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Chicago Steez: An Insider’s Guide to the Best Winter Dinner Spots

Chicago Steez: An Insider’s Guide to the Best Winter Dinner Spots

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Chicago Steez: An Insider’s Guide to the Best Winter Dinner Spots

I can’t pretend to be unbiased on this one: I’m a Chicago girl - now and forever - and the 312 is v close to my heart. The raunchy summer heat rolling across Lake Michigan, the nights strolling through freezing-beyond-belief winter chill, the endlessly delicious eeeeats in Lincoln Park, Hyde Park, the Gold Coast, the weird off-kilter suburbs populated with shady-but-smoke show ramen bowls and falafel sandwiches. These are the snippets which filled my childhood (not to mention that I grew up in my mom’s catering kitchen in the West Loop). So basically: Chicago is dear to me and its cuisine is the overture to the cinema of my life, you dig?

I’m going to share the best spots for you, yes you, to enjoy in the depths of winter. I’m talking about negative 20 wind chill, four of your grandmother’s Sonia Rykiel sweaters wrapped around you, cold as-a-b evenings when the only solution is a rich Pinot Noir and a bowl of something miraculously steaming delivered into your waiting hands. 

Let’s begin, class.

ATHENIAN ROOM

Athenian Room is the single most comforting dining experience you’ll ever have. When you walk in, you’ll be greeted by Anna (hi Anna!) who will usher you past huge tilting gyros orbs (the flames won’t lick ya, don’t worry) to a cozy lil table in the corner. From there, you’ll order off a plastic menu depicting ancient gods and settle on a "villager’s salad", some woefully (and deliciously) salty taramasalata, thick cut fries, and a gyros platter, hamburger or the chicken "kalamata style". Someone will retrieve a Sam Adams from the bar next door and you’re on your way. Equal parts screaming babies, high school run ins and criminally yum Greek meat, this is an OG Chicago favorite. 

Photo credit: Yelp

MON AMI GABI

Mon Ami Gabi is a French bistro nestled into the first floor of a Chicago apartment building. It’s the kind of spot where you’ll be sandwiched between old ladies in knockoff Chanel, with 4 layers of lipstick on the rims of their martinis. Which is to say, it’s glorious. Between the piping hot baguettes with baked garlic and pats of butter, escargot, steak frites, and deep leather booths, it’s a dreamy scenario. 

Photo credit: Steve Dolinksky 

PITA INN

Pita Inn - a diamond in the rough and an RCP favorite. Granted, it’s not Chicago proper (it’s in Skokie) but it’s totally worth the shlep. What you're in for: the perfect consistency of the hummus (a 50-50 split between silky and satisfying), the crispness of the falafel as it comes right out of the deep fryer, the jazzy, fizzy Coke from the fountain and the Jerusalem salad, diced ever so evenly and swimming in a little pool of some Mediterranean dressing (what is in there?). Aaaand the entire meal costs maybe $8. Gas up your whip, it’s time to go. 

Photo Credit: foodspotting.com

PISOLINO

Pisolino is a gem. It’s a newcomer to Chicago’s Avondale but is quickly becoming a neighborhood fave. The dishes are soulful but beautifully light - from the crispy, heavenly, oily “Fata Madrina” pizza with onion, capers, stracciatella, mozzarella, basil, tomato puree (seriously some of the best ‘za in Chicago, need to be real with you) to the al dente orecchiette with fennel sausage. Throw back a little Chianti and let the good times roll. 

Photo Credit: Rachel DeMarte 

PICCOLO SOGNO

Piccolo Sogno - as elegant as it is tasty. So good, in fact, that the last time I was in there I spotted Mark Wahlberg having a drink at the bar (sorry Marky Mark, had to be said). Featuring an impressive all Italian wine selection and rustic food that emphasizes simplicity and locality, it’s the perfect end cap to a blustery day in freezing winds. Word to the wise: you’re going to order the cecina fritta and the tagliatelle bolognese. 

Photo Credit: Serious Eats

That's the end of our tour, friends, but if (when) we're hungry (circa 1am) we can always hit up Weiner Circle for a Chicago dog with celery salt and sport peppers. It's kind of mandatory. 

Athenian Room,
Mon Ami Gabi,
Pita Inn,
Pisolino,
Piccolo Sogno

About the Author

Hi! I'm a writer, producer and storyteller. I'm the creator behind Yum Yum Fun - an experiential food blog at the intersection of adventure, memoir, and delicious eats. I've lived in Chicago, Baltimore, Rome, San Francisco and New York - and have used food as a means to explore them all. V excited to be part of the Chowhound editorial crew and for the #YYF trips ahead. Peep the adventures on IG: @rcpatrizio