Rooftop Bars in Chicago (2025)

Chicago Athletic Association’s glass‑topped perch marries lake views with a serious cocktail program and seasonal Midwestern cooking. Frequently praised by Condé Nast Traveler and Eater Chicago, it remains a definitive downtown rooftop without feeling generic.

Wicker Park’s 13th‑floor lounge is a locals’ go‑to for skyline sunsets and well‑made classics. Regularly recommended by Eater Chicago and travel writers, it feels intimate and unmistakably neighborhood despite the postcard views.

A laid‑back sixth‑floor pool bar with frozen drinks, tacos, and neighborhood views. Covered by The Infatuation and local press, it’s Wicker Park’s only public rooftop pool scene—casual, social, and distinctly Chicago summer.

Above The Second City, this playful Old Town rooftop leans into games, DJs, and big‑format drinks. Covered by Eater Chicago and Time Out Chicago, it’s rowdy in the best way and rooted in a classic Chicago comedy address.

A true neighborhood original atop a beloved sausage shop in Lincoln Square. Seasonal, wood‑grilled brats, draft beer, and Euro wine under grapevines. Frequently cited by local journalists and Condé Nast Traveler for its community feel.

A multi‑level River North institution with a lush, year‑round rooftop garden. Known for classic‑leaning cocktails and late‑night energy, it’s been highlighted by Block Club Chicago and local critics for that indoor‑outdoor charm.

Peruvian cocktails and cebiches meet a lively second‑floor terrace. OpenTable and Condé Nast Traveler call out the pisco program; locals love the weekday happy hour and the late‑evening Pisco Disco nights upstairs.

One Off Hospitality’s seasonal rooftop channels Iberian seaside snacks with downtown views. Frequently recommended by Eater Chicago and Choose Chicago, it’s relaxed, food‑forward, and distinctly local in ownership and spirit.

A West Loop favorite from a Chicago‑born group, with a year‑round rooftop patio and a deep list of Mediterranean spirits. Regularly featured by Condé Nast Traveler and local media for its scene, mezze, and garden‑like design.

Devereaux’s successor brings Southeast Asian flavors, baos, and a cocktail list built for golden hour. Covered by Block Club Chicago and hotel editors, it adds fresh energy to the Gold Coast’s rooftop landscape.

West Town’s garden rooftop above Roots Handmade Pizza serves seasonal menus amid planters and vertical gardens. Eater Chicago continues to recommend it for farm‑leaning dishes, desserts, and a mellow, neighborhood feel.

A Loop standby with a retractable roof and South American rhythms. Frequently cited by Condé Nast Traveler and hotel guides, it suits post‑work drinks or late‑night salsa under the glow of the glass canopy.