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A Guide to Chicago in the Cold

Guide to Chicago in the Cold

There’s a reason Drake’s lyric is not,

Weekend in Chicago, tryna study by the pool.

Even from the beginning of the time, it’s like I’m always in Chicago in the middle of January. This has become such a clear pattern that our followers have started tweeting at us, “Why are you always in Chicago in winter?” Hah. That is a great question.

So, in keeping with my annual trip to the arctic tundra Chicago, I’ve been running from business to business, strategically planning crosswalks and occasional Walgreens stops to warm-up (and look for more chapstick), and sitting in coffee shops, or any indoor establishment way past our warm welcome. But it is all good though, because as Kristen Newman, author of What I Was Doing While You Were Breeding, would say,

You gotta do the thing, in the place.

And I guess Chicago’s “thing” is frostbitten toes, numb fingers, and sore earlobes. So as my fingers slightly warm up as I type at a turtle’s pace, here is my good friend Dom and I’s guide to Chicago…in the cold.

Holiday Jones

[See also: How to Spend a Day in Wicker Park]

Our home-base, and also my second time staying here. This hostel is the kind of hostel I’d want to take my skeptical family to. There’s an empanada café at the entrance, where I ate spinach and cheese empanadas daily and where a former New Yorker-turned-Chicagoan wrote us a list of cool things to do in Chicago – in other words, she basically came up with this entire blog.

Holiday Jones Chicago Review | Guide to Chicago in the Cold

Garfield Botanical Conservatory

Imagine it’s 5 degrees fahrenheit and you’re trying to do something off-the-beaten path – aka a @damonandjo video. When my friend Dominique came across the Garfield Botanical Conservatory, we looked at each other and shrugged, “Why not?” We arrived expecting to have to awkwardly give a donation (always wondering if it’s enough), but we found it was only $5. I think the botanical conservatory in my hometown of Fort Wayne, Indiana even costs more and is two times smaller. This is one of those places you have to walk slowly and kind of get lost in your mind, really looking at all the details of the plants. If you simply see the plants as just plants, you’re not going to enjoy this one. It’s an awesome place to feel outside inside the winter time.

Chicago Garfield Botanical Conservatory 6 | Guide to Chicago in the Cold

Chicago Garfield Botanical Conservatory 6 | Guide to Chicago in the Cold

Chicago Garfield Botanical Conservatory 5 | Guide to Chicago in the Cold

Chicago Garfield Botanical Conservatory 4 | Guide to Chicago in the Cold

Chicago Garfield Botanical Conservatory 3 | Guide to Chicago in the Cold

Chicago Garfield Botanical Conservatory 2 | Guide to Chicago in the Cold

Chicago Garfield Botanical Conservatory | Guide to Chicago in the Cold

Magnificent Mile

C’mon, we had to. No, we literally had to because I really did show up to Chicago with a baby coat, no gloves, no scarf, and nothing to protect my ears.  I drug Dominique around Magnificent Mile, Chicago’s 5th Avenue, going from store-to-store until we reached the bridge with the picturesque view of the Chicago river and skyscrapers, where we didn’t stay too long because, again, imagine the wind power near a river when it’s 5 degrees outside. That’s ok, Chicago, you’re still beautiful – although my skin now isn’t.
Chicago Magnificent Mile | Guide to Chicago in the Cold

Pequod’s Deep-Dish Pizza

I’m not an extreme foodie, so I can’t exactly tell you if this really was the best deep-dish in all of Chicago – although the employees at the hostel seemed to believe so. Last year, I ate a pizza at Chicago pizza chain Lou Malnati’s, and was impressed that even such an obsessed health-freak like myself could manage to eat a whole-wheat, gluten-free if I wanted, deep-dish pizza. At Pequod’s, I didn’t get that option, but I still got a gooey cheese, basil, and saucy deep-dish that I appreciated in the moment, and slightly despised afterwards when I had continuos stomach pains. Yum.

Pequod's Chicago Deep-Dish Pizza | Guide to Chicago in the Cold

The Bean

The Bean, or Cloud Gate, is one of Chicago’s biggest tourist attractions. Not often do you get to snap selfies in a jellybean shaped public sculpture, but 2004 Chicago decided that needed to change. I like The Bean, cuz it’s different. Yes, it’s almost always packed with other tourists but it’s one of those “things to see” that is both a tourist attraction and a piece of art when you want it to be.
Literally chillin' at the Bean | Guide to Chicago in the Cold

Nicki MInaj at The Bean | Guide to Chicago in the Cold

The Bean | Guide to Chicago in the Cold

Wicker Park’s Milwaukee Ave

The staples of a quintessential hipster neighborhood are as follows: vintage thrift stores, used book stores, coffee shops with couches, unnecessarily expensive restaurants, and probably a donut shop. Wicker Park’s Milwaukee Ave and immediate area around the Damen station has got it all. My favorites: Filter Café,  Stan’s Donuts, and Myopic Books.

Damon Dominique Damen Station Chicago | Guide to Chicago in the Cold

Filter Cafe Milwaukee Ave | Guide to Chicago in the Cold

Stan's Donuts Damen Station | Guide to Chicago in the Cold

La Colombe Coffee Roasters Damen | Guide to Chicago in the Cold

Damon & Damen | Guide to Chicago in the Cold

Damen Station Chicago | Guide to Chicago in the Cold

Dominique and I also managed to hit up Kingston Mine’s Jazz club, the Design Museum in the Loop that really wasn’t much of a museum at all,  the Streeterville Cinemas to see La La Land for a second time, and the Arcade in the same building to brush up on our knockoff DDR skills ($10 gets you about 7 games.)

On my next trip to Chicago (for winter, most likely), where should I go?

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  • winston

    You hit a lot of the good stuff. There’s more great stuff for warmer seasons that is free. The Chicago Botanic Garden is far away but free and BEAUTIFUL. Ravinia (outdoor concert venue) is nearby and quite a great place for an evening picnic on the lawn while listening to the Chicago Symphony Orchestra or your favorite acoustic performers live (not free). There are some cool Frank Lloyd Wright homes (not free). The University of Chicago main campus in Hyde Park is incredibly pretty and also eerily futuristic in some parts (free); there are lots of little cafés to check out while you are there. Walking, running, or biking the lakefront trail is incredible; in the summer, there are often pickup volleyball games there to join in on (free).

  • Ivan Contreras

    I want to go to CHI now

  • Excellent recommends, I just got back from Pequods and will soon be sharing my notes from Chicago as well! 🔮🙏

    http://www.patientexplorers.com

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