Midwesterners describe Chicago as a “big city with a small town heart.” It boasts many of the same great features as other major metropolises—robust access to public transit, great food and drinks, and plenty of noticeably Chicago backgrounds to show your Instagram followers that yes, you were definitely here.
What’s different is that alongside the hustle and bustle of city life is a deep grounding in community and connection. Each neighborhood has its own little quirks and idiosyncrasies, as well as its own collection of beloved businesses, community groups, and funky scenery ranging from intriguing to… oddly suggestive? Chicago coffee shops serve as gathering spots, deeply ingrained within and committed to supporting people in the surrounding areas.
As you prepare to fly out to Chicago for Specialty Coffee Expo 2024, here’s a non-exhaustive list of what to check out.
Coffee
While expansion often leads to a reduction in beverage quality, we know that when there’s a will, there’s a way. Local staples Metric, Metropolis, Goddess & The Baker, and Dark Matter have managed to continue serving up delectable bean water even as they’ve opened up additional shops across the city. With multiple locations to choose from, it’s easy to work a visit into any of your various Chicago escapades.
Looking for divine food and drink, a pristine interior, and access to nature? It doesn’t get much more curated than the world-renowned Dayglow Coffee. Dayglow sits at the base of The 606, a picturesque elevated trail that comes alive at the start of each spring as Chicagoans emerge en masse from their winter slumber.
Chicago is also home to a number of themed coffee shops, which deliver high quality coffee and tea beverages served up with niche slices of pop culture.
The Brewed, located on the border of Avondale and Logan Square, is a horror-themed coffee shop serving up Halfwit Coffee with a side of frights. As a bonus, the shop is attached via glass door to Bric-a-Brac Records, which sells a wide variety of vinyls and assorted collectibles.
If you’re a fan of Twin Peaks, consider checking out Damn Fine Coffee in Logan Square. With numerous easter eggs to the classic 1990s crime film, this multi-roaster shop will leave you feeling like yeah, I could probably solve a murder today.
Thespians and theater-lovers alike will delight in perusing the shelves of The Understudy Coffee & Books, Chicago’s debut theater-bookstore-slash-coffee shop that’s quickly become an Andersonville staple.
Enter a wormhole into the 1980s with a visit to Wicker Park’s aptly-named Wormhole Coffee. This grungy neighborhood spot offers a variety of vegan donuts, in addition to rotating seasonal beverages. Nestled along a strip of cute shops and restaurants, stop by Wormhole before an afternoon of thrifting or an evening out with friends.
You’ll have to plan ahead to visit the now-renowned Everybody’s Busy, an exclusive-yet-accessible appointment-only coffee shop by 2021 Sprudge 20 Honoree, Melissa Stinson.
Additional fan favorites include Sawada Coffee, Four-Letter Word (often stylized as 4LW), Side Practice, Magnífico, Gaslight Coffee Roasters, New Wave Coffee, and VietFive.
Food
Chicago locals know that the true Chicago pizza is not in fact Deep Dish, as is our reputation, but a classic, gooey, crunchy thin-crust pie—often cut into strips instead of slices. With plenty of accommodations for dietary restrictions, local favorites include Dimo’s, Sarpino’s, and Paulie Gee’s.
Vegans and vegetarians alike will have no shortage of food options to choose from. For seated dining or takeout, check out the selection at Penelope’s Vegan Taqueria, Pick Me Up Cafe, Kopi Cafe, Alice & Friends, Urban Vegan, Kale my Name, Bloom Plant-Based Kitchen, and Chicago Diner (“Meat Free Since ‘83!”). Brand new to Uptown, X Market is a grocery store and food hall-style eatery featuring an all plant-based selection of goodies. For pastries and grab-and-go, you can’t go wrong with Middle East Bakery, Liberation Kitchen, or Sam & Gertie’s Vegan Jewish Deli.
