Things to do in Chicago

There’s so much to do in Chicago! Frank Sinatra is not the only one to sing Chicago’s praises; Vinnie Van GO is quite partial to the city as well. He loves its Lake Michigan beaches, vast network of parks, and Willis Tower. Plus, it’s the perfect city for sports fans: Cubs, White Sox, Bears, Bulls, Blackhawks, and more! Not to mention some quirkier attractions throughout the Windy City.

While the top tourist sites include Navy Pier, the Museum of Science & Industry and the Art Institute, Vinnie has a few out-of-the-way suggestions you might enjoy as well. There’s always something to do in Chicagoland. Book a Chicago shuttle or explore Chicago on your own!



Things to do in Chicago


Here are just a few of the annual events happening in Chicago! Book a GO shuttle to enjoy events without worrying about the road.

Chicago Auto Show

The Chicago Auto Show at McCormick Place is one of the largest auto shows in the US. Over one million visitors attend the Chicago Auto Show each year. Held around Valentine’s Day, sometimes nothing says “I Love You” quite like the auto show. Hundreds of cars are on display from the latest models to classic cars to one-of-a-kind cars you may never see again!


St. Patrick’s Day Parade

It’s simply not St. Patrick’s Day in Chicago until the Chicago River is dyed green! Besides the green river, Chicago’s St. Patrick’s Day Parade is known for drawing crowds by the thousands and green beer served at downtown bars, but remember parking is limited.


Printers Row Lit Fest

Originally called the Printer's Row Book Fair, the Lit Fest has become an annual tradition of the past 30 years and dubbed “the Midwest's largest celebration of the written word.” The festival features readings, panel discussions, workshops, children's programming and poetry slams. Over 150,000 book lovers attend the Printers Row Lit Fest each year.


Taste of Chicago

Known as the Taste, the Taste of Chicago is a local favorite. Held in Grant Park, the Taste of Chicago is week of great food, music, and fun. More than 70 local restaurants participate in the Taste each year with live entertainment provided on multiple stages throughout the park. But remember that while The Taste of Chicago is free, the food is not.


Chicago Air and Water Show

The Chicago Air and Water Show has become a lakefront event for over 50 years. The free, two-day experience features aerial thrills and chills and brings in over two million sightseers on Lake Michigan. The Air and Water Show has demonstrations by military and civilian aircrafts, boats, and diving and parachute teams.


Chicago Jazz Festival

Every Labor Day for the past 30 years, The Chicago Jazz Fest brings the best musicians from around the world to downtown Chicago. The Chicago Jazz Festival features stages at the different locations throughout the city: Chicago Cultural Center, Millennium Park and Grant Park. The Chicago Jazz Festival is not nearly as packed as other annual events in Chicago, making for a much more relaxed environment.


Things to do in Chicago

Photo Credit: Eric. X via Yelp


Chicago is a sports lovers dream! If you’re looking for something to do, check out a game or concerts at any of Chicago’s arena. Avoid arena and stadium parking with a shuttle service.

Chicago Bears

Soldier Field
1410 Museum Campus Dr
Chicago, IL 60605


Chicago Cubs

Wrigley Field
1060 W Addison St
Chicago, IL 60613


Chicago White Sox

Guaranteed Rate Field
333 W 35th St
Chicago, IL 60616


Chicago Bulls & Chicago Blackhawks

United Center
1901 W Madison St
Chicago, IL 60612


Chicago Fire

Toyota Park
7000 Harlem Ave
Bridgeview, IL 60455


Things to do in Chicago


If you’re headed to a Chicago landmark, our shuttle and car services can help get you there!

