Things to do in Chicago: What to See, Do, Eat, + Enjoy

Things to do in Chicago: What to See, Do, Eat, + Enjoy

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Planning a trip to Illinois and looking for the best things to do in Chicago?! You’ve come to the right place!

The Windy City promises a plethora of breathtaking architecture, stunning sculptures and arts, world cuisines, musicals and operas, comedy and sports, and free activities for every type of visitor to the city.

Here are some tips to plan an enjoyable trip:

  • Chicago has great public transportation and the CTA sells unlimited 1, 3 or 7 day passes. Most things to do in Chicago are easily accessible by the Loop or ‘L’ train or bus.
  • Book a hotel in the Loop or Magnificent Mile neighborhoods to make the most of your trip.
  • The key to enjoying Chicago is to be ready for the weather. Summer and winter are both extreme; pack a hat and sunscreen if traveling in summer and heavy-duty jacket and snow shoes for the cold season. Dress in layers during spring and fall when the day is pleasant, but evenings can get chilly quickly, especially on the water. The best time to visit Chicago is during summer when the entire city comes alive with music and colors.

Things to do in Chicago:

1 | Gaze at your reflection in the Cloud Gate sculpture

Planning a trip to the windy city soon?! Check out this post for loads of helpful tips and best things to do in Chicago!

Commonly called ‘The Bean’, the Cloud Gate sculpture is a giant mirrored surface that beautifully reflects Chicago’s dramatic skyline. Visitors throng to take their photo with the Bean and this is one of the most popular things to do in Chicago. The sculpture looks equally stunning in winter when snowflakes drift over it. The Cloud Gate sculpture is located in Millennium Park.

2 | Take a stroll around Millennium Park

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The Bean is not the only attraction in Millennium Park; the park also boasts excellent gardens, tulips in a myriad of colors, various sculptures, and the striking Crown Fountain – two giant glass display towers that spout water and display videos. The Park is also home to an open air steel pavilion with a shell designed by Frank Gehry. Free concerts are held in the pavilion in summer. A big part of the park is converted into an ice rink in winter and skating is a popular holiday activity.

3 | Conquer your fear of heights at Skydeck Ledge, Willis Tower

Planning a trip to the windy city soon?! Check out this post for loads of helpful tips and best things to do in Chicago!

Willis Tower is the tallest building in Chicago and 2nd tallest in the US. Its 103rd floor is occupied by Skydeck, which offers visitors stunning views of Chicago. The main attraction of the Skydeck is the Ledge, a glass box that extends from the building. While standing on the glass floor and watching Chicago streets and traffic underneath is an exhilarating experience; it is not for those with a fear of heights.

4 | Be inspired by renowned paintings at the Art Institute of Chicago

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The Art Institute of Chicago boasts a vast collection of 300,000 pieces of art and ranks among premier museums in the world. The museum collection is incredibly diverse and features Monet, Renoir, Van Gogh, Picasso, and Warhol, among others. The building also has excellent grounds with shady trees and fountains. Taking a picture with the impressive lion sculptures at the entrance is one of the most popular things to do in Chicago. Plan to spend minimum of 2-3 hrs at the Art Institute.

5 | Hang out at the Navy Pier

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Families love Navy Pier; it is among the best things to do in Chicago if you have children. Navy Pier boasts an incredible amount of activities targeted towards children, including a Ferris Wheel and other rides, fun mirrors, a Children’s Museum, and IMAX theatre. It also has lots of stores and restaurants for adults. The Navy Pier also offers great views of the Chicago skyline and one of the most popular things to do at the Navy Pier during the summer is to take a cruise (more info below)!

6 | Watch the music and lights show at Buckingham Fountain

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Buckingham Fountain, located in Grant Park, runs only in summer. The 20 min music and lights fountain show in the evening is beautiful, as is the center water jet that shoots up in the sky!  Visitors enjoy standing by the fountain and getting misted by water sprays on a hot summer day. This is also another place to get great shots of the skyline!

7 | Take in the city with a relaxing cruise

Planning a trip to the windy city soon?! Check out this post for loads of helpful tips and best things to do in Chicago!

In summer, a bevy of cruises depart from Navy Pier. Take the Chicago River architectural cruise and learn about the history and architecture of the city. Alternatively you can take a Lake Michigan cruise and jet around the lake in a speedboat or sail a tall ship or relax with a dinner and music 3 hr cruise on a big ship or charter a yacht tour. The options are nearly endless and all cruises offer beautiful views of the stunning Chicago skyline. The sunset cruises are very popular and among the best things to do in Chicago.