Fans of The Bear inclined to follow in the footsteps of Chef Sydney Adamu should get their stomachs primed for a whole lotta eats. Season 2, Episode 2 featured a montage of Ayo Edibiri’s character dining her way across the city, with stops at Kasama, Avec, Publican Quality Meats, Pizza Lobo, Giant, Lao Peng You, and Margie’s Candies.
Fans of ramen need look no further than Ramen-San. With ingredients made fresh in-house daily and plenty of allergy-friendly offerings, this classic establishment never fails to satiate your palate and your appetite.
No trip to The Windy City is complete without a trip to Portillo’s. Most famous for their Chicago-style hot dogs, the classic eatery has been serving the Chicagoland area since 1963.
To cap off the evening with dessert, it doesn’t get more quintessential Chicago than Jeni’s Splendid Ice Creams. With a rotating selection of flavors, scoops and pints, and many locations across Chicagoland and beyond, make sure to stop in before you head home.
Bars
Though not as much of a late night city as New York, Chicago still has plenty of great nightlife and bars you won’t want to miss.
If beer is your drink of choice, you’ll have to stop by one of Chicago’s many taprooms and breweries. Undoubtedly the most famous is Goose Island Taproom, located in the heart of West Town. With dozens of beers available and a rotating selection of seasonal offerings, there’s an option for every beer lover. Other fan favorites include Solemn Oath Brewery and Half Acre Taproom, which also offers food service on select days of the week.
For a side of arcade games with your libations, check out Replay Lincoln Park or the various locations of Emporium. Both businesses offer a robust selection of beer, alongside select house cocktails and various other alcoholic and nonalcoholic beverages.
Whether you’re gay or simply adore The Gays™, there are queer bars a’plenty in the Windy City, primarily concentrated within Boystown and Andersonville. Looking for gay sports with billiards and darts? The North End is the spot for you. Karaoke more your speed? Spend an evening at Bobby Loves. For a more lowkey evening, check out The Closet, Dorothy Downstairs, Nobody’s Darling, or Atmosphere on a weeknight. If you’re looking for a sweaty rager with tons of dancing and loud music, enjoy an evening of debauchery, drag, and queer fun at Sidetrack, Spybar, Smartbar, Progress, Charlie’s, Roscoe’s, or Hydrate Nightclub.
Chicago also has a collection of themed bars with carefully curated experiences to enjoy. Beauty Bar, themed after a 1960s hair salon, sits within Chicago’s West Town neighborhood. For a mystical evening filled with tarot readings and “eclectic entertainment,” check out Chicago’s first spirit lounge: King of Cups. Step into a ski lounge at Bunny Slope, a “retro private party lounge” located in downtown Chicago.
Return to the prohibition era at Blind Barber, but not until you’ve gotten a fresh new cut. This quaint establishment is a barber shop by day, but as the lights go down, you’ll find something unique: a speakeasy-style cocktail bar behind an unmarked door.
Are you in Chicago, or New Orleans? You won’t be sure during your trip to Storyville, The Windy City’s very own Big Easy-themed craft cocktail bar and restaurant.
Nature & Sight-Seeing
Chicago has a wide variety of museums and tours and is particularly famous for its unique and storied architecture. While you’re in town, check out the Art Institute of Chicago, the Museum of Science and Industry, the Leather Archives & Museum, and climb aboard Chicago’s First Lady for a river boat architecture tour.
Other key sights include Cloudgate (AKA “The Bean”), Buckingham Fountain at Grant Park, the Chicago Riverwalk, Chicago Botanic Gardens, Humboldt Park, and Garfield Park and Lincoln Park Conservatories.
Chicago Has Much to Offer
The Windy City has something for everyone, beyond this non-exhaustive list. Most importantly: have fun, explore the city, and eat and drink as much as you can.
Arielle Rebekah a freelance journalist and creator of Trans and Caffeinated. Read more Arielle Rebekah for Sprudge.
