat cruise.

Our Fleet

From breweries and cocktail bars to museums and summer concerts, our private car service has taken countless groups around Chicago. We’re sure there’s something in our fleet to perfectly fit your requirements.

Sedans and SUVs

  • Lincoln Continental
  • Mercedes-Benz S-Class
  • Cadillac Escalade
  • Chevy Suburban
  • Cadillac XTS


  • Limousine-Style Mercedes-Benz Sprinter
  • Turtle Top
  • Executive-Style Mercedes-Benz Sprinter

Executive Buses

  • 24-Passenger Executive Bus
  • 39- to 43-Passenger Executive Bus
  • 55-Passenger Motor Coach

Special Occasion Vehicles

  • 30-Passenger Trolley
  • 36-Passenger Limousine Style Party Bus

Arrange Group Transportation Around Chicago Today

If you’d like to find out more or schedule your next group outing, all you need to do is contact Signature Transportation Group today.