The One-Two Punch is our two-stop plan for dinner and drinks in the same neighborhood. And when it’s way too terrible outside to be traveling more than a few feet, it becomes even more critically important. Because let’s face it, unless you have your own portable warming station (something you should patent immediately), it’s just too cold to be wandering around right now. All these bars and restaurants are within a short walking distance of each other - and in some cases, they’re even in the same building.
Get the rest of The Chicago Winter Survival Guide here.
Au Cheval/Lone Wolf
Au Cheval doesn’t need much explanation. You’re here to eat the best burger in Chicago, but it’s not going to be easy. To test your strength and purity of heart, Au Cheval is going to make you wait.
Lone Wolf, right next door, is the best place to do that - especially when it’s freezing out. This bar pretty much lives off the people waiting for tables at Au Cheval, and it’s far less crowded than Au Cheval’s clown car of an entrance. If at any point over the course of your five-hour wait, you happen to get hungry, order a Chicago hot dog and some very good fries to tide you over.
Daisies/The Pink Squirrel
Chicago clearly appreciates a good theme, because a new themed spot seems to open up every time we sneeze. And at both Daisies and The Pink Squirrel in Logan Square, the theme is essentially “Midwestern.” With Daisies, what this means is that the pasta-focused menu has a lot of seasonal vegetables (which somehow continue to grow even though our winter landscape is about as hospitable as Mars). To drive the message home, there are cheese curds, too.
When you’re ready to be reminded even further that you’re in the Midwest, just head southeast on Milwaukee until you hear the sound of tiny bowling balls hitting tiny bowling pins. That’s when you’ll know you’ve reached this cocktail bar designed to feel like a supper club/bowling alley. Come for a Wisconsin Old Fashioned (made with brandy), and follow that up with a milkshake and some duckpin bowling.
If there’s anything we took away from The Revenant (besides a healthy fear of bears), it’s that human beings are adaptable. Hence Chicago’s abundance of restaurants with separate cocktail bars attached, so that we do everything possible to avoid going outside. Momotaro and The Izakaya are a perfect example of this. Start your evening upstairs, with some sushi and Japanese small plates from Momotaro’s very long menu, and then head down to the smaller basement bar.
This place is in Momotaro’s basement, you can get to the entrance outside, or better yet, just take the stairs behind the first-floor bar. There you can get some more Japanese small plates (like donburi, or a burger on a housemade bao bun). Also note the lack of windows, which will help you to ignore the six inches of snow slowly accumulating outside.
Giant is one of our favorite restaurants in the whole city, and it’s just a few doors down from Scofflaw, a gin-focused bar. The food here is new American, and the options change all the time, so you never have to worry about getting bored. That said, there are some classics that are always on the menu, like the crab salad with waffle fries, and the tagliatelle with chili butter. Both of which are perfect winter comfort foods.
Scofflaw is not only close by, but it also happens to be exactly the kind of place we want to hang out in during the winter. First, because it has a fireplace, and second, because gin tastes like pine trees, and pine trees make us think of sleigh rides through the woods. Plus, if you stay past midnight, you’ll get free, fresh-baked chocolate chip cookies. If that doesn’t make you happy, we’re a little concerned.
Piece is a very good pizza place in Wicker Park that specializes in New Haven-style pies. It’s ideal for watching sports, and occasionally it has karaoke. So depending on the talent level of your fellow diners, you might want to leave before that starts.
Luckily, you can go straight to Dorian’s - a bar nearby that’s hidden in the back of a record shop. This place has a long list of house cocktails, including some that are perfect for winter (like the “Sorry, Eh,” with whiskey, maple, and prickly pear, which comes in a snowman-shaped glass). It’s just what you need when you’ve been hurdling over piles of dirty snow all day.
Lonesome Rose/Golden Teardrops
Lonesome Rose is a brightly-lit Tex-Mex spot in Logan Square, and Golden Teardrops is the kind-of-hidden basement bar right underneath it. You’re here to eat some excellent chili con queso and fish tacos, and hopefully forget for at least a couple of minutes that the plants stationed around the dining room would probably survive for less than an hour if someone carried them outside.
While Lonesome Rose looks like it was teleported straight in from Southern California, Golden Teardrops has the dark atmosphere we feel most comfortable in after a vitamin D deficiency has taken hold. This place is perfect for an old-school nightcap - order a martini and talk about how back in the day they used to plow the main roads and the side streets.
River North is full of spots owned by Chicago’s culinary overlord, Rick Bayless. (If you’re new to the city, know that it’s his shadow, not a groundhog’s, that tells Chicagoans how many weeks of winter we have left.) Besides being a meteorological oracle, Bayless also has some fantastic Mexican restaurants. Like Frontera, which has been around for over 30 years and is still one of our favorite places in the neighborhood. It has consistently great dishes like carne asada and enchiladas, and it’s great if you’re spending the evening with an out-of-towner who happens to watch the Cooking Channel - or if you just want a casual sit-down Mexican meal.
Dinner at Frontera is great on its own, but even more enjoyable if you follow it up with a trip to Bar Sotano, the speakeasy-style cocktail bar hidden in the alley right around the corner. There’s a long drink menu with lots of mezcal, including a cocktail called the “tacos al pastor,” which has pineapple and is poured over chorizo fat. It should impress anyone who’s not a vegetarian.
Saint Lou's Assembly/Moneygun
St. Lou’s Assembly always has a lot going on, and it appreciates winter enough to turn its patio into a tree lot during the month of December. This place is vaguely cafeteria-themed (with patty melts and upscale takes on “meat and threes”), but unlike most cafeterias, it also has dishes like biscuits with foie gras ganache. Also unlike most cafeterias, it has the entrance to a bar (Moneygun) right inside it.
As mentioned, to get here after dinner, you don’t even have to set foot outside at all. Moneygun is a bar with big leather booths and old-school drinks like White Russians, negronis, and daiquiris, and you can also play arcade games like Pac-Man and Tetris. We’re just waiting for them to open up a hotel so that we can actually stay here all night.
You can try to get through a Chicago winter without a trip to Soule in West Town, but we wouldn’t recommend it. This restaurant has The Feel Good Factor™, meaning the friendly service and delicious soul food will put you in a good mood even if your apartment radiator sounds like Jacob Marley on amphetamines. Just know that since you’re not the only person in the city trying desperately to find a sliver of joy, there’s likely to be a pretty long wait.
Spend that wait at Cleo’s, the dive bar right next door. Head over there for drinks, eat shrimp and grits and banana pudding at Soule, and then go back to Cleo’s to finish the night brimming with your new serotonin.
Monteverde/The Press Room
Monteverde and The Press room are actually about a four-minute walk from each other, but both are so enjoyable that they’re worth the frostbite risk. Monteverde has some of the best pasta in the city (the cacio e pepe in particular is great) - and the ragu alla Napoletana (fusilli with sausage, meatball, and pork shank), while fantastic, will probably make you grateful for the chance to take a walk afterwards anyway.
The Press Room is a low-key wine bar you could happily hang out in all night. And to celebrate the fact that you got a reservation at Monteverde, you should do just that. The bartenders here are friendly, and won’t make you listen to any long-winded lectures on varietals while trying to convince you to spend $500 on a bottle. So bundle up after dinner and make a run for it.