Even during the pandemic, over 30 million folks visited Chicago in 2021. This 2023, the city’s tourism office projects the tourism sector to recover fully.

There are, after all, so many sites to see, places to visit, and fun things to do in Chicago, Illinois. So much so that in 2021, the city generated about $1.3 billion in tourism tax revenue.

But with Windy City having so much to offer, which ones should you include in your itinerary?

We’ve listed the top ones you can’t miss below, so read on.

1. A Stroll at the Millennium Park

Your first trip to Chicago won’t be complete if you don’t visit the iconic Millennium Park. This 24.5-acre space is where you can find the Crown Fountain and Cloud Gate, more fondly called “The Bean.” A photo of your reflection here is a must-have souvenir of your Chicago vacation.

The Bean, a public art, is one of the world’s most massive permanent outdoor installations. As its nickname suggests, it resembles a bean, albeit a 66-foot long, 33-foot high one. It’s an incredible masterpiece reflecting Windy City’s famous skyline and surrounding green space.

Considering the park measures nearly 25 acres, there’s much more to do after your selfie by The Bean. For example, you can head to the Boeing Gallery North. It’s an open-air gallery with rotating art exhibits.

If you visit Chicago in the summer, head to the park’s Pritzker Pavilion. Enjoy free movies, participate in events, or catch concerts here.

Millennial Park is also home to the Lurie Garden, a 5-acre botanical garden. It’s open year-long, is free to explore, and features majestic flora.

2. Marvel at Grant Park’s Manicured Grounds

Also known as “Chicago’s front yard,” Grant Park is a vast green space measuring over 300+ acres. Entry is free, and you get to behold its majestic manicured grounds. More than that, it’s home to many attractions, at the heart of which is the Buckingham Fountain.

The Buckingham Fountain is one of the world’s largest fountains. Featuring 133 jets that shoot water into the air at heights of up to 150 feet, it’s a sight to behold. You can catch one of its 20-minute choreographed displays every hour, from 8 AM to 11 PM, from early May to October.

Many of Chicago’s famous sites, such as The Field Museum, are in Grant Park, too. Another is the Art Institute of Chicago, visited by over 1.4 million folks yearly and home to over 270,000 objects.

If you only want to chill and relax, you can go on a waterside picnic at Grant Park. You can spread a blanket, sit by one of the space’s installed benches, and enjoy food and drinks.

3. Shop at the Magnificent Mile

The Magnificent Mile, sometimes shortened to Mag Mile, is Chicago’s premier commercial district. Upscale shops, posh hotels, luxury outlets, and fantastic restaurants dot this 13-block stretch. Over 450 retailers, from jewelry stores to travel-related shops, call it home.

Even if your Chicago vacation isn’t all about shopping, a trip to the Mag Mile is still a must. A good enough reason is that this is where you can find some of the city’s most incredible architecture. These include the Wrigley Building, Chicago Water Tower, and John Hancock Center.

4. Go on a Chicago Architecture River Cruise

Were you aware that Chicago is the birthplace of skyscrapers? It is, after all, the location of the world’s first skyscraper, the Home Insurance Building. It’s also home to five buildings towering over 1,000 feet tall.

So whether you’re an architect or simply love archi, Chicago is a perfect vacation spot. And the best way to learn more about its iconic buildings is with an architecture river cruise. Go on one, and you’ll hear incredible stories about the buildings along the Chicago River.

Most boat tours run throughout the day, but you can also enjoy one at night. Sunset tours are also a great way to catch the city’s architecture bathed in the soft light of the setting sun.

5. Get Some Family QT at the Navy Pier

Navy Pier, a 3,300-foot-long pier on the Lake Michigan shoreline, is one of Chicago’s most fam friendly spots. For starters, it’s home to the Centennial Wheel, a Ferris wheel that soars to a height of almost 200 feet. A ride here can give you and your entire family breathtaking views of Windy City and Lake Michigan.

If you’re looking for something more posh, you should try the Wheel’s VIP gondola. It boasts not only plush seating but also a glass bottom.

Other rides for young kids include the pier’s historic carousel and Tea Cups. Older kids may enjoy the Funhouse Maze, Time Freak Game, Atomic Rush Game, Light Tower, and Wave Swinger.

After the rides, you and your offspring can explore the Chicago Children’s Museum. With exhibits like fire trucks and treehouses, they’ll surely love to spend time here.

You can also book an architectural cruise from the pier. Alternatively, you can enjoy a more exciting ride by going on one of the speedboat tours.

Navy Pier also often hosts events and publishes their schedules online. So, check its website to see what’s in store during your planned visit to the city.

Also, consider going on a Wednesday or Saturday night. These are the days the pier schedules its twice-a-week fireworks display.

6. Work Your Brain Out at an Escape Room

Are you visiting Chicago with co-workers or teammates? Then consider trying one of the city’s escape rooms.

According to experts, escape rooms can encourage teamwork and enhance problem-solving. They’re also exciting and can even promote analytical thinking.

An escape room with your mates can be an exciting start or finale to your Chicago vacation. Find an escape room here to see which can work out your and your teammate’s brain cells the most.

Have a Blast With These Fun Things to Do in Chicago

There are many fun things to do in Chicago, but the ones listed here are perfect for first-time visitors. So, if you’re visiting for the first time, include the ones we discussed in your itinerary. You can then explore the rest of the country’s “Best Big City” during your next trips.

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