If you’re planning an epic first trip to Chicago, you’re in for a real treat. I recently made my first visit to this vibrant city.
As someone who has always been a huge fan of New York, I honestly didn’t expect anything could come close. But Chicago completely won me over in ways I didn’t anticipate.
The city is full of incredible history, world-first landmarks and a unique energy that’s hard to describe.
From the moment I landed, I loved its walkable streets and diverse neighbourhoods. Getting around is easy, thanks to the famous L Loop train.
Are you into art? Maybe you’re a foodie or enjoy architecture? Whatever floats your boat, Chicago makes you feel at home.
At the same time, it excites you with something new around every corner. I left feeling like I had barely scratched the surface. Still, I knew I’d definitely be back.
If you want to make your own epic first trip to Chicago unforgettable, here’s how to get the most out of it. 
Discover the World’s First Skyscraper on Your Epic First Trip to Chicago
Chicago is known as the birthplace of the world’s first skyscraper.
The Home Insurance Building, built in 1885, was the pioneer with its steel-frame structure. Although the original building no longer stands, its legacy lives on in the city’s towering skyline.
Walking through downtown, you’ll see how this innovation influenced the city’s architecture. The city embraces its history while pushing design boundaries with modern skyscrapers.
One of the best ways to admire these buildings is by hopping on the L Loop train. This elevated train circles the central business district, making stops near the top landmarks.
I loved sitting by the window, watching the cityscape unfold while cruising the Loop.
Experience the Original Ferris Wheel at Navy Pier
The Ferris wheel was invented in Chicago for the 1893 World’s Fair. Visiting the Navy Pier’s Ferris wheel today feels like stepping into history.
Riding it at sunset is unforgettable. The views of Lake Michigan and the city skyline bathed in golden light are breathtaking. I felt connected to Chicago’s innovative spirit while enjoying the gentle breeze above the lake.
The Navy Pier itself is a lively spot, with restaurants, shops, and entertainment options. It’s perfect for a relaxing afternoon or evening.
Snap a Selfie at Cloud Gate — The Iconic Bean
No epic first trip to Chicago is complete without seeing Cloud Gate in Millennium Park. Known as The Bean, this reflective sculpture captures the city, the sky and you.
I spent a good while here, fascinated by the way it changes with the light and weather.
The park itself is great for a stroll, with beautiful gardens and art installations nearby.
If you visit during the summer, check the schedule for free outdoor concerts at the Jay Pritzker Pavilion. It’s an incredible way to soak up local culture.
Indulge Your Sweet Tooth at Nutella Cafe
If you love sweets, the Nutella Cafe is a must-visit. Every menu item includes the famous hazelnut spread — from waffles to creamy hot chocolate.
I tried the Nutella latte and a rich Nutella crepe. The cozy atmosphere makes it perfect for a relaxing break during a busy day of sightseeing.
Visit the World’s Largest Starbucks Reserve Roastery
Coffee enthusiasts will love the Starbucks Reserve Roastery on Michigan Avenue. It’s the world’s largest Starbucks and feels more like an immersive coffee museum.
You can watch beans roasting, sample rare brews, and enjoy gourmet pastries. I found it fascinating to see how much care goes into every cup.
This spot is perfect for a mid-morning or afternoon pick-me-up while exploring the city.
Dive into Art at the Art Institute of Chicago
The Art Institute of Chicago is a treasure trove for art lovers. It houses classic works like American Gothic and The Bedroom by Van Gogh.
Spending a few hours here lets you dive deep into American and international art history.
Explore Little Village on Your Epic First Trip To Chicago
For something more colourful and community-driven, visit Little Village.
This vibrant Mexican neighbourhood features stunning street art and murals that tell stories of culture and resilience.
Walking the streets of Little Village, I felt the city’s rich diversity come alive. It’s a side of Chicago many first-timers don’t expect but absolutely should experience.
Cruise the Chicago River
A riverboat cruise offers a unique way to see Chicago’s famous architecture.
Expert guides share stories about buildings, architects, and the city’s rebirth after the Great Fire of 1871.
The calm river waters provide beautiful reflections of the skyline. I found this cruise relaxing and educational, a must-do for first-timers.
Take in Breathtaking Views from Willis Tower Skydeck
The Skydeck at Willis Tower is not for the faint-hearted. Standing on the glass ledge that juts out 1,353 feet above the city is thrilling.
On a clear day, you can see up to four states. The panoramic city views left me speechless.
It’s one of those experiences you’ll remember forever.
Relax at Oak Street Beach by Lake Michigan
Chicago’s Oak Street Beach offers a refreshing lakeside escape. Though it’s a freshwater lake, the vibe is beach-like.
I enjoyed walking along the sand and watching people play volleyball or cycle nearby.
It’s a great place to chill, especially after exploring the bustling city streets.
Stroll and Shop Along the Magnificent Mile
The Magnificent Mile is Chicago’s shopping hotspot. It’s packed with luxury brands, boutiques, and plenty of places to grab a coffee.
The architecture along Michigan Avenue is stunning too. I loved wandering between shops and admiring the mix of historic and modern buildings.
Discover Route 66 on Your Epic First Trip to Chicago
Chicago marks the start of the legendary Route 66, the highway that stretches nearly 2,500 miles all the way to California. I made sure to stop by the iconic Route 66 sign downtown – it’s a piece of Americana you simply can’t miss.
This historic route has inspired countless road trips, songs and stories.
Even if you don’t have time to drive it yourself, standing at the starting point feels like stepping into a classic American adventure.
Along the way, you’ll see diners, motels and quirky roadside attractions that capture the spirit of a bygone era, all beginning right here in Chicago.
Chicago’s Chocolate Brownie Legacy
Chicago also claims to have invented the chocolate brownie. The Palmer House Hilton hotel introduced the treat in the early 1900s. Visiting the hotel, I grabbed a recipe card and admired the grand lobby.
If you’re a fan of history and food, these stops are fun additions to your trip.
Where to Stay to Make Your Epic First Trip to Chicago Perfect
Where you stay shapes your whole experience. If you’re travelling solo or on a budget, HI Chicago Hostel in the Loop offers affordable dorms and a social atmosphere.
For families, the Hyatt Regency Chicago provides spacious rooms and easy access to major sights.
If you want to treat yourself, the Langham Chicago offers luxury with stunning river views and a relaxing spa.
For a boutique stay with a trendy vibe, The Robey in Wicker Park features a rooftop bar and artsy design.
If you want to escape the busy downtown vibe or need a relaxing breather after exploring the city, DuPage County is the perfect spot.
Check out my blog post on Discover DuPage: An Ultimate 2-Day Guide For A Girl’s Trip to see how to make the most of this nearby getaway.
