As much as we miss it when it’s gone, the truth is that summer in Chicago is a huge source of stress. There’s the pressure to always be outside while it’s nice out, coupled with three months of low-level anxiety that you’re not doing enough to fully take advantage of the warm weather. Not to mention the constant doomsday clock counting down the seconds till fall.
Let’s face it, winter is our safe space. Huddling in a warming station on the L platform, digging cars out from under six feet of snow, going to a fancy dinner dressed like a snowmobiler - these are the situations we’re most comfortable in. Here’s where to go when you need to be reminded why we still live here between January and March.
In the summer, we make a big deal out of the huge outdoor patio at Kaiser Tiger. It’s one of the few places where you and 13 of your friends can always get a table outside, and share some beers along with a five-pound sausage wrapped in bacon. During the winter, though, this whole area becomes a curling rink. This means you no longer need to rely on the Winter Olympics or YouTube videos at 2am to enjoy a sport that proves exactly how bored and desperate winter can make people.
Scofflaw is the perfect winter bar, in large part because the inside has a large and very cozy fireplace you can sit next to. Also, after midnight they give out free, fresh-baked chocolate chip cookies. So basically, it might be a trap set for grown-ups by the witch in Hansel and Gretel. But it’s still fun.
Moody’s has been around since 1959, and the atmosphere doesn’t seem like it’s changed much since then. In the summer, we recommend coming here primarily because of the large beer garden where you can sit and eat a burger. But the indoors is a fantastic place to hang out when it’s cold, too. It feels like a hunting lodge, with two very old-looking stone fireplaces that seem like they could plausibly have been built in the Middle Ages. Sit next to one of them and try to remember something about medieval history.
Summer weather makes us feel bad for doing indoor things we really enjoy (and also happen to be good at), like drinking, eating, and watching sports on very nice television sets. But when it’s cold out, The Moonlighter in Logan Square lets you take full advantage of the fact that no one expects you to to be outside. You’ll find plenty of TVs, great bar food, and a wood-burning fireplace that will even make you secretly glad it’s snowing. Again.
If you’ve watched Downton Abbey, you might suspect that winter would be a lot more charming if you lived with the Crawleys. And you’re probably right, which is why you should head to The Darling in the West Loop. This two-floor cocktail bar is designed to look like an old English manor, so you can have drinks and small plates by the fireplace while surrounded by old-timey bookshelves and elegant leather couches and chairs. Don’t think too hard about the fact that in real life, you’d probably be one of the servants.
Just because we know we can get our food at Trader Joe’s instead of chasing it across the plains for three days doesn’t mean that our DNA does. And that must be why the moment the temperature drops, the biological imperative to start preparing our bodies for winter begins. You can do this very effectively at Chicago Pizza And Oven Grinder, home of the pizza pot pie. This thing is essentially a pound of bread and cheese, and one serving is guaranteed to last you through all of the cold months. Plus, the basement space is warm and cozy, and pretty ideal for holing up until you can hear birds again.
No place takes humanity’s desire to conquer the elements as seriously as Frontier - which, as the name suggests, is a pioneer-themed restaurant. During the winter, the outdoor patio (complete with huge fireplace) is enclosed, and you can order from a menu with things like rabbit and antelope that will make you feel like you’re possibly on the Oregon Trail. Just with less typhoid and dysentery.
Gibsons Italia is a fancy Italian restaurant in River West from the same owners as Gibsons Steakhouse, and it works really well for special occasions and/or any meal where you get to use a corporate card. While the main dining room is filled with people impressing out-of-towners over dinner, the third floor is the slightly more casual lounge area. It has comfortable (but still expensive-feeling) chairs and couches, a fantastic view of the river, and a nice sitting area around the fireplace. Plus, you can order the full menu there. Despite the name of this restaurant, you shouldn’t actually focus on the Italian dishes - just order anything that looks like it belongs in a steakhouse.
Cherry Circle Room is the upscale restaurant inside the Chicago Athletic Association Hotel. But unless you’re Nicole Kidman’s children from The Others, it’s kind of a bummer to eat here when it’s nice out - because it’s windowless, dark, and located all the way in the back on the second floor. In the winter, though, it’s perfect, because the main design elements are wood and overstuffed leather chairs, and it basically reminds us of a fancy turn-of-the-century lodge. Plus, the rustic menu (with plenty of roasted meat) fits the ambience. So you can spend all day here and never regret that you haven’t felt sunshine on your skin in four months.
This is the bar you have to walk through to get to Cherry Circle Room. Although you might not ever get there, because Game Room’s atmosphere and activities are a lot of fun on their own. This place also looks like it belongs in an old mansion, with big leather seats, billiards tables, and a bocce court. Plus, it serves well-made classic cocktails. Basically, coming here will make you want to wear a monocle and/or purchase Baltic Avenue.
The outdoor patio at Parson’s is fantastic. It’s huge, and it has its own bar and ping pong table. So you might not even be aware that there is actually an inside to this restaurant. But there is, and it’s a fun place to spend time in the winter, when the ping pong table is brought inside for tournaments, and they play movies on a projector. In fact, coming here is a little like having a self-imposed snow day, just with fried chicken and hushpuppies that you didn’t have to make at home.
Before we go on a five-mile run or 20-mile bike ride along the Lakefront trail during the summer, we’re probably not fueling up on sausages and spaetzle. But when our weekend plans involve a lot of Netflix and falling asleep on the couch, those things are perfect. Funkenhausen, a German-inspired restaurant in West Town, has exactly the kind of delicious (and heavy) food we’re talking about. Get dishes like the French onion spaetzle or a huge platter of cider-glazed pork shoulder with roasted apples, and then go take a nap.
Park And Field is another spot that has a fantastic outdoor patio and refuses to let winter ruin it. You’ll find multiple fire pits here all winter long - plus blankets, warm drinks, and snacks. So you can sit outside, make s’mores, and show everyone how much you actually love winter in this city.