In 2022, nearly 49 million tourists visited Chicago, Illinois. While lower than its 2019 record of 60.8 million visitors, it’s still an impressive 80% of that count. That goes to show how famous and loved the Windy City is.
This 2023, the city’s authorities are aiming for a higher number: 54 million visitors. If that comes to pass, it will help Chicago’s tourism sector to recover completely.
So if you’ve always wanted to tour the Windy City, too, now’s an excellent time to create a Chicago bucket list.
If you’re unsure where to start or what to include in your list, don’t worry. We’ve rounded up the top must-see sights and must-do things in Chicago, so read on.
Chicago Architecture River Tour
Fun fact: Chicago is the location of the world’s first-ever modern skyscraper. This is none other than the Home Insurance Building. It may no longer be around, but it still led to Chicago being the city that forever changed architecture.
Today, the Windy City is home to five buildings with heights of over 1,000 feet. It boasts many other architectural wonders, like the Wrigley Building and Marina City. Other notable landmarks are the Tribute Tower, Navy Pier, and Lyric Opera, to name a few.
One of the best ways to see these architectural Chicago attractions is aboard a boat. These architecture river tours aren’t just fun but also educational. They run throughout the day, but some companies offer sunset and night tours.
Private Luxury Yacht Cruise
Would you prefer to go on a Chicago River tour with only your family or friends? Would you also like to have lip-smacking lunch and custom cocktails with them?
If so, consider going all out by renting a private luxury yacht. Here’s a guide about these private rentals; check it out and see if they’re right up your alley.
Millennium Park
One of the first places you must head to when you visit Chicago is the 24.5-acre Millennium Park. A good enough reason is that it’s home to the Crown Fountain and Cloud Gate, more popularly known as “The Bean.” You can’t say you’ve visited the Windy City if you don’t have a photo of your reflection on this iconic landmark.
Aside from The Bean, Millennium Park is also home to the Boeing Gallery North. This open-air gallery is a must-visit for its rotating art exhibits.
Grant Park
If you thought the 24.5-acre Millennium Park was impressive, wait till you see Grant Park. Fondly known as “Chicago’s front yard,” this green space encompasses over 300 acres.
One of the top must-see sights at Grant Park is the Buckingham Fountain. It’s among the largest fountains worldwide. It also boasts 133 jets powerful enough to shoot water at heights of 150 feet.
The natural history Field Museum is another landmark located in Grant Park. There’s also the Art Institute of Chicago, one of the largest and oldest art museums in the U.S.
Willis Tower
The Willis Tower is one of the many skyscrapers you’d see on a Chicago Architectural River cruise. It’s undoubtedly a must-see, considering it’s the Windy City’s tallest building at 1,450 feet. But if gazing at it from the outside isn’t enough for you, worry not, as you can do the opposite.
A ticket to the Skydeck Ledge will give you access to the inside of the Willis Tower. But that’s not all; the Ledge is a glass balcony extending from the iconic building’s 103rd floor. Each ticket costs over $40 for adults, but if you want to see the city from a high vantage point, that price may be worth it.
360 Chicago
Like the Skydeck Ledge, 360 Chicago is also an observatory. It’s older than the former, though, having been around since 1969. However, it sits lower than the Ledge since it’s on the John Hancock Building’s 94th floor.
Despite that, 360 Chicago affords views just as magnificent as the Ledge. Tickets are cheaper, too, at only $30 per adult, and waiting times are typically shorter than at the Ledge.
If you don’t have budget constraints, consider visiting both observatories.
Magnificent Mile
Magnificent Mile is where all the best shopping action in Chicago happens. Also known as Mag Mile, it’s Windy City’s premier commercial district. Over 450 retailers have set up shops here, so you’ll undoubtedly find your favorites.
Even if you don’t plan to shop till you drop, Mag Mile is still a must-visit for its many Chicago landmarks. There’s DuSable Bridge, The Tribute Tower, and The Wrigley Building, to name a few.
Navy Pier
Stretching along the Lake Michigan shoreline is the 3,300-foot-long Navy Pier. Also known as the People’s Pier, it’s the world’s largest public pier and the most visited site in Illinois. About nine million people visit this site yearly.
A good enough reason is that Navy Pier hosts many attractions, events, and activities for all ages. It’s home to the Centennial Ferris Wheel, offering majestic city views from 200 feet up high. It also has numerous games and rides like the Wave Swinger, Tea Cups, and Light Tower.
This is also where the Chicago Children’s Museum and Chicago Shakespeare Theater are. It even offers boat and bus cruises and tours, many of which allow pets.
Original Chicago Eats
Touring Chicago won’t be complete without trying its popular dishes and beverages. So on your visit, feast on deep-dish pizza, the Original Rainbow Cone, and Chicago-style hot dogs. Windy City is also famous for its unique take on Italian beef sandwiches and steak.
Chicago-Made Cocktails
As for beverages, don’t go home without trying Chicago’s famous “Old Fashioned.” Some folks regard it as the original cocktail drink.
You may also want to try The Chicago, the Chicago Fire Extinguisher, and the Mamie Tayler. Just remember to drink responsibly!
Time to Complete Your Chicago Bucket List
You can add many other items to your Chicago bucket list, but the ones above are a great place to start. They’re perfect for first-time vacationers and those who’ve already visited the Windy City. You could even fit most, if not all, of them into a 3-day or even a weekend stay in Chi-town.
So, as early as now, add our ideas to your bucket list so you can plan for your trip ASAP.
Ready for more travel tips? Then check out our ultimate guide on money-saving travel hacks.