8 | Walk down the Chicago Riverwalk

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The Chicago Riverwalk is an excellent alternative to the Chicago River architectural cruise. You can simply walk along the Chicago River and take in the beautiful buildings of Chicago downtown. The views are stunning and there are many restaurants and bars with riverside patios along the Riverwalk if you get hungry. It is a great place to walk, jog, bike or just hang out and people-watch.

9 | Shop on Magnificent Mile

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Magnificent Mile is a shopper’s absolute delight!  The area is home to Macy’s, Saks Fifth Avenue, Chanel, Bloomingdale, Rolex, Nordstrom, and a variety of luxury labels and department stores. This part of Michigan Avenue is full of beautiful sculptures and stunning architecture. Walking down the Magnificent Mile is a delight in spring when colorful tulips frame this popular tourist attraction. In winter, the Magnificent Mile Lights Festival brings holiday cheer and lights up the entire area; viewing the Tree Lighting ceremony on Magnificent Mile is one of the most popular things to do in Chicago in winter.

10 | Visit the Museum Campus

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Museum campus, in the South Loop, offers an excellent choice of attractions. The Shedd aquarium is among the best aquariums in the United States and exhibits sharks, stingrays, tropical fish and many other specimens in its Caribbean Reef section. The Field Museum of Natural History is home to Sue, the dinosaur. Sue is the largest Tyrannosaurus rex fossil ever found and a favorite with children of all ages. The Adler Planetarium and Astronomy Museum, founded in 1930, is the first planetarium in the country and a must for space buffs. Visiting any of these attractions can take 3-4 hrs to an entire day, so plan accordingly.

11 | Relax at the beach

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The Windy City has many beautiful beaches on the Lakefront and spending a day at the beach is one of the most popular things to do in Chicago in summer. North Avenue beach is the best beach in Chicago with excellent amenities and hosts the annual Chicago Air and Water show. Oak Street beach, close to Downtown, offers an excellent swimming area to beat the summer heat.

12 | Watch a Broadway musical in Theatre district

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Chicago’s lively theatre district is home to many majestic theatres like the Cadillac Palace Theatre and Oriental Theatre. The several venues feature a variety of musicals, ballet, and operas; past shows include Broadway hits like Disney’s ‘The Lion King’ and ‘The Wicked’. You can also see theatre life behind the scenes with a public Theatre tour on Saturdays.

13 | Meet the animals at Lincoln Park Zoo

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Lincoln Park Zoo has some of the best wildlife in the country and has excellent interactive programs and events. The best part, entry to the Zoo is completely free. The Zoo is extremely popular with families and children can come face-to-face with polar bears, giraffes, kangaroos, gorillas, seals, wolves, and more.

14 | See the Nine-Dragon wall in Chinatown

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Few people know that Chicago’s Chinatown, located on the South Side, is the third largest in the country. Big red ‘Welcome’ sign attracts visitor’s attention while Chinatown Murals and Chinatown Square offer showcase excellent artwork. The nine-Dragon wall, with its nine different Chinese dragons, is beautiful and mystic. This area is an excellent place to sample exotic Chinese foods and buy paper lanterns, teas and lucky bamboo plants.

15 | Attend a show recording at NBC Tower

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The NBC Tower in Chicago, located a block away from the Magnificent Mile, is an excellent example of postmodern Art Deco architecture in the city. Judge Mathias Show, the recently concluded Steve Harvey Show and few other shows are recorded in the studios. Visitors can call to see if free show tickets are available. Don’t forget to take pictures with the NBC daytime show posters that line the wall of the lobby while you are there. If not attending a show taping, you can take a quick picture with the colorful peacock logo and check out Chicago’s other attractions.

16 | Commute with the Water Taxi

Planning a trip to the windy city soon?! Check out this post for loads of helpful tips and best things to do in Chicago!

Chicago offers various ways to commuters; the ‘L’ trains and buses being the most popular one. Many tourists see the city by biking the Downtown or taking Segway Tours; but few tourists know about the water taxi that is operational from May to September. The water taxi is a great way to reach Chinatown from the many stops in Downtown. You can buy the all day pass that lets you take unlimited water taxi rides and explore all the great things to do in Chicago.

Have you been to Chicago before?  Planning a trip there anytime soon?!

Thanks to Ketki for this wonderful guest post on things to do in Chicago!

Ketki Sharangpani is a travel writer and blogger on a quest to illustrate the world through travelogues & photoessays. Currently she is basking in the sun and breathing salty air off the Gulf Coast. Read her free guide on spending a perfect day in Chicago and follow her attempt at captioning the world on Dotted Globe.

// *THIS POST MAY CONTAIN AFFILIATE LINKS. This means that if you make a booking after clicking on one of these links, I may make a small commission at no extra cost to you. Thanks for the support and help keeping the site free of charge for everyone to enjoy!

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