This is part of my remote work travel series where I review places I visit as a digital nomad. Check out the rest of my posts and follow me on Instagram, YouTube, Substack, or on TikTok for more travel content! This post contains affiliate links*, meaning I may make a small commission at no additional cost to you. Thanks for supporting my blog!

I'm writing this from the Chicago airport, awaiting my flight to Barcelona — aka, the land of Gaudí and paella. I'm looking forward to eating only tapas and exploring this city for the next week!

As part of the first leg of my trip, I've spent 48 hours in Chicago, and wanted to share some favorites if your travels wind you up in the windy city:

Where to Stay in Chicago, Illinois for Digital Nomads and Remote Workers

As a millennial, I have a bit of an allergy to traditional hotels. In the past, I’ve stayed in Airbnbs and other unconventional dwellings, but for this quick trip I wanted a space that was affordable, good for a short-term stay, and in a walkable location. 

We landed on Selina (now since closed), a remote-worker/digital nomad-forward accommodation that has co-working spaces, phone booths, and other work-live-laugh-love traveler amenity favorites. It was located right next to Magnificent Mile, and a quick walk to Oak Street Beach and Millennium Park. 

I’ll be honest and say that this location had a great co-working space, but the rooms left some things to be desired. However, it was affordable and the location was great, so if you’re only in Chicago for a few days, it’s a good choice. Otherwise, you might want to pick another accommodation for a longer stay. The next time I return I’m going to try Kasa* — which looks amazing and is in the same are.

RELATED: The Best Travel Cards for Digital Nomads

Where to Eat for Digital Nomads in Chicago, Illinois

As I only spent 48 hours in Chicago, I only have two dinner places to recommend:

• Ramen-san. This was one of my favorite ramen spots I've been at in a while -- definitely try their crunchy tofu bun and vegetable ramen. Cool spot, great food for a casual dinner.

• Alinea. This restaurant won Restaurant of the Year -- the same year that the head chef lost his sense of taste due to an illness. His story is really cool (and shared on Netflix's Chef Table), and worth the trip if you're a foodie. Reservations are hard to get and you'll need to book way in advance (like, months in advance.) Their signature dish is the banana split "paint" where they paint a silicon mat like a canvas and it's an edible dessert.

I did break my veganism and do the deep-dish pizza thing — on two separate occasions — but I was very underwhelmed by the gumminess of the cheese and the dryness of the crust with the two famous places we tried. I’d recommend instead hopping on a flight to Naples and getting a 6-euro gigantic slice of some of the best pizza you’ll have in your whole life.

What to Do in Chicago, Illinois for Digital Nomads

For full transparency, I probably won’t need to come back to Chicago again. I wasn’t a fan of the city and other American cities have more things to do, but out of everything we saw and did these were my favorites:

• Ghosts and Gangsters walking tour.* This tour was run by my favorite tour guide of all time, Andre (and I've been on quite a few tours!) and this hilarious history of Chicago's crime lords was fun and dynamic. The tour stops at a former speakeasy and ends at the Chicago Cultural Center, and you'll definitely get your steps in as Andre tells you all about how Al Capone wielded his "Chicago typewriter" to terrorize opposing gangs!

• The Art Institute of Chicago*. I'll be honest: I'm not really a museum person if there isn't a story-based guided tour involved, but the Art Institute has some fancy paintings if you want to catch some Monets and Van Goghs up close. They also have a Van Gogh special exhibit up now.

• I missed the American Writers Museum*, so if you're wanting some writer history that might be something to add to your list, too.

Chicago is a bookish city, and this quote was etched into the ceiling of the Chicago Cultural Center (which was formerly a library, and is home to one of the largest Tiffany glass domes in the world):

"Books are the legacies that a great genius leaves to mankind which are delivered down from generation to generation as presence to the posterity of those who are yet unborn."

-Addison

There was another quote that I can't find, but translated to be something like, "what was learned yesterday but remembered today is wisdom gained."

*chef's kiss*

For the last few years, I've joked to my partner Kyle that I'm on a quest to understand what "Books 2.0" will look like in the future.

In reality, it's evident that while the form of how we share our ideas may change, the experience of absorbing curated, long-form ideas and stories from our peers is and remains a deeply human experience.

Write on, fellow authors --

-- and I'll write to you next from Spain! ☀️

Thanks for Your Love and Amazon/Goodreads Reviews of My New Book

🙏 I also wanted to say THANK YOU to those of you who are leaving reviews on my new book, Six-Figure Freelance Writer.

The love is so appreciated -- thanks for playing a pivotal role in helping others find the book as well and furthering their journies as freelance writers ✨ If you haven’t already, please leave a review for me on Amazon and Goodreads.

Thank you!

If you liked this post, be sure to subscribe to my newsletter and check out the rest of my remote work series. You can also follow me on Instagram, Twitter, or on TikTok to join me in my journeys in real-time. I can’t wait to continue to share my travels with you!

✍️ Find High-Paying Writing Jobs on My Job Board

Lots of cool writing jobs come across my desk — and I'm here to share these curated opportunities with you. Want to work remotely from Paris or at home in your PJs? Subscribe now to get high-paying writing work straight to your inbox!

Pin for Later!

p.s. I create my blog voiceovers and my podcast episodes using the tool Wondercraft AI, a text-to-speech tool that speaks in YOUR voice. 🎙 Use my code SUTO50 or this link to get 50% off your Wondercraft AI subscription!*

*These are affiliate links. Thanks for supporting this blog!