Working Remotely from Chicago: A 5-Day Itinerary
Ah, the joys of remote work! When your office can be anywhere with Wi-Fi, why not choose a city that’s equal parts breathtaking architecture, deep-dish pizza, and some of the coolest museums on this side of Lake Michigan?
Over four days, I balanced my work hours with exploring the must-see spots and eating my way through Chicago’s iconic dishes. Spoiler: it was a bit of a balancing act, but well worth it. Here’s my ultimate “work-from-Chicago” itinerary!
Day 1: Saturday – Arrival and Evening Exploration
Morning Flight to the Windy City
Start your journey bright and early with a flight that probably leaves at a time most people are still dreaming. Coffee? Yes, please. Excitement? Definitely. I was all set to head to the Windy City, where the only thing blowing harder than the wind was my list of things to eat and see.
Arrival & Check-In at HI Chicago Hostel
Pro-tip: landing in Chicago doesn’t mean you’re quite “there” yet. It’s about 1.5 hours from O’Hare to Chicago Loop, so budget in some extra time for the journey. By the time I reached the hostel, I’d felt like I’d traveled halfway across the country. I’d try to avoid the evening rush hour that I got caught in on my way to the hostel from 3pm — 5pm.
Checked in around 5:30PM, freshened up, and got ready to hit the streets. I may or may not have done a little happy dance after surviving the commute and was ready to see what the evening had in store.
HI Chicago, The J. Ira and Nicki Harris Family Hostel — HI USA
This is one of the best working hostels I’ve ever stayed at! The beds are spacious, the washrooms are spotless, the service is outstanding, and it’s quite affordable too.
Dinner & Drinks at Elephant & Castle
Nothing says “Welcome to Chicago” like finding a cozy pub. Elephant & Castle is a classic, with hearty food and drinks to kick off your first evening in the city. Plus, it was just what I needed after a long day of travel.
Day 2: Sunday – Museum Day and Deep Dish Pizza
Start the Day at Peet’s Coffee
Sunday morning = coffee time. Chicago has some amazing local coffee spots, but I kicked off my morning at Peet’s because, sometimes, you just need a little familiar caffeine kick to start the day.
Peet’s Coffee Store Locator | Find a Peet’s Near You | Peet’s Coffee
Explore Museum Campus
Chicago’s Museum Campus is a must-visit. There’s the Field Museum, Shedd Aquarium, and Adler Planetarium all in one place. I opted for the Field Museum, where I spent 4–5 hours geeking out over fossils, ancient artifacts, and, yes, SUE the T. Rex. It was a bit like entering nerd heaven.
The Museum has three levels, and here are my top highlights from each one:
Ground Level
- Inside Ancient Egypt
Main Level
- Maximo the Titanosaur
- The Ancient Americas
- Field Bistro
Upper Level
- Evolving Planet
- SUE the T.rex
- Restoring Earth
Lunch at Lou Malnati’s for Deep Dish Pizza
Next on the Chicago checklist? Deep dish pizza! Lou Malnati’s is a legend, so I dove into a gooey, cheesy slice of heaven. Honestly, I’d give it a solid 3/5 – not life-changing, but definitely worth a try. Chicago deep dish is more of a savory pie than a pizza, and I’m glad I wore my stretchy pants.
LOU MALNATI’S PIZZERIA, Chicago — 439 N Wells St, River North — Menu & Prices — Tripadvisor
Mexican Dinner at Senoritas Cantina
After the pizza feast, I went for some Mexican flavors at Senoritas Cantina. Let’s just say, my stomach was very happy that day. Quesadillas and some good ol’ fashioned? Yes, please.
Drinks at Bar Louie – Printer’s Row
The night wasn’t over yet. I wrapped up with drinks at Bar Louie in Printer’s Row – a great spot for a relaxed vibe and to soak in some local nightlife. Not bad for my first full day in Chicago!
Day 3: Monday – Work, Millennium Park, and Chicago’s Comics Scene
Morning Coffee & Bagels at Hero Coffee and Bagel Bar
Started the day with a Smooth Criminal Bagel and coffee from Hero. This place is tiny, so I got my stuff to go. But the bagel? Criminally good. Knuckled down for a productive work session (because, you know, that’s why I’m here too). Chicago has a way of inspiring you, even if it’s just through the coffee and bustling atmosphere around you.
Lunch at Millennium Park & Oasis Cafe
Took a midday break at Millennium Park. There’s something special about eating lunch near the iconic Cloud Gate (“The Bean”).
If you’re wandering around Grant Park in Chicago and stumble upon a crowd of giant, headless, armless bronze legs — don’t worry, you haven’t accidentally walked into a Tim Burton movie set. Welcome to Agora, a unique art installation created by Polish artist Magdalena Abakanowicz.
