Drop Pin • Chicago's Coffeeshops & Cafes

Years ago, back in 2012 or so, when I was first getting my bearings as a writer in the scene I often found myself hugely broke. Unwilling to take a 9-5 exit, I often found myself hacking into freelance pieces for various sites and outlets while working from home or the best alternative. Most often, that alternative was a coffeeshop and in the months and years since those experiences of hopping from one caffeine outlet to the next resulted in a largely useless knowledge of some of the best spots to grab a cup almost anywhere in the city. I definitely don't claim to know them all, I'm sure there's a bearded dude with a top-bun in Logan Square that's more cultured, but this is what we think are the best places to get your fix around the city.

Cafe Mustache


Cafe Mustache holds a distinctly special place in my heart. One of the first coffee spots I found myself going to regularly, the original spot at 2313 N. Milwaukee has been a mainstay for years. Between 2012 and 2015 you'd be hard-pressed to find me anywhere else, often making good on the bottomless cup of coffee served in a kitchy mug that would last me from the morning well into the afternoon hours. Recently, it's grown to include a bar and ample entertainment space which is welcome, but has seemed to lose some of the intimacy of the original space. While not the best for much more than coffee, they serve Bridgeport and have some of the best aesthetics Logan Square can offer. Perfect for getting lost in a book on a rainy Fall day.

New Wave Coffee


A mainstay along Milwaukee Ave in Logan Square, New Wave Coffee is admittedly a hit & miss spot depending on the day and time. Despite that, the cafe setting, assortment of seating options and diverse menu that offers sandwiches as well as coffee make it the perfect spot to settle in for a long afternoon to get some real work done. With communal areas it also allows for a welcome meeting space if needed. For me, it would always served as a perfect stop-over to grab a quick bite to eat and a large coffee, my favorite sandwich being the 'Caddyshack' which I can't attest to still being on the menu. Careful in the winter, anywhere near the doors will keep you in a perpetual chill so make sure to find a spot tucked away.

Gaslight Coffee Roasters


While Gaslight may have served as the initial nose-up-hipster hot spot in Logan Square, the spot couldn't be more centrally-located at the corner of Fullerton and Milwaukee and definitely knows a thing or two about their coffee. True to their name, Gaslight roasts their own beans and is hands-on with just about every step of the process, a true coffee-lover's type of cafe. It can be tricky to catch a table or spot to sit so be sure to take a look around before ordering, the bar to the left of the cash registers is actually a fairly cozy catch, offering service while seated. I used to celebrate the end of big stories with their 'Big Hoss' sandwich, a marvel of a bagel sandwich with turkey, jalapenos and god knows what else. Alas, I don't remember seeing it on the menu last time I was through.

Filter Cafe


While Wicker Park may not be the center of creativity it built its name on in the 90s, there are still plenty of solid places to settle in for a cup and some solid work. Among those options, Filter offers the most hospitable setting from which to do your thing. With a full kitchen and living-room feel with plenty of room, it has just about anything you can ask for. Alas, you are in Wicker so time your stops in around the newfound locale depending on the vibe you're looking to achieve. Located ideally between the six corners and Division, it serves as a perfect stop over to bang out a quick blog post or sit down for an interview. They also run tabs if you're trying to avoid the .50 credit card charge.

Star Lounge Coffee Bar


Star Lounge is a gem that sits just off the 'coffee highway' I've assembled here. It's inclusion is necessary though, as it serves as one of the best spots anywhere in the city to get a cup of coffee. They may have taken down the iconic Star Lounge sign, it can now be seen inside, the cafe has maintained a cosistently cozy vibe, with a porch for the summer months, an actual bar to sit at if you're in the mood and an upstairs that offers plenty of room to stretch out. Best tip? Try to grab the spot on the second floor by the window, it's one of the best seats in town. It's also right across the street from Soundscape Studios and has proven a reliable place to camp out if you're early for a session or meeting.

Sip Coffee House


Sip is certianly not the sexiest coffeeshop on this list, but it is certainly one of the most reliable. Tucked away in a residential-looking blue building on Grand Ave, Sip has been a mainstay on my treks across the city for many years now. The main reason? Their yogurt parfaits. Often on a short budget and somewhat health-conscious, eating muffins, bagels and sandwiches all day started making the biking tough and Sip somehow has perfected the parfait which pairs perfectly with this amazing toffee muffin they offer. They also have an excellent reclining chair near the stairs, one of my favorite single spots in town, a quiet upstairs that can be easily overlooked and a pair of patios that make it one of the few places to grab a cup in the summer and enjoy the weather while getting some work done. The family-owned shop also is never without a smile. 

Sawada Coffee


A newcomer to Chicago and the country at-large, Sawada is an interesting escape from your everyday cup of coffee. The first U.S. location of world-renowned coffee connouisseur Hirsoshi Sawada offers a new take on some favorites while introducing new ideas set amongst a very cool industrial build-out in the bustling West Loop. The first noticeable thing about Sawada is their use of green tea-based Matcha, especially in their ever popular Military Latte which is well-paired with the Camoflage doughut provided courtesy of Doughnut Vault. In a quickly-changing neighborhood with spots like Starbucks and Colombe just around the corner, Sawada is a nice escape from the mundane. Careful on the weekends, the new West Loopers often line up out the door.

Kristoffer's Cafe & Bakery


I discovered Kristoffer's Cafe when I moved to Pilsen back in 2015 and since then it has become one of my favorite places in the whole city. The no-frills, family-owned stop is as reliable as it is endearing, allowing for a quiet spot along Halsted to get an array of coffee drinks from an Americano to the surprising Horchata Latte. The staff there is as friendly as can be and it's a real gem, tucked away right on the corner of 18th street and Halsted. Go a couple times and the Kristoffer's team will invariably pre-empt your next order. While Jumping Bean and La Catrina down the way are reliable as well, Kristoffer's possesses a sort of quaint modesty as well as awards for some of the best Tres Leches cake in town. Tip? Try to get the spot in the window up front. 

Bridgeport Coffehouse


Ah, good old Bridgeport Coffeehouse. The no-frills Bridgeport mainstay on the corner of Morgan and 31st has been a solid decision for as long as I can remember and a perfect stop-in for the stories that took me a bt further south than Pilsen. A great variety of options, a friendly staff and a true neighborhood feel makes this one feel like you're right at home. Also, they roast their own beans, and also provide Cafe Mustache with theirs, so you know it's real.