The Best Boat Up Restaurants & Bars in Chicago

Written by Kristen Rogers
June 22, 2018

Last Updated on January 13, 2022 by Boatsetter Team

Cruise through the city of Chicago

Interstate’s and Ubers are a hassle worth giving up. Ditch the drive and set sail on the wide open waterway. Boatsetter, a peer-to-peer boat rental company, has taken the idea of hailing a ride to a whole new territory – the water. Boatsetter allows you to browse and pick the perfect boat for your party to sail out on.Gather your closest friends and turn your usual outing into an unforgettable experience. Dock up along the way or end your cruise at one of these Chicago favorite boat up bars and restaurants.

SMITH & WOLLENSKY – This is one of the beautifully fitting establishments on Chicago’s riverside. A top eatery, it is the perfect spot to stop before, during, or after any boating excursion. The restaurant is home to a plethora of alcohol including ciders, daiquiris, and Revolution Anti-Hero. The drink list isn’t the only endless thing Smith & Wollensky has to offer. The tall windows offer stunning panoramic river views that make this restaurant a must see!

ESTATE ULTRA BAR – If South Beach moved North for the summer, it would look something like this place where club music, hot servers, and one of the best rooftops in the city conspire to steal your afternoon. And as the late afternoon mules and sangrias give way to nighttime bottle service, thank God you can order $800 bottles of bubbly.

RIVER ROAST – This former location of Fulton’s on the River pulls a major upgrade with a serious craft beer list including Penrose and Boulevard, not to mention a beautiful patio to enjoy your unique summer cocktails with names like Unicorn Tears and Dragon Kisses on. And did we mention the hand-carved meats?

Flatwater – The somewhat hidden from the street restaurant has a small elevator near the river’s edge and actually shares its address with the American Bar Association. However float up from the water, and Flatwater is easy to spot with its large, elegant bay windows and river-level terrace. River rats can dock for free at Flatwater and either dine on their boats “take-out” style (same menu, but boaters receive their orders in take-out packaging) or in the restaurant. Dark-stained wood floors and a 54-foot marble bar distinguish the restaurant’s interior while the outside area sports couches and tables, giving it an almost lounge-like feel. But it’s Flatwater menu that is the main attraction, with upscale versions of American contemporary cuisine such as Kobe beef mini-burgers and salmon carpaccio.

Green Dolphin Street -This spot may be easy to miss, but the food is worth the find. The small orange-and-brown dock leading up to Green Dolphin Street, if you’re cruising the river’s North Branch, is where you’ll dock, tie up for free, and head up the stairs to enjoy an upscale restaurant. This spot is also home to live music every night. The dinner menu offers an assortment of steak, chops, chicken and fish entrees. Patrons can also mix ‘n’ match their entrees with several side dishes, including a tasty truffle macaroni and cheese, Parmesan garlic mashed potatoes and assorted sauteed mushrooms. Neither on-boat or take-out service is available, but with indoor and outdoor seating available, you’ll want to dine on the premises, then stay for the music.

O’BRIENS RIVERWALK CAFE – Pregame before taking an architecture boat cruise at this cool little patio spot along the riverwalk. Take in stunning building views and stiff summer cocktails, that will leave all of your senses happy. 

City Winery Chicago at the Riverwalk – City Winery on the Chicago Riverwalk provides Chicagoans and visitors a way to engage with the city in a unique way. Guests have a truly special experience with local and sustainably-made products. Located in the West Loop, City Winery Chicago is the perfect place to stop and unwind before moving to your final destination.

In all, just go with the flow. Let the river lead you through the many different places Chicago has to offer, you won’t be disappointed.

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