Navy Pier

Navy Pier has become is a popular destination for out-of-towners and is known for its iconic Navy Pier Wheel, carnival rides, restaurants and shops. It is one of the most visited destinations in the Midwest and Chicago's top tourist attraction.
Address: 1400 S Lake Shore Dr, Chicago, IL 60605


Millennium Park

The 24.5-acre park has over 25 million annual visitors, and features video displays, outdoor theater, Crown Fountain, and the world famous, reflective "Bean" sculpture.
Address: 201 E Randolph St, Chicago, IL 60602


Art Institute of Chicago

Flanked by iconic bronze lion statues, the Art Institute of Chicago features some of the best in modern and contemporary art as well as shops specializing in art books, jewelry, and souvenirs.
Address: 111 S Michigan Ave, Chicago, IL 60603


Willis Tower

Originally the Sears Tower (and still referred to by my many), The Willis tower is a 110-story fixture in the Chicago skyline. Check out the expansive views of Chicago from the 103rd-story Skydeck!
Address: 233 S Wacker Dr, Chicago, IL 60606


Field Museum of Natural History

The Field Museum is one of the largest natural history museums in the world. It features a combination state-of-the-art exhibits and scientific specimen and artifacts, as well as the biggest Tyrannosaurus Rex in the world!
Address: 1400 S Lake Shore Dr, Chicago, IL 60605


Things to do in Chicago


Outdoor Art

Don’t want to spend your time indoors at a stuffy museum? Chicago boasts a world-class collection of iconic public art from such prominent artists as Pablo Picasso, Joan Miro, Jean DuBuffet, Henry Moore, Marc Chagall, and Alexander Calder. Equally outstanding are newer works including Magdalena Abakonwicz’s stunning “Agora,” which features 106 headless figures and is located at Michigan Avenue and Roosevelt Rd. Also see Claes Oldeburg’s Pop Art “Batcolumn,” at 600 W. Madison; Anish Kapoor’s bean-shaped “Cloud Gate” and Jaume Plensa’s “Crown Fountain,” both at Millennium Park. To help you plan your tour, see “The Chicago Public Art Guide,” which identifies more than 100 sculptures, mosaics and paintings on public display in downtown Chicago.


Graceland Cemetery

Chicago’s history is written in the tombstones of Graceland Cemetery (founded in 1860, where the city’s founders, architects, industrial and commercial forefathers are buried. Among its permanent residents are Cyrus McCormick, Philip Armour, George Pullman, Marshall Field and boxer Jack Johnson. One of the largest shrines is the final resting place of Potter and Bertha Palmer, who together were the social, cultural and economic leaders of Chicago in the Victorian era. And don’t miss the “Cemetery of Architects,” where such luminaries as Louis Sullivan, Daniel Burnham and Ludwig Mies van der Rohe are buried. The cemetery offers a free self-guided tour map or you can sign up for a two-hour walking tour conducted by the Chicago Architectural Foundation.


Maggie Daley Park

The city’s newest attraction is Maggie Daley Park, a brand new children’s park with lots for grown-ups to love: an ice-skating/rollerblading ribbon, a climbing wall, field house, tennis courts and a play garden. The latter is a high-concept playground which is divided into several distinct areas designed to appeal to different age brackets. They include The Sea, The Watering Hole, The Harbor, Enchanted Forest, Wave Lawn and Slide Crater. The park is located on East Randolph Street – walking distance from Millennium Park, another major Chicago attraction.


Things to do in Chicago


The City of Chicago has a corps of volunteers who serve as city greeters and will show you around their particular neck of the woods. Explore any one of 25 diverse neighborhoods -- including Hyde Park, home of the University of Chicago; Old Town, with historically preserved homes that predate the Chicago Fire; Pilsen, which features outdoor murals reminiscent of Mexico City, and Chinatown, home to Chicago’s Chinese population since the 1860s. There are also special interest tours for foodies, history buffs, families with children and the LGBT community. Sign up 10 business days prior to the requested visit.

Chicago offers numerous options to see the city from the water. There are several boat operators at Navy Pier, including Chicago’s own Tall Ship. Interactive programs include the Real Pirates of the Inland Seas, Spirit Ships & Haunted Harbors, fireworks cruises and more. One of the most popular tours is provided by the Chicago Architecture Foundation (CAF). The CAF-certified volunteer tour guides interpret more than 50 buildings along the Chicago River, revealing how the city grew from a small back-country outpost into one of the world’s most important crossroads in less than 100 years.


For more travel tips and recommendations
visit Vinnie’s blog “Going Places".

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