9 venues with rooftop seating

Cindy's rooftop terrace offers breathtaking Lake Michigan views paired with exceptional seasonal cocktails, curated wines, and local craft beers. Despite the tourist crowds, the magical city sunsets and quality shared plates make securing a reservation worthwhile.

Perched atop a Wicker Park hotel, Kennedy Rooftop offers panoramic Chicago skyline views, craft cocktails worth their price tag, an impressive beer selection, and full food menu. Heated sections make it enjoyable year-round—perfect for happy hours or impressive date nights.

Perched 22 floors up, LondonHouse's tri-level rooftop offers eye-level views of Chicago's architectural icons and the winding river below. Creative cocktails complement the Instagram-worthy backdrop, making sunset drinks here worth both the reservation planning and the price tag.

Perched above the city, The Prospect offers rooftop magic with substance—thoughtful local craft beers, creative cocktails, and chef-driven food that complements the stunning skyline views. Perfect for impressive yet comfortable date nights, especially at sunset.

Elevated 24 floors above the Magnificent Mile, Aire pairs breathtaking Chicago skyline views with exceptional seasonal cocktails, heated year-round outdoor seating, and shareable upscale bites. Live music enhances the sophisticated yet unpretentious atmosphere.

Arlington Ale House boasts a spacious rooftop with neighborhood views, an impressive craft beer selection, and live music that strikes the perfect volume balance. Bring your own food, enjoy cornhole games, and embrace the energetic atmosphere that transforms from casual daytime hangout to vibrant nightspot.

Cerise Rooftop offers breathtaking wraparound Chicago skyline views with an exceptional cocktail program featuring bourbon and local honey specialties. Enjoy live jazz against the backdrop of Lake Michigan, paired with crowd-favorite truffle fries. Book ahead for sunset—this popular spot fills quickly.

Elevated six floors above Michigan Avenue, Z Bar offers panoramic Chicago views and artfully crafted cocktails in a sophisticated atmosphere. The rooftop venue features elegant shareable bites, live sunset music, and an impressive cocktail program worth the splurge despite the touristy crowd.

Tony's Rooftop Bar pairs stunning 360-degree city views with unpretentious vibes, offering expertly crafted cocktails and a global beer selection. Perfect for sunset dates or post-work unwinding, with a full food menu to complement your elevated drinking experience.