Living in Wisconsin and itching to explore major American cities? The first city that pops into my mind is Chicago, famous for its deep-dish pizza. It’s just a four-hour drive from Appleton. Chicago also ranks as the second most-visited city in the U.S. after New York. After finally finding time amidst our busy schedules, Kyle and I managed to plan a trip to Chicago.
We set out in the morning and arrived around 3 p.m., heading straight to our Airbnb, located about 20 minutes from downtown Chicago. Exploring the third-largest city in the U.S., located on the southwestern shore of Lake Michigan, required some preparation. Known as the “Windy City,” Chicago called for warm clothing. Late December’s weather was manageable, though the wind was intense. For me, a coat alone wasn’t enough, so I layered a thick sweater underneath and wore leggings under my pants, along with gloves and a scarf. Since I didn’t tie my hair up, I had to deal with it getting messy from the wind. Besides the strong winds, parking in downtown Chicago is expensive, so we opted to park near the Airbnb and take the “L,” or Loop, train into town.
Exploring American cities is just as exciting as visiting European destinations, as each city has its own unique charm. Chicago attracts visitors with its contemporary architecture and abundant green spaces, offering plenty of public art to enjoy. Here are some top things to do and see in Chicago:
1. Millennium Park
This gigantic park, located in downtown Chicago near The Loop business district, is perfect for hanging out, picnicking, or running. The park is also home to “The Bean,” a contemporary art piece that has become a Chicago icon. The Bean, officially named Cloud Gate, was created by Indian-born British artist Sir Anish Kapoor. It’s hugely popular, so be prepared for lines to get that perfect selfie, even in winter!
2. The Loop
If you enjoy urban landscapes, the Loop is a must-visit. I was blown away by Chicago’s skyscrapers, both day and night. I explored the high-rise-filled area, crossed the street to the Chicago Riverwalk, and admired the gleaming buildings, including the Trump building. Although the wind and rain kept us from visiting the nearby boutiques, Kyle and I spent time in The Loop, dining and hanging out at bars.
3. Navy Pier
Navy Pier, on the edge of Lake Michigan, has breathtaking views of the lake and the Chicago skyline at night. The pier features an indoor area with shops, restaurants, and the Chicago Children’s Museum. Try the Centennial Wheel, a Ferris wheel with $12 tickets. Just beside the pier, you’ll find contemporary art installations, including Crystal Gardens, an indoor garden with 80 palm trees, fountains, and sparkling lights. Navy Pier also hosts monthly events, so check their website for updates.
4. Try Deep Dish Pizza
Chicago’s signature deep-dish pizza is much thicker than traditional Italian pizza. Originally created by Pizzeria Uno, this style is now famous nationwide. We opted for California Pizza due to long waits but recommend Giordano’s if you can wait. A slice of deep-dish pizza at Giordano’s costs around $20.
5. Willis Tower (Sears Tower)
Once the world’s tallest building, Willis Tower stands at 442 meters. You can take an elevator up to the Skydeck on the 103rd floor for incredible views of Chicago and Lake Michigan. Skydeck tickets cost around $24.
6. Art Institute of Chicago
This renowned museum exhibits works by famous artists across various media, from photography to textiles. Admission is $25. Other notable museums include the City History Museum, Oriental Institute Museum, and The Field Museum of Natural History.
7. The ‘L’ (Chicago Transit)
Chicago’s elevated train system, known as the ‘L,’ makes getting around easy. Tickets for one ride cost $2.25, with unlimited visitor passes available for 1-day ($10), 3-day ($20), and 7-day ($28) options. Other transportation options include buses, Uber, and Lyft.
8. Chinatown
I visited Chinatown for a taste of Asian food, finding various Chinese and Korean restaurants, Asian hair salons, and markets. For dinner, we had roast duck at a Chinese restaurant, where we unexpectedly met an Indonesian staff member from Medan!
9. Fashion Outlets Chicago
Located at 5220 Fashion Outlets Way in Rosemont, Illinois, this outlet mall features famous brands at discounted prices. It’s near the airport, so prepare for hours of shopping.
Chicago offers a blend of history, culture, and vibrant city life—definitely worth a visit!