Is there a better way to spend a summer afternoon than cruising around the Chicago River with some boozy drinks? We think not! Now that summer humidity is upon us, it’s time to grab your crew and hit Lake Michigan for all-around blissful entertainment. This is the perfect time to set sail on a Chicago booze cruise if you enjoy sipping on tasty cocktails, dancing the evening away, and taking in Chicago’s majestic skyline.
1. Swiftie Booze Cruise
Attention all Swifites—have you ever just wanted to shake it off on the Chicago River? While Taylor Swift takes her tour internationally, you can pretend you left Chicago for a few hours as you listen to all your favorite T-swift songs to Lake Michigan. Enjoy music, drinks, and great company as you take in breathtaking city views through the river and into the lake.
📍 Location: 900 S Wells St, Chicago
👤 Age requirement: 21+ with valid ID
🎫: Purchase tickets to the Swiftie Booze Cruise here
2. Labor Day Sunday Funday Sunset Booze Cruise
Celebrate Labor Day the right way with a fun party cruise on the Chicago River. On this booze cruise, you’ll sail all along the river until you reach Lake Michigan, where you’ll dance the night away to your favorite tunes. With some of Chicago’s best house music artists and two fully-stocked bars, you’ve got everything you need to make a memorable Labor Day weekend.
📍 Location: 900 S. Wells St., Chicago
👤 Age requirement: 21+ with valid ID
🎫 Purchase tickets to Labor Day Booze cruise here
3. Boozy Brunch Cruise
Prepared to be enthralled with the Chicago aroma—the city and the delectable scents of a morning brunch—all while becoming slightly tipsy from the endless mimosas. If that doesn’t convince you, the Dj’s electrifying beats just might. Think about it—as you soar down the river, the wind in your hair, you’ll be frocking with dazzling skyline views and delightful music. This Chicago booze cruise will have your taste buds in overdrive while catering to your rumbling stomach.
📍 Location: TBD
👤 Age requirement: None
♿ Accessibility: Wheelchair Accessible
🎫 Get your tickets to Chicago Signature Brunch Cruise here
4. The Lake House Day
Save the trip to Michigan, Wisconsin, or another small town near Chicago for another day because, believe it or not, your party lake day awaits you on the Chicago River. This Chicago booze cruise will have intoxicating house music reverberating on the boat. As you admire breathtaking views, you’ll be swinging and turning with delicious drinks in your hands. It will probably be hard to get off this Chicago booze cruise.
📍 Location: 900 South Wells Chicago, Illinois, 60607
👤 Age requirement: 21+ with valid ID
🎫 Get your tickets to “The Lake House” Day Cruise here
5. Sunday Funday Booze Cruise
Have you ever stayed up until sunrise, still slightly inebriated, and thought to yourself, “How do I keep the party going?” Your wishes have been answered—set sail and experience the ultimate party at the Sunday Funday Booze Cruise. Once stepping aboard, the music will blare, and you’ll be dancing to a DJ’s mix of songs you can’t get out of your head—all of this and multiple cocktails in hand. There is no slowing down on this Chicago booze cruise as you speed through the river and watch Lake Michigan glimmer.
📍 Location: 900 South Wells Chicago, Illinois, 60607
👤 Age requirement: 21+ with valid ID
🎫 Get your tickets to Sunday Funday Booze Cruise
6. Sights & Sips
If house music isn’t your thing, and you want to experience a more decadent booze cruise, Sights & Sips is the place to go. This cocktail cruise has creative cocktails, wine, beer, and a full list of scrumptious Hors D’oeuvers, including bruschetta, skewers, a Mediterranean station, and more. For a few hours, you can cosplay guests from Below Deck and enjoy being catered to as revel in Chicago’s views.
📍 Location: River Esplanade 455 N Cityfront Plaza Drive Chicago, IL
👤 Age requirement: none
🎫 Get your tickets to Sights & Sips here
7. Chicago River Architecture
Boozy history is one of our favorite activities—is there anything better than spending the day sailing down the river, learning about the architecture with a drink in hand? The Chicago Lake and River Architecture Tour happens to have all that and is one of our favorite tours.
📍 Location: 400 N Michigan Ave Suite C100, Chicago, IL , 60611
👤 Age requirement: None
♿ Accessibility: Wheelchair Accessible
🎫 Get your tickets to Chicago Lake and River Architecture Tour here
8. Floating Tiki Bar Cruise
In Chicago, we’re one of the few cities where we can dig our toes beneath the sand and jump into the waves to cool off; even with humidity at an all-time high, we’re still far from a tropical paradise with palm trees and coconut-sippy cups.
However, one way is to head to a tiki oasis without spending hundreds on a plane ticket. At this floating tiki bar, you can cruise down the Chicago River while soaking in tropical tunes and the city’s stunning architecture.
This is a unique tiki Chicago booze cruise experience, from bascule bridges to the Tower buildings.
📍 Location: 355 Chicago Riverwalk, 60601
👤 Age requirement: 21+ with valid ID to consume alcohol
♿ Accessibility: Not Wheelchair Accessible