Chicago comes alive during the summer season; it’s an awakening that must be experienced. A great way to do this is by holding an event at one of the spectacular rooftops to soak up the summer rays, breathe in the fresh air, and take in the aesthetic Chicago skyline with a craft cocktail in hand. Although the city is home to a plethora of rooftops, here are five that exhibit diversity in ambiance, guest capacity, and location so that you can begin to explore which would offer the ideal experience for your event.

Terrace 16

Terrace 16 is a rooftop restaurant and bar located on the 16th floor of the Trump International Hotel and Tower donning a business and chic casual feel. Its terrace looks right onto the serpentine Chicago River, which showcases a magnificent view of Lake Michigan and the surrounding historic, downtown architecture. The locale is comprised of the Terrace Patio, the Tower Room for main dining, the private River Room, the Terrace Reception area outside the River Room, and the semi-private Bridges Room. The terrace portion is open from mid-May to the end of September. The Tower Room serves lively new American fare with an extensive variety of cocktails, wines, and spirits.

Cerise Rooftop

Right across the river is the Cerise Rooftop of the Virgin Hotel embodying a trendy, funky vibe that will have you feeling like you’re in a loft in London.  Located on the 26th floor in the heart of the Loop, the Cerise Rooftop offers its guests a wrap-around terrace with north, west, and southside views that immerse you into the formidable skyline. The venue can hold up to 220 guests in both its indoor and outdoor installations, which offers a fireplace, a private bar called the Trophy Room, and comfortable, swanky furniture where you can mingle and nibble on delicious bar bites, sip on exquisite cocktails, and enjoy live DJ entertainment.

Utopian Tailgate

Heading about 15 minutes north of the Loop, we arrive at the Utopian Tailgate located in Old Town; its home is the rooftop of the Second City Comedy Club, which views the downtown city skyline.  This restaurant-bar, which can host 20 to 150 guests, has been famously dubbed the playground for grownups due to its swings; bungalows; bright and colorful furniture; a tire swing; super-size versions of Connect 4 and Jenga; putter ball; corn-hole; foosball; and beer pong. Not to mention their menu offers highly prismatic, Instagram-able cocktails; smoothies; an extensive beer list; and finger-licking pub grub, such as sliders, hot dogs, wings, fries, and nachos.

Cindy’s Rooftop

Overlooking the crystal-blue waters of Lake Michigan, the Art Institute of Chicago, and Millennium Park, Cindy’s Rooftop is a picturesque modern restaurant-bar with a subtle hint of antiquity attributed by the Chicago Athletic Association Hotel it sits atop. Located on the 13th floor, crowned with a glass atrium, Cindy’s smart-casual vibe offers event spaces that include semi-private lakeview couch sections; a private dining area called The Library that holds up to 30 seated guests; and complete buyouts. A portion of the proceeds from The Library are donated to the Chicago Public Library. The venue serves new American fare for brunch, lunch, and dinner, along with tasty bites, cocktails, beer, and wine to satisfy your palates.

Offshore Rooftop

The Offshore Rooftop Bar at Navy Pier, surrounded by the azure waters of Lake Michigan with the coast-lined city as its backdrop, creates a panoramic vista like no other. It holds the Guinness World Record for the largest rooftop bar with a 36,000 square feet indoor lounge and a 20,000 square feet terrace. It has a retractable roof, two private lawns, seven fire pits, and gaming and entertainment areas.  The Offshore can host 15-275 people for a semi-private event; 350 guests for a seated dinner; and 750 guests for a cocktail-style event. Whether it’s lunch in the sun or dinner under the stars, the view, fresh air, innovative cocktails and eclectic menu will undoubtedly make your event a most memorable experience.

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