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Where To Go To Pretend It’s Not Winter

The guide for when you’d really just rather be on vacation.

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15 Spots
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17 Spots
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After the fun of the holidays is over, there’s January through March - the long, bleak hallway toward spring that seemingly goes on forever. And just when you think the end is in sight, it’s 15 degrees again and/or you wake up to another eight inches of snow. It’s like living in Groundhog Day, with more catching colds on the CTA and less Andie MacDowell.

Even people who’ve lived in this city for a long time and know better than to get their hopes up can use a respite. So here are 16 bars and restaurants with heated patios, covered rooftops, and lots and lots of plants - places where you might plausibly convince yourself, for a second or two at least, that you’re hundreds of miles away. Or at least just in a city where winter doesn’t physically hurt.

Featured In

The Spots


$$$$ 200 N Green St

Cabra is like a terrarium sitting on top of the Hoxton hotel. It’s a plant and light-filled rooftop restaurant that has a great view of the West Loop, and also serves some very good Peruvian-inspired food. The best things here are the ceviches (the bass with leche de tigre and the duck are stand-outs), and the shrimp tacu tacu which comes on a delicious crispy rice cake. It’s a great spot for a fun date night, and for remembering back when plants could grow.

Sandy Noto


$$$$ 1604 W Chicago Ave

Beatnik is very big on atmosphere, and that atmosphere is best summed up as “Wes Anderson movie that takes place in a hot climate.” That means you’ll find lots of tropical plants, a big skylight, and ornate furniture (like a huge daybed from Bali covered in pillows). The menu is varied, with dishes like Lebanese lamb, beef cheek arepas, and red curry noodles. It’s a nice change of pace from eating all those canned goods and root vegetables.

Sandy Noto


$$$$ 938 W. Webster Ave.

This pizza place in Lincoln Park has also spent a lot of time curating its atmosphere, but in this case the atmosphere is more like “college apartment on a CW show.” There are big, comfortable couches with lots of space for groups, and light-up signs that remind you to “be awesome.” Homeslice also has a fantastic outdoor patio, and during the winter goes to extreme lengths to make sure that patio is still usable and comfortable (it’s covered in plastic and temperature controlled). So it feels a little bit like eating in a tent from Outbreak, but with pizza and adult-size swing sets.

Sandy Noto

90 Miles Cuban Cafe

$$$$ 2540 W. Armitage Ave.

It’s remarkably easy to forget how terrible it is outside when you’re eating empanadas and Cubanos on the heated outdoor patio at 90 Miles. This Logan Square spot is BYOB, so invite some friends and remind them all to pick up wine on the way. It’s about a thousand times better than inviting them to your expensive winter destination wedding.

Three Dots And A Dash

$$$$ 435 N. Clark St.

Tiki bars are an excellent line of defense against winter. And even though it’s somewhat hidden in an alley, Three Dots And A Dash in River North is Chicago’s most popular and well-known one. There are plenty of large booths, not to mention over-the-top drinks that are great for sharing (including one in a smoking treasure chest that’s meant for six people). Since the whole bar is in a basement, there are also no windows to shatter the illusion that you’re on a tropical island, and not surrounded by piles of old grey snow that refuses to melt away.

Lost Lake

$$$$ 3154 W. Diversey Ave.

Another great tiki bar, this time in Logan Square. While Three Dots is large, Lost Lake is small and cozy, but it’s still very into its theme - the decor and menu both go all-in on the tropical island atmosphere. The strong, not-too-sweet drinks are served in elaborate glassware, and some come with extra touches like a banana peel carved to look like a dolphin. You might have to wait a little bit to get in, but after 30 minutes here you’ll forget the whole reason you’re wearing a coat that looks like a sleeping bag in the first place.

Jeff Marini


$$$$ 302 N Green St

There’s pretending it’s not winter, and then there’s outright denial. Aba, a Mediterranean spot in the West Loop, encourages this second strategy. It has a partially enclosed rooftop patio with heat lamps, fire pits, and blankets - but if sitting outside in sub-zero temperatures doesn’t sound appealing, the inside of the restaurant has so much foliage that you can pretend you’re in Fern Gully. If only the people who drive five miles an hour on Lake Shore because they see one flurry could be as deep in denial as you are.

The Duck Inn

$$$$ 2701 S. Eleanor St.

