I’ve always been drawn to Chicago—the city of skyscrapers, deep-dish pizza, and vibrant cultural landmarks. It had been on my travel bucket list for years, so when the opportunity arose, I jumped on it. Spoiler alert: Chicago did not disappoint. Here’s a detailed recap of my whirlwind 4-day adventure, complete with deep-dish pizza, riverside strolls, and plenty of iconic landmarks.

Table of Contents

• Why Chicago?
• The Logistics
• What I Did on My Trip to Chicago
• If I Had More Time in Chicago
• Travel Tips

Why Chicago?

Chicago has always stood out to me as a city that blends urban sophistication with Midwestern charm. Its iconic skyline, rich architectural history, and world-class cultural scene made it an easy choice for a quick getaway. I was drawn to its legacy as the birthplace of the skyscraper and couldn’t wait to see landmarks like the Willis Tower and the stunning riverfront architecture. Food was another big pull—Chicago is famous for its deep-dish pizza, vibrant local eats, and an exciting culinary scene.

Beyond that, summer in Chicago promised vibrant energy, with waterfront walks, music, and plenty of outdoor fun. Add the city’s walkability and excellent night-life, and it was the perfect pick for a 4-day adventure.

The Logistics

Where I Stayed

I stayed at the HI Chicago Hostel, located in downtown Chicago’s Loop neighbourhood near Millennium Park. It was an amazing spot with clean, modern accommodations, a welcoming vibe, and an unbeatable location. Staying here made it super easy to explore the city on foot and by public transit. Plus, it’s a great place to meet other travellers—I even shared some deep-dish pizza with new friends one of the evenings!

Getting Around

Chicago’s public transportation is reliable, affordable, and easy to navigate, making it my go-to way to get around. Here are some helpful tips:

• Transit Pass: Get a Ventra Card, which works for both buses and trains. You can buy one at kiosks in “L” stations or some convenience stores. Load it with money or buy a daily/weekly pass for unlimited rides.
• Subway (the “L”): The “L” is short for “elevated train,” though some lines go underground. It’s colour-coded (e.g., Red Line, Blue Line), and the signage is clear.
  • For tourists, the Red Line is great for accessing downtown, Wrigley Field, and the North Side. The Blue Line takes you to O’Hare Airport if needed.
• Buses: Chicago’s buses cover routes not serviced by the “L,” and they’re easy to use with a Ventra Card. Google Maps integrates seamlessly with Chicago Transit Authority (CTA) schedules, so it’s simple to find routes.
• Walking & Biking: Chicago is a walkable city, especially downtown. If you prefer biking, look into Divvy bikes, a bike-share program with stations all over the city.
• Rideshares: While Uber and Lyft are widely available, they’re often more expensive than public transit and not always faster during rush hour.

If you’re visiting from out of town, don’t hesitate to ask locals or staff at transit stations for help—they’re usually happy to guide you.

What I Did on My Trip to Chicago

Day 1: Arrival, Riverwalk, & Deep-Dish Delight

Once I arrived in Chicago, I checked into the HI Chicago Hostel, which felt like a little home away from home, especially with all the friendly people around. After settling in, I headed straight to the Chicago Riverwalk for a stroll, which is one of the city’s most scenic spots. I hopped on the Architecture Boat Cruise, where I learned all sorts of fun facts about Chicago’s famous skyline. A particularly fun tidbit I learned: contrary to popular belief, the Great Chicago Fire wasn’t caused by a cow knocking over a lantern! It’s a myth that’s been debunked—who knew, right?

For dinner, I indulged in a classic Giordano’s deep-dish pizza. I grabbed a whole pie to go and shared it back at the hostel with some fellow travellers. Pizza always brings people together, and we swapped stories about our trips while munching on cheesy, deep-dish goodness late into the night.

Day 2: Iconic Sights & Harry Potter Magic

Day two began with a free breakfast at the hostel, which was a great way to fuel up for a busy day ahead. I caught up with my friends from the night before, talking about the fun things we had planned for the day. My first stop was Cloud Gate, aka The Bean. It’s one of the most famous landmarks in Chicago, and I couldn’t resist snapping a selfie in front of the shiny sculpture.

In the afternoon, I went to the Nederlander Theatre to see Harry Potter and the Cursed Child. The special effects were absolutely incredible, but my favourites were definitely the Dementors—so chilling the way they floated eerly across the stage! I also loved the scene where the characters travelled back in time, and the stage seemed to vibrate as the magic swirled around them. It was a show that really brought the magic to life.

For dinner, I went to The Purple Pig, a Mediterranean-inspired spot that never disappoints. The lively atmosphere and delicious dishes were the perfect way to end a magical day in Chicago.

