Last Updated on August 13, 2024

Chicago, also known as the “Windy City”, is one of the most iconic and vibrant cities in the United States. It’s a place where you can experience everything from world-class museums and beautiful architecture to delicious food and exciting nightlife. If you’re visiting for the first time, there are many things to do in Chicago that will make your trip unforgettable.

In this blog post, we’ll take a deep dive into the best things to do in Chicago over a weekend. Pack your bags and let’s explore this amazing city together!

How To Spend A Weekend In Chicago As A First-Time Visitor

Explore the Magnificent Mile

The Magnificent Mile is a must-visit for any traveler to Chicago. This iconic stretch of Michigan Avenue is home to some of the city’s most famous landmarks, including the historic Water Tower and the John Hancock Center. It’s also where you’ll find some of the best shopping in the city with high-end stores like Gucci, Louis Vuitton, and Tiffany & Co.

But don’t just stick to window-shopping on this mile-long strip. Make sure to take a stroll down Oak Street for designer boutiques or head over to Rush Street for a taste of Chicago’s vibrant nightlife scene.

Take A Walk Through Millennium Park

Located in the heart of downtown Chicago, Millennium Park is another must-see attraction in Chicago, and for good reason. This 24.5-acre urban park is home to some of the city’s most famous landmarks, including the iconic Cloud Gate sculpture (affectionately known as “The Bean”), Crown Fountain (the coolest splash pad in Chicago), and the Jay Pritzker Pavilion.

Take a leisurely walk through the park and admire the stunning art and architecture or catch one of the many events that take place throughout the year, such as concerts, film screenings, and outdoor yoga classes.

Wander The Chicago Riverwalk

If you want to experience the beauty of Chicago’s architecture and riverfront, then a stroll along the Chicago Riverwalk is a must. This 1.25-mile promenade offers stunning views of the city skyline and is lined with restaurants, outdoor cafes, and boat tours.

Take a break from your walk and grab a bite to eat at one of the many options along the way or hop on a river cruise for an up-close view of some of Chicago’s most famous buildings like the Wrigley Building and Tribune Tower.

Enjoy Grant Park And Buckingham Fountain

Located just south of Millennium Park, Grant Park is often referred to as “Chicago’s front yard.” This expansive green space features gorgeous views of Lake Michigan and the city skyline, making it a popular spot for picnics, concerts, and festivals.

At the center of Grant Park sits Buckingham Fountain, one of the largest fountains in the world. Designed in a neoclassical style, this iconic Chicago landmark features hourly water displays and stunning light shows at night.

Visit Navy Pier

Located on Lake Michigan, Navy Pier is a popular tourist destination in Chicago. It offers something for everyone with its array of shops, restaurants, boat tours, and even an amusement park with a giant Ferris wheel.

Take a stroll along the pier and enjoy the beautiful views of the lake, or catch a fireworks show during the summer in the evening. You can also hop on a boat tour to get an up-close look at Chicago’s impressive skyline from the water.

Indulge In Deep-Dish Pizza

No trip to Chicago is truly complete without indulging in a slice of its iconic deep-dish pizza. This mouthwatering delight features a thick, buttery crust that serves as a delicious base for a generous layer of gooey cheese, tangy tomato sauce, and an array of delectable toppings. Unlike its classic flat counterpart, this deep-dish creation resembles a savory pie, offering a unique pizza experience.

Fortunately, Chicago boasts an array of eateries vying for the title of the best deep-dish pizza in town. Why not go on a culinary adventure and sample the offerings at renowned spots such as Lou Malnati’s, Giordano’s, and Pequod’s? Each establishment brings its own twist to this beloved dish, ensuring a delightful exploration of flavors that will tantalize your taste buds and leave you craving more.

Catch A Game At Wrigley Field

Home to the beloved Chicago Cubs baseball team, Wrigley Field is a must-see for sports fans. Located in the Wrigleyville neighborhood, this historic ballpark has been standing since 1914 and is known for its ivy-covered outfield walls and iconic red marquee.

Even if you’re not a die-hard Cubs fan, attending a game at Wrigley Field is an experience like no other. The energy of the crowd, the classic charm of the stadium, and the delicious ballpark food make for a memorable day out in Chicago.

End your visit by taking a stroll around the neighborhood filled with charming homes and local bars and restaurants. You may even catch some live music or street performers on game days.

Alternativey, check out a White Sox game at Guaranteed Rate Field, located on the South Side of Chicago. While not as historic as Wrigley Field, this stadium offers a more modern and updated experience for sports fans.

Take A Tour Of Wrigley Field

Even if you’re not a die-hard sports fan, taking a tour of Wrigley Field is still worth adding to your Chicago itinerary. You’ll get an inside look at the stadium’s iconic features such as the ivy-covered walls, manual scoreboard, and historic bleachers.

You’ll also learn about the history of the Cubs and some memorable moments that have taken place at Wrigley Field. And who knows, you might even catch a glimpse of the team practicing or warming up on the field!

Relax At Oak Street Beach

When the weather is nice, head to Oak Street Beach for some fun in the sun. This popular beach offers stunning views of Lake Michigan and is a great spot for swimming, sunbathing, and people-watching.

There are also nearby bike and walking paths if you want to explore the area further. And don’t forget to snap a photo with the iconic Chicago skyline in the background – it’s a must-have shot for your trip!

