Chicago Spring Break

Explore top Spring Break tours in Chicago including skyline cruises, tiki bar parties, and day trips to Milwaukee. Book your Chicago Spring Break adventure today!

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2-Hour Chicago Wine and Cheese Cruise

This Wine & Cheese Cruise is a world class Chicago experience for locals and visitors. Board our famous tour boats at Michigan Avenue, and enjoy the Chicago Riv

★ 4.2 (6)

From $70.00 USD

Astounding Chicago Bar Crawl: Chi-Town Showdown

"Dive into adventure with Let’s Roam, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to b

From $14.99 USD

Burning Spirits Haunted Pub Crawl

Step into the shadows of Chicago’s past on this adults-only haunted pub crawl, where ghost stories, historic landmarks, and legendary nightlife collide. Beginn

★ 5.0 (1)

From $34.99 USD

Chicago Lake Michigan Skyline Sunday Funday Party Cruise

Kick off your Sunday the right way—with mimosas, Bloody Marys , and unbeatable views of Chicago’s stunning skyline aboard Enchantment, our flagship vessel. This

★ 4.5 (10)

From $42.00 USD

Chicago Local Brewery Expedition with Homemade Guacamole

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; wh

★ 5.0 (4)

From $63.00 USD

Chicago River Floating Tiki Bar Cruise Friday and Saturday

Set sail for an unforgettable evening aboard the River Star or Island Time, where the drinks are flowing and the views are unmatched. Enjoy a refreshing beverag

★ 4.8 (24)

From $42.00 USD

Chicago River Sunday Funday Mimosa or Bloody Mary Party Cruise

Sunday Funday Mimosa Cruise – Chicago’s Floating Tiki Bar Adventure! Sundays are Fun-Days aboard our vibrant floating tiki bar, Island TIme, where the drinks a

★ 4.3 (31)

From $42.00 USD

Chicago River Tiki Bar Party Cruise from Chicago River Wednesdays

See Chicago the Island Party Way. Our floating Tiki Bar offers you the opportunity to take in all the sights and sounds as you relax and enjoy a beverage. Have

★ 4.0 (128)

From $42.00 USD

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board

★ 3.9 (37)

From $42.00 USD

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davids

★ 4.5 (12)

From $125.00 USD

DIY Cocktail Candle and Wine Bottle Cutting Class in Chicago

Get ready to unleash your creativity at the BYOB Candle-Making Class at Chicago Candle Co. This hands-on workshop invites you to craft stunning, personalized ca

★ 5.0 (1)

From $60.00 USD

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective ri

★ 5.0 (1)

From $179.00 USD

Paint Night and Cocktails at Trendy Venues Across Chicago

Ready for a night that’s equal parts laughter, creativity and cocktails? Join this hands-on paint and sip class in Chicago hosted through!, and rediscover how f

From $60.00 USD

Wind and Souls an Adults Only Ghost Tour in Chicago

Leave the little ones at home and step into the shadows for a spine-chilling evening designed exclusively for adults. Not all spirits in Chicago are content to

★ 4.2 (46)

From $34.99 USD