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Chicago is the perfect destination; it has something for everybody. Whether you’re interested in architecture, history or food, Chicago has it all—including unique tours that cater to these interests.
Having grown up in the Chicagoland area, I didn’t even know there were so many tours in Chicago. I guess you don’t really think about your hometown being a place that you would look for a tour for. I think even locals would be interested in most of these! The tours I found offer a really unique way of viewing Chicago, whether through learning more about the city’s architecture, history or food.
In this post, you’ll find a roundup of the most unique architecture tours, history tours and food tours Chicago has to offer. Each tour is unique and fun, and I hope you choose at least one of these on your trip to Chicago. A guided tour is a great way to experience a city, whether it’s your first time in Chicago or whether you’re a local!
I truly believe that there is a tour for everybody in this list of unique tours in Chicago. Happy searching!
One of the things that Chicago is most known for is its architecture. It was one of the first cities in the world to build skyscrapers, and from old historic buildings to revolutionary modern buildings, you will find that Chicago’s architecture offers a peek at both the past and the future. Here are some of the most unique ways to tour the architecture of Chicago.
This architecture tour takes you a bit into the past—1920s Chicago to be exact. Chicago has some of the most beautiful Art Deco skyscrapers in the world, and you’ll explore them in great detail on this tour. In addition to entry to five Art Deco buildings, you’ll also have admission to the exhibits in the Chicago Architecture Center.
Alternatively, this architecture tour focuses on more modern buildings. Chicago is the best place to learn about Modernism because it’s a world leader in this style of architecture. Learn more about skyscrapers in the city where they were skeleton frame is said to be first used, and visit the most iconic Modern buildings in Chicago. This tour also includes admission to the exhibits in the Chicago Architecture Center.
The Loop is at the heart of downtown Chicago, and it’s where you can find some of Chicago’s most impressive and famous buildings and architecture. Therefore, this is the best place to tour Chicago’s architecture. You’ll visit some of the best architecture the city has to offer with an expert guide and get to see the inside of six of the buildings.
This tour focuses specifically on one impressive part of Chicago architecture: Tiffany glass works. You’ll visit buildings with Tiffany glass or mosaics all around Chicago while learning about Tiffany from your guide. You’ll also see one of the largest collections of Tiffany art glass in the United States, and the tour includes admission to the exhibits in the Chicago Architecture Center.
This architecture tour is unique because it allows you see Chicago from a more local immersion. It’s a walking tour, but you also take the “L”, which is Chicago’s elevated train system. Your fare for the “L” is included in the price, and you will get a unique view of architecture in Chicago from the elevated platforms. This will get you closer to details you might have otherwise missed from the street. The tour also includes admission to the exhibits in the Chicago Architecture Center.
This is one of the most unique architecture tours in Chicago because it takes place on a boat. Most of Chicago’s most impressive buildings are along the Chicago River, so you get a really interesting perspective of them from the river. Your guide will narrate the history of the city’s skyline and point out the historic buildings you’ll be passing. The boat has both an open-air deck and climate-controlled interior, so you can go on this tour in any weather.
If you prefer faster boats, there’s an architectural cruise on a speedboat too! This tour will move faster, meaning that you’ll also have time to cruise around Lake Michigan in addition to the Chicago River. The tour also offers a narration of the architecture you’ll be passing, and I personally think the Chicago skyline looks stunning from the lake.
Duration of Tour: 75 minutes
Best History Tours in Chicago
Chicago is perhaps not a very old city (less than 200 years old), but it has an absolutely fascinating history. From the revolutionizing architecture to the glitz and glam of the Golden Age, Chicago has also had a darker side to its history. From gangsters to serial killers to criminals, you can explore topics of Chicago’s dark past in more alternative tours than your typical history tour.
This tour explores the Loop. Now an area with tall, sleek office buildings, this was once where gangsters like notorious Al Capone partied and conducted business. A historian will guide you around this area and show you the supposed haunted spots and old crimes scenes in this area form the 20s and 30s.
If you don’t fancy too much walking, this tour will also show you some gangster-related historical spots around the city but from the comfort of a bus. The great thing about this tour is that you get to cover more than just one neighborhood of Chicago and you can do this tour even in bad weather. This tour also covers famous crimes from all of Chicago’s history, not just the 20s and 30s.
This is for those who don’t want to focus on the dark side of Chicago’s history. Instead, this tour takes you into the world of arguably Chicago’s best part of history: the Golden Age. Sure, there were many problems back then, but the 1890s to 1930s was when Chicago was one of the most exciting places in the world. It’s when Chicago transformed from an industrial city to a cultural one, with its leading architecture and the World’s Columbian Exposition of 1893. Learn all about this exciting time on this tour. (It’s especially great for those interested in both Chicago history and architecture and want a unique tour that offers both.)
