Cutting through the Windy City's bustling urban core is the Chicago River; a scenic stretch often used for boat cruises, running routes and plenty of engagement photo ops. While the river itself is mesmerizing, the addition of numerous paths and establishments along its shoreline have made it all the more alluring. From wining and dining to taking a simple stroll, we've mapped out the best eateries and scenic spots so you don't miss a moment on one of Chicago's finest walks.

The River Theater

LaSalle Street to Clark Street

Last summer, a revamped section of the Chicago Riverwalk, stretching from LaSalle St. to State St., debuted. Start your journey down Chicago’s waterfront walkway at the new River Theater, where staggered steps that double as seats claim the perfect people-watching space. Water taxis and boats dock alongside the path, while sweeping steps shaded by trees lead up to the city’s bustling Upper Wacker Drive.

Tiny Hatt

55 West Riverwalk South

Make Tiny Hatt your first stop along the Riverwalk journey. Sip on custom, barrel-aged cocktails and sink your teeth into a gourmet burger at this riverfront lounge.

The Cove

Clark Street to Dearborn Street

Take a look around while you enjoy one the aforementioned mixed drinks. You’re sitting in the Riverwalk’s newly opened Cove; a slice of path that mimics a natural waterfront with its gentle slope to the river’s edge.


27 West Riverwalk South

No summer day is complete without ice cream, and, thankfully, the Riverwalk has you covered with sinfully delicious concoctions from gelato shop, Frost. Order a scoop of cinnamon apple pie if you’re feeling adventurous, or if you’re a sucker for the classics the dark chocolate will surely call your name.

City Winery

11 West Riverwalk South

City Winery is a staple of Chicago’s West Loop, and this summer the libations spot has set up a sister location alongside the river. Order a glass – or carafe – of Riverwalk White or Red and watch the colorful city life pass by on both land and water.

Marina Plaza

Dearborn Street to State Street

Both Frost and City Winery are settled in the Riverwalk’s Marina Plaza. The Plaza connects the Vietnam Veterans Memorial – a stunning architectural highpoint – to the Riverwalk’s new spots.

O’Briens Riverwalk Cafe

45 East Riverwalk South

O’Briens is a classic Old Town restaurant with a beer garden, and its Riverwalk location keeps the same delicious flavor. Enjoy a light summer salad under the afternoon sun, or dig in for a full meal with a succulent steak.

Cyrano's Cafe on the River

233 East Riverwalk South

This wine bar is another sister location – Cyrano’s Bistro and Wine Bar resides in River North. The Cafe on the River takes some of the original’s best dishes, and interprets them into a lighter menu. Enjoy elegant French dishes – steak frites or traditional escargots – at the riverfront. Bonus: pet lovers can bring their pups to this dog-friendly restaurant.

Island Party Hut

355 East Riverwalk South

Finish up your Riverwalk crawl with the ultimate summer party stop. Savor slow-smoked pulled pork and tropical, boozy creations at the Island Party Hut. Who could resist imbibing the Lime in the Coconut or mouthwatering Wiki Wiki Root Beer Float?

Looking for more things to do this summer in Chicago? We've got all the festivals in one place

*Feature image credit: LilyyyB via Flickr Original Image / CC BY 2.0