Why Chicago is the best big city in the US
By Cathy Rose A. Garcia, Editor-in-Chief
FOR FIRST-TIME visitors like myself, Chicago makes an unforgettable first impression.
I found myself bug-eyed as my Uber entered downtown, filled with towering skyscrapers and impressive architecture everywhere. Then I stepped out of the car and was immediately hit by a strong gust of wind — “Windy City” indeed!
Chicago was named Best Big City in the United States by Readers’ Choice Awards last year. It’s not hard to see why.
It has an iconic skyline, beautiful buildings, a scenic lakefront and a river walk, expansive parks, world-class museums, and good restaurants. Plus it’s home to famous sports teams like the Bulls, the Bears, and of course, Pope Leo’s beloved White Sox.
Here are a few things I loved about Chicago even though I only stayed for a few days:
PUBLIC ART
Art is everywhere in Chicago. And I’m not even talking about architecture.
You can’t go to Chicago without seeing the iconic Cloud Gate by Anish Kapoor. Also known as “The Bean,” the stainless-steel public sculpture is a tourist magnet that draws thousands of people to Millennium Park. The surface reflects the skyline and the clouds, providing the perfect background for those social media posts.
Also found in Millennium Park is the Crown Fountain by Spanish artist Jaume Plensa. The fountain features two 50-foot glass towers showing giant video portraits of ordinary Chicago residents. It’s a playful work that invites kids and adults to splash around the reflecting pool.
Walk a little more and you’ll find the untitled 50-foot-tall steel sculpture by Pablo Picasso. Located in Daley Plaza, this was the first monumental abstract public artwork in the downtown area. It was the artist’s gift to the city of Chicago in 1967.
Other public artworks in the city include Joan Miro’s sculpture called Chicago, a mosaic by Marc Chagall called Four Seasons, and Alexander Calder’s bright red Flamingo sculpture on Federal Plaza.
ARCHITECTURE-FIRST CRUISE
Everyone — and I mean every single person who has been to Chicago — told me to go on an architecture river cruise. Yes, I can confirm that there is no better way to see Chicago’s most beautiful buildings than from a boat on the river.
Make sure to pick the “Chicago Architecture Center (CAC) River Cruise” aboard the First Lady. It was voted one of the best experiences in the US in Tripadvisor’s 2026 Travelers’ Choice “Best of the Best” awards.
The “architecture-first cruise” features docents that are architecture buffs and trained by the CAC, a nonprofit cultural organization. It is a 90-minute trip down the river, where you’ll learn about the city’s history (the Great Chicago Fire of 1871) and the stories behind the beautiful buildings like the Willis Tower (formerly the Sears Tower), the Wrigley Building, the Tribune Tower, the Merchandise Mart, and Marina City (with its twin corn-cob towers).
The St. Regis Chicago and Aqua Tower, both designed by American architect Jeanne Gang, are some of the most eye-catching buildings. The St. Regis is the tallest building in the world designed by a woman.
Beyond the architecture, it was fascinating to learn about the Chicago River’s transformation. Once a dumping ground for industrial waste and sewage, it has been revitalized into a clean, inviting waterway, so much so that multi-million-dollar homes now line its banks, proudly facing the river. Maybe there’s hope for the Pasig River yet.
After hopping off the boat, you can take a walk along the Riverwalk that stretches along the edge of the river. It’s filled with restaurants, bars, cafés, and public art. It’s a vibrant area filled with people just relaxing after a long day at work.
For fans of architecture visionary Frank Lloyd Wright, the city is littered with his work including the Frederick C. Robie House and the Unity Temple which were declared as UNESCO World Heritage sites. The Wright Home & Studio is widely considered the birthplace of the Prairie style of architecture.
MUSEUMS
The Art Institute of Chicago is one of those museums that you simply cannot miss. It’s so good that even Ferris Bueller spent part of his day off at this museum.
Since not everyone has the luxury of time, one has to prioritize seeing the masterpieces like Edward Hopper’s Nighthawks, Grant Wood’s American Gothic, Georges Seurat’s A Sunday on La Grande Jatte, Vincent Van Gogh’s Self-Portrait, and Georgia O’Keeffe’s Sky Above the Clouds IV.
Marc Chagall also designed and presented a stained-glass piece called America Windows to the museum as a gift in 1977 to commemorate America’s bicentennial.
Across the Art Institute, you can find the Route 66 sign marking the start of the nearly 4,000-kilometer highway that goes all the way to Los Angeles. America’s “Mother Road” is celebrating its centennial this year.
Other notable museums in Chicago include the Field Museum of Natural History, the American Writers Museum, and the Griffin Museum of Science and Industry.
The Griffin Museum is inside the only remaining building from the “White City” of the 1893 World’s Columbian Exposition.
The Obama Presidential Center, located within Jackson Park, is scheduled to open to the public on June 19. The museum will have an exhibit highlighting former President Barack Obama’s time at the White House. It also features a replica of the Oval Office, decorated as it was when Mr. Obama was in office.
Part of the museum’s facade shows concrete words from Mr. Obama’s famous “You Are American” speech. Once it opens, the museum will become a must-visit for everyone.
On a side note, for the best view of the Chicago skyline, head to the shore in front of the Adler Planetarium on the Museum Campus. This is where you can find the widest angle of the Chicago skyline, at least on a clear day.
DEEP DISH PIZZA, ANYONE?
Chicago is synonymous with deep dish pizza, which is simply a thick pie baked in a cast-iron skillet with lots of cheese and tomato sauce.
There’s an long-standing debate on which deep dish pizza is the best — Lou Malnati’s Pizzeria, Giordano’s, Uno Pizzeria, or Pequod.
Uno is widely regarded as the birthplace of the deep-dish pizza, making it since 1943, while Lou Malnati’s is known for its signature buttercrust and an exclusive sausage blend. Lou Malnati and his father had worked at Uno, developing deep dish pizza.
With all the hype about it, I was inevitably disappointed when I tried the Chicago-style deep-dish pizza. Maybe the extremely thick, almost bread-like crust wasn’t to my taste. However, when I asked some Chicago natives, it turns out most locals actually prefer the tavern-style, thin-crust pizza.
Even the Chicago-born Pope Leo XIV is said to be a fan of a thin crust pizza, particularly the one from Aurelio’s Pizza. There’s even a clip of the Pope stopping the Popemobile to receive a box of Aurelio’s Pizza from the crowd at St. Peter’s Square (https://tinyurl.com/5c5y5f22).
If I had more time, I would probably visit Kasama — the first Michelin-starred Filipino restaurant in the world — and Mr. Beef, the inspiration for the Italian beef sandwich place in The Bear.
Overall, Chicago feels like one of those big cities that doesn’t feel the need to impress you. But one look at that skyline and you’re already halfway to falling in love with the place.
It is rich in culture, character, and charm (and relatively clean compared to New York City or San Francisco), yet it’s still down-to-earth and doesn’t feel too touristy.
At the end of my trip, I totally understood why Frank Sinatra once said, “Chicago is my kind of town.” I only spent a few days here, and yet I felt Chi Town just might be my kind of town as well.
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