If you’re looking for where to watch the Bears game in Chicago and you want more than a packed sports bar with sticky floors, let me put you on to Utopian Tailgate.
It’s a 10,000-square-foot rooftop in Old Town — indoor and outdoor — built like a tailgate party for grownups. Big screens everywhere, picnic tables, string lights, turf under your feet, and the Chicago skyline behind it all. We went for their Gourmet Tailgate event and honestly, it might be the most fun way to watch a Bears game in the city.
What Utopian Tailgate Is Like on Game Day
Picture this: you walk in and there’s a DJ going, a disco ball spinning, Bears fans everywhere in their jerseys, and the game on screens you can actually see from wherever you’re sitting. Inside there’s a full bar and lounge areas with cozy nooks. Outside on the rooftop, it’s picnic tables, oversized games like Jenga and Connect 4, hanging plants, and colorful Adirondack chairs.
It’s 21 and over, so the whole vibe is adult tailgate — loud in the best way, but nobody’s stumbling around.
What We Ate and Drank
The food setup is vendors, not a sit-down menu. When we were there: tacos al pastor carved right off the trompo, fresh-baked cookies, sangria, and a full bar inside. The tacos were the standout — get them if they’re there when you go.
Drinks-wise, they’ve got cocktails, a big draft selection, and everything you’d want for a game day. Prices are moderate — think typical Chicago rooftop, not stadium robbery.
Why It’s One of the Best Places to Watch the Bears Game in Chicago
Here’s what sold me: you can actually watch the game. Some Chicago rooftops are all vibe and you end up squinting at a tiny TV in the corner. Not here. Screens are big, placed well, and the crowd is locked in. When something big happens, the whole rooftop reacts together. That’s the energy you want on a Sunday.
Between plays, there’s plenty to do — the games, the food, the skyline views. It never feels like you’re just killing time waiting for the next snap.
Good to Know Before You Go to Utopian Tailgate
Where it is: 1608 N Wells St, in Old Town. It’s the rooftop above Second City at Piper’s Alley — enter through the building at North and Wells and head up. Look for the Second City entrance; the rooftop is upstairs.
Hours: Monday through Thursday 4pm to 11pm, Friday noon to 1am, Saturday 11am to 2am, Sunday 11am to 10pm. For a Sunday Bears game, get there early — it fills up.
Parking: There’s a public lot nearby. Street parking in Old Town on a game day is ambitious, so plan ahead. Rideshare is honestly your best bet.
Reservations: They’re encouraged, and you can book indoor, patio, or field (picnic table) seating through their site. Walk-ins are welcome until they hit capacity. Fridays and Saturdays are first come, first served — so don’t roll up at kickoff expecting a table.
Age: 21+ only. Leave the kids at home for this one.
Price: Moderate — food and drinks in line with other Chicago rooftops. Expect $31–$50 per person for food and a couple of drinks.
The Honest Take
I’ve been to a lot of game-day spots in Chicago, and most of them are either a bar with TVs or a rooftop that happens to have a game on. Utopian Tailgate is the rare one that’s built for both. The tailgate theme isn’t just decor — it’s the whole point. You eat, you drink, you play games, you watch the Bears with a crowd that’s actually into it, and you do it all with the skyline behind you.
Worth the trip? Absolutely. Especially for a Sunday game.
Disclosure: We were invited to the Gourmet Tailgate event by Chicago Gourmet (via Kinship Company) with complimentary tickets. All opinions are my own — I only share spots I’d actually go back to.
Planning a trip to Chicago? Check out my Chicago travel guide for my full local itinerary.
More Chicago game-day ideas: Top 5 Spots to See the Chicago Skyline and Best Hotels to Stay While Visiting Chicago
