A lively crowd is the perfect backdrop for dinner on an outdoor patio or drinks up high in a rooftop bar. We’ve got suggestions for 10 top Chicago patios and rooftop bars that are local favorites and great places to do some summer in the city people watching.  

1. ROOF on theWit

ROOF theWit

THE VIBE: Young professionals cutting loose after a long week of work in the Loop crowd this lively rooftop lounge on the 27th floor of theWit hotel. With its modern design, glittering city views and nightclub atmosphere, it’s no wonder Travel + Leisure named it one of the top three rooftop bars in the world.

MUST TRY: Go for dishes like the stuffed scallops or grilled beef kebab, followed by a Lululemon Lemon Drop shot (vodka, fresh citrus and lavender).

2. Cindy’s

Cindy's at Chicago Athletic Association Hotel

THE VIBE: Inspired by a Great Lakes beach house with its glowing string lights and picnic table seating, this rooftop restaurant perched atop The Chicago Athletic Association Hotel draws downtown execs with its jaw-dropping views of Millennium Park and Lake Michigan.

MUST TRY: Share the shellfish platter and pair it with a Howl at the Jun (an elixir of gin, Kombucha, grapefruit and sparkling rosé).

3. Dusek’s Board & Beer

Tack Room

THE VIBE: Music lovers flock to this Pilsen hot spot for the all-in-one entertainment under one historic roof: Dusek’s beer-centric restaurant, indie bands at the upstairs Thalia Hall, spiked punch at the lounge-like Punch House, and craft cocktails with live piano music in the Tack Room.

MUST TRY: Sample the paprika-glazed suckling pig with purple carrots at Dusek’s, then grab a seat on the Tack Room’s cozy patio and order a Mint Julep (tequila, sugar and mint).

4. Parson’s Chicken & Fish

Parsons Chicken & Fish

THE VIBE: This Logan Square hot spot features a leafy outdoor patio outfitted with cheery picnic tables topped with red-and-white-striped umbrellas, string lights and ping-pong tables, just for fun.

MUST TRY: The fried Amish chicken goes surprisingly well with the signature Original Negroni Slushy (gin, bitters and sweet vermouth).

5. The Dawson

The Dawson 

THE VIBE: In trendy West Town, local young professionals and couples can be found on the welcoming rustic outdoor patio with its own bar and French doors that lead into the beautiful restaurant housed in a historic former fireplace mantle factory.

MUST TRY: Pair the wood-grilled Spanish octopus swimming in black garlic vinaigrette with the popular frozen Mai Tai.

6. The Promontory

The Promontory

THE VIBE: Stylish Hyde Parkers and University of Chicago students populate this combination restaurant and music venue that boasts two levels of open-air patio seating in an industrial-chic space.

MUST TRY: Go for the grilled Gulf prawns with black pepper barbecue and cheese grits, then toast the evening with an herb-infused Booze & Botany (vodka, dry vermouth and celery bitters). 

7. Athena Restaurant

Athena Restaurant

THE VIBE: The spacious outdoor patio of this Greektown restaurant with a smashing skyline view is packed in the summertime with West Loop workers, residents, large groups and families, along with tourists who are looking for a little Opa!

MUST TRY: You can’t go wrong with the rich pastitsio: baked macaroni mixed with beef and cheese, topped with bechamel sauce. For dessert, sip the Buttered Rum Cake Martini crowned with whipped cream.

8. Oak Street Beach Food + Drink

Oak Street Beach

THE VIBE: Set on the sands of Oak Street Beach in the shadow of the towering 875 N Michigan (formerly the John Hancock Center), this breezy lakefront eatery attracts sun-loving Chicagoans and out-of-towners who know the beach is the place to be.

MUST TRY: A summertime match made in heaven are the fish tacos paired with a refreshing mango Oak Street Mojo Mojito.


9. Raised – An Urban Rooftop Bar


THE VIBE: Guests staying at the Renaissance Chicago Downtown Hotel and locals in the know flock to this sleek rooftop deck that features an indoor/outdoor bar and a private VIP greenhouse that’s right in the middle of the action.

MUST TRY: Pass around shareable plates like the beef tenderloin sliders with truffle cheese and split a decanter cocktail for six, such as the Parley (rum, seasonal berries and mint).

10. Shanghai Terrace

Shanghai Terrace

THE VIBE: Shades of deep red and an elegant Asian decor create a vintage 1930s supper club feel at this fourth-floor oasis in The Peninsula Chicago hotel that is a favorite of the well-heeled Magnificent Mile crowd.

MUST TRY: Order the Cantonese dim sum, including barbecue pork buns and spicy beef pot stickers, sided with a Lost in Shanghai (vodka, lychee and cassis).

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