Working in Chicago: America’s metropolis

Commonly referred to as the Second City, Chicagoans will confidently (and politely) argue that their home is second to none. Clocking in at over 2.7 million residents, Chicago is America’s third largest city, and possibly its best metropolis. Cleaner than NYC, more accessible than LA, and more affordable than San Fran, Chicago offers big city life amidst a warm, friendly atmosphere.

Chicago is and has always been a welcoming home for transplants, many of whom are looking for a work-life balance without having to sacrifice their careers or the thrills that only a big city can provide. What makes people stay though is the quality of life they can have in Chicago. It’s often praised for its ample access to green spaces, exceptional transportation system, a world-class food scene, numerous cultural offerings, art spaces, and more. But what really makes the world’s best and brightest call Chicago home is the midwestern values and positive attitude that’s put on display daily.

There are infinite reasons to call Chicago home. Here’s just a taste of what makes working remotely in Chicago so special.

Work friendly cafes: kick back, grab a coffee, connect to the free WiFi, and let’s get some work done.

Botanical Cafe

  • Winters in Chicago are cold (very cold) which is why during those gray months it’s important to cherish the places that make you want to get out of those sweats and hit the streets. Enter Botanical Cafe: part cafe, part oasis in the winter months that is packed floor-to-ceiling with lush greenery. While enjoying your cortado, you’ll be surrounded by monstera leaves, cacti, succulents, palms, you name it. Best of all, this cafe is also a part-time plant store, meaning you can take some of that greenery home with you.

Hexe Coffee

  • Hexe Coffee is the ideal spot for those coffee aficionados who are looking for a truly special cup of java to get them through the workday. Roasted and barrel-aged in-house, Hexe focuses primarily on specialty coffees, which offer some new and exciting flavors. With its industrial feel and ample indoor and outdoor seating options, Hexe is the perfect place to focus on your to-do list.

Good Ambler

  • Few places hit so many sweet spots for remote workers as Good Ambler. Literally, this place does it all. Part cafe, part bakery, part chocolatier, Good Ambler is a large and welcoming space that’s open seven days a week. It offers an array of sweet and savory pastries, hand-crafted assortments of individual chocolates, house-made candy bars, cakes, and everything else your sweet tooth can handle.
Chicago Dropboxers gathering for coffee

It’s happy hour! Well, almost… Here are some great places to grab a drink while sending those last few emails.

Hopleaf Bar

  • Nothing beats a cozy pub to cap off the workday, and Hopleaf may just be the perfect one. Offering Belgian-style pub grub and a spectacular selection of Belgium’s best beers, Hopleaf always hits the spot. Not to mention, Hopleaf’s no TV policy means you can finish all those last-minute tasks on your to-do list in peace and quiet.

Three Dots and a Dash

  • Even though winters can get 20 below freezing, that doesn’t mean you can’t feel like you’re on a tropical island. Three Dots and a Dash is world-renowned for being one of the nation’s best tiki bars, and is perfect for meeting colleagues during happy hour to discuss workflows… all while sipping down some Zombies.

The Welcome Back Lounge

  • A relative newcomer to Chicago’s hipster scene, The Welcome Back Lounge is a ’70s and ’80s-themed bar that makes everyone feel welcomed. Their outdoor patio is our favorite spot to enjoy happy hour drinks and no-fuss grub like mini-corn dogs from this funky establishment’s outdoor bar. Spoiler alert: the bar is a technicolored, neon bus. Also, if you want to start the week off right, don’t forget to hit up their bingo on Monday nights, where a portion of the proceeds will go to a rotating charity.
Chicago Dropboxers gathering for coffee

Embrace all the culture that Chicago’s rich history has to offer


  • The city might be known for its frigid winters, but nothing’s quite as lovely as a Chicago summer. SummertimeChi makes the most of the few months of warm weather with a roundup of all the can’t-miss cultural, arts, music, nightlife, and culinary events for you to relish. If spontaneous outings are more your thing, you might want to take in the beautiful night air at a Cubs game at Wrigley Field, join a Chicago Sport and Social team for some friendly competition, catch a comedy show at Second City, or hit Lakefront Trail for however you like to get your cardio in.

Art Institute of Chicago

  • When people think of the nation’s best art museums, the Art Institute of Chicago always comes to mind. Known as one of the city’s most important hubs for arts and culture, the Art Institute of Chicago displays close to 300,000 artworks in its permanent collection alone, in addition to the impressive repertoire of rotating exhibits throughout the year.

Chicago History Museum

  • Founded in 1856 by the Chicago Historical Society, the Chicago History Museum proudly holds the title for being Chicago’s oldest cultural institution. Housing millions of historical objects, images, and documents, the museum is devoted to “collecting, interpreting, and presenting the rich multicultural history of Chicago, as well as selected areas of American history.”[1] It’s a wonderful way to spend a day learning about this important city’s rich and impactful history.

Museum of Science and Industry

  • The Museum of Science and Industry is one of the world’s largest science museums, where attendees can explore over 400,000 square feet of hands-on exhibits designed to spark scientific creativity and your imagination. Step inside a simulated tornado, explore the mirror maze, check out the restored U-505 German submarine, or immerse yourself within a simulated coal mine and a recreation of a Chicago street at the turn of the century. Honestly, you’ll never experience a dull moment at this museum.
Dropboxer Katherine biking around the city

Working remote at Dropbox

At Dropbox, our Virtual First policy is here to champion your successes, personally and professionally. And there’s no better place to reach your career goals than in America’s favorite metropolis. Come meet us in Chicago, and join a fast growing workforce of career-minded individuals who cherish all that the big city has to offer.

You can check out job openings here.



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