Looking for the best things to do in Chicago?
I’ve got you covered!
Nestled along the shores of Lake Michigan, Chicago is a vibrant city full of history, culture, and natural beauty.
In this post, I’ve put together all the top attractions, must-see landmarks, and local favorites of Windy City that you don’t want to miss.
Let’s dive in.
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Chicago Essentials
Top Tours & Experiences In Chicago
- Chicago Architecture River Cruise
- Chicago Sunset Cruise
- Gangsters and Ghosts Tour in Chicago
- Skydeck Chicago Admission Ticket
- 360 Chicago Observation Deck Admission
Where To Stay In Chicago
- citizenM Chicago Downtown ($)
- Sofitel Chicago Magnificent Mile ($$)
- Thompson Chicago ($$$)
- Viceroy Chicago ($$$)
- The Langham Chicago ($$$$)
Related: 10 Best Hotels In Chicago
1. Take a picture at “The Bean”
Officially titled Cloud Gate, “The Bean” is the nickname for the famous public sculpture located in the beautiful Millennium Park located right in the heart of downtown Chicago.
The nickname “The Bean” comes from its distinctive shape resembling a massive, polished stainless steel bean.
Visually stunning and easily recognizable — the sculpture’s reflective surface offers endless opportunities for photos.
Whether it’s reflecting the colorful leaves of fall, the glistening snow of winter, or the vibrant energy of summer, each season provides you its own unique perspective.
“The Bean” is more than just a cute photo op though, it’s a multi-dimensional experience that combines art, architecture, and the urban environment, making it a must-do activity for anyone visiting Chicago.
Make sure to get there as early as possible, if you want photos without the crowds!
2. Explore Millennium Park
After you’ve stopped by The Bean, make sure to check out the rest of Millennium Park.
This park provides something for everyone, making it an essential part of the Chicago experience.
With its perfect location in downtown Chicago, it offers panoramic views of the city’s iconic skyline while also being a great spot to relax, take a stroll, or have a picnic while enjoying the scenery.
Kids can even enjoy playing in the Crown Fountain, which has interactive video projections and fun water features.
And just a short walk away is the famous Lurie Garden, a serene and beautifully landscaped garden that offers a peaceful escape from the hustle and bustle.
It features a variety of native plants and a design that changes with the seasons, providing a tranquil and educational space with plenty of photo opportunities.
3. Visit the Riverwalk
The Riverwalk is a vibrant waterside promenade along the Chicago River in downtown Chicago.
It features pedestrian walkways, landscaped gardens, art installations, and sitting areas.
You’ll find some of the best views and photo spots on Wabash Bridge.
Whether you’re indulging in a leisurely stroll or enjoying a riverside picnic, the Riverwalk is a must-see in Chicago.
4. Take an Architecture Boat Tour
Due to its role in pioneering modern architectural concepts, the city of Chicago is renowned for its architecture.
Chicago birthed the world’s first skyscraper, housed influential architects like Frank Lloyd Wright, and boasts iconic structures like the Willis Tower (formerly the Sears Tower).
Exploring Chicago’s famed architecture from the comfort of a boat provides a one-of-a-kind perspective that combines education and relaxation.
With the tour’s mix of visual sights, historical significance, and the chance to create fun memories, it’s an ideal activity for anyone desiring a sophisticated adventure in Chicago.
I recommend this insanely highly-rated Chicago Architecture River Cruise on Viator.
Click here to check availability on Viator.
5. Explore the Magnificent Mile
Exploring the Magnificent Mile in Chicago offers an amazing fusion of upscale shopping, delectable dining, and captivating sights.
With iconic stores like Saks Fifth Avenue, Nordstrom, and Louis Vuitton, the Magnificent Mile is a shopper’s haven, where luxury meets variety.
Amidst the shopping spree, you can savor culinary delights at renowned restaurants such as The Signature Room, known for its panoramic views, and The Purple Pig, offering exquisite Mediterranean-inspired cuisine.
Beyond its retail and dining options, Magnificent Mile’s proximity to Lake Michigan adds an extra touch of beauty.
Seasonal events like the Lights Festival infuse the area with vibrant festivities.
Overall, Magnificent Mile’s blend of shopping, dining, and landmarks makes it a quintessential Chicago experience that embodies the city’s glitz.
6. Experience Skydeck Chicago
Located in the world-famous Willis Tower (formerly the Sears Tower), Skydeck Chicago is a must-see.
It’s an exhilarating experience that combines breathtaking views and Insta-worthy moments.
Stepping onto the iconic glass ledge known as “The Ledge,” is sure to offer an adrenaline rush.
From there, you’ll take in panoramic vistas of the city’s skyline and Lake Michigan from over 1,300 feet high.
Beyond the thrill, the Skydeck offers a blend of cultural and architectural appreciation, allowing you to engage with Chicago’s rich history and one of its most iconic landmarks from a birds-eye vantage point.
Click here to check availability on Viator.