Day 3: Zoo, Beach, & the Best Tacos

Day three was a day of adventure. I met up with a friend from the hostel, and we headed to Lincoln Park Zoo – which is completely free by the way. Although we were a bit bummed we didn’t spot any meerkats or penguins, we were super excited when we found the giraffes and lions. Afterwards, we also visited the Lincoln Park Conservatory. Built between 1890 and 1895, the historic Lincoln Park Conservatory displays lush, exotic plants from around the world in four display houses – The Palm House, Orchid House, Fern Room, and Show House. 

We then grabbed some tacos from a food truck near Millenium Park, which was the perfect snack. These tacos were absolutely delicious and hit the spot after a day of sightseeing.

In the evening, I went solo to Navy Pier and I took in the iconic Centennial Ferris Wheel, the view of Lake Michigan, and the beautiful skyline. I finished the evening by heading to a local Chicago beach called Ohio Street Beach where I got the perfect views of the sunset. On my way back to my hostel, I was able to get a quick night shot of The Bean and I was wowed by the city’s reflection in the mirrored surface.

Day 4: Art, Culture & Departure

Before heading to the bus station, I stopped for lunch at Ramen-san, a delicious local Japanese restaurant. The ramen and bao buns were out of this world and were the perfect meal before the long travel ahead.

Then came the less-than-ideal part of the journey…the Greyhound bus ride to Toronto. Let’s just say it wasn’t a smooth ride. Thankfully, I wasn’t alone in this adventure—another friend from the hostel joined me, making the whole experience a bit more bearable.

Our first bus didn’t show up at all, and we ended up spending the night at the Greyhound bus station. The place was, well, not exactly a five-star establishment—let’s just say it was full of people who didn’t exactly match the travel brochure’s expectations. But eventually, we caught a morning bus to Detroit, and from there, we transferred to another bus bound for Toronto.

Despite the rocky travel experience, my time in Chicago was unforgettable. The city offered so much to explore, and I left with amazing memories and a full heart—definitely worth every adventure, both the easy and the not-so-easy parts!

If I Had More Time in Chicago

Though I had an amazing 4-day trip, there’s so much more I would have loved to explore if time had allowed. Here are a few more things to do and places to eat that I would recommend if you find yourself with extra time in Chicago.

Things to Do:

1. Skydeck Chicago at Willis Tower
   For incredible panoramic views of the city, head to the Skydeck. Don’t miss the glass-floored “Ledge” for a thrilling view straight down!
2. Museum of Science and Industry
   A fascinating museum filled with interactive exhibits. It’s perfect for science lovers and families, offering everything from space exploration to historical exhibits.
3. Wrigley Field Tour
   Take a tour of this iconic baseball stadium and soak in the rich history of the Chicago Cubs. If you’re there during baseball season, catching a game would be a must!
4. The 606 Trail
   If you enjoy walking or biking, the 606 Trail is a former rail line turned elevated park and trail that stretches across several neighbourhoods. It’s a perfect spot for a scenic walk or a bike ride while experiencing Chicago’s hidden gems.

Food Spots:

1. Lou Malnati’s Pizzeria
   Known for its buttery crust and cheesy goodness, Lou Malnati’s is a Chicago deep-dish pizza institution. A must-try for pizza lovers.
2. Portillo’s
   Grab a classic Chicago-style hot dog at Portillo’s. It’s the best place to try this iconic dish, loaded with all the traditional toppings.
3. Garrett Popcorn Shops
   Don’t leave Chicago without trying Garrett’s famous caramel and cheese popcorn mix. It’s a delicious snack to take with you while exploring the city.

Travel Tips

Walkability:
Chicago is incredibly walkable, especially in areas like Millennium Park, the Riverwalk, and the Loop. Many attractions are within walking distance, so you can easily explore the city on foot. Comfortable shoes are a must, as you’ll likely do a lot of walking.

Safety:
While I generally felt safe during the day and in busy tourist areas like Millennium Park and Navy Pier, there are some areas that felt a bit sketchy, especially at night. Like any major city, it’s best to stay aware of your surroundings and stick to well-lit, busy areas after dark. If you’re venturing farther out or feel uncomfortable, using a rideshare service is a good option.

Would I Return to Chicago?

Absolutely. After just four days, I felt like I had only scratched the surface of what Chicago has to offer. The city is rich in culture, history, and energy, and I know there’s so much more I could explore. Chicago’s energy is infectious, and I definitely see myself coming back.

So, if you’re considering a trip to Chicago, go for it. It’s a city that can surprise you, and whether you’re a first-time visitor or someone looking for a return visit, I think you’ll find it’s a place worth exploring over and over again.

Safe travel,

Carina

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