Chicago was the American city that exceeded every expectation I had. Set on the southwestern shore of Lake Michigan — a body of freshwater so vast it looks and behaves like an ocean — Chicago is a city of stunning architecture, world-class museums, an obsessive food culture, and a lakefront that gives its residents a quality of life that other major cities can only dream of. I arrived thinking I’d like it. I left completely in love 🇺🇸🏙️.

I flew into O’Hare International Airport and took the CTA Blue Line train directly to downtown — a 45-minute ride that costs just $5 and drops you in the heart of the Loop, Chicago’s central business district. Chicago’s “L” (elevated train) system is iconic and efficient, and watching it rattle through the city on those elevated tracks that snake between skyscrapers is one of those distinctly Chicago experiences. Pro tip: the Brown Line loop gives you a free architectural tour of downtown from above 🚂.

Getting There & First Impressions

The architecture is what sets Chicago apart from every other American city. After the Great Fire of 1871 destroyed most of the city, Chicago rebuilt itself as the birthplace of the modern skyscraper, attracting architects like Louis Sullivan, Frank Lloyd Wright, and Mies van der Rohe. The Chicago Architecture Center river cruise is widely considered the best tour in the city — a 90-minute boat ride down the Chicago River where a guide points out dozens of architectural masterpieces. The Tribune Tower, the Wrigley Building, Marina City (the “corn cob” towers), and the Aqua Tower with its undulating balconies were all incredible, but it was the overall effect — an entire city designed as a showcase for architectural innovation — that blew my mind 🏗️.

Millennium Park is Chicago’s outdoor living room and one of the greatest urban parks in the world. The Cloud Gate sculpture (affectionately known as “The Bean”) — a massive, mirror-polished stainless steel sculpture by Anish Kapoor that reflects the city skyline in its curved surface — is mesmerizing from every angle. The Jay Pritzker Pavilion, a Frank Gehry-designed bandshell with a lattice of steel pipes, hosts free concerts throughout summer. The Crown Fountain, with its two 50-foot towers projecting video faces that “spit” water, had kids (and adults) playing in the splash pool all afternoon. All of this is free 🎭.

Top Highlights & Must-See Spots

The Art Institute of Chicago is one of the greatest art museums in the world. Home to over 300,000 works, its Impressionist collection rivals the Musée d’Orsay in Paris. Standing in front of Seurat’s A Sunday Afternoon on the Island of La Grande Jatte, Grant Wood’s American Gothic, and Edward Hopper’s Nighthawks — all in one museum — was a pinch-me moment. The Modern Wing, designed by Renzo Piano, is stunning 🎨.

Chicago’s food scene is legendary and fiercely debated. The deep-dish pizza battle between Lou Malnati’s and Giordano’s is practically a civil war (I tried both — Lou Malnati’s buttery crust won my heart). But Chicago food goes far beyond pizza: Italian beef sandwiches dripping with jus and topped with giardiniera, Chicago-style hot dogs (never, ever put ketchup on them — locals will correct you), and the incredible Mexican food in neighborhoods like Pilsen. I had the best tacos al pastor of my life on 18th Street 🍕.

The Lakefront Trail is Chicago’s crown jewel — 30 kilometers of paved path along the shore of Lake Michigan, connecting parks, beaches, harbors, and museums. I rented a bike and rode from the Museum Campus in the south (home to the Field Museum, Shedd Aquarium, and Adler Planetarium) to North Avenue Beach, and the experience of riding along that glittering lakefront with the skyline beside me was pure joy. Chicagoans treat the lakefront as their collective backyard, and in summer, the beaches are packed with swimmers, volleyball players, and families barbecuing 🚲.

More Things to See & Do

I explored neighborhoods that showed me different sides of the city. Wicker Park and Bucktown for their creative energy, independent boutiques, and craft cocktail bars. Pilsen for its vibrant Mexican-American culture and incredible street art. Hyde Park for the University of Chicago campus, Frank Lloyd Wright’s Robie House, and Obama’s former neighborhood. Each one felt like its own small town within the larger city 🏘️.

Final Thoughts

What I didn’t expect about Chicago was how friendly it would be. Midwestern warmth is real — strangers gave me directions, bartenders shared their favorite spots, and everyone I met seemed genuinely proud of their city and happy to share it. Combined with the architecture, the lake, the food, and the culture, Chicago became the American city that surprised me the most ❤️.

Planning a trip to Chicago? 👉 Check out my full Chicago travel page for all the details and tips!