7. Visit 360 Chicago
360 Chicago is a popular observation deck located at the top of the Hancock Tower.
It offers stunning views and an immersive journey into Chicago’s history and architecture.
The interactive exhibits and informative displays provide a deeper understanding of the city’s iconic landmarks, bridging the past and present.
Coupled with the option to step onto the TILT glass platform, which tilts outward from the building, this experience blends thrill and cultural enrichment.
While at the top, make sure to grab a drink at the Cloud Bar.
Click here to check availability on Viator.
8. Relax on the beach
Relaxing on one of Lake Michigan’s beautiful beaches is one of the best things to do in Chicago on a sunny day.
North Avenue Beach stands out as one of the city’s most popular lakefront destinations.
It encapsulates Chicago’s lively beach atmosphere, while offering a picturesque lakeside experience.
It has sandy shores, blue water, and great amenities like bathrooms, showers, and a beachside restaurant.
You’ll also find a variety of activities here, such as kayak and paddle board rentals, sand volleyball, and frequent events.
If you’re looking for a more laid back atmosphere, head to Oak Street Beach.
This beach is smaller and quieter, with fewer amenities but smaller crowds.
Overall, Chicago’s beaches offer a unique blend of natural beauty and city views for a fun day in the sun.
9. Try deep dish pizza
As a beloved local specialty, it wouldn’t be a true Chicago trip without indulging in an authentic Chicago-style deep dish pizza!
If you haven’t heard, it features a thick, buttery crust that lines the sides and bottom of a deep pan.
The toppings are then layered in reverse order, with cheese often at the bottom, followed by meat, vegetables, and a rich tomato sauce on top.
Amongst Chicagoans, there are a few top spots to lose yourself in this iconic dish.
Lou Malnati’s Pizzeria is a classic choice, celebrated for its perfectly balanced flavors and flaky crust.
Giordano’s is another renowned option, famous for its stuffed deep dish pizza that boasts layers of ingredients and cheese.
These establishments have garnered both local and international acclaim, making them essential stops for anyone looking to savor an authentic and delicious deep dish pizza experience in the city.
10. Spend the evening at Navy Pier
The Navy Pier is one of the best places to visit in Chicago for families with kids, or couples looking for a romantic outing.
This iconic destination combines fun activities, entertainment, shopping, and dining along Lake Michigan’s beautiful shoreline.
Here, you’ll find the famous Centennial Wheel (a giant ferris wheel), the Chicago Children’s Museum, and Pier Park which houses a carousel and mini golf.
The Pier includes an array of dining options, from upscale restaurants to casual eateries.
If you visit around sundown, you may even catch a dazzling firework show.
Related: 31 Magical Things To Do In Chicago At Christmas
11. Have a spa day at AIRE Ancient Baths
If you’re looking for something unique to do in Chicago, look no further than AIRE Ancient Baths.
Drawing inspiration from ancient Roman baths, AIRE transports visitors to a realm of relaxation and rejuvenation.
The baths’ opulent design, including pools of different temperatures and indulgent spa services, exude tranquility.
Situated in the heart of the city, AIRE offers a sanctuary from the hustle and bustle, making it a must-see for those seeking relaxation in Chicago.
12. Visit Art Institute of Chicago
As one of the oldest and largest art museums in the United States, The Art Institute of Chicago boasts an impressive collection spanning centuries and continents.
Within its halls lies a diverse array of artwork, from timeless classics to cutting-edge contemporary pieces.
The museum’s ambiance provides a serene and inspiring atmosphere for self-reflection and exploration.
Renowned pieces, such as Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte,” offer opportunities to view iconic masterpieces firsthand.
The museum’s commitment to fostering a dialogue between art and its viewers, combined with its central location in downtown Chicago, makes it an essential stop.
13. Visit the Chicago Theater
The Chicago Theater is a cultural landmark, known for its historical significance and striking architecture.
If you time your visit right, you may be able to catch a live show and witness the theater’s grandeur firsthand.
If not, still stop by to snap a picture of the theater’s iconic sign.
This iconic and ornate marquee sign has become synonymous with Chicago itself.
14. Enjoy the Lincoln Park Zoo
If you’re looking for one of the best free things to do in Chicago, head to the Lincoln Park Zoo.
This zoo offers a family-friendly environment with year round activities and beautifully landscaped habitats.
Its commitment to education and conservation makes it a great place to spend the day in Chicago.
15. Catch a game at Wrigley Field
Wrigley Field stands as one of the premier attractions in Chicago due to its rich history, captivating tradition, and enduring charm.
As one of the oldest ballparks in Major League Baseball, it exudes an irresistible nostalgic allure.
The ballpark’s ivy-covered walls, iconic hand-operated scoreboard, and daytime games create a distinctive atmosphere.
Whether you’re a serious baseball fan or just an adventurous traveler, Wrigley Field offers an opportunity to experience a piece of sports legacy and Chicago’s culture.
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