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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
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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

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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

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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

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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

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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

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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

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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

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Chicago’s 9 Best Spots for Brunch with a View of Lake Michigan

Along the southern shores of Lake Michigan, many of Chicago’s best restaurants serve up stunning water views alongside mimosas and eggs Benedict, either from lakeside locations or lofty rooftop lounges.

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The Surprising Sea Life of Lake Michigan

While visiting Chicago, you may be wondering what kind of marine life lives in Lake Michigan. Not all the fish species that call it home are native species—in fact, Lake

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Wedding Rehearsal Dinner on the Water

A wedding rehearsal dinner is almost as important as your wedding day. During your rehearsal, you’ll be practicing the events for your wedding, ensuring your special day occurs without any

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.