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15 Best Things To Do In Chicago

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Things To Do In Chicago, IL

Located along the shores of Lake Michigan, Chicago is the largest city in the midwest. With iconic buildings, lovely open spaces and great museums, there’s an endless amount of things to do in the Windy City.

To help you plan your trip, here are our picks for the 15 best things to do in Chicago. Millennium Park

1. Millenium Park

Things to do in Chicago
Millennium Park, Chicago | Photo Credit – Teo Romera

Millennium Park is without a doubt one of the best things to do in Chicago. Part of Grant Park, Millennium Park is home to some of the most famous attractions in the city, and includes incredible art, architecture and landscaping.

Take a selfie in front of Cloud Gate (more commonly known as “The Bean”), Anish Kapoor’s mirrored, stainless steel art piece. Be dazzled by the reflecting pools and projected visuals of the Crown Fountain. Admire contemporary sculptures outdoors at the Boeing Galleries. Or wander among the Lurie Gardens. And from spring to fall, enjoy live shows as the Frank Gehry-designed Pritzker Pavilion.

Free guided garden and architecture tours are also available during this time. The park and its exhibits are all free.

2. The Magnificent Mile

Things to do in Chicago
The Magnificent Mile, Michigan Avenue, Chicago, Illinois
Photo Credit – Ken Lund

Shop until you drop, and admire amazing architecture, along the Magnificent Mile. This iconic stretch of Michigan Avenue runs between the Chicago River and Oak Street.

Considered Chicago’s grandest street, it’s home to more than 450 retails. From grand department stores and brand name retail chains to luxury boutiques, you’ll find it all here. The Mag Mile is also home to some of the most impressive buildings in the city. Highlights include the Tribune Tower, Hancock Center, Wrigley Building and the Historic Water Tower.

Even if you don’t plan to do any shopping, it’s worthwhile just to stroll along this incredible street. Along the way, you’ll also come across many hotels, galleries, restaurants and bars

3. Willis Tower Skydeck Chicago

Things to do in Chicago
Willis Tower, Chicago | Photo Credit – Bari D

Visiting Skydeck Chicago in the Willis Tower (formerly Sears Tower) is one of the best things to do in Chicago. Located on the 103rd floor of Chicago’s tallest building, you can see for more than 50 miles and across four states on a clear day.

Enjoy sweeping views on all four sides. If you’re brave enough, there are also four clear glass-bottomed boxes that extend out over the side of the building. There are also an array of interactive exhibits, including one on notable Chicagoans and the Knee-High Chicago exhibit for kids. You’ll also learn some interesting facts as you go up the elevator.

The Skydeck is extremely popular and there are often lines. You can purchase a fast pass to cut down on waiting times. Alternatively, try 360 Chicago Observation Deck on the 94th floor of the John Hancock Center.

4. Chicago Riverwalk

Things to do in Chicago
Chicago Riverwalk | Photo Credit – Payton Chung

Walking along the Chicago Riverwalk is one of the best things to do in Chicago. It stretches for 1.25 miles along the banks of the Chicago River, and offers many dining, drinking, recreation and entertainment options.

It’s made up of six different themed “rooms,” or coves that offer different activities. Walk or run along the pedestrian path. Take a break and watch the world go by in stadium seats. Enjoy stunning views of the city and architecture.

Rent a boat or kayak. Explore a floating garden. Admire public art. Learn about bridges and the river at the McCormick Bridgehouse & Chicago River Museum. Go fishing. Or just enjoy a nice meal and drinks al fresco. 

5. Grant Park

Things to do in Chicago
Buckingham Fountain, Grant Park, Chicago, Illinois | Photo Credit – Ken Lund

Known as “Chicago’s front yard,” chances are you will spend some time at Grant Park during your visit. Spanning 319 acres, it’s home to some of Chicago’s top attractions.

Highlights include Millenium Park, the Museum Campus (home to the Field Museum, Shedd Aquarium and the Adler Planetarium), Maggie Daley Park and Soldier Field, home of the Chicago Bears NFL team.

In addition, you can enjoy manicured grounds, lovely gardens, nice trails, tennis courts, baseball diamonds and great city views. The park is free to visit, though certain attractions may charge an entrance fee.

6. River Cruise

Things to do in Chicago
River Cruise, Chicago | Photo Credit – Bill Ward

Going on a boat cruise is one of the best things to do in Chicago. One of the most popular cruises is an architecture river cruise. Chicago is known for its wealth of landmark and historic buildings.

Enjoy great skyline views while expert guides share the history and background of these amazing buildings, including the Wrigley Building, Willis Tower and the John Hancock Building. While many companies offer these cruises, most people recommend the Chicago Architecture Foundation cruise one the First Lady. 

Other cruises options are available. Try a wine and cheese cruise, a lunch cruise or a dinner cruise. Or go on a guided kayak tour, or a ghosts and gangsters kayak tour.

7. Try Some Pizza

Things to do in Chicago
Lou Malnati’s Pizzeria, Chicago | Photo Credit – Lauren Topor

No visit to Chicago would be complete without trying some pizza. Chicago is known for its signature deep dish pizza, with layers of sauce, cheese and toppings. Some of the best places to try some include Lou Malnati’s Pizzeria, Pizzeria Uno, Giordano’s, Gino’s East and Pequod’s Pizza.

If you’re feeling extra indulgent, you can even try a stuffed version. Or for a lighter option, try some thin crust tavern style pizza. To sample a variety of pies, try a guided pizza tour, or a pizza and cocktail tour.

You can even learn to make deep dish pizza in a cooking class. To sample more than just pizza, try a guided food tour.

