You’ve Never Seen Chicago from the Water Like This: 4 Boat Rides That Bring the Party

The second after most first-time Chicago visitors pick their jaw up off the floor after getting a look at the Chicago River and the city’s gleaming skyscrapers reflecting off the downtown lakefront, their next question is how to get on the water. Now. Like right now.

Luckily, you’ve got options. Because if you’re not on the water during Chicago summer, you’re doing it wrong. Very wrong.

Island Party Boat

If you’ve always wanted to rent your own floating Tiki bar complete with waterslides (which you can zip down with your dog), look no further than this colorful collection of thatched structures on the Chicago Riverwalk.

Island Party Boat’s range of rentals includes 65-foot floating monsters and more intimate thatched pontoons. Seeing these BYOB and BYOF (bring your own food) Polynesian beauties cruising down the river is a sure sign that summer in Chicago is in full swing. You can also buy tickets for a 75-minute cruise if you don’t want to rent your own boat.

After your ride, keep the party going at the outfitter’s Riverwalk location, where you’ll have access to live island music most summer days, games like ping-pong and bag toss, and food, including burgers and slow-smoked pulled pork paired with island drinks.

Chicago Boat Rentals

You’ll find Chicago Boat Rentals hidden from the tourist crowd in a nondescript location near an industrial section of the city at the foot of Estate Ultra Bar. Blink and you might miss this small pontoon boat rental service, which turns you loose on the Chicago River in whatever direction you so choose.

Pack the 8- or 12-person pontoon with a cooler full of “essentials” and, after a quick lesson for newbies, be on your merry way. You can pilot the vessel toward downtown (where most of the larger boats dominate the river), but for a less touristy and more unique experience, point the GPS toward Chinatown and admire a gritty yet eerily beautiful landscape of urban decay rather than the glistening buildings downtown.

Whatever you do, resist the urge to jump in the river — unless you want a free trip to boat jail.

Mystic Blue Craft Brew Cruises

It’s no secret that beer and boating go together like, well, beer and boating. And true brew aficionados know to sail with this outfitter, which teams up with Brewfest Partners to offer guests craft beer–themed trips during summer months that center around offerings from regional brewmaking powerhouses.

After 20 beer samples you’re bound to get a little peckish, at which time you can set your sights on the boat buffet for brew-pairing bites like chicken wings, Italian meatball sliders and cheese platters.

You’ll also find a live DJ, dance floor and bar games like foosball aboard this two-hour early afternoon booze cruise, and no one would be surprised if you took the rest of the day off.

Chicago’s First Lady

Vince Vaughn popularized the art of the hyped-up Chicago tour guide in the 2006 comedy “The Break-Up,” where his character’s job involved taking tourists out on the water via boat.

And while there are many architecture boat tours you can board in this world-renowned design city, the First Lady tour is the only one that partners with actual docents from the Chicago Architecture Foundation.

Sure, they may not be as raucous or hilarious as Vince Vaughn, but they certainly know their stuff. Grab a spot indoors or outdoors on this beautiful custom-designed vessel and discover facts about the city that you will actually be interested to learn aboard this 90-minute, fully narrated tour (with cash bar, of course). Not since you majored in leisure studies in college has learning been this fun.

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