Chicago Things to do

Chicago Things to do

Chicago has tons of things to do for all ages and all interests. Take a sightseeing tour of the city to enjoy some of the architectural marvels and famous spots around town. Get the best views of the city by zooming up to 360 Chicago or step out onto the Skydeck Chicago at Willis Tower. There are also world-class museums to explore, like the Art Institute of Chicago and The Field Museum. Of course, attending a performance at one of Chicago’s historic theaters is also a great way to spend an evening in Chicago. Be sure to buy Chicago show tickets early to get the best seats!

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One of the country’s longest-running dinner attractions, Medieval Times Dinner and Tournament Illinois offers a fun and exciting way to enjoy a meal with family or friends. Guests can enjoy a hearty four-course meal, served banquet-style (without silverware), while watching as six brave knights compete in games of skill atop their beautiful Andalusian stallions. Details
$63.95 $48.95
You Save: $15.00
Immerse your family into one-of-a-kind LEGO® exhibits, rides, 4D theaters, and so much more at the LEGOLAND® Discovery Center in Chicago. Tour the LEGO® factory, ask a pro builder all of your questions, and build to your heart’s desire! From the DUPLO Village to MINILAND Chicago, there’s so much to explore. With 11+ attractions to enjoy, it’s fun for the whole family. Details
$24.95 $19.95
You Save: $5.00
Chicago Crime Tours offer luxurious 90-minute tours of the Windy City, revealing some of its darker history of infamous criminals and gangsters. Guests can ride comfortably in a luxury, climate-controlled bus while learning about Al Capone, John Dillinger, Terrible Tommy, and more, while seeing famous crime scenes, like the Biograph Theatre, Clark Street Bridge, Holy Name Cathedral and more. Details
3 Reviews
$45.00
Embark on the bike tour that’s been recognized by National Geographic, USA Today, and the Associated Press. This leisurely bike tour of Chicago’s Near North Side neighborhoods will captivate you as you view the skyscrapers, visit Lincoln Park, and bike along the Lakefront Trail. Bring a camera along for the ride so you can capture these memories for a lifetime. Details
$49.99

Best of Chicago - Grand Tour

Gray Line Chicago • Chicago, Northern Illinois
Best of Chicago - Grand Tour

This is a comprehensive tour of everything Chicago has to offer. Travel through both the North Side and South Side business and residential districts. All the points of interest covered in the North Side and South Shore tours are included in the Grand Tour. Details
$52.95
Hop on your bike and get ready for a tasty tour through Chicago’s most diverse and delicious neighborhoods. You’ll stop at local eateries loved by locals all while learning about Chicago’s history, notable landmarks, and restaurants. This four-hour tour includes all food and beverages, along with bikes to ride if you don’t have one. Details
$84.99

Chicago Day Bike Tours

Fat Tire Tours • Chicago, Northern Illinois
Hop on a bike and pedal from Grant Street to Lincoln Park! This tour takes you through eight prestigious neighborhoods and makes numerous stops for incredible photo opportunities. You will hear the history of Chicago from a knowledgeable guide as you appreciate the stunning city architecture and beautiful lakefront. This tour is a fantastic way to see Chicago’s most famous sites! Details
$42.51
Get ready to sample Chicago’s iconic food, including deep dish pizza, the original chocolate brownie, and local craft beers. This walking tour brings you around to some of the most renowned restaurants and bars in the city. Along the way, you’ll come across Chicago’s landmarks, well-known neighborhoods, and historic spots. This tour is not recommended for kids under the age of 17. Details
$62.99
An affordable and convenient way to see some of the best attractions Chicago has to offer, the Chicago Explorer Pass offers exclusive discounted rates for up to 30 days after its first use. Guests can enjoy saving up to 40% on several different hotspots, including Adler Planetarium, Art Institute of Chicago, Field Museum and Museum of Science and Industry. Details
2 Reviews
$83.00
For authentic cuisine with a rich history, embark on a Chinatown food and walking tour with Bobby’s Bike Hike, America’s longest running city bike tour company. As you stroll through Chinatown’s neighborhoods on this 2.5-hour tour, you’ll sample Cantonese dim sum and tea, try Portuguese-Chinese baked goods, and so much more. Plus, you’ll learn about the history behind the cuisine and culture. Details
$62.99
Operated by Bobby’s Bike Hike, America’s longest running city bicycle tour company, this 2.5-hour bike tour brings you around to Chicago’s greatest landmarks and sights. You’ll see everything from Museum Campus to Cloud Gate, and Grant Park to Buckingham Fountain. If you’re looking to maximize your time in Chicago while staying active, this is the perfect tour for your trip. Details
$49.99

Historic Chicago - South Side Tour

Gray Line Chicago • Chicago, Northern Illinois
Historic Chicago - South Side Tour

This land tour will take you past all the sights of Chicago’s Historic South Side. You will head south out of the Loop down Michigan Avenue past Art Institute of Chicago, the starting point of historic Route 66, Grant Park, and the site of Chess Records. Your journey will continue along Lake Michigan on South Lake Shore Drive. Traveling on, you will see President Obama’s home, Robie House, University of Chicago and Jackson Park, and the Museum of Science & Industry. The return trip will take you through Museum Campus and past Buckingham Fountain. Details
$34.95
There’s nothing more magical than Chicago during the holiday season. Embark on a walking tour through Chicago’s most festive neighborhoods and restaurants. Sample the city’s best pizza while marveling at sights and decorations along the Magnificent Mile, strolling through Christkindlmarket, and sipping on the Windy City’s best craft beer. It’ll be a holiday season unlike any other! Details
$69.99
Scenic Chicago - North Side Tour

This is the tour for those looking to experience the vitality and excitement of Chicago! You'll drive through Chicago's main business section, one of the busiest financial centers in the world. You'll tour the famous "Loop" and State Street - the great street where Chicago's fame began. Next, travel by the striking Richard J. Daley Plaza with its acknowledged masterpiece, the Pablo Picasso sculpture, created specifically for Chicago. You will take a ride on Wacker Drive, the double-decked thoroughfare that winds its way under the city. Also, journey over the Chicago River, which flows backward due to one of the world's greatest engineering feats.

On this tour, you'll see the famous white Wrigley Building that announces the beginning of the Magnificent Mile and Michigan Avenue, where Chicago's most exclusive stores exhibit their wares. You'll see Chicago's elegant seven-level shopping complex, the renowned Water Tower Place, alongside one of the tallest buildings in the world, the John Hancock Center. You will also travel through Lincoln Park, a thousand acres of greenery, lagoons, flowers, and zoo. You'll see Wrigley Field - the home of the Cubs (visits not on game days), the Botanical Gardens, Chicago Historical Society, Newberry Reference Library, and an Indian Totem Pole. Also, enjoy a twenty minute stop at the Lincoln Park Conservatory.

If you're looking for a day of adventure in Chicago, then this is the tour for you! Details
$34.95

Two Hour Chicago Segway Tour

City Segway Tours • Chicago, Northern Illinois
Segway is the newest trend when it comes to touring because you can cover more ground. Plus, it’s just plain fun! You will have numerous Instagram-worthy photo opportunities as you travel to the best spots in Chi-Town including Grant Park, Buckingham Fountain, the Crown Fountain, and so much more! Your knowledgeable guide will reveal interesting facts and history of Chicago along the way. Details
$70.85