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Top Things to do in Chicago

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Chicago is the second most visited city in the United States with over 54 million travelers flocking to The Windy City annually. Chicago is a city rich in history and culture and loaded with things to do.  Be sure to pack to a comfortable pair of shoes for all the walking and sightseeing. I logged more steps in Chicago during my last trip than a day at Disneyland. If you aren’t a fan of cold weather, you will want to plan your visit in May through October. There is a ton of stuff on this list to do for free in Chicago, but purchasing a City Pass

can save you up to 50% off admission to several top attractions. That means more money in your pocket to spend on souvenirs for the kids. Without further delay, here is our list of top things to do in Chicago. Check out the 40+ free audiotours for things to do in Chicago to learn more about many of the attractions on our list.

Grant Park

Located in the Loop, Grant Park is 319 acres of urban park located within the city’s central business district. Grant Park is a favorite place for locals and visitors to unwind and hang out. The largest food festival in the world, Taste of Chicago Festival is a free event that happens in mid-July. In October, Grant Park is the start and finish line for the Chicago Marathon.

Kids 12 and under will enjoy letting out a little excess energy at the Maggie Daley Park, located in the northeast corner of Grant Park. This playground is unlike any you are used too. Cool off at the Watering Hole, walk through the Enchanted Forest, enjoy a family picnic, climb a rock wall, or go for a round of mini-golf.

Make a wish at Buckingham Fountain. The fountain is was built in 1927 of Georgia pink marble and stands nearly 24 ft. tall has nearly 200 jets, and a sits in a pool measuring over 250 ft. across; making it one of the largest fountains in the world.

Buckingham Fountain, Grant Park; Chicago
Buckingham Fountain, Grant Park; Chicago

Museum Campus is a 57-acre sub-set of Grant Park that is home to five of Chicago’s most notable attractions: Adler Planetarium is America’s first planetarium. Soldier Field is home to the NFL’s Chicago Bears.Shedd Aquarium was the largest aquarium in the world when it was first built and is still considered one of the top aquariums in the world. With 24+million objects, the Field Museum of Natural History is one of the best and largest natural history museums in the world. The star of Field Museum is the 122 feet long Titanosaur, Patagotitan mayorum (pat-uh-go-tie-tan my-or-um), a giant, long-necked herbivore from Argentina that has affectionately been named Máximo for his incredible size. Máximo has recently ousted Sue, the T-Rex, as the most popular dinosaur on the block.McCormick Place is Chicago’s premier convention center, offering the largest amount of exhibition space in North America (2.6 million square feet).

Field Museum of Natural History
Field Museum of Natural History

Millennium Park is another area sub-set within Grant Park. The iconic Cloud Gate is the centerpiece of Millennium Park and is affectionately known as “The Bean”.  Cloud Gate is a reflective arch comprised of 168 stainless steel panels which are perfect for getting an amazing picture for the Gram.

Crown Fountain is another crowd favorite. Two 45 ft. tall LED towers face each other across a reflecting pool. Crown Fountain is animated with facial expressions from local citizens that happens to spout water from the lips. During hot summer months, the reflecting pool and waterfall from the towers is a pleasant place to cool off and kids especially enjoy splashing in the shallow waters.

The Jay Pritzker Pavilion is a band-shell that seats 11,000. From spring to autumn, you can find a packed calendar of concerts. One of the totally free events at Jay Pritzker Pavilion and other spots in Millennium Park is the four-day Chicago Jazz Festival that takes place over Labor Day weekend. The Jazz Fest includes the biggest names in jazz as well as up-and-comers.

Cloud Gate
Cloud Gate

Navy Pier

Navy Pier is home to a 15-story Ferris wheel, modeled after the original one that debuted in Chicago in 1893 World’s Columbian Exposition. You will also find a Funhouse Maze, fair rides and other amusements here. This attraction is guaranteed family-friendly fun. Navy Pier is home to the Crystal Gardens botanical garden and the Chicago Children’s Museum. Navy Pier hosts weekly fireworks shows in the summer as well as productions at the Chicago Shakespeare Theater.

Navy Pier
Navy Pier

Pedestrian Trails

Throughout the Loop and Millennium Park, there are over 700 works of public art including pieces by famed artists; Picasso, Chagall, Miró and more. The entire area is one big outdoor gallery.With a number of outdoor walking paths, it is easy to get around Chicago by foot and see them all.

Lakefront Trail is 18 miles of Chicago shoreline that threads through all four of the city’s lakeside parks and attractions such as Navy Pier and the Shedd Aquarium.

Go underground and experience the Pedway which spans more than 40 blocks with a vast network of tunnels. You’ll find numerous works of art along the tunnels down under including 22 stunning stained glass panels.

The Chicago Riverwalk is a 1.25-mile walkway along the south bank of the Chicago River and offers up magnificent views of the city skyline. From here, you can catch boat tours and kayaking. You may want to stick to the Riverwalk during the warmer months as the wind rolling off the river can be bone chilling.

While exploring by foot, be sure to wander down the Magnificent Mile. Many of the sights and attractions on our list are along the Mile or a stone’s throw from it. The Magnificent Mile has 275 restaurants and more than 450 retailers here. Take note of Tribune Tower and the Wrigley Building as well as the second oldest surviving water tower in the U.S., the castle-like Chicago Water Tower.

Crown Fountain in Millennium Park
Crown Fountain in Millennium Park

Museums, Museums, and Museums

For lovers of art, knowledge, science, and history, there is no shortage of museums to get lost in. We have already mentioned a few of Chicago’s awesome museums but we would be doing you a great disservice if we left out these jewels.

