A Month of Remote Work in Chicago: Q&A

We completed our second month of travel remote work!

If you aren’t familiar with our situation, my partner and I lived in San Francisco and are now digital nomads, traveling through a few different cities this summer and fall.

We started in Denver for the month of July and then traveled to Chicago for the month of August. The density of the city was shockingly different at first, but we soon adjusted to our city views, visually rich morning walks, and plethora of options for food and entertainment in an around our building.

Chicago is a wonderful city, especially in the summer. The lake has crystal clear water and sandy beaches, famous architecture can be found on nearly every city block, and there are so many restaurants and bars to try. We thoroughly enjoyed our stay.

Here are a few elaborations on our trip- question and answer style!

How did we rent our unit?

We rented this month through Airbnb. We negotiated a monthly discount with our host and loved how vibrant our neighborhood was. We also had great views from our spot!

Where did we stay? What did we like the most about our rental unit?

We stayed in the River North neighborhood of Chicago in an apartment tower. The complex was about two blocks from the Magnificent Mile, closer to Trader Joe’s, and near public transit. We thought this was a great area for a temporary stay as it was a bit busy and close to the tourist hub, but we loved the proximity to grocery stores, cafes, and activities.

Our unit had one bedroom, a spacious living area, and office nook. We enjoyed the complex’s gym, outdoor pool, and rooftop deck with BBQ areas.

What restaurants did we like?

Rooh (randomly ended up here and the food was SUPERB)
Bar Avec (cute rooftop)
McDonald’s (this is an honest recommendation; their downtown location is beautiful!)
Fairgrounds Cafe (super cute cafe with many seating options, including swings, and coffee flights)
Velvet Taco (so many strange, but delicious flavors)
Duneyrr Fermenta Brewery (deliciously combines the fermentation of wine and beer)

What restaurants didn’t live up to our expectations?

Urban Space Food Hall (food was delicious, but there are so many vacancies!)
Starbucks Roastery (gigantic lines and for a non-coffee drinker, not too many other exciting options)

What tourist sites do we recommend?

Art Institute of Chicago (extensive museum with iconic works of art that everyone will recognize)
Chicago Architecture River Cruise (there’s way too much hype for this attraction, but it was fun and informative)
The Second City- (attend a drop-in class or an improv jam (I went to both!))
John Hancock Tower Restaurant (go at dusk for beautiful views and twinkling lights)
Wrigley Field (Iconic. Arrive early to grab a drink in the neighborhood)
The River Walk (beautiful views and a lovely place to enjoy lunch or an after-dinner drink)
All of the architecture!! Mies Van der Rohe, Jeanne Gang, & Frank Lloyd Wright rule this town

How did we get around?

Our feet!
Uber and Lyft Cars (+/- $12 within the city)
Zipcar for longer day trips ($7 monthly fee, plus $150ish a day to rent a car with insurance and gas included)
Public transit- we took both trains and busses

Favorite day trip?

Edith Farnsworth House
We reserved our tours in advance.
Drove through Utica and grabbed lunch and a drink on the way back.
We drove about 40 minutes farther to visit Starved Rock State Park. We hiked an easy path through a few of their beautiful canyons.

Favorite Unexpected Find?

The Green Mill and the Paper Machete
The Paper Machete is inspired by the “Living Newspaper” plays and showcases burgeoning comedic and musical talents with a nod to current events. It was unbelievable, quirky, and so much fun.