Explore Chinatown

Chicago’s vibrant Chinatown neighborhood is a must-visit for its bustling streets, unique shops, and delicious food. Take a stroll down Wentworth Avenue and you’ll find an array of Chinese restaurants, bakeries, and markets selling traditional goods.

Be sure to check out the Nine Dragon Wall, a stunning mosaic wall featuring nine dragons that symbolize good luck and prosperity. And if you’re in town during the Chinese New Year celebrations, don’t miss the colorful parade that takes place in this lively neighborhood.

Chicago’s Chinatown is the second largest Chinatown in the United States.

Experience Art At The Art Institute Of Chicago

Home to over 300,000 artworks from across the globe, The Art Institute of Chicago is an essential destination for any art enthusiast. Its diverse collection, which spans centuries and cultures, has earned recognition as one of Tripadvisor’s “Best of the Best” attractions in the US for 2024. With iconic pieces by Monet and Van Gogh alongside contemporary masterpieces by Picasso and Warhol, there is something for everyone to admire and enjoy.

Be sure to stop by the iconic “American Gothic” painting by Grant Wood, as well as the Thorne Miniature Rooms, which feature intricately detailed miniature replicas of historical rooms from different time periods and cultures.

Learn About History At The Chicago History Museum

For those interested in learning more about Chicago’s rich history, a visit to the Chicago History Museum is a must. This museum features interactive exhibits, artifacts, and photographs that showcase the city’s past, including its role in important events like the Great Fire of 1871 and the World’s Columbian Exposition of 1893.

Be sure to check out their extensive collection of Abraham Lincoln memorabilia and don’t miss their rotating special exhibitions that offer in-depth looks at various aspects of Chicago’s history.

Architecture River Cruise

Chicago is known for its stunning architecture, and one of the best ways to experience it is through an architecture river cruise. These narrated boat tours take you along the Chicago River, showcasing iconic buildings like the Willis Tower (formerly known as the Sears Tower) and the Wrigley Building.

Learn about the city’s history and how its skyline has evolved over time while taking in breathtaking views from a unique perspective. Many tour companies offer different variations of this popular activity, including sunset cruises and themed tours focused on specific architectural styles or famous architects.

Go For A Paddle On The River

If you prefer a more hands-on approach to exploring the Chicago River, consider renting a kayak or stand-up paddleboard. Paddleboards and kayaks can be rented from several locations along the river.

This is a great way to get some exercise while enjoying the city’s beautiful skyline from a different angle.

Explore The Neighborhoods

Chicago is known for its diverse neighborhoods, each with its own unique culture and charm. Take some time to explore different areas of the city and discover their hidden gems.

Visit Chinatown for authentic Chinese cuisine and cultural experiences, or head to Pilsen for colorful street art and delicious Mexican food. Don’t miss out on the vibrant music scene in Wicker Park or the trendy shops and restaurants in Logan Square.

No matter where you go, you’ll find something new and interesting to discover

Skydeck Chicago At The Willis Tower

For the adrenaline seekers and thrill-seekers, a visit to Skydeck Chicago at the Willis Tower is a must. This observation deck located on the 103rd floor of the tallest building in Chicago offers stunning views of the city and Lake Michigan from its glass-enclosed deck.

But it’s not just about the views here – Skydeck Chicago also offers visitors a unique experience with its famous “Ledge.” Step onto this glass balcony that extends out from the building, giving you a bird’s eye view of the streets below.

360 Chicago Observation Deck

For another incredible view of Chicago’s skyline, head to the 360 Chicago Observation Deck located in the John Hancock Center. Similar to Skydeck Chicago, this observation deck also offers a glass-enclosed viewing platform and the opportunity to step out onto “Tilt,” a glass balcony that tilts you out over the city at a heart-pumping angle. Be prepared for an extra fee for the TILT experience, as well as to pay a premium for a photo, since cameras are not permitted inside.

In addition to its views, 360 Chicago also features interactive exhibits and an impressive bar with craft cocktails and small bites. It’s the perfect spot for both thrill-seekers and those looking for a unique experience while taking in the cityscape.

The Chicago Theatre District

Known as the birthplace of modern American theater, Chicago’s Theatre District is a must-visit for any art and culture enthusiast. Located in the Loop neighborhood, this area is home to over 15 different theaters and performance venues, showcasing everything from Broadway hits to experimental shows.

Catch a show at the iconic Chicago Theatre, known for its marquee sign and dazzling interior décor. Or head to the Goodman Theatre, one of the oldest and most respected regional theaters in the country. No matter which show you choose to see, you’re bound to be entertained by some of the best talent in the industry.

Afterwards, take a stroll down bustling State Street and admire the historic architecture while grabbing a bite to eat at one of the many restaurants in the area. And if you’re visiting during the summer months, be sure to check out the free outdoor performances at Millennium Park’s Jay Pritzker Pavilion.

With its vibrant culture, breathtaking architecture, and endless entertainment options, Chicago truly caters to everyone. Whether you’re exploring the city’s iconic landmarks or immersing yourself in its flourishing arts scene, a visit to the Windy City promises to be an unforgettable experience.

There’s always more to discover in this remarkable city—be it savoring local delights at renowned deep-dish pizza spots or participating in one of the many festivals held throughout the year. Don’t overlook Chicago’s rich history, from its pivotal role during the Prohibition era to its stunning skyline; there’s a captivating story waiting to be uncovered at every turn.

Pack your bags and get ready to uncover all that this dynamic city has to offer. See you in Chicago!

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