At the Museum of Science and Industry, you can see a giant Tesla Coil or a view a tornado vortex at the Science Storms exhibit. Other exciting sights include a full-size German submarine, the Pioneer Zephyr, and relics from the Apollo missions.

Museum of Science and Industry
Museum of Science and Industry

The Chicago History Museum is a step back in time through the history of the city. Themed exhibits let you experience what Chicago was like through historical eras such as the Civil War, Women’s Suffrage, and Civil Rights, as well as climb aboard the L train or step into a jazz club. Kids will love the Sensing Chicago exhibition which is both interactive and informative.

The Museum of Contemporary Art is dedicated to surrealism, conceptual art, pop art, and minimalism works of art from 1945 to present. Showcased artists include René Magritte, Andy Warhol, Jasper Johns, Francis Bacon, Richard Serra, and Ann Hamilton just to name a few.

See exhibits such as a statue of King Tutankhamen and a giant human-headed winged bull from Assyria at The Oriental Institute at the University of Chicago. There is a whole treasure trove of artifacts from Turkey, Israel, Egypt, Iran, Iraq, and Syria that would make Indiana Jones jealous.

The Art Institute of Chicago has the largest Impressionist and Post-Impressionist pieces outside of Paris. This includes more than 30 paintings by Monet and works by Renoir, Cézanne, van Gogh, and Toulouse-Lautrec. Fans of more modern art will appreciate works by Jasper Johns, Matisse, Jackson Pollock, and Andy Warhol. Iconic pieces such as American Gothic by Grant Wood and Nighthawks by Edward Hopper are also on display here.

American Gothic by Grant Wood Art Institute of Chicago
American Gothic by Grant Wood Art Institute of Chicago


With six major championship teams, Chicago is easily one of the top sports cities in the country. Regardless of when you visit, there is sure to be a game to go to.

Soldier Field, situated along Museum Campus in Grant Park is home to football’s Chicago Bears. The Bears are a founding franchise of the NFL and winner of Super Bowl XX. You can see the Bears between August and December. On select game days, the team hosts free Chicago Bears Ultimate Tailgate parties on the stadium green and features live music, games, food and autograph signings.

October through April the United Center pulls double duty for NBA’s Chicago Bulls and NHL’s Chicago Blackhawks. The Blackhawks hockey team won their sixth Stanley Cup in 2015 and is one of the original six National Hockey League teams founded in 1926.

The Chicago Bulls are known for having one of the NBA’s greatest dynasties, winning six NBA championships between 1991 and 1998. The Bulls keep the tradition of great basketball alive in the city and will keep fans on the edge of their seats. Be sure to visit the five-story atrium and snap a selfie with the statue of the legendary Bulls player, Michael Jordan.

Chicago Cubs
Chicago Cubs

Normally, Chicago locals are pretty tight knit when it comes to sports teams, but with baseball, fans become a town divided. The Cubs-White Sox rivalry refers to the geographical rivalry between Major League Baseball’s Chicago Cubs on the North Side of town and South Sides Chicago White Sox. The Cubs are part of MLB’s National League Central division and play at Wrigley Field which is the second oldest ballpark in Major League Baseball.  The White Sox are part of the American League Central division and play at Guaranteed Rate Field. The terms “North Siders” and “South Siders” are synonymous with the respective teams and their fans, setting up an enduring rivalry. Baseball season runs April through September.

The Chicago Fire is a Major League Soccer (MLS) team that exploded onto the scene in 1998, named in honor of the Great Chicago Fire of 1871. The team won the MLS Cup Championship in its debut year and has taken home the U.S. Open Cup an astounding four times. You can catch all of the exciting soccer action at Toyota Park.


The Willis Tower, formerly the Sears Tower, stands at 1,450 feet tall and is the second tallest building in the United States. The Skydeck is an observation deck that sits on the 103rd floor of Willis Tower. It has an encased glass ledge that extends four feet into the Chicago skyline giving way to magnificent views of the city that spans over 50 miles and four states. Venturing out on the ledge is not for the faint of heart and may certainly induce a heart palpitation or two.

360 Chicago

Similar to the Skydeck, 360 Chicago takes you to the 94th floor of the John Hancock Building that has a tilting glass lookout at 1,000 feet in the air. The 360 Chicago observation deck overlooks the Magnificent Mile and gives breathtaking views of Lake Michigan.

Pizza Capri of Hyde Park
Pizza Capri of Hyde Park


No trip to Chicago would be complete without having a slice of artery-clogging Chicago-style deep-dish pizza. There’s no denying that the best deep dish pizza in Chicago is a truly unique dining experience. Pizza Capri of Hyde Park serves up a pie so delicious you’ll think you’ve entered pizza paradise. There are of course no shortage of great eateries around town to get your nosh on. Giordano’s is a local favorite with several locations but you won’t go wrong by trying Pequod’s in Lincoln Park or one of Lou Malnati’s Pizzeria locations. Lou’s has a trademark buttery crust that melts in your mouth.

Boat Tours

When you get ready for a break from all the walking, take a break with a boat tour. You can admire the beautiful cityscape from a different vantage point, all while sitting back and relaxing. Lake Tours will run about 40-minutes and allow for some pretty amazing sights.

The Chicago River Architecture Cruise is a little more laid back and takes about 90-minutes. You will get a clear view of more than 40 listed landmarks accompanied by commentary from an expert guide.

For those who prefer a little more giddy-up, you can get your adrenaline pumping with a speedboat Architecture Cruise that leaves from Navy Pier and heads upriver as far as the Willis Tower.


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