Best Rooftop Restaurants in Chicago (2025)
Cindy's Rooftop
Restaurant · Loop
A signature Chicago experience atop the historic Chicago Athletic Association, pairing sweeping Millennium Park and lake views with seasonal, market‑driven cooking and inventive cocktails. Celebrated by Time Out and Condé Nast Traveler; reservations are wise, especially at sunset.
bar avec
Mediterranean restaurant · River North
One Off Hospitality’s rooftop sibling to Avec channels Iberian seaside vibes: spritzes, tinned-fish riffs, and those famed chorizo-stuffed dates—plus knockout skyline sightlines. Frequently featured by Eater Chicago for both its food and its view-forward terrace.
SIFR
Middle Eastern restaurant · River North
From the team behind Indienne, this Middle Eastern charmer cooks over live fire and serves a thoughtful mezze‑to‑grill menu on an all‑season rooftop. Recognized with a Michelin Bib Gourmand and praised by local critics for value and verve.
Tanta Chicago
Peruvian restaurant · River North
River North’s Peruvian staple brings the party upstairs with a retractable‑roof terrace, pisco‑driven cocktails, cebiches, and anticuchos. Highlighted by Time Out and Eater; look for rooftop events like late‑night pisco nights in warm months.
Lonesome Rose (Logan Square)
Mexican restaurant · Logan Square
A Logan Square favorite from Chicago’s Land & Sea Dept., this leafy rooftop pairs tacos, queso, and agave spirits with easygoing neighborhood vibes. Featured on Eater’s rooftop list; cap the night downstairs at Golden Teardrops.
BiXi Beer
Brewpub · Logan Square
Chef‑owner Bo Fowler’s Logan Square brewpub marries house beers with Chinese, Korean, and Vietnamese‑influenced dishes. The sunny rooftop and dim sum brunch draw locals; repeatedly recommended by Eater Chicago and neighborhood guides.
Utopian Tailgate
Restaurant · Old Town Triangle
A 21+ rooftop playground above The Second City with whimsical, shareable tailgate fare and skyline views. Covered zones keep the party going year‑round. Frequently cited by local press for its big‑fun energy and solid bar food.
Taxim
Greek restaurant · Wicker Park
Chef‑owner David Schneider’s modern Greek spot features a rooftop herb garden terrace, an all‑Greek wine list, and regionally driven dishes. Long praised by Chicago critics; a Wicker Park original with real neighborhood roots.
Gene's Sausage Shop and Delicatessen
Deli · Lincoln Square
A family‑run Lincoln Square institution with a seasonal rooftop serving wood‑grilled sausages, pierogi, and European wines. A simple, communal setup that locals love; typically open weekends, weather permitting, per the shop’s updates.
Homestead On The Roof
Temporarily Closed
Above Roots in West Town, this garden‑lined rooftop hosts seasonal pop‑up menus with wood‑fire cooking and pastries from acclaimed local talent. Time Out and Chicago Food Magazine spotlight its summer openings and chef‑driven approach.