Discover the Best Things to Do in Chicago – Your Ultimate Guide

photo of high-rise building

Welcome to our comprehensive guide to the best things to do in Chicago! As one of the largest cities in the United States, Chicago has something for everyone. From its stunning architecture to its cultural attractions, delicious food, and thriving nightlife, you’ll never run out of things to do in this vibrant city.

Chicago is famous for its architecture. The city boasts some of the world’s most iconic skyscrapers, including the Willis Tower and the John Hancock Center. Visitors can also explore the Chicago Riverwalk, a popular destination for outdoor walks and river tours.

In addition to architecture, Chicago is known for its rich cultural scene. The city is home to many world-class museums, including the Art Institute of Chicago and the Museum of Contemporary Art. Music lovers will also appreciate Chicago’s deep history in blues and jazz music.

No visit to Chicago would be complete without indulging in its delicious cuisine. Whether you’re in the mood for deep-dish pizza, hot dogs, or upscale fine dining, this city has it all. Make sure to check out the famous Taste of Chicago and Chicago Gourmet festivals for a sampling of the city’s best food and drink.

If you’re looking to enjoy the great outdoors, Chicago has plenty of options for you. The city is home to many beautiful parks, including Grant Park and Millennium Park, as well as stunning beaches along Lake Michigan.

For those who love to shop, Chicago won’t disappoint. With everything from luxury stores on the Magnificent Mile to unique boutiques in Wicker Park, there’s something for every shopper.

Chicago is also famous for its nightlife. From bars and clubs to theaters and comedy shows, there’s always something to do in the evening. And for sports fans, Chicago’s passionate sports culture is not to be missed. Cheer on the Cubs, Bears, or Blackhawks at one of the city’s many venues.

Finally, we’ve included a section with frequently asked questions to help you plan your trip. From transportation options to safety tips and the best time to visit, we’ve got you covered. So pack your bags and get ready for an unforgettable trip to Chicago!

Explore the City’s Iconic Architecture

Built after the Great Chicago Fire of 1871, Chicago’s architecture is a fascinating mix of old and new. From the historic skyscrapers of the Chicago Loop to modern designs such as the Cloud Gate in Millennium Park, the city’s buildings are a must-see for any visitor.

Chicago’s skyline is one of the most recognizable in the world, with towering structures that showcase the city’s engineering and architectural prowess. The Willis Tower (formerly known as the Sears Tower) was the tallest building in the world until 1998 and remains a popular tourist attraction. Visitors can take an elevator to the Skydeck on the 103rd floor to experience breathtaking views of the city.

Building Location Height (ft)
Willis Tower 233 S Wacker Dr 1,450
John Hancock Center 875 N Michigan Ave 1,128
Aqua Tower 225 N Columbus Dr 876

Besides the towering skyscrapers, Chicago’s Riverwalk is another architectural marvel worth exploring. The promenade follows the Chicago River and offers stunning views of the city’s bridges and buildings. Visitors can enjoy a leisurely stroll, dine at one of the many riverside restaurants, or take a boat tour to learn more about the city’s history.

Chicago’s unique architectural style can be traced back to the late 1800s when the city became a hub for steel production. The use of steel frame construction allowed for taller buildings, and architects began to experiment with decorative features such as terra cotta and stained glass.

The Best Buildings to Visit

While Chicago is home to many awe-inspiring structures, some buildings are considered must-sees:

  • The Rookery Building: A historic office building designed by Frank Lloyd Wright and Louis Sullivan.
  • The Chicago Cultural Center: A stunning Beaux-Arts building that houses free art exhibits and performances.
  • The Tribune Tower: A neo-Gothic skyscraper that features fragments from famous buildings from around the world embedded in its exterior.

Chicago is not the most beautiful city in the world, but it is one of the few in which the beauty of the architecture is so central and pervasive.

– Paul Goldberger, architecture critic.

Immerse Yourself in Art and Culture

Chicago is a cultural powerhouse, home to world-renowned museums and art galleries. Whether you’re interested in ancient history, modern art, or natural sciences, there’s something for everyone in the Windy City.

One of the most famous museums in the city is the Art Institute of Chicago, which is home to over 300,000 works of art from around the world. Visitors can marvel at iconic pieces like Grant Wood’s American Gothic and Georges Seurat’s A Sunday on La Grande Jatte.

Another must-visit museum is the Field Museum of Natural History, which is home to Sue, the largest and most complete Tyrannosaurus rex skeleton in the world. Visitors can also explore exhibits on ancient Egypt, dinosaurs, and the natural world.

If modern art is more your thing, check out the Museum of Contemporary Art, which features rotating exhibits of contemporary art from around the world. The museum also hosts performances, film screenings, and lectures throughout the year.

