By Loukia Zigoumis
Navy Pier. The Bean. Chicago “dogs.” Deep-dish pizza. Cheesecake. Ferris Bueller’s Day Off. Chicago Cubs. The Bears. No matter what comes to mind when you think of Chicago, one thing is certain. It’s a city worth visiting in any season.
In 2024, Chicago was voted the Best Big City in the United States for a historic eighth year in a row—because of its hospitality, stunning architecture, historic landmarks, museums, art galleries, unique neighbourhoods (77 of them!) outdoor festivals, shopping, stunning waterfronts and world-class dining. It’s one of those travel destinations that’s ideal right through the year, because there’s always something special to see and experience.
What to explore
Into sports? As home to the Cubs, Bears, Red Socks and Bulls, Chicago is definitely a sports lovers’ city. It’s also a revered by foodies, shoppers, culture enthusiasts and architecture buffs. Here are some things you should add to your itinerary:
Navy Pier: Located on Lake Michigan, Navy Pier is a standout attraction that’s home to parks, restaurants, attractions, retail shops, games and rides, including the Centennial Wheel at Pier Park, Chicago Shakespeare Theatre and even a fitness trail. Bike rentals and boat tours are also offered. navypier.org
Millennium Park: In the heart of downtown Chicago, Millennium Park is a top spot for arts, entertainment, architecture and events. It’s home to The Bean (also known as Cloud Gate), a famous sculptural work of art with a reflective surface that mirrors the skyline and surroundings. A skating rink in the winter, free events, interactive fountains, gardens and green space are other highlights. Millenium Park hosts the Chicago Blues Festival, Chicago Jazz Festival and other annual fests. In the summer months you can also enjoy outdoor workouts, such as free yoga and tai chi classes.
Boat tours: Boat tours are the thing to do in Chicago. There are offerings on both the Chicago River and Lake Michigan, as well as many different types of excursions on the water. Popular options include the architecture tours showcasing stunning landmarks, as well as the river cruises with dinner and dancing.
Skydeck Chicago: If you’re feeling adventurous and aren’t afraid of heights, a visit to Skydeck Chicago is a fun way to see the sights from the very top. One of the world’s most famous skyscrapers, it offers jaw-dropping views and thrills. Step out on to The Ledge, a glass box hovering 1,353 feet in the air at the Willis Tower—one of the tallest buildings in the world. The all-glass floor gives you stunning views of the Chicago River and Lake Michigan; on clear days, you can see up to four different states.
360 Chicago: Another cool adventure is a visit to the 360 Chicago observation deck inside the former John Hancock Centre on Michigan Avenue. You can experience TILT, an enclosed platform that tilts you out and over Michigan Avenue at 1,030 feet.
Magnificent Mile: Chicago’s Magnificent Mile is one of the world’s most iconic retail destinations. The streets are full of boutiques, shops, dining spots and luxury hotels. The area is very walkable and captivating, as you’re surrounded by the city’s stunning architecture and top attractions are all within walking distance.
Dining options
It’s common to book a trip to Chicago for the restaurant scene alone. After all, the city is legendary for its signature treats, like Chicago “dogs,” deep-dish pizza, “Chicago mix” popcorn and cheesecake. Most of all, Chicago is known for its Michelin-star restaurants.
Garrett Popcorn: Dating back to 1949, Garrett Popcorn Shops are part of Chicago culture, with 14 locations throughout the city. Garrett’s is most recognized for its Garrett Mix, a combination sweet CaramelCrisp® and savory CheeseCorn® that’s beloved around the world. Garrettpopcorn.com
Giordano’s: Renowned for its deep-dish pizza and fun atmosphere, Giordano’s is an excellent place to stop for lunch. Lou Malnati’s and Uno Pizzeria (considered the first restaurant to serve deep-dish) are also great places to enjoy the authentic Chicago-style pizza.
Cindy’s: Located on the 13th floor of the Chicago Athletic Association hotel, Cindy’s is a year-round rooftop restaurant and open-air terrace, complete with stunning views of Millennium Park and Lake Michigan. The menu features American dishes and seasonally-inspired fare.
Luxbar: Located in Chicago’s Gold Coast neighbourhood, Luxbar dishes all-American, feel-good food and handcrafted cocktails. It’s a great place to stop for a bite after sightseeing or shopping.
Mr. Beef: Acclaimed for its old school sandwich-shop vibe and iconic Italian beef sandwiches, Mr. Beef is featured on the hit TV show The Bear. Expect long lines and people snapping pictures outside. It’s worth the wait. Order an Italian beef and enjoy a bite of classic Chicago.
Where to stay
One place you’ll want to consider is the Chicago Athletic Association Hotel, a distinctive downtown landmark, built in 1893, that used to be a private members’ club. Today it houses some top local haunts, including Cindy’s, and it has been awarded One Michelin Key.
Other notable hotels: The Blackstone Hotel; Langham Chicago.
