Poshmark City Guide: Chicago, IL

Not only is this city known for its delicious food but local Poshers dished about all the other hidden gems to check out.


First things first, shopping!

  • Cinnamon Boutique (2104 W Roscoe St)
    “Cinnamon has been open for more than 10 years and is run by a local mom who does a wonderful job giving back to our community. Cinnamon has a beautifully curated mix of casual yet stylish clothes, workwear, evening wear, and even beachwear! I love that I can walk down the street and get anything I might need” – @anneray405
  • Bottomline Boutique (2208 W Chicago Ave)
    “The proceeds of this shop go to support a nonprofit called Bridge to Success that enhances employment opportunities for at-risk, low-income, no-income men, women, and young adults,” says @anneworth522015. Grab your Marc Jacobs, Prada, and YSL items here!
  • Squasht Boutique (2556 W Chicago Ave)
    If you’re all about shopping local, this is your go-to! All the items sold are 100% locally handmade. What better way to find something unique while supporting the local community?


Fuel up before taking on the city.

  • Hero Coffee Bar (Multiple locations)
    Grab your drink and ‘gram it too. These coffee spots are small but mighty with the menu featuring a greek yogurt “salad bar.” One Posher can’t wait to try their new bourbon barrel-aged coffee. Yum!
  • Intelligentsia Coffee (Multiple locations)
    Intelligentsia may be seen around the country but there’s no place like home. It’s deemed as a “Chicago classic,” so take a sip of history.
  • Caffe Streets (1750 W Division St)
    Whether you come for the coffee or the aesthetic, Caffe Streets has it all. This is a perfect spot to turn into your workplace for the day. “The coffee tastes so smooth and delightful, and they’re serious about it, offering pour over, drip, lattes, and clearly communicating the origins of their products,” says @anneworth522015.

Honorable Mentions: The Wormhole Coffee, Ipsento 606


Chicago has some of the best places to meet up with your PFFs!

  • Three Dots & a Dash (435 N Clark St)
    This place was deemed “one of The World’s 50 Best Bars by Drinks International” so you know they HAVE to be good! We’re sold.
  • Kaiser Tiger (1415 W Randolph St)
    The back outdoor patio is calling you and your PFFs names to talk all things Posh. Fun fact: During winter, the entire patio is transformed to a place for everyone to brush up their Curling skills.
  • The Darling (905 W Randolph St)
    This place is quite literally, darling. Head here if you’re feeling a bit fancy. Pinkies up!
  • Punch Bowl Social (410 N Greet St)
    Keep things light in this fun, game center. Grab a drink and play video games, go bowling, have a fun meal with your PFFs in a place with great vibes.

Honorable Mentions: Pops for Champagne, The Northman, City Winery Chicago at the Riverwalk, Sugar Factory, The Map Room, AceBounce, Federales, Soho House Chicago, Goose Island Brewhouse, Rainbow Lounge


Chicago does not disappoint when it comes to food!

  • Bellemore (564 W Randolph St)  
    This place does not lack in food or decor. The food alone will be having you asking for more! Bellemore food is classified as “Artistic American” featuring a menu fit for all tastebuds.
  • Pequod’s Pizzeria (2207 N Clybourn Ave)
    Chicago is known for its deep dish. Several Poshers swear you MUST try this local favorite. “Their caramelized cheese crust is everything!” says @trendyende.
  • Giant (3209 W Armitage Ave)
    Opposite of its name, this restaurant is NOT giant so book your reservations in advance. “Your tastebuds will thank you,” says @anneworth522015.
  • Giordano’s (Multiple locations)
    Another local Posher favorite! Reserve your spot early and get ready for a wait, but don’t worry. It’s worth it! Each deep dish takes approximately 1 hour to finish. You’ll be ready to dive in right away! 

Honorable Mentions: Chicago Pizza and Oven Grinder Company,  Dimo’s Pizza, Kaufman’s, Kuma’s Corner,  The Purple Pig, Dick’s Last Resort, Au Cheval, Gyu-Kaku Japanese BBQ, Legend Tasty House, Flo, RM Champagne Room, Ēma  


  • “Chicago is authentic and fun. Chicago may be the largest city in the Midwest, but it’s home to the nicest people. Chicagoans are very friendly!” – @trendyende
  • “Chicago, often referred to as the Windy City, is known for its architecture, sports teams, and deep dish pizza.  It has a friendly Midwestern vibe, with all the amenities of a big, bustling city. You can spend the day on the beaches of Lake Michigan, explore the history, art, and science at one of the many museums, or shop the day away on the Magnificent Mile.” – @anneray405
  • “We’re friendlier than most cites (at least I think so!!) We love our sports!!  LET’S GO HAWKS!! Go Cubs Go! Da Bears!” – @rockcandystyle
  • “The Windy City is iconic all around the world for so many reasons! Navy Pier, Millennium Park, Sears (Willis) Tower, the historic theaters and architecture, and Wrigley Field Home of the CHICAGO CUBS! Everything you want to do can be done in this beautiful city. It is modern, it is cool, it is hip, and there is something for everyone in this city.” – @valeriemae28
  • “My city is full of great museums and architectures with variety of food. We are a vibrant city with so much to do from riding a bike on the lakefront to having a drink while playing ping pong, pool or bowling to hitting the town for some live music and dancing.” – @alena821
  • “Chicago is a multifaceted city known for sports teams, hot dogs without ketchup, good music and amazing restaurants. I truly believe that Chicago offers options for whatever hobby or interest you may have. Try Googling it to prove me wrong. You may have to go off the beaten path to find that record shop, a Peruvian restaurant, comic store, or 4 am bar that plays Prince and Bowie videos, but it’s out there, waiting for you to find it. My personal favorite part of Chicago is the food. I believe Chicago has the best restaurants in the U.S. Explore Eater Chicago for restaurants that suit your style.” – @anneworth522015
  • “Chicago is a city of neighborhoods. You can go 6 blocks in any direction and be in a totally different environment. If you are a newcomer, don’t be afraid to venture out of downtown. Pick a few key train stops, and get out and walk around nearby. You’ll get so many different experiences and not have to worry about navigating too much.” – @nina_in_the_chi


Suitcase must-haves:

  • Bring a jacket or two (You never know what the weather is going to be like.)
  • A good pair of shoes for dancing!
  • A windbreaker
  • Cash (“Believe it or not but even in 2019 but a lot of the best Chicago hangouts are cash only still. Most have an ATM inside in case you forget. The Boiler Room gives you a free shot of Jameson to make up for the ATM fees!” says @nina_in_the_chi)

Thank you to @trendyende, @anneray405, @clothesliveon, @rockcandystyle, @valeriemae28, @alena821, @nina_in_the_chi, and @anneworth522015 for contributing to the Chicago Posh City Guide.

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