Tales of a Digital Nomad: How I Spent the Summer Living in Chicago

Nothing beats sweet home Chicago—and I’m not just referencing the song. I was born and raised in the Chicago suburbs, and I’ve spent the past five years living at the tippy-top of the city, all the way up in Rogers Park. When John’s music career brought us back to the city for the summer, we were excited to get to experience Chicago in a whole new way: downtown style. 

Here’s how we made the most of this new experience during our three months living in Chicago: 

Where to stay in Chicago

Streeterville, The Gold Coast, and Lincoln Park are great locations to be close to the lake during the summer. We stayed in a gorgeous Landing apartment near Ohio Street Beach and Navy Pier. We were nice and close to the tourist activities we wanted to do but still within walking distance of grocery stores, gyms, and other necessities. Since our Landing apartment came fully furnished, moving in was a breeze. After a few hours of settling in, we were ready for a summer in the city!

It’s cooler by the lake: All the ways to experience Lake Michigan 

Without a doubt, the highlight of spending the summer in Chicago is being so close to Lake Michigan. We were lucky enough to live in an apartment with a gorgeous view of the lake, including the Playpen, a famous area of Lake Michigan where boat owners and renters alike drop anchor to enjoy the few beautiful summer months Chicago has to offer. 

There are so many ways to experience Lake Michigan, and we vowed to try as many as possible and rank them for fellow digital nomads thinking about making their way to Chicago next summer: 

1. Kayaking 

Urban Kayaks provides an affordable and fun way to explore Lake Michigan (or the Chicago River, if you prefer a little more architecture as you paddle along). We chose to take our kayaking journey on the lakefront, and with a two-hour rental, we got more than enough exercise and plenty of spectacular views of the city. The highlight was certainly getting to see Buckingham Fountain from the lake. 

If you have an afternoon and about $50 to spare, I highly recommend taking an urban kayak for a spin. Just make sure to bring a waterproof phone case (or buy one from the kayak rental) so you can snap pics on the boat without the risk of drowning your phone! 

2. The Lakefront Trail 

Chicago’s lakefront trail stretches just over 18 miles from the south side of the city all the way to the Edgewater neighborhood on the north side. The trail is open 24 hours a day and is completely free for the people of Chicago to enjoy on foot, bike, or scooter. A stroll along the lakefront trail is a must-do for anyone visiting Chicago in the summertime. 

If you’re extra brave, you can even try walking the full 18 miles in one day! Bucket list item? Check. 

3. Rent a boat 

No ranking of ways to experience Lake Michigan would be complete without taking the more luxury experience for a spin. While we didn’t get a chance to get out on the famous Chicago Playpen during our time in the city, if you have the budget, I highly recommend hiring a captain to take you out on the lake. 

4. Hit the beach

There’s no shortage of beaches on the beautiful shores of Lake Michigan. Ohio Street Beach is perfect for families; Oak Street Beach is a must-see if you’re from out of town; North Avenue Beach is pure party territory; and Loyola Beach, while a hike, is the calmest, least-crowded option for a quiet day in the sand. Whatever you choose, the beaches of Chicago are not to be missed. 

Where to eat in Chicago 

Chicago isn’t all Italian beef and Chicago-style hotdogs (although you’d be missing out if you didn’t get both during your time in the Windy City)! Here are a few restaurants that might fly under the radar of most tourists but absolutely shouldn’t be missed if you have time to spare while exploring Chicago: 

1. Virtue

Head down to Hyde Park on the near south side of the city to taste some of the best southern food you’ve ever had. Don’t believe me? Consider the fact that Virtue’s Chef Erick Williams was the only Chicago chef to win a James Beard award in 2022—and it wasn’t his first win, either. 

Reservations are harder to come by since his second win, so be sure to book in advance! We were lucky to snag a table on a weekend, and in my many years of navigating a dairy allergy, I’ve never had a restaurant be so accommodating and enthusiastic about guaranteeing I have the full tasting experience while demonstrating complete and utter care toward my dietary restrictions. 

The menu changes seasonally, but you should be able to snag their life-changing mac and cheese and “oh my god” collard greens, regardless of the season. 