Yes, the specialty at this American restaurant in Bridgeport is duck. And yes, this is another spot with a dome, so you can sit inside while you’re technically also outside. If you’re wondering the difference between doing this and just eating in your car, it’s that the dome has better food and fewer empty Starbucks cups. Plus, it has a fancy name - “The Duck Chalet.” You can reserve it for groups of four to eight people, with dinner and brunch packages starting at $55-$75 per person.

3 Arts Club Cafe

$$$$ 1300 N. Dearborn St.

Hanging out at 3 Arts during the winter is like being in the terraformed biodome our great-great-great-great-great-great-grandchildren will be living in after they’re forced to flee Earth. Just with more expensive couches. It’s a huge space with a glass ceiling, and lots of full-sized trees surrounding the tables. Come to the all-day cafe here for breakfast or lunch (with dishes like soft scrambled eggs and truffled grilled cheese), and to discuss key topics like how you’re going to tap the sun’s core for energy.

The J. Parker

$$$$ 1816 N Clark St Fl 13

Rooftops are an important part of enjoying summer in this city, because you get beautiful views of the skyline and the lake, and you can eat and drink outside without being bothered by buses or our fragrant sewers. But trying to hang out on a rooftop during the winter is like being trapped on the ski lift from Frozen (the 2010 horror movie, not the lovable Disney cartoon, which only becomes a horror movie once you’ve watched it 300 times). All that being said, The J. Parker in the Hotel Lincoln is a rooftop bar that’s perfect for winter - because it’s completely encased in glass, giving you a 360-degree view of city, and probably even some vitamin D.

Christina Slaton


$$$$ 12 S. Michigan Ave.

Cindy’s is another rooftop (in the Chicago Athletic Association Hotel downtown), and it has one of the best views of the city. So it’s a great place to take a group of out-of-towners for brunch or dinner, impress them with our skyline, and hope they don’t notice that Lake Michigan looks like it might be where they filmed the The Terror. On warmer winter days (a.k.a. False Hope Days), they have fire pits and warmers so you can hang outside and act like it’s not 11 degrees. Who knows, you might even be able to see someone breaking into your car.

Happy Camper

AmericanBar FoodPizza  in  Old Town
$$$$ 1209 N Wells St

Remember when you were a kid and you set up a tent in the backyard and acted like you were camping in the woods? Happy Camper is a pizza place and sports bar that lets you play pretend in the same way. This place is from the same owners as Homeslice, and while it doesn’t have a patio, it does have design touches like tire swing barstools and a full-size airstream camper. You won’t quite earn points for being a survivalist, but at least you can come here and actually enjoy yourself. Although depending on how bad it is outside (or how much you drink), you still might need someone to come get you.

Sandy Noto

Paradise Park

$$$$ 1913 W North Ave

This is the newest restaurant in the trifecta of themey pizza places that includes Happy Camper and Homeslice. Paradise Park has the same menu of tasty pizzas, salads, and bar snacks, and the theme here is literally “trailer park.” The outdoor patio is decorated with swings, lawn furniture and ornaments (like pink flamingos), and a Winnebago - plus, it’s heated and covered. So you can rest easy knowing that winter doesn’t have to interfere with your dreams of using a “pushin’ broom” to turn the lights off in your RV.

Sandy Noto

Lonesome Rose

$$$$ 2101 N. California Ave

You know that friend who moved to California a few years ago and never misses an opportunity to mention that he went to the beach in January? That person is really annoying. So when it’s the middle of winter and his sun-drenched pictures of tacos are making you jealous, head to Lonesome Rose. It’s a Tex-Mex restaurant in Logan Square that has a bright interior filled with plants, along with some very good fish tacos. Add in an order of queso and some excellent cocktails, and you can pretend you’ve taken a long weekend away. Then call your friend and tell him you hope he’s not too worried about all the earthquakes.

Sandy Noto

Summer House Santa Monica

$$$$ 1954 N Halsted St

We’re on the fence about how much this place actually allows us to pretend it’s not winter. Mainly because it has a literal countdown of days left until summer posted on the wall, which forces us to relive the disappointment of all the false springs. But it can’t be denied that the California theme, large skylight, and avocado-heavy menu do help a little bit. Plus, there’s also a case full of really tasty baked goods. And not even a terrible Chicago winter can ruin the joy of eating a brown butter Rice Krispy treat.

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