Savoring Chicago wines on a riverfront patio, going island style under light-strewn shade trees, devouring gastropub goodies with a tantalizing craft cocktail — and all with views of the Chicago River.

City Winery Chicago Riverwalk

11 Chicago Riverwalk

People eating at drinking at City WineryPhoto: Ranvestel Photography

For the quintessential Chicago Riverwalk wining and dining experience, grab a seat on the patio at City Winery Chicago Riverwalk and try a glass of the house Riverwalk White or Rosé. Watch the boats glide by and do some serious people watching as you listen to live music and snack on Mediterranean bites like the dolmades stuffed with rice, mint and spices. Note that this is, in fact, City Winery’s outpost location. Its original site is located in the West Loop, where you’ll find Chicago's premier fully operational urban winery. Wine is served through a unique tap system to showcase the company's commitment to sustainability.

Island Party Hut Tiki Bar and Grill

355 E Riverwalk South

Island Bar Hut RiverwalkPhoto: Ross Buchanan Moore

Get into the island vibe of Island Party Hut Tiki Bar & Grill. Listen to live island music as you sample slow-smoked pulled pork and quench your thirst with a refreshing tropical cocktail -- think Mai Tais and margaritas. You can also book a charter aboard Island Party Boats and enjoy the city from the water. The entire Tiki Boat fleet has upper decks and water slides for swimming in the lake!

O’Brien’s Riverwalk Café

45 E Riverwalk South

O'Briens at Chicago Riverwalk

Photo: Ranvestel Photography

Grab a seat under one of the bright yellow umbrella-topped tables and dine on bar grub favs sided with a vodka lemonade at O’Brien’s Riverwalk Café. Menu favorites include the steak sandwich, half-pound certified Angus beef burgers and buffalo chicken wings. Weekend breakfast is available from 9am to 11am.​

Tiny Tapp Riverwalk

55 W Riverwalk

RiverwalkPhoto: Ross Buchanan Moore

It all started with Lincoln Square’s Tiny Lounge, and we're so glad there's now a Riverwalk outpost. Tiny Tapp brings its signature craft cocktail concept to Chicago’s Riverwalk, located in the Riverwalk Cove between Dearborn and Clark Streets. Check out the calendar of entertainment and events, and get your fill of locally roasted coffee, fresh baked pastries, ice cream, and more. 

The Northman Beer & Cider garden

The team behind Chicago's first cider-focused pub brings a traditional European-style beer garden to the Riverwalk. Grab a spot at one of the picnic tables and take your pick from homemade ciders, beer, wine and cocktails. If you get hungry, order up one of the great snack options, like artisanal Chicago-style hot dogs, sausages, salads, soft pretzels and their signature Döner Kabob Sausage.

Frost Gelato

Frost serves up scoops of sorbet and authentic Italian gelato all summer long. Made fresh daily, their decadent creations comes in a rotating array of flavors — so you'll have to come back to try them all, naturally. 

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