2. Avec

Have you ever had a slice of bread that made you second guess every other piece of bread you’ve ever eaten? That’s how I felt eating at Avec. This Mediterranean-meets-the-Midwest restaurant offers incredible plates that are built for sharing. If you’re a “little bit of everything”’ eater who sometimes thinks tapas servings are a little too small, Avec is the perfect restaurant for you. 

Whatever you do, don’t miss the chorizo-stuffed bacon-wrapped dates. It sounds like a lot, but it’s exactly the right amount. Pinkie promise. 

Heads up: Avec has two locations—one more intimate dining experience in the West Loop and one more bar-oriented restaurant in River North. We chose the River North location solely out of convenience, but there is a slight difference in the menu between the two restaurants. If there’s something you have your heart and stomach set on, make sure you check in advance that they’re serving that dish at your location of choice. 

3. Cafe Ba-ba-reeba!

Two words: spicy potatoes. Need I say more? This Spanish tapas restaurant is a favorite among Chicago locals, and for good reason. You truly can’t miss with anything on the menu. 

Unlike Avec, the Cafe Ba-ba-reeba! servings err on the smaller side, so order more than you think you need. Your stomach will thank you.

4. Pequod’s

If you haven’t tried Chicago deep dish, it’s an essential for any visit. Giordano’s is the go-to for tourists, but in my opinion, Pequod’s makes the better pie. They’re famous for their caramelized crust and, in my opinion, the perfect ratio of sauce to cheese. 

Pro tip: Be sure to order ahead of coming to the restaurant or way in advance of when you want it delivered. Deep dish can take up to an hour to bake!

The best music, theater, and culture in Chicago

Chicago is well known for its theater, improv comedy, and live music scenes. With so many options, it was tough to narrow down our can’t-miss experiences of the summer. Here are the standouts that I’d recommend to anyone spending summer in the city. 

1. Millennium Park Concerts

Iconic venue + awesome artists + totally free? Yes, please! Check out the weekly free concerts at Millennium Park. I saw Jeff Tweedy from Wilco on a Tuesday and had the time of my life! Be sure to get there early if you want to be up close—otherwise, sit back on the lawn with a snack and a beverage and enjoy the tunes. 

2. The Art Institute of Chicago

This museum is far more than just a scene in “Ferris Bueller’s Day Off” (although I do recommend recreating your Ferris Bueller moment in front of “A Sunday on La Grande Jatte”). Block off a rainy or extra-hot summer day to wander the museum and see the work of Georgia O’Keefe, Jackson Pollock, Picasso, and Van Gough, along with plenty of contemporary and modern art. 

3. Windy City Smokeout 

This three-day festival brings out the country in even the most urban of city slickers. Located in the parking lot of the United Center, Windy City Smokeout features some of the biggest names in country music and a huge variety of food from 50 different barbeque restaurants across the country. I’ve yet to experience any other festival quite like it!

4. Wrigley Field 

Any baseball fan knows that Wrigley Field is one of the most iconic MLB parks—what you might not know is that they put on some of the biggest concerts of the summer, too! I caught multiple Cubs games and saw Lady Gaga from the same seats I usually catch foul balls! 

Take the Red Line to the Addison stop for easy transportation, or grab a ride with Uber or Lyft (but expect to walk a block or two—the roads will be closed off around Wrigley Field!) 

5. The Infinite Wrench 

If you enjoy live theater, I cannot emphasize this enough: Do not miss a production at the Neofuturarium. The Infinite Wrench is a modified version of the longest-running show in Chicago theater history, “Too Much Light Makes the Baby Go Blind.”

A small cast of actors attempts to perform 30 original plays in 60 minutes. Your program is a menu of plays, which you can “order” by shouting them out. The timer ticks down as they attempt to perform them all, but when it goes off, the show is over, regardless of whether they’ve performed one play or 30. The plays are autobiographical, sometimes hilarious, sometimes political, and sometimes too abstract and experimental to understand. The Infinite Wrench is ever-evolving, different every weekend, and constantly changing. 

So long, Chicago—it’s been spectacular! We are off to wrap up our year in the mountains of Boulder, Colorado! If you’re interested in hearing more about our adventures living with Landing, check out our other blog posts: 

• Tales of a Digital Nomad: How I Spent Six Weeks Living in Seattle
• What I Learned About Being a Digital Nomad in Los Angeles
• Tales of a Digital Nomad: How I Spent Three Months Living in Boulder, Colorado