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 that the city was the birthplace of the car radio and remote control?

Chicago is also known for the Nation’s first open-heart surgery, the first televised Presidential debate, and the world’s only backward-flowing river. 

Originally named Chigagou, an Algonquian word meaning “onion field”, the Windy City offers plenty of opportunities to immerse yourself in the past. Take a historical tour if you want to find out what makes Chicago the city it is today. It may surprise you that it is actually not the windiest city! 


Bus Tours

The Chicago Trolley Tours are a convenient way to see the city. It is much easier to look around and take in the scenery when you do not have to be worried about traffic and you can sit back, relax, and enjoy all there is to see. This tour includes stops at Buckingham Fountain, Millennium Park, the Sears Tower, and more. A variety of other bus tours are available in Chicago, such as the Chicago Crime and Mob Tour. It takes you to all the famous places that Al Capone and Chicago’s notorious gangsters frequented, like the Biography Theater, Holy Name Cathedral, and the site of the bloody St. Valentine’s Day Massacre.

You can also take the Big Bus Hop-On, Hop-Off Tour to explore Chicago’s architectural wonders and key landmarks. Then there is Gray Line’s Chicago Grand City Tour, which drives through the city’s magnificent parks.

Chicago River with boat going under a bridge


Boat Tours on the Chicago River

Chicago is a city of water. So, whether it’s Lake Michigan or the Chicago River, expect to find yourself surrounded by this precious resource. Being on a boat is an unforgettable way to experience Chicago’s incredible skyline-from the water.  

Chicago’s skyline is known for its architectural and engineering landmarks. Boat tours operated by the Chicago Architecture Foundation and the Chicago History Museum provide an opportunity to see these icons up close without dealing with heavy traffic or crowds of tourists.


Walking Tours

Put on your walking shoes and stroll through history as you learn about Chicago’s storied architecture, neighborhoods, and culture. These intimate tours will provide you with a deeper knowledge about the city and maybe some new friends too! 

The Chicago: Night Crimes Tour starts at the Chicago Police Museum and continues to some of Chicago’s most famous crimes, including the Great Chicago Fire and neighborhoods like Chatham and Old Town.

The Gangsters and Ghosts Tour takes you to historic gangster hangouts and haunted sites like the Congress Hotel, Palmer House, and Death Alley.

The Chicago Architecture: A Walk Through Time Tour will guide you through the city’s rebirth after the Great Chicago Fire of 1871.

The Historic Chicago Walking Bar Tour takes you to the best local watering holes in the heart of downtown Chicago to get a drink and learn about the city’s history.

The Chicago Crime and Gangster tour is a free stroll (available only Saturdays) through Chicago’s infamous mob history. (Are you noticing a theme here?)

Giordano's Pizza sign Chicago

Food Tours

Food tours are trendy among travelers interested in tasting new dishes from around the world. Foodies will not be disappointed with the extensive cultural food scene and delicious cuisine.There is one thing all of Chicago neighborhoods have in common and that is amazing food! Although Chicago is famous for its pizza and hot dogs, it has much more to offer. Did you know that the twinkie was created in this beloved city? There is so much variety, you will be guaranteed to leave with a full heart and stomach. A Chicago food tour takes you to several hot spots where you can try local, unique cuisine from the city’s most influential kitchens.

Typically, food tours are walking tours. If you’re traveling with someone with limited mobility, talk to the trip organizer ahead of time to find out what accommodations they can make. Some food tours can accommodate food allergies, but others can’t, so ask about that if it’s a concern.

Here are other tasty tours:


Self-Guided Tours

You have plenty of options if you like to plan your own schedule without a structured tour group. And Chicago has many fascinating places to explore all on your own, from historic homes to underground freight tunnels.

Or maybe you’ll want to travel far back into prehistory at Chicago’s Field Museum of Natural History, where you’ll get a first-hand look at dinosaur bones, ancient Egyptians, and some of the museum’s 40 million artifacts. The city of Chicago is sure to impress you with their impressive architecture, passion for sports, delicious international foods, hipster bookshops, cocktail bars, lush green spaces, and amazing art galleries. Whatever type of historical tour you decide upon, there is something for everyone in the Windy City. 

FAQs – Historical Tours in Chicago

Why choose City Experiences for historical tours in Chicago in 2024?
City Experiences offers expertly guided tours that bring Chicago’s rich history to life. They provide a blend of historical insights, storytelling, and local knowledge that makes each tour a memorable experience.

What types of historical tours does City Experiences offer in Chicago?
City Experiences offers a variety of historical tours in Chicago, including walking tours of significant neighborhoods, river cruises focusing on architectural history, and themed tours exploring specific aspects of Chicago’s past.

Can City Experiences accommodate private groups for historical tours?
Yes, City Experiences can cater to private groups, offering customized tours tailored to the interests and needs of the group, whether it’s a family outing, educational trip, or a special event.

What are the highlights of City Experiences’ historical tours in Chicago?
Highlights include expert guides, immersive storytelling, a mix of well-known landmarks and hidden gems, and insights into the cultural, architectural, and historical fabric of Chicago.

How long are the historical tours offered by City Experiences?
Tour lengths vary, ranging from short walks of a couple of hours to more extensive tours that can take up half a day or more, depending on the itinerary.

Do City Experiences’ tours operate year-round in Chicago?
While most tours are available year-round, some may be seasonal, especially boat tours. It’s best to check their website or contact them directly for current offerings and schedules.

What should I bring on a City Experiences historical tour in Chicago?
Comfortable walking shoes, weather-appropriate clothing, a camera, and a sense of curiosity are recommended. For boat tours, sunglasses and sunscreen might be useful.

What are some must-see historical sites in Chicago?
Chicago is rich in history, with must-see sites including the Willis Tower, The Art Institute of Chicago, The Field Museum, Millennium Park, and historic neighborhoods like The Loop and Bronzeville.

Can I find walking tours that focus on Chicago’s history?
Yes, Chicago offers a variety of walking tours that delve into its architectural, cultural, and historical heritage. These tours often cover significant landmarks and tell stories about the city’s past.

Are there any historical boat tours in Chicago?
Chicago features several historical boat tours, particularly along the Chicago River, providing perspectives on the city’s architectural marvels and historical developments.

What unique historical experiences are available in Chicago?
Unique experiences include tours focusing on Chicago’s Prohibition-era history, its role in the jazz and blues scenes, architectural tours, and visits to historic sites like the Chicago Cultural Center.

Original post date: November 10, 2022