Essential Chicago

Experience the best of Chicago with City Experiences! Take a sightseeing or dining cruise on the Chicago River or Lake Michigan, explore the city with a walking tour, take a speed boat thrill ride on Seadog, enjoy package deals and more.

Recommended Experiences in Chicago

  • City Cruises

    Sightseeing and dining cruises, iconic attractions, private events, and more
  • Walks

    Beautifully designed tours in cities around the world
  • Other City Experiences

    More essential tours & activities
Blog Image

Aboard City Cruises During Chicago Restaurant Week

Behind the Scenes of Chicago Restaurant Week with Chef Francesco Simone aboard City Cruises Chicago Only steps away from the Magnificent Mile, just east along the Chicago Riverwalk, Francesco Simone,

Blog Image

Where to See the Best Fireworks in Chicago This July 4th

Fireworks. Chicago. July 4. Some things just go together, like America and apple pie. If you plan on celebrating Independence Day in the Windy City, you’re in for a real

Blog Image

8 Unique Ways to Celebrate Mom on Mother’s Day in Chicago

Every day is a day to show your mother how much you love and appreciate her, but Mother’s Day is the day to truly pull out all the stops. With

Blog Image

Reasons to Explore the Rich Architectural History of Chicago

There are endless reasons to love Chicago. From the city’s vibrant arts and music scene to its many fantastic green spaces and top-notch dining options, the Windy City has plenty

Blog Image

How to Find Chicago’s Hidden Jazz Clubs

From blues to hip-hop, Chicago is a fantastic city for live music. Of all the musical genres that define the city, jazz is arguably the best-known, and it’s not a

Blog Image

Fun Places to Eat in Chicago

Chicago is an ideal city to try new foods and drinks. We’ve gathered a few of the most unusual and fun places to eat in the Windy City. If you

Blog Image

Historical Tours in Chicago

You may think of Chicago as the home of deep-dish pizza and Al Capone. But did you also know that America’s first skyscraper was built in Chicago (in 1885), and

Blog Image

Unique Ways to Celebrate a Birthday in Chicago

Planning on spending your special day in the Windy City? If you’re looking for birthday ideas, Chicago has plenty of unique local ways to celebrate, from sailing on Lake Michigan

Blog Image

The Turbulent History of the Chicago River

The history of the Windy City is deeply intertwined with the history of the Chicago River—the waterway’s imposing presence can be felt throughout the city, and its impact on the

Blog Image

Tour Chicago for the Sights, The Great Foods, and Iconic Dishes

Chicago is the “largest city of the American Midwest” and “the third largest city” in the U.S. Founded in 1830, the city was “Established as a water transit hub; the

Frequently Asked Questions

Top things to do in Chicago

There are plenty of fun things to do in Chicago! For instance, you can explore the city’s many museums and historical sites, enjoy its diverse food and drink scene, or take part in one of its many annual festivals. Of course, Chicago is also home to a variety of sports teams and outdoor activities, so there’s something for everyone to enjoy in this vibrant city. Lake Michigan is also a popular spot for fishing, swimming, and kayaking, so be sure to check it out if you’re looking for some fun in the sun! You can also take boat cruises down the Chicago River and river to take in the sights of Chicago from a different perspective. Whatever you’re looking for, you’re sure to find it in Chicago!

What do I need to know before visiting Chicago?

Chicago is an amazing city full of culture, history, and great food. If you are planning on visiting Chicago, make sure to research everything beforehand so you can make the most of your trip! If it is your first time in the city, be sure to book a fun tour like an architecture boat tour. Both the Chicago River and Lake Michigan offer some of the best views! And of course, dress accordingly depending on the time of year you are visiting.