Can you actually live a little in a super-expensive city while barely spending anything? That’s what I set out to discover. With the rise of remote jobs Chicago offers some interesting possibilities for budget-conscious digital nomads, but is it really feasible? This is a kind of on-the-ground report from my budget remote work trip.
My target: Chicago. My limit: $100 for two days. That had to cover food, getting around, a little bit of fun stuff, and basically, just being there. My “offices” were the main library downtown, a random coffee place, and, well, sometimes a park bench.
I’ve always had this tricky relationship with big cities – wanting to do everything but knowing what I can realistically afford. Chicago? Forget about cheap. Everyone knows that. I’ve usually managed by crashing with friends, which is exactly what I did this time, saving a ton on hotels. But, I get it, not everyone can do that. So, these next two days were about seeing how low I could go, still getting some work done, and, you know, having some kind of experience. I wanted to taste some real Chicago food, hang out with friends, and feel the city a little bit.
Day 1
9 a.m., Breakfast on the Go
I walked from where I was staying to the big library downtown. Walking saves money on rides, plus it’s a way to see the city, even the touristy parts. I grabbed a Chicago-style hot dog from a street vendor for breakfast. I skipped the extras to save a few bucks.
Cost: Around $5.
Noon, Library Work Session
The library was packed, people taking pictures of everything. I was there to work, though. I found a quiet spot and got down to business. Free Wi-Fi, outlets – the whole deal. It was super quiet, which was great, but then I had to make a call and had to go outside. Lesson learned: think about call spots ahead of time.
4 p.m., Quick Bite
I was starving. Needed something cheap, especially since I was meeting friends for dinner later. I ducked into a grocery store and got a simple salad.
Cost: About $8.
6 p.m., Park Time
I wandered through Millennium Park for a bit.
7 p.m., Dinner with the Crew
Met up with friends at a local place. I’d already told them I was on a tight budget. We ordered a bunch of food, family-style. I hoped the bill wouldn’t be too crazy. When they asked about more drinks, I just got water.
Dinner was $30 each.
Cost: $30.
Day 1 Total: $43
Day 2
9 a.m., Coffee Shop Work
The first coffee shop was slammed. Found another one nearby that had a few tables and Wi-Fi. Got a coffee and a pastry.
Cost: Around $7.
12 p.m., Riverwalk Stroll
Took a break and walked along the Riverwalk.
1 p.m., Park Lunch
Grabbed a sandwich and ate it in Grant Park.
Cost: About $10.
3 p.m., Museum Hop
Went to the Art Institute – luckily, it was a free admission day.
6 p.m., Last Bite
Grabbed another hot dog before heading out.
Cost: About $5.
Day 2 Total: $22
Trip Total: $65
What I figured out
Doing Chicago on $100 for two days? Possible, but you have to be really careful. You can’t eat at fancy places or do all the touristy stuff. But there are free things to do. The library was great for working. Coffee shops are a gamble. Sometimes they’re perfect, sometimes not. One big thing I learned: stick with one work spot if you can. Running around trying to find places killed my productivity.
