Chicago bars with waterfront views

The perpetually swanky bar and balcony perched above the Chicago Athletic Association Hotel is the perfect place to enjoy an innovative cocktail and a view that stretches all the way to Lake Michigan and beyond. The enticing drink menu includes a refreshingly honeyed matcha latte (available both boozy and as-is) and a sustainably produced Sugarfoot cocktail playfully dubbed the Foot in Mouth.

Located just north of Navy Pier, Caffé Oliva is a true beach bar offering fresh food with a heavy Mediterranean influence. Drinks, on the other hand, are tropical and fun, with classic options like mojitos, mules and margaritas. Just steps away from the sand and water, it's an ideal place to day-drink before the sun goes down.

This romantic, Michelin-starred restaurant and bar in Lincoln Park is the perfect place to celebrate special occasions. Crouched beside the tranquil body of water from which it derives its name, North Pond is the closest you’ll come to a cabin in the woods while in the heart of Chicago’s North Side. Sit back and sip wines and gorgeously balanced cocktails. 

Watch yachts float down the Chicago River as you sip rosé, bubbly, whites and reds. Located along the Riverwalk, City Winery feels like a boozy oasis in the thick of the city, offering stellar views of the river and surrounding architecture. 

The decadent steak isn't the only thing you'll be fawning over at this classic riverside restaurant. Situated at the foot of Marina City, Smith & Wollensky boasts gorgeous views of the Chicago River, which only get better as the sun sets. You'll find seating indoors and out, a menu of classic cocktails, red meat galore and a bevy of seafood.

Award-winning chefs Tony Mantuano and John Hogan serve up expertly executed takes on American tavern fare alongside flowing beverages and the glistening Chicago River. For three dollars more, you can take home a River Roast koozie to remember the visit.

This family-friendly option is attached to the Adler Planetarium and surrounded by stunning views of the city skyline and Lake Michigan. It’s a perfect place to come back down to earth after staring up at the stars. The over-21 set can pick from a selection of wines and premium and domestic beers.

Enjoy upscale, inventive cocktails alongside stunning views of Chicago at this Michelin-starred Streeterville destination located on the 16th floor of the Northwestern Memorial Hospital complex. The outstanding cocktail menu, loosely inspired by Chicago’s Irish heritage, includes drinks like the Hinky Dink, a sunny combination of dandelion, honey and Power’s John's Lane Single Pot Still Irish whiskey.