Best Hotels with Rooftop Bars & Pools in Chicago (2026)

Occupying the lower floors of Mies van der Rohe's iconic IBM Building above the Chicago River, The Langham is the finest hotel in the city by almost any measure — the Chuan Spa, Paul Kahan–informed dining, and rooms with soaring Miesian windows over the river are extraordinary. Service is consistently ranked among North America's best.

• River North
• Luxury
• Architecture

★ 9.5 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

Floors 30–46 of 900 North Michigan Avenue make this the highest perched luxury hotel in the city, with views stretching to Lake Michigan's horizon on clear days. The jewel-toned rooms are among Chicago's most beautifully appointed, and Allium Restaurant serves one of the best power lunches in the Loop.

• Magnificent Mile
• Luxury
• Views

★ 9.3 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

A stunning conversion of the 1923 London Guarantee Building at the confluence of the Chicago River and Lake Michigan, with a triple-tiered rooftop bar that claims some of the best urban views in the country. Rooms blend the building's Classical Revival exterior with a lively, colourful interior palette.

• Loop
• Rooftop
• Views

★ 9.1 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

Richard Branson's take on the boutique hotel, set in a magnificent 1928 Mayan Revival skyscraper with rooms reimagined as 'Chambers' featuring a clever dressing room foyer, adjustable climate and lighting, and a fridge stocked at grocery-store prices. The Commons Club restaurant and bar is one of River North's most reliably enjoyable dining rooms.

• River North
• Boutique
• Design

★ 9.0 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

Named for Gwendolyn Brooks, Illinois's first Poet Laureate, this Art Deco hotel blends Chicago literary heritage with Marriott's Luxury Collection polish. The gold-leaf lobby ceiling and rooftop bar with Mag Mile views are defining features of this mid-range luxury sweet spot.

• Magnificent Mile
• Art Deco
• Views

★ 8.9 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation

The neighbourhood's original creative-class hotel, with rooms featuring local artist commissions, a lobby designed for lingering, and a rooftop with fire pits and a view of the West Loop skyline. The ground-floor restaurant and coffee bar hum with the energy of Chicago's creative and tech communities.

• Fulton Market
• Creative
• Rooftop

★ 8.7 Hotelier's Choice score, 40+ criteria · Many rooms include free cancellation