Chicago invented the skyline, and drinks on top of it: Cindy's glass atrium over Millennium Park, LH Rooftop's triple-deck view where the river meets Michigan Avenue, and the J. Parker looking down Lincoln Park to the lake.
Tap a gold pin to see the rooftop and jump to its card below.
A glass-house rooftop over Millennium Park inside the Chicago Athletic Association, the Bean and the lake below.
Pip’s Tip Reserve. Glass house over Millennium Park with the Bean and the lake straight below.
Three stacked terraces where the Chicago River meets Michigan Avenue, the postcard corner of the city.
Pip’s Tip Three stacked terraces where the river meets Michigan Avenue. The top level is the postcard.
Hotel Lincoln's 13th-floor rooftop, Lincoln Park rolling out to the lake, with a retractable roof for the shoulder seasons.
Pip’s Tip Retractable roof, so it works in shoulder season. Thirteen floors over Lincoln Park to the lake.
Six floors above Michigan Avenue at The Peninsula Chicago, this refined lounge pairs globally inspired cocktails with a plush outdoor terrace.
Sixteen floors up at Trump International Hotel & Tower, Terrace 16 pairs a New American menu with iconic skyline-and-river views.
Eight floors up in River North, this covered rooftop channels the casual seaside diners of Spain and Portugal with seafood-forward shared plates.
Atop the Godfrey Hotel, a retractable roof and heated winter igloos keep this southern-skyline lounge going year-round.
This five-story terrace at The Gwen offers a closer, architecture-forward view of River North, turning into a cozy winter lounge with curling in season.
Twenty-seven floors above Streeterville, Riu Plaza's glass-balcony terrace pairs Latin-and-American bites with sweeping 360-degree views.
Near the Magnificent Mile, this al fresco terrace mixes fire pits and lounge seating with Mediterranean-leaning small plates and lake views.
One of the largest al fresco terraces downtown, this Loews Chicago Hotel rooftop offers gourmet American classics and skyscraper views built for a crowd.
Recognized by Guinness World Records as the largest rooftop bar in the world, Offshore's Navy Pier perch spans a glass lounge and lakefront terrace.
Eleven stories above Restaurant Row, Nobu's rooftop pairs a sleek lounge and airy terrace with sushi and Asian-inflected cocktails.
Atop The Hoxton in Fulton Market, Cabra channels Peruvian flavor into a bright, plant-filled rooftop with year-round dining.
This sun-splashed Fulton Market terrace serves handmade Roman-style pizza and spritzes, with a rotating DJ lineup into the evening.
Atop the Hyatt Place in Wicker Park, this modern lounge leans into its neighborhood with panoramic skyline views from a four-season terrace.
Crowning Wicker Park's tallest building, The Robey's 13th-floor lounge pours crafted cocktails behind floor-to-ceiling glass.
Rising 22 floors above the Motor Row/South Loop area near McCormick Place, VU's spread offers three bars and unobstructed views toward Lake Michigan.
Twenty-four floors up at the Hyatt Centric in the Loop, AIRE's open-air terrace wraps 360 degrees around downtown, with fire pits for lingering.
A Cote d'Azur-inspired garden 24 floors above the Pendry Chicago, pairing rose and a picnic-basket menu with sun-drenched skyline views.
At Park Hyatt Chicago, NoMI Garden's open-air terrace offers a quieter respite amid the skyscrapers, paired with an artisanal cocktail program.
Eighteen floors up at the Viceroy Chicago, Pandan's lush, tropical-leaning lounge sits beside the rooftop pool with sweeping Gold Coast views.
A glass atrium floating over Millennium Park, Chicago's most beautiful room, indoors or out.
Rooftops are one chapter of Pip's Lifestyle, find the lounges, whiskey bars, jazz clubs and the Domino Club below.
