Hold onto your hats because fall group activities in the windy city of Chicago just got real. With a little something for everyone, your crew can pedal their way through the picturesque Chicago River on water pedal tours, soak up the breathtaking views on a paddleboard, or hop from one lively venue to another on an epic party bar-hopping tour.
The windy city sure blows us away. Scroll through our picks of the best activities for groups in the fall and see why.
Party Cruise on the River is the perfect pregame before hitting the windy city bars. Step aboard the lively riverwalk, located between the iconic Wells Street and LaSalle Street bridges, and cruise up and down the Chicago River. This venue is about as unique as it gets—because it’s a floating one!
Special features: BYOB (coolers and ice provided); a unique hang; stunning views
Duration and party size: 1.5 to 2 hours, up to 26 passengers
In need of a peaceful morning? Enjoy a scenic and relaxed paddle through Lake Michigan as you coast alongside Chicago’s beautiful skyline. The team of experienced instructors will help get you started and paddling in no time. All the gear is included, so you just need your swimsuit (and maybe a morning coffee or mimosa to stave off the hangover?)
Special features: Perfect whether you wanna make it a workout or just laze along the lakefront; budget-friendly; an adventurous way to spend the day
Duration: Up to 50 — 1 hour and 30 minutes
The Epic 60-minute Escape Room Adventure is the perfect activity to kill some time. As the leading provider of escape rooms, their immersive experiences unfold like thrilling Hollywood blockbusters. Does your group do well under pressure? Bond with your group and see if you can solve the puzzle in time.
What You’ll Do: You’ll have twists, turns, and jaw-dropping surprises around every corner. Choose something like the Heist and recover a stolen priceless piece of art! Plus, Mission Mars, Prison Break, Gold Rush, or Special Ops: mysterious market.
Special features: This will make for awesome team building; plenty of laughs; pictures.
Group Size & Duration: Up to 8 People & 1-Hour
One of our favorite ways to explore Chicago is from the water. The Private Shoreline Tour Boat, on a former military Williard Marine, provides an opportunity to see the city from a unique perspective. The engaging crew will provide you with great historical content on the city, as well as an exhilarating experience through the use of high-speed runs and spins while using our own storytelling approach
Special Features: BYOB; a one-of-a-kind experience; the photos will be to-die-for
Duration and party Size: 1.5 hours, up to 6 guests
If you’re on the hunt for a wild night, The Private Bar Crawl on a shuttle bus will deliver. The best part? You choose the bars while they take care of the driving. It's basically the adult version of a field trip, but instead of museums, you'll be exploring the bottomless pits of questionable decision-making.
Special Features: Choose where the bus stops, and stay at each bar as long as you like.
Duration and Party Size: Up to 16 — 3 to 6 hours
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