8. Field Museum of Natural History

Things to do in Chicago
Field Museum of Natural History, Chicago | Photo Credit – Curtis & Renee

Learn about history, natural science and more at the Field Museum of Natural History.

It’s one of the largest natural history museums in the world, with a whopping 24 million items in its collection. There’s everything from fossils to ancient artifacts to gems and more. Popular exhibits include SUE, the most complete T. rex fossil ever found. Also noteworthy are a giant Titanosaur and flock of pterosaurs.

The ancient Egypt exhibit is also fantastic and includes a reconstructed 3-story Egyptian tomb. Be dazzled by an incredible gem collection. Learn about conservation, or genetics. There’s so much to do here, so be sure to leave yourself enough time.

9. Art Institute of Chicago

Art Institute of Chicago | Photo Credot – vagueonthehow

The Art Institute of Chicago is one of the best things to do in Chicago for art lovers. Considered one of the top art museums in the world, the museum has a collection of more than 300,000 works of art.

It’s home to one of the best collections of Impressionist paintings in the world. See works by famous artists such as Monet, Van Gogh and Renoir. The museum also has a notable collection of ancient Egyptian sculptures, Japanese fabrics and modern American art.

Join a gallery tour to learn more. Special exhibitions, performances and other programs are also available from time to time.

10. Wrigley Field

Things to do in Chicago
Wrigley Field, Chicago | Photo Credit – Rob Pongsajapan

Even if you’re not a baseball fan, Wrigley Field is worth visiting. One of the top landmarks in Chicago, it’s the second oldest stadium in Major League Baseball.

Built in 1914, it’s also one of the most distinctive ballparks in the sport. It’s best to watch a Cubs game here if you can. Depending on the game and opponent, upper-level seats can be quite reasonably priced. Check out the ivy-covered exterior, famous red marquee entrance and iconic manual scoreboard.

Don’t forget to treat yourself to a hot dog. Even if you can’t make a game, consider taking a guided tour of the ballpark. Tours on non-game days even include a visit to the team clubhouse.

11. Shedd Aquarium

Shedd Aquarium, Chicago | Photo Credit – Josh Hallett

Located within the Museum Campus portion of Grant Park, Shedd Aquarium is one of the largest indoor aquariums in the world. It’s home to more than 32,000 animals.

While most of the residents here are aquatic, there are also birds, reptiles, small monkeys and more. See animals in many different habitats, such as the Amazon Rising, Caribbean Reef, Polar Play Zone and Waters of the World. Special experiences, including tours, animal encounters and feedings, are available for an additional fee.

Over the summer, enjoy live jazz on Wednesday nights. The aquarium is very popular, so it’s best to book your ticket in advance to minimize waiting times. CityPASS holders also get to skip the line.

12. Navy Pier

Navy Pier, Chicago | Photo Credit – Dawn

This is one of the best things to do in Chicago, especially for families. Located on a prime spot that extends out over Lake Michigan, it’s one of the top attractions in Chicago.

Take a ride on the iconic Ferris Wheel and enjoy sweeping city and lake views. There’s also a popular carousel and swing ride. The pier is also home to the Chicago Children’s Museum, the Chicago Shakespeare Theater, an indoor botanical garden, miniature golf, an IMAX theater, restaurant, shops and a cruise ship dock.

During the summer, the pier often hosts free concerts, theater performances and fireworks shows. It’s free to walk around the pier, but rides and attractions will cost extra.

13. Chicago Lakefront Trail

Chicago Lake Front Trail | Photo Credit – bradhoc

Enjoy the outdoors and plenty of attractions along the Chicago Lakefront Trail. The trail is an 18-mile path that hugs the shoreline of Lake Michigan.

You’ll pass through all four of Chicago’s lakefront parks. Walk, jog, run or bike the paved trail. Along the way, enjoy green spaces, beaches, recreation facilities, art installations, cultural institutions and dining and entertainment options.

The trail also offers some of the best lake and skyline views in the city. There are also plenty of restrooms, hydration stations and concession stands along the path. Many bike and Segway tours will cover a portion of the trail as well.

14. The Second City

Chicago Theatre | Photo Credit – GPA Photo Archive

If you like comedy, then you must catch a Second City show. The Second City is the oldest continuously running and one of the top improv comedy theaters in America.

Famous names such as Bill Murray, Stephen Colbert, Steve Carrell and Tiny Fey all got their start here. There are seven different locations across Chicago. Their Mainstage can be found in Old Town near Lincoln Park.

There are shows every night of the week. The shows are not kid-friendly, but they are hilarious. Second City also offers comedy classes for aspiring comedians, as well as private dinners and events.

15. Chicago Cultural Center

Things to do in Chicago
Chicago Cultural Center | Photo Credit – Brian Crawford

Built in 1897 as Chicago’s first public library, today the Chicago Cultural Center is an architectural gem and a popular attraction.

The building boasts two beautiful stained glass domes and an ornate interior of rare marble, hardwood, stained glass and mosaics. There’s also a visitor information center here, which is a great resource for tourists. Stop by to pick up maps and other tourist information. Or join a guided tour.

There’s also a permanent exhibit on Chicago’s architectural gems and preservation efforts. The center also hosts around 1,000 free exhibitions and cultural programs a year, including art exhibits, concerts, plays, film screenings, lectures and family events.

If you plan on sightseeing in Chicago, a multi-attraction pass, such as the CityPASS or Go Chicago Explorer Pass, offer great value. For a custom tailored experience, book a private tour. Opt for a hop-on hop-off bus tour to explore at your leisure. There are also many tours tailored for certain interests, such as a gangster tour, prohibition tour, street art tour, bike tour and Segway tour.


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