Blues Music and Live Venues

In addition to its museums, Chicago is also known for its rich musical history, particularly the blues. Fans of the genre won’t want to miss a visit to the Chicago Blues Museum, which showcases the contributions of Chicago to the blues scene.

For those looking to experience live music, there are plenty of venues to choose from. The Green Mill Cocktail Lounge is a historic jazz club that has hosted legendary performers like Von Freeman and Patricia Barber. For a more modern vibe, check out Thalia Hall, which hosts popular indie bands and up-and-coming artists in a beautifully restored historic venue.

Indulge in Delicious Food

One of the best things to do in Chicago is to immerse yourself in its diverse food scene. From deep-dish pizza to hot dogs to upscale fine dining, there is something for every taste and budget.

Chicago is famous for its deep-dish pizza, and two of the best places to try it are Lou Malnati’s and Giordano’s. Both restaurants have multiple locations throughout the city, so you can easily find one near you. If you’re looking for something a little different, try Pequod’s Pizza, which is known for its caramelized crust.

Chicago is also famous for its hot dogs, which are typically topped with mustard, relish, onions, pickles, tomatoes, and peppers. Two of the best places to try them are Portillo’s and Superdawg. If you’re feeling adventurous, try a Chicago-style Italian beef sandwich, which is a local specialty that is typically served with giardiniera, a spicy pickled vegetable relish.

If you’re looking for upscale fine dining, there are plenty of options in Chicago. Some of the most popular restaurants include Girl & the Goat, Alinea, and The Chicago Chop House. Just be sure to make a reservation in advance, as these restaurants tend to fill up quickly.

Chicago Food Festivals

In addition to its many restaurants, Chicago is also famous for its food festivals. The Taste of Chicago is one of the city’s most popular events, featuring food from some of its best restaurants. Other popular festivals include the Chicago Gourmet and the Chicago Hot Dog Fest.

Restaurant Specialty Location
Lou Malnati’s Deep-dish pizza Multiple locations
Giordano’s Deep-dish pizza Multiple locations
Pequod’s Pizza Deep-dish pizza with caramelized crust 2207 N Clybourn Ave
Portillo’s Chicago-style hot dogs Multiple locations
Superdawg Chicago-style hot dogs 6363 N Milwaukee Ave
Girl & the Goat Upscale American cuisine 809 W Randolph St
Alinea Molecular gastronomy 1723 N Halsted St
The Chicago Chop House Steakhouse 60 W Ontario St

Experience the Great Outdoors

Chicago offers more than just city streets and skyscrapers. The city is also home to a variety of outdoor recreation opportunities, including beautiful parks and beaches.

Visit Grant Park

Grant Park, also known as “Chicago’s front yard,” is a 319-acre park located in downtown Chicago. The park features stunning gardens, art installations, and monuments, as well as the famous Buckingham Fountain. Visitors can also enjoy outdoor concerts and events at the Jay Pritzker Pavilion.

Explore Millennium Park

Millennium Park is another popular destination for outdoor recreation in Chicago. The park features unique architectural features, such as the Cloud Gate sculpture (affectionately known as “The Bean”), as well as beautiful gardens and green spaces. Visitors can also take advantage of the park’s free outdoor fitness classes and concerts.

Relax on the Beach

Chicago is home to many beautiful beaches along the shores of Lake Michigan. North Avenue Beach is a popular destination, with a beach house, concession stands, and water activities such as kayaking and stand-up paddleboarding. Montrose Beach is another great option, with a dog-friendly area and volleyball courts.

Take a Bike Ride

One of the best ways to explore Chicago’s outdoor spaces is by bike. Visitors can rent a bike from the city’s bike-sharing program, Divvy, and explore the city’s many bike trails and paths. The Lakefront Trail offers stunning views of Lake Michigan, while the 606 Trail is a unique elevated trail built on a former railroad.

Shop ‘Til You Drop

If you’re a shopaholic, Chicago won’t disappoint. With its eclectic mix of upscale stores, independent boutiques, and vintage shops, you’re sure to find something to fit your style and budget.

Begin your shopping adventure on the Magnificent Mile, which boasts an array of high-end designer stores, including Burberry, Gucci, and Louis Vuitton. If you’re in the mood for something more unique, head to Lincoln Park, where you’ll find a variety of local boutiques and specialty shops.

Shopping Destination Location
Magnificent Mile Michigan Avenue between Oak St and the Chicago River
Lincoln Park Armitage Avenue between Halsted and Racine
Wicker Park Milwaukee Avenue between North and Division

If you’re looking for something a bit more affordable, head to Wicker Park, where you’ll find a variety of thrift and vintage stores, such as Kokorokoko and Knee Deep Vintage.

