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Upcoming Second City Rooftop Bar to Offer Discounts to Those Braving Winter’s Cold

Utopian Tailgate should open soon in Old Town and will feature magicians, boozy paletas, and more

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A green drink in a highball glass with a novelty marijuana leaf flag.
The “Gin and Chronic” features gin, Green Chartreuse, CBD oil, lime, and triple sec.
Utopian Tailgate/Sarah Zelman
Ashok Selvam is the editor of Eater Chicago and a native Chicagoan armed with more than two decades of award-winning journalism. Now covering the world of restaurants and food, his nut graphs are super nutty.

Ownership of the new rooftop bar on top of Second City, Old Town’s esteemed comedy club, bills it as the antidote for customers who want to do more than play with their phones out in public. Utopian Tailgate, 1608 N. Wells Street, could open as early as the end of August, just in time for the starts of the NFL and college football seasons. The rooftop venue at the corner of North Avenue and Wells Street will feature several “large format” table and outdoor games – the kind of games sports fans or concertgoers would play in parking lots before attending an event, hence the word tailgate in its name.

The new venue is a partnership between Second City — the comedy troupe that’s produced legends like Stephen Colbert, Bill Murray, and Amy Poehler — and Fifty/50 Restaurant Group, the company that started with its namesake sports bar in Wicker Park. Fifty/50 has since shifted from more of a neighborhood model into opening spaces closer to Downtown Chicago, including its newest restaurant, 90th Meridian.

Fifty/50 co-founder Greg Mohr described his oddball (on some days it’ll have a magician), outdoor wonderland as full of games and high-tech TVs with screens the cut down glare, designed specifically for outdoor use. One of the many games it’ll have on the roof is Putterball. It’s kind of a cross between mini-golf and beer pong. Management will surround the putting green with stadium seating, creating a ridiculous scene to watch players. This is representative of what Utopia Tailgate is about, Mohr said.

“The only rule is it can’t make a lot of sense,” Mohr added.

A pink drink garnished with mint in a styrofoam cup, with a giant red foam fan finger on the left.
The Punch Face CHampion cocktail is playful.
Utopian Tailgate/Sarah Zelman

Mohr’s new spot will also have cornhole and a giant Jenga set that’s unique. Almost like a fortune cookie, each block will have a saying. A player would pull a block from the Jenga tower and then read something like “high-five a stranger.” There’s also cabana seating and giant Connect Four boards.

Football fans are accustomed to braving frigid temperatures while tailgating. Mohr said his new spot will encourage customers to bundle up and hang out outside by offering discounts on food and drink to outdoor customers during winter months. The space features a bar that goes from the 3,500-square-foot indoor portion of the space through the 6,500-square-foot outdoor portion. Garage doors separate the indoors from the outdoors.

This is Fifty/50’s first Old Town location, and the neighborhood is a bit of an anomaly. Many bar owners in other area lament younger customers who prefer to stay at home and drink. However, Mohr said Old Town is full of twenty-something residents who venture out along Wells Street.

“I don’t where they come from, it’s not cheap to live around here,” Mohr said. “If you walk down the street there’s so many young customers and so many who are dining and drinking. It’s already very social, it’s a very cool vibe.”

Cocktails are huge parts of the ambience at rooftop bars, and Utopian Tailgate will have some fun stuff in store from bar manager Michael Barnes (with an assist from Dylan Seo, bar manager at Fifty/50’s Lincoln Square bar, the Sixth). Barnes worked at Broken English Taco Pub. Their drinks have creative glassware, props, and names like “Gin and Chronic,” “Punch Face CHampion” (served in a disposable cup), and “Big Piña.”

The space will have 32 draft lines for beer. But the secret weapon is the paletas. Fifty/50 is working with suburban Blue Island dessert maker La Michoacana on boozy popsicles. Flavors include piña colada and boozy watermelon. Also expect table-side keg service.

Amber Lancaster was the previously announced chef but she left to take another job. Nate Hensler, Fifty/50’s chef at Portsmith (its River North seafood restaurant) has taken a larger role with the company and is now handling Utopian Tailgate’s food. His menu consists of “the best tailgate food you’ve ever had” said Mohr. Korean-style steak kebobs, Chinese-style spare ribs, and Doritos-style nachos are on the menu.

Fifty/50 is also opening another location of its Quad City-style pie shop, Roots Handmade Pizza, downstairs. Mohr said the partnership with Second City is “like a dream come true.”

“I pinch myself sometimes,” Mohr said. “It’s amazing, Old Town is awesome, it’s vibrant and there’s a lot going on.”

Stay tuned for more details in the coming days.

Utopian Tailgate

1608 North Wells Street, , IL 60614 (312) 210-7799 Visit Website