Three women enjoying cocktails and bites atop the city of Chicago.

Outdoor Dining with a City View

With warmer weather on the way, dining out at downtown Chicago restaurants tops the list of things to do. To really experience Chicago restaurants like a local, check out our recommendations for al fresco and patio dining around The Magnificent Mile. Soak up the sun, feel the breeze and take in some of the best views the city has to offer. And of course, a little people-watching never hurt!

  • Beatrix

    You Can't Beat This Patio!

    Beatrix is a neighborhood restaurant, coffeehouse and meeting place, with two locations around The Magnificent Mile. Take a seat at either the sidewalk café or at the open window wine bar for a summer’s night signature cocktail.

    Beatrix - River North
    519 N. Clark Street, Chicago, 60654 | (312) 284-1377

    Beatrix - Streeterville
    671 N. St. Clair Street, Chicago, 60611 | (312) 642-0001

  • Cindy's Rooftop

    The City's Top View

    Cindy’s is a rooftop restaurant and open-air terrace atop the historic Chicago Athletic Association Hotel, with panoramic views of Millennium Park, the Art Institute, Lake Michigan and beyond. With seasonal freshness reflected in both food and drink, the rooftop dons the relaxed ambiance of a Great Lakes beach house with a view.

    Cindy's Rooftop
    12 S Michigan Ave, Chicago, 60603 | (312) 792-3502

  • Fremont

    Nightlife in the Sky

    Fremont, located in the heart of Chicago's River North area, will take you from an eclectic dining experience into elevated nightlife. And up on the second story, the retractable roof might just make for your new favorite summer spot.

    15 W Illinois Street, Chicago, 60654 | (312) 874-7270

  • Labriola Café & Ristorante

    Italian in The Sun

    Indulge in lunch and dinner - plus house made gelato for dessert - out on the patio at Labriola Café & Ristorante, just steps away from The Magnificent Mile along the Grand Avenue pedestrian walkway. The ecletic venue houses an elegant full-service Italian restaurant and private event space with seasonal outdoor seating for lunch and dinner, a cocktail lounge that serves food from the restaurant, and a bakery café that sells baked goods, including Stan’s Donuts, and serves breakfast and lunch.

    535 N Michigan Ave, Chicago, 60611 | (312) 955-3100


  • Quartino

    Shareable Plates on the Patio

    Quartino is a bustling restaurant and wine bar just a few blocks off The Magnificent Mile. The distinctive Italian small- plates menu is full or regional specialties which are perfect to share with friends! 

    626 N State Street, Chicago, 60654 | (312) 698-5000

  • Streeterville Social

    Social with a Skyline

    With sweeping skyline views, The Bistro at Streeterville Social provides a casually chic environment to take in the city’s favorite season with inventive bites and refreshing sips. The sun-soaked urban escape at Loews Chicago Hotel has everything for laid-back days, happier happy hours, and picture-perfect nights.

    Streeterville Social
    455 N Park Drive, Chicago, 60611 | (312) 840-6617

  • I|O Godfrey

    Where Every Season is Rooftop Season

    At I|O Godfrey, every season is rooftop season thanks to the indoor|outdoor space’s retractable glass roof. Guests can enjoy sweeping city views from underneath the transparent enclosure or from the open-air portico, while snacking on elevated bar bites and signature Kitchen Cocktails.  I|O Godfrey is open 2 p.m.-2 a.m. Monday through Friday, 11 a.m.-3 a.m. Saturday, and 11 a.m.-2 a.m. Sunday. Reservations can be made via OpenTable or by calling 312.374.1830.

    I|O Godfrey Rooftop Lounge
    127 W Huron Street, Chicago, 60654 | (312) 374-1830

  • LH Rooftop

    Al Fresco From Above

    The tri-level restaurant and rooftop venue at LondonHouse Chicago showcases magnificent architecture, river, and lake views from the hotel’s apex. The 22nd floor’s outdoor terrace provides a spot to enjoy jazz-age-inspired cocktails and reimagined American fare from Executive Chef Jacob Verstegen. The 23rd floor Cupola boasts 360-degree views in a beaux-arts, domed space – perfect for a enjoying a drink or renting for an intimate event.  LH Rooftop is open 11 a.m. to 12 a.m. Monday-Friday and 10 a.m. to 12 a.m. Saturday-Sunday. Brunch and lunch reservations can be made via OpenTable. Reservations for dinner can be made by calling 312.253.2317.

    LH Rooftop
    85 E. Wacker Drive, Chicago, 60601 | (312) 357-1200

  • Terrace 16

    Outdoor Dining With A City View

    Terrace 16's seasonal rooftop patio offer breathtaking views of the Chicago River, Lake Michigan, and the city's prized architecture. Terrace 16 is an American restaurant with high-quality, approachable dining and a vivacious atmosphere located on the sixteenth floor of Trump International Hotel & Tower® Chicago.  

    Terrace 16
    401 N Wabash Ave, Chicago, 60611 | (312) 588-8030

  • Upstairs at The Gwen

    Artfully Crafted Cocktails, Small Bites and Big Views!

    A standout among rooftop terraces & lounges in downtown Chicago, Upstairs at The Gwen focuses on the art of craft cocktails paired with shareable small plate fare and cityscape views from among the Art Deco-infused architecture.
    Upstairs at The Gwen
    521 N Rush Street, Chicago, 60611 | (312) 645-1500

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