The Freelance Creative

The 5 Best Coffee Shops for Freelancers: Chicago Edition

Working from a coffee shop may seem romantic to those who don’t do it on a consistent basis, but it can often be a disaster. Slow WiFi, no outlets, uncomfortable seats, and terrible music are just a few of the elements I’ve encountered trying to write remotely. And it’s hard to research the best places to work when online reviews usually only cover the quality of coffee and service.

So I decided to investigate the old-fashioned way—by pounding the pavement at more than 30 coffee shops in my city, Chicago, and subjecting each place to the following criteria:

—Free WiFi

The only time I’m paying for WiFi is if I’m desperate to finish work on a plane.

—Plenty of outlets

My laptop is old and does not hold a charge for long. I often carry around an extension cord thanks to a severe case of outlet anxiety.

—Great ambiance and lighting

If I’m leaving my house, I better be headed somewhere that inspires me to be productive.

—Food made in-house

Baked goods can only go so far. I need some serious lunch options beyond scones, cookies, and croissants.

—Good music

I always carry headphones just in case the music sucks, but I’d rather enjoy some legitimate ambient noise.

—Plentiful, comfortable seating

I’m not asking for much, but if my butt falls asleep after 10 minutes, we’re in trouble.

“Quality local coffee” is always in the back of my mind as I visit these shops, but I can’t get too picky. After indulging in many iced coffees, cappuccinos, and croissants over the past year, I’ve landed on the top five freelancer-friendly establishments in Chicago:

1. Filter Café, 1737 N. Milwaukee Ave.

This Wicker Park free-WiFi haunt is about as reliable as you can get. The space feels roomy and cozy and mixes vintage couches and lamps with traditional tables and chairs. Also, there are enough outlets to power a small army of freelancers. Thanks to the kitchen, you can work a full day and go from a tofu scramble to a Filter Salad to a spicy steak wrap with sweet potato fries. Filter is cash only, but they accept LevelUp, which lets you pay with a credit card from a smartphone.

The only unreliable component of this coffee shop is the music selection. Bring headphones just in case today’s DJ irks you.

Image via Diane G. / Yelp

2. Bourgeois Pig Café, 738 W. Fullerton Ave.

Nearby DePaul students often frequent this café, so be prepared for the occasional pajama-clad study group discussion. Beyond that, the Bourgeois Pig is a one-of-a-kind establishment: sandwiches to the left, coffee to the right, free WiFi all over. Above the coffee shop, you’ll find a sequence of cozy rooms mixed among the vintage portraits and woodwork of this historical home. When you’re hungry, head downstairs and pick up a Hamlet, Hobbit, or a Midsummer Night’s Dream—the salad and sandwich menu is full of literary allusions. The food may be a bit overpriced, but the all-day jazz soundtrack should keep you relaxed.

Image via Bourgeois Pig Cafe

3. Heritage Bicycles General Store, 2959 N. Lincoln Ave.

Not many coffee shops can claim to fix your bike while you sip a latte, but Heritage Bicycles General Store can. Whether you’re taking advantage of the bicycle repair shop or the Free Wifi, this light-filled space is hipster catnip, and the music is perfect for that crowd. Seating inside is somewhat limited but overflows onto the sidewalk. Beyond your typical bakery treats, sandwiches and soups from nearby Southport Grocery are available. Warning: You’ll want to buy one of their custom bicycles after spending time here, and they don’t come cheap. But they sure are gorgeous.

Image via Sydney T. / Yelp

4. Dollop Coffee & Tea, 345 E. Ohio St.

Tall floor-to-ceiling windows make Dollop Coffee & Tea a sunny Streeterville destination for getting work done. There’s plenty communal seating, and outlets line the bright and airy space. Metropolis Coffee and Hoosier Mama Pie headline a menu of pastries, sandwiches, and salads also available at Dollop’s South Loop location.

Image via Dollop Coffee & Tea / Yelp

5. Gaslight Coffee Roasters, 2385 N. Milwaukee Ave.

Open spaces and clean lines define this unique space in Logan Square—that and the taxidermy. This coffee shop can be found at the tip of the Fullerton Ave. and Milwaukee Ave. intersection, which means both sides are lined with welcoming windows. Bar seats, a picnic table in back, and traditional table and chairs give freelancers a few different options for seating. A small but thoughtful menu elevates traditional coffee-shop fare with salmon and pimento tartine, scrambled duck eggs with prosciutto, and homemade gazpacho. While the menu sounds incredibly fancy, the space doesn’t try too hard to be hip, and the food is very affordable. Just how Logan Square likes it.

Image via Matt G. / Yelp

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