Chicago winters are usually something we just try to survive. You bundle up, you trudge through slush, and you count the days until May. But then there’s the curling at Upstairs at The Gwen. It’s weirdly addictive. Honestly, sitting on a rooftop in the middle of a January deep freeze sounds like a terrible idea until you’re actually up there with a cocktail in your hand and a stone in your stride.
The Gwen Hotel, tucked away in the McGraw-Hill Building on North Michigan Avenue, does things differently. While every other tourist is fighting for space at the Millennium Park ice rink, the locals are heading to the fifth floor. Upstairs at The Gwen is an Art Deco-inspired retreat that transforms its outdoor terrace into a "Curling & Cocktails" experience every winter. It isn’t about Olympic-level precision. It’s about the vibe. It’s about that satisfying clack of the stone hitting the target while the Chicago skyline glows around you.
How Curling at Upstairs at The Gwen Actually Works
Forget everything you think you know about professional curling. There are no brooms here. You won't see anyone frantically scrubbing the ice to adjust the speed of the stone. At The Gwen, they use "iceless" curling rinks. This is basically a high-tech synthetic floor that mimics the glide of real ice without the mess or the need for a massive cooling plant. It’s smart. It means you can play even if it’s a relatively "warm" 40-degree Chicago day without splashing through puddles.
You book a slot—usually 30 or 45 minutes—and you get a dedicated lane. It’s $30 per person, but that usually includes a signature cocktail to keep the engine running.
The stones are smaller than the heavy granite ones you see on TV. They’re manageable. Even if you have the upper body strength of a wet noodle, you can get a good slide going. The goal is the "house"—that bullseye at the end of the lane. You’re basically playing shuffleboard’s cooler, more sophisticated cousin. It’s competitive but in a "let’s see who buys the next round of sliders" kind of way.
The Atmosphere is the Real Draw
You’re five floors up. The architecture of the Magnificent Mile surrounds you. It’s intimate. Unlike the massive rinks at Maggie Daley Park, this feels like a private club. They’ve got fire pits. They’ve got heat lamps that actually work.
The Gwen's terrace is famous for its Art Deco soul. That doesn't disappear in the winter. They just add faux fur throws and a lot of whiskey. If you’re lucky enough to be there when it’s lightly snowing, the whole place feels like a movie set. It’s arguably one of the most Instagrammed spots in the city for a reason, but it doesn't feel plastic or fake. It feels like Chicago.
The Drink Menu: More Than Just an Afterthought
Let’s be real. You’re here for the drinks. The curling at Upstairs at The Gwen is the activity, but the beverage program is the anchor. They lean heavily into the "Alpine" aesthetic.
Think hot toddies that actually taste like spices instead of just watered-down bourbon. They usually have a seasonal "Gwen Spritz" or some variation of a boozy hot chocolate that hits the spot when the wind picks up off the lake.
- The Chili Hot Chocolate: It’s thick. It’s got a kick. It’s the kind of drink that stays hot longer than two minutes.
- The Seasonal Old Fashioned: Usually involves some kind of maple or walnut bitters situation.
- The Mocktails: They don't ignore the non-drinkers. The ginger-based warmers are legit.
The food is solid too. You aren't getting a five-course meal on the curling rink, but the small bites—like the wagyu sliders or the truffle fries—are exactly what you want when you're outside. It’s elevated bar food. You can eat with one hand while you wait for your turn to throw.
Why People Get This Place Wrong
A lot of people think you can just wander up and start playing. You can't. It’s popular. If you show up on a Friday night without a reservation, you’re going to be disappointed, staring at the rink from the bar through the glass.
Another misconception: it’s only for hotel guests. Nope. While The Gwen is a Luxury Collection hotel, the rooftop is very much a public-facing venue. You’ll see a mix of hotel guests in expensive coats and locals who just finished a shift in the Loop.
Is it expensive? Kinda. It’s Michigan Avenue prices. But you’re paying for the view and the exclusivity. If you want cheap, go to a bowling alley in the suburbs. If you want to feel like you’re winning at life in Chicago, you come here.
Comparing The Gwen to Other Chicago Winter Spots
| Feature | Upstairs at The Gwen | Millennium Park |
|---|---|---|
| Surface | Synthetic Iceless | Real Ice |
| Crowd Level | Low/Controlled | Extremely High |
| Vibe | Sophisticated Lounge | Family Chaos |
| Beverages | Craft Cocktails | Hot Cocoa Stand |
| Reservations | Required | Recommended/Walk-up |
The Gwen wins on comfort. If you have a low tolerance for shivering in line with a thousand strangers, the rooftop is your sanctuary.
Logistics: What You Need to Know Before You Go
The curling season at The Gwen typically runs from late November through February, or sometimes into March if the weather stays crisp. Chicago weather is a fickle beast, so they play it by ear.
Location: 521 North Rush Street. You enter through the hotel lobby, head to the elevators, and hit the button for the 5th floor.
Dress Code: Don't be the person who shows up in a cocktail dress and heels. It’s a rooftop. It’s Chicago. Wear boots with grip. Wear a coat that allows you to move your arms. You’re throwing stones, not walking a runway. However, because it’s The Gwen, "athleisure" should be the fancy kind.
Group Size: It’s perfect for groups of 4 to 6. Any more and you’re standing around too much. Any fewer and the $30-per-person cost feels a bit steep for a quick game.
The Strategy of the Stone
If you actually want to win, remember that the synthetic surface is faster than you think. You don't need to hurl the stone. It’s all in the release. Smooth. Level. Follow through with your hand like you’re reaching out to shake someone’s hand.
Most people overcompensate for the cold by being too aggressive. Relax. Sip your drink. Let the stone do the work. The beauty of curling at Upstairs at The Gwen is that even if you're terrible at it, the scenery makes up for your lack of athletic prowess.
Actionable Steps for Your Visit
- Book Two Weeks Out: Seriously. If you want a weekend slot, you need to be proactive. Use their website or OpenTable.
- Check the Wind Chill: If the wind is coming hard off the lake, the 5th floor can get drafty. Check the forecast and add an extra layer.
- Arrive Early: Get to the bar 20 minutes before your slot. Get your drinks ordered and in your hand so you don't waste your 30 minutes of play time waiting for a server.
- Validate Parking: If you’re driving, valet is pricey. There are apps like SpotHero for nearby garages, but the hotel can sometimes help with validation if you're spending enough at the bar.
- Plan an "After" Spot: The Gwen is right next to The Shops at North Bridge. Once you’re done curling, you’re steps away from some of the best dining in the city. Head to Purple Pig or Joe’s Seafood to warm up for real.
The whole experience is a reminder that Chicago doesn't have to be miserable in January. Sometimes, all it takes is a synthetic ice rink, a glowing heater, and a stone sliding toward a target to make the winter feel a little bit shorter. Curled up at The Gwen, the city feels small, quiet, and surprisingly warm.