Finally, if you’re in need of some retail therapy but don’t want to deal with the crowds, head to one of Chicago’s many shopping malls, including Water Tower Place and the Shops at North Bridge.

  • Water Tower Place
  • The Shops at North Bridge
  • 900 North Michigan Shops

Pro Tip:

If you’re looking to save some money on your shopping trip, head to the city’s outlet malls, such as Fashion Outlets of Chicago and Chicago Premium Outlets, which offer discounts of up to 65% on designer brands.

Unwind with Nightlife

Chicago is known for its vibrant nightlife scene, with options for every type of visitor. Whether you’re looking for a laid-back night at a local bar or an energetic dance party, the city has something to offer.

If you’re a comedy fan, be sure to check out Second City, where many famous comedians got their start. For live performances, head to the Chicago Theatre or the Metro Chicago.

Bars and Clubs

Chicago has a plethora of bars and clubs, ranging from casual neighborhood hangouts to upscale lounges. For a rooftop bar experience, check out Cindy’s Rooftop or The J. Parker. If you’re looking for a unique themed bar, try The Violet Hour or The Aviary.

For clubbing, head to the River North neighborhood where you’ll find venues like Tao Chicago and Sound Bar. And for those who enjoy a good sports bar, check out The Cubby Bear or The Sportsman’s Club.

Live Music Venues

Chicago has a rich history of music, particularly in the blues and jazz genres. For live music, head to Buddy Guy’s Legends or Kingston Mines for some blues. If you’re looking for jazz, try the Green Mill or Andy’s Jazz Club.

For larger concerts, check out the United Center or the Aragon Ballroom. And if you’re visiting during the summer, be sure to catch one of the many outdoor music festivals, such as Lollapalooza or the Chicago Blues Festival.

Tip: Chicago has a thriving underground music scene, so keep an eye out for local shows and events happening throughout the city.

No matter what type of nightlife experience you’re looking for, Chicago has plenty to offer. Be sure to explore the city’s diverse options and immerse yourself in its vibrant culture.

Attend a Sports Game

If there’s one thing that Chicago is known for, it’s the city’s passionate sports culture. Sports fans from all over the world come to Chicago to experience the thrill of live sporting events and to cheer on the city’s beloved teams.

The Chicago Cubs are one of the city’s most celebrated baseball teams, playing in the historic Wrigley Field. The stadium is an experience in itself, with its ivy-covered walls and classic scoreboard. Catching a Cubs game is a must-do for any visitor to Chicago.

If football is more your style, head to Soldier Field to catch the Chicago Bears in action. The stadium has a prime location right on the lakefront, making for a stunning backdrop to your sports viewing experience.

Hockey fans won’t want to miss a game at the United Center, where the Chicago Blackhawks play. The stadium is known for its raucous fans and electric atmosphere.

If you’re looking for a sports bar to watch the game with fellow fans, head to Joe’s Bar on Weed Street. This lively bar has over 110 TVs and a huge selection of drinks and bar food.

Whether you’re a die-hard fan or just looking to experience the excitement of a live sporting event, attending a game in Chicago is a must-do on your trip to the Windy City.

Frequently Asked Questions (FAQs)

As you plan your trip to Chicago, you may have some questions about the city and what to expect during your visit. Here are some common questions and answers to help you prepare:

What’s the best time of year to visit Chicago?

Chicago is a great city to visit year-round, but the best time to visit is during the summer months, from June to September. During this time, the weather is warm and there are many outdoor activities and festivals to enjoy. However, if you prefer cooler weather, the fall months are also a great time to visit, as the city is full of beautiful fall foliage.

How do I get around the city?

Chicago has an extensive public transportation system, including buses and trains that can take you to all the major attractions. You can purchase a Ventra card at any train station or online, which can be used for both buses and trains. Taxis and ride-sharing services are also widely available.

What are some must-see attractions in Chicago?

Some of the top attractions in Chicago include the Willis Tower, Navy Pier, the Art Institute of Chicago, and Millennium Park. Be sure to also check out the city’s famous architecture and museums, and try some of the local cuisine!

Is Chicago a safe city to visit?

Like any big city, Chicago has some areas that are more dangerous than others. However, if you stick to the tourist areas and take the usual precautions, such as staying aware of your surroundings and not walking alone at night, you should have a safe and enjoyable trip.

Where can I find more information about visiting Chicago?

For more information about visiting Chicago, check out the official tourism website at or stop by one of the city’s visitor centers for maps and brochures.


Please enter your comment!
Please enter your name here