Where to Find Exclusive Rooftop Bars in Chicago

1.

LH Rooftop at LondonHouse

Perched above the Wacker & State intersection, LH Rooftop gives you sweeping panoramas of the Chicago River, downtown skyline, and Lake Michigan. The design balances sophistication with energy — polished cocktail menus, ambient lighting, and comfortable terrace seating. Because it's part of the LondonHouse hotel, the rooftop feels elevated (literally) yet accessible, and many guests time their visit for sunset to see the city transition from day to night.

2.

Cindy's Rooftop

Situated atop the Chicago Athletic Association Hotel, Cindy's overlooks Millennium Park, Lake Michigan, and the Art Institute. The bar has a glass atrium / "winter garden" feel alongside an outdoor terrace, which makes it usable nearly year-round. The menu is refined and the crowd tends toward tastemakers and architecture lovers — it's not just about drinks, but moments framed by iconic views.

3.

Upstairs at The Gwen

On Michigan Avenue, Upstairs at The Gwen is an elegant rooftop haven that feels pampered yet relaxed. By day, it's calm — morning coffee, brunch. By night, the vibe shifts toward atmospheric lighting, craft cocktails, and stellar skyline views. It leans boutique and intimate rather than rowdy, making it a favorite for couples or small groups wanting a refined rooftop experience.

4.

ROOF on theWit

ROOF on theWit sits 27 stories above State Street and embraces performance and design. The space offers sweeping views, bold décor, and a rooftop that's both lounge and nightclub — often featuring DJs or bottle service. The experience feels like being part of a high-end party above the city, where the architecture and the skyline become part of the show itself.

5.

Raised | An Urban Rooftop Bar

This spot in the theater district delivers a more industrial-chic rooftop bar, with open roof decks, river views, and drink menus that match the creativity of the space. It's not always "ultra-exclusive," but its design, elevated ambiance, and the city-view vantage make it feel special. On slow nights or off-peak windows, the terrace becomes a quietly potent spot with its own charm.