Agora consists of 106 nine-foot-tall iron legs, each posed in a variety of slightly different stances. It’s a little unsettling (where are their heads?), but that’s the point. Abakanowicz wanted to create a reflection on the concept of crowds and individuality — or maybe she just thought Chicago needed a few dozen creepy leg sculptures to liven up the park. Either way, Agora definitely makes an impression.
So, if you’re ever in Grant Park, stop by and take a “leg selfie.”
After all the “legwork”, I wanted to have something filing and I found the perfect spot for lunch — Oasis Cafe. Here, I went for the Chicken Kebab Plate. So delicious, it could almost distract me from the incredible views around me. Almost.
Don’t be misled by the entrance, which looks like (and probably is) a jeweler’s shop. At the very end, you’ll find a cozy café. Perhaps they share the same owners. Either way, I can’t complain — it’s a clever use of space!
Afternoon Comic Book Stop at Graham Crackers Comics
As a comic book fan, this was a non-negotiable stop. Graham Crackers Comics has an impressive collection, and I could’ve spent hours browsing through indie gems and well-known classics. Highly recommend it if you’re a fan of graphic novels and superhero stories.
Evening Architecture Cruise by Wendella’s
One of the best ways to appreciate Chicago’s architecture? On a river cruise. Wendella’s 45-minute tour gave me a new perspective on the skyline, complete with stunning views and fascinating history lessons. It’s touristy, yes, but so worth it.
Chicago’s Original Architecture Tour® — Wendella Tours & Cruises
Day 4: Tuesday – Work Day and Classic Chicago Bites
Morning at Goddess & The Baker
Goddess & The Baker is one of those spots that just feels cozy and cool. I ordered the Leo Omelette and a Pumpkin Apple Butter Latte (yes, it’s as amazing as it sounds). It’s also a great place to set up shop with your laptop if you want to work remotely with a side of creativity. Spent the day getting things done, powered by the caffeine from Goddess & The Baker. Sometimes, working remotely can feel like a chore, but when you’re surrounded by such a lively café, it’s anything but.
Evening Riverwalk Stroll
After wrapping up work, I took a walk along the Riverwalk. It’s one of the best places to unwind in Chicago, with beautiful views and people-watching galore. Perfect way to recharge after a day on the laptop.
Chicago Hot Dog at Chicago Brewhouse
Finally checked “Chicago hot dog” off my food bucket list! Chicago Brewhouse did not disappoint with their classic dog. Pro-tip: don’t ask for ketchup. It’s basically a crime here.
Chicago Brewhouse | Celebrating Chicago’s Craft Brewing Industry and Neighborhood Food.
Drinks at Emerald Loop Bar & Grill
Ended the day at Emerald Loop. A fun, laid-back spot with great drinks and atmosphere. It was the perfect place to toast to my last full night in the city.
Emerald Loop | Irish Bar & Grill in Chicago’s Theater District | Open Late
Day 5: Wednesday – Work & Last Meal in Chicago
Work from Intelligentsia Coffee
Intelligentsia is a Chicago staple, and they take their coffee very seriously here. It’s a fantastic place to work from, and the vibe is chill enough to help you focus while you sip on high-quality brews.
Monadnock Coffeebar | Chicago Locations | Intelligentsia Coffee
Try their Apple Honey Latte! Uff.
Lunch at Maharaja India Grill
I took a break from deep dish and hot dogs to savor some delicious Indian food. Maharaja India Grill hit the spot with all the spices and flavors I’d been craving. I got some Chicken Tikka Masala, Garlic Naan, and Rice.
Dinner at Girl & the Goat
Last meal in Chicago? Girl & the Goat. This spot is a bit of a splurge, but it’s worth every penny. The food is creative, the vibe is electric, and it’s the perfect way to end a week of mixing work with play in Chicago. Here’s what I had:
Drinks: Spicy Boy, Goat Fashioned (5/5)
Food: Goat empanadas, Shrimp Salad, Sautéed Green Beans (5/5), Sticky Glazed Pork Shank (5/5)
Dessert: Sticky Toffee Pumpkin, Spice Cake (10/5)
Girl & The Goat | Los Angeles & Chicago | Chef Stephanie Izard
Reflecting on my “work-from-Chicago” adventure, I can honestly say this city makes remote work an absolute joy. From delicious coffee shops to iconic foods and jaw-dropping sights, Chicago is perfect for anyone looking to balance productivity with exploration. So if you’re considering a remote-work getaway, why not make Chicago your next stop?
And there you have it! A blend of work, play, and a ton of great food to keep you fueled along the way.
