This family-owned coffee company does mostly wholesale business these days — its roastery is in Avondale — but the cafe where it all began is still in Edgewater, where it’s been for the past 18 years, and it’s still a friendly place to sit with a laptop or a book or a friend and sip coffee and maybe nibble a pastry (from Phlour) and watch the world go by.

A love letter to Chicago’s unique storefront theater scene, The Understudy serves as both a stylish spot for caffeine and a bookstore featuring scripts, memoirs, historical tomes, and more. Co-owners and spouses Adam Todd Crawford and Danny Fender (an actor and stage manager respectively) unveiled the eagerly-anticipated cafe in 2023. They’ve set the business apart from other coffee shops in the neighborhood with a specialized Ground Control coffee brewer, which creates batch coffee while maintaining the flavor of a pour-over cup. It’s the second of its kind in Chicago, only otherwise seen at Gaslight in Logan Square.

This tiny coffee shop, across the street from Amundsen High School, is cozy and features drinks find nowhere else in the city, many flavors are Filipino. Purple chai comes with ube syrup. The Pandan Paradise combines pandan, vanilla, and macadamia nuts. Furthermore, if you become a regular, the barista will get to know you and craft drink based on your preferences.

Osmium Coffee Bar is the Lakeview sibling in the Dark Matter family, which is spread out all over the city. Enjoy some strong coffee in a funky space with neon lights and graffiti-style artwork. There’s also a patio for outdoor sipping. Dark Matter has locations in West Loop, West Town, and Avondale.

This small takeout-only coffee window has serious seasonal specials that will make regulars come back. For fall, for example, grab a chai-pumpkin cider or a Belgian cookie con panna (a double espresso with cookie butter — yes, cookie butter), whipped cream, caramel, and a Biscoff cookie. Eggnog lattes and more are on their way for winter. One of the most creative coffee shops in Chicago. Might as well go a few doors down and grab a treat from Sugar Moon. You deserve it. There’s a larger location in Printer’s Row where they offer sugar-free syrups.

It’s only been only since January, but the first American location of Soloway Coffee appears to be a runaway hit in Lincoln Park. This Ukrainian chain features croissants and other pastries — like Basque cake, and all the traditional espresso drinks. They also brew Spirit Tea, Chicago’s hometown tea maker.

Ipsento 606, nestled between Milwaukee Avenue and the 606, is always busy. The enthusiastic energy makes a nice backdrop for enjoying a Nutella or Ipsento latte (the latter made with coconut milk, honey, and a sprinkle of cayenne) or a fresh mini-doughnut.

Inside the Kimball Arts Center, this West Coast import serves some of the most creative drinks in town. Concoctions like Defund the Military (matcha, milk chocolate, espresso, bourbon vanilla, milk) make this sleek place special.

The owners of Mano Modern Cafe want to open more locations, using their new formula — a kind of Filipino American spin on Panera Bread. This cozy West Town cafe has lumpia, pastries, and rice bowls. The drinks feature fun syrups like pandan and ube.

Despite its name, there is seating at this charming little West Town coffee shop and art gallery. The coffee is Dark Matter, and the food menu features Do-Rite Donuts, Italian subs, and a meatball sub collaboration with Flour Power, the pasta powerhouse from Schwa alum Wilson Bauer and partner Alice Richter (it’s a few blocks west). There are also vintage 16-bit video game systems set up for Mortal Kombat in case there are gamers in the house who need to kill some time. Fatality!

Metric Coffee opened its first cafe in 2016 at its West Town roastery, where it serves coffee brewed from freshly roasted beans and doughnuts from Brite. There are only a few seats indoors, but during warmer months customers can sit at sidewalk tables. The cafe gives baristas a chance to serve experimental drinks that other cafes don’t have. The team is working on a major expansion, including an all-day cafe in, that’s set to open in Avondale. When that space debuts, the West Town cafe with close.

The joy of Vietnamese coffee isn’t exactly a secret, but Chicago’s community of spots serving versions of the sweet, buzzy beverage seems to be growing at a noteworthy rate. Among the strongest contenders is Vietfive, where robusta beans are sourced from the owners’ family farm in Buôn Ma Thuột and brewed into hair-raising hot or iced drinks.

One of the first Black- and women-owned record labels in America, Vee-Jay Records holds a historical niche in Chicago’s South Loop. Taking over Vee-Jay’s former headquarters is Overflow Coffee and the space is decorated with memorabilia from the space’s past. This gives the space an incredible feel, and the drinks are always solid with syrups made by staff.

This neighborhood cafe grinds out some of the city's best coffee using beans procured from across the world, which it sells by the pound.

Chicago entrepreneur Trez Pugh oversees a burgeoning empire of local coffee shops with his chain Sip & Savor, which has five locations across Bronzeville, Hyde Park, South Loop, and Edgewater. A go-to for strong brews and a community-friendly atmosphere, the 47th Street location also recently became a shared space with Turner Haus Brewing, which brought a rare Black-owned taproom to the neighborhood in late 2023.

This European-style cafe on the University of Chicago campus features a full assortment of coffee drinks and pastries, plus breakfast, lunch, and wine. It's a collaboration between Kevin Heisner (Heisler Hospitality) and former Little Branch partner Soo Choi. The patio affords nice views of the Frank Lloyd Wright Robie House.

Kusanya Cafe opened when Phil Sipka came over from Robust Coffee Lounge to give Englewood a coffee shop and alternative to fast food. He uses beans from Bridgeport Coffee and serves sandwiches and all-day breakfast. The coffeehouse also hosts community events, like open mic nights and yoga classes.

Located across the street from the South Shore Cultural Center and just a few blocks from Lake Michigan, South Shore Brew is a bright, sunny space that serves up a solid menu of coffee drinks, including the surprisingly good coffee lemonade, as well as oatmeal and panini sandwiches.

Afro Joe’s has been a revelation since Kendall and Aisha Griffin open their first location in Auburn Grehsam. Great food — the short-rib grilled cheese is amazing — quality coffee, and a community gathering space; places like this are sorely needed in the neighborhood. They’ve since moved to Beverly and have continued to perfect their formula.