The Best Tours in Chicagoland

September 9, 2021
Holiday
jason wolfe
Yelp

Chicago has a lot to offer in terms of food, entertainment, and art. It also has a pretty colorful history. With all of the amazing people who've called this city home, you can't help but feel a bit of their influence in the city streets and individual neighborhoods.

Local Chicagoans are proud of their city, but the history is such a large tapestry that even people who've lived here their whole lives have new things to discover and explore. That's why the many tours that are offered throughout Chicago make for a great experience. Local school kids and adults alike can get something out of one of the tours offered in the city and surrounding neighborhoods. There's something special for every taste.

Of course, tourists often look for these excursions, and they do offer a great way to see the city. But they're just as awesome for lifetime Chicagoans to get to know a bit more about the people who came before them, the architecture, the art, and the many things this city and its people have to offer.

Whether you're a local looking for something fun to do on a date, or a tourist looking to get to know the city, check out our list of tours. Pick up a virtual GiftYa card to gift that friend or family member to use on their next awesome excursion. Check out the list below. You'll be amazed at the eclectic mix of topics and tour locals just waiting for you to explore.

We're splitting this list into a few categories. That's how many tours there are. There really is something for everyone, whether you're looking for traditional, odd, or unique.

Boat Tours

You might not think about water or boats when you think of Chicago, but you'd be wrong. We have one of the most amazing skylines in the world and the Chicago River runs right through the heart of the city, making this one of the most visually stunning locations you can see. Our boat tours are something to experience, whether you want to enjoy a dinner cruise or learn a little more about the city you love. Here are a few of our favorites.

Chicago Line Cruises

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Chicago Line Cruises offer a wealth of information for the history buff. Get deep into Chicago's beginnings, learn about the architecture and see the current sites with a guide who is fully trained and offers a great take on the history of the city and the people who built it.

SeaDog Tours

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This is the perfect tour for someone who likes a bit of excitement. The SeaDog takes you on a rollercoaster ride, no slow amble for these tourists. Through the course of the tour, you get some background on the city itself, when you're not holding on and getting splashed.

Chicago's First Lady Architectural Tour

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If you mention a boat tour to a Chicagoan, they will undoubtedly ask if you took the architectural tour. Some of the best and most innovative architects in the United States' history went into building this city and used those innovations to develop modern marvels across the globe. The architectural boat tours give you one of the best views possible of these extraordinary buildings and Chicago's First Lady offers a great one.

Urban Kayak

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Want to pilot your own boat? Then Urban Kayak is the tour for you. They give you a brief training session to learn how to pilot your kayak and you can join in on one of their fun group tours.

Architectural Tours

We mentioned one of the Architectural boat tours in the section above, but there are actually several of these and all of them are highly rated. Chicago is big on architecture though, so there are also bus and walking tours you can take that are fantastic. Like these:

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Chicago Architecture Foundation Bus Tour

This tour is put on by the actual CAF, so it's an amazing and really well-thought-out architectural tour. They hit all of the great sites in a full 3-hour tour. This one is highly educational. That makes it the best bet for architects, budding architects, and big history buffs.

Big Bus Tours

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These tours are also educational but they give you a little more color commentary. They also like to stop at the various sites and let you get out and look around, up close and personal. You get some of the most famous sites in Chicago on these tours and the Big Bus Tours offer a double-decker tour when it's not cold, so you can take in all the city grandeur under the stars and lights.

Segway Architectural Tours

Segway tours get you off your feet but not as far removed as a bus or a boat. There are walking tours if you prefer. But these tours provide a lot of fun. They're light on education, just covering the basics in the way of the architects and designs. But the tours themselves are still very enjoyable and highly rated.

Historical Tours

Chicago in a Day: Food, History, and Architecture Combo

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Really, what more could you want here? This tour brings you some of the most famous dishes, local history, and architecture all in one great package. These tours sell out fast, so reserve ahead of time.

Chicago Crime and Mob Bus Tour

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This is one of the most popular tours in the city, for locals and tourists. Chicago has a colorful past and that includes famous figures like John Dillinger and Al Capone. Explore the criminal background, prohibition-era speakeasies, and famous figures like the Untouchables who helped bring them down. More than a great idea for a movie, this stuff actually happened here. Your tour guide gives you the real story and shows you the actual locations.

Haunted Tours

You might not think of the paranormal with Chicago, but the city has a ton of ghost stories from a very storied history. The haunted tours of Chicago are a staple. They gain popularity around Halloween, but they're available year-round. From the alley where Dillinger was gunned down, to local legends, like Resurrection Mary. There's a tour to give you the history of the ghost story and fill you in on what people have experienced in those places.

Ghostly Pub Tours of Chicago

This is a great tour for anyone who likes to imbibe in a few spirits themselves. The pub tour features haunted bars in the Chicagoland area and gives you chance to grab a drink at each of them. Fun for everyone involved. They also tour you through actual prohibition-era locations and give you the backstory on what happened there and which famous (and infamous) characters are said to haunt the premises.

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Haunted Tours of Historic Prairie Avenue

Some of the old homes in Chicago still exude the importance of the wealthy owners who originally built them. These homes can be pretty impressive, just from a design element. But the structures on Prairie Avenue have a bit more history to them. If local legends are correct, this is one of the most haunted neighborhoods in Chicago.

The Leopold and Loeb Tour

If you're into true crime, this is the tour for you. The Chicago History Museum takes you on a tour of these infamous and cold-blooded killers and their entire criminal history. You'll see actual locations and get the real information beyond what you might have read in short end notes.

Chicago Hauntings Tours

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This tour company bills itself as The Original Chicago Ghost Tour, and it's definitely worth the trip. They offer a bunch of different tours, so you're bound to find something you like. Some favorites include The Original Chicago Hauntings Ghost Tour, Prairie Avenue Ghost Hunt, and Devil in the White City. If you've ever read the book Devil in the White City or if you've read up on America's first serial killer, this one is sure to keep you riveted.

All of the tours are highly rated. The ghost hunts are especially interactive to keep you engaged.

Tours for Foodies

You can't talk about Chicago without talking about the food. We can give you a long list of the best types of restaurants from every type of cuisine. Plus, Chicago also has a cuisine all its own that rivals any other place in the world. You'll never find a beef quite like ours because we invented them.

When people come to Chicago, the first thing they want to do is eat... and when people move from Chicago, the thing they miss most is the food. So, of course, we have to give you at least one tour just for the foodies.

Chicago Food Tours

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Chicago Food Tours offers a variety of tours that are all about the cuisine. They break it down by neighborhood and food type. Some great tours include The Chinatown Adventure Food Tour, The Tacos and Tequila Tour in Pilson, and the Gateway to the West Loop Food Tour. If you're in the mood for a little something quintessentially Chicago, try the Iconic Foods of Chicago Tour. You'll walk away with a new appreciation for everything culinary we have to offer.

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