One of my favorite books set in Chicago is The Devil in the White City. It’s one of the best non-fiction books I’ve ever read and it gave me an insight on the past of a city I called home most my life. So naturally, this tour caught my interest. Inspired by the book, this tour will take you around the place where the World’s Columbian Exposition took place and H.H. Holmes’ “Murder Castle,” among other POI from the book.
This tour is unique because it will educate you on a part of the city’s history that most Chicago tour wouldn’t focus on since it’s not in the conventionally tourist hot spots. Specifically, this tour is about the expansion of the city, and you’ll also learn about the history behind the beautiful cottages in this neighborhood. Which, by the way, is one of my favorite areas in Chicago—it’s so beautiful!
Do you love a good pub crawl and have an interest in Chicago’s famous historical speakeasies? Say no more, because I have the perfect Chicago tour for you. This private tour will take you to speakeasies that still exist in Chicago, and a local historian will tell you all you need to know about them. It’s a must for history lovers traveling to Chicago!
This is a more affordable option for those looking for a Chicago history tour merged with a pub crawl. The group pub crawl has a haunted theme, and in between three pub stops you’ll hear some spooky stories and pass by haunted spots from Chicago’s dark past.
This is a great tour to choose if you’re on a budget or if you want flexibility. That’s because this is a self-guided scavenger hunt in which you hunt for the ghosts of the Chicago River on an app. A fun, unique and cheap history tour of the ghosts of Chicago!
Duration of Tour: About 2 hours
Best Food Tours in Chicago
Chicago is a melting pot of different cultures. It always was. Because of this, Chicago is a foodie paradise, and you can sample food from all over the world. Whether you want to try the food Chicago is famous for or sample some local eats, any foodie would love all of these food tours that are unique to Chicago!
Looking for a food tour that lets you sample all the food Chicago is most known for? You found the right place here. You’ll get to try deep-dish pizza (probably my favorite food!), Italian beef sandwich, Chicago-style hot dog (in my biased option, the best kind of hot dog in the world) and Italian pastries. Don’t expect to leave this tour without feeling full!
This tour is the best place to explore Chicago’s Chinatown if you’re a foodie. You’ll be trying Chinese food from different regions in China, while also learning about the history of this Chicago neighborhood. It’s a Chicago tour that is a great fusion of food and history!
Possibly one of the most unique food tours you’ll go on, this tour takes you to several donut shops in Chicago. While Chicago might not be world-famous for donuts, it should be. It offers several gourmet donut shops, and I’ve become kind of a donut snob because of them (Dunkin Donuts is ruined for me). These shops have super interesting flavored donuts, so have a sample of some of them!
Instead of a walking foodie tour, burn off more calories with a biking foodie tour! This is a great option because you’ll get to visit food joints in multiple neighborhoods in Chicago. From pizza to hot dogs to brownies to beer, be ready to fall in love with Chicago’s food.
If Chicago’s famous deep-dish pizza is what excites you most about your visit to Chicago, this is the tour for you. Although this isn’t what we locals eat on a regular basis (I don’t think the human body is capable of that!), it definitely my favorite annual treat, and I don’t think any tourist should leave Chicago without trying deep-dish pizza. The great thing about this tour is that you visit four pizzerias in different Chicago neighborhoods and you get to try a slice from each one. If you go on this tour, let know which one you think was the best!
I recommend this tour because Wicker Park is a great place to go out eating. It’s not as touristy as, say, the Loop or River North area, and it’s a really youthful part of the city. That means you’ll be sampling food that locals *really* eat instead of just the stereotypical deep-dish pizza and hot dogs. The itinerary includes authentic tacos, gourmet butcher shop, donuts, fried chicken and red velvet donuts. This is also interesting neighborhood historically, so you can learn about that on this tour too.
This tour has it all; explore Chicago’s food, architecture and history in just one unique tour. It’s a great option if you’re interested in all of the above tours but have only one day to budget for a tour. And although it’s one of the more expensive tours in this list, you’ll be saving money by lumping your architecture, history and food interests into one tour rather than trying to fit several tours into your Chicago itinerary. It’s the ultimate unique Chicago tour!
Duration of Tour: 5 hours
So there they are! 20+ of the best and most unique tours in Chicago, Illinois! Which are you most excited to go on? I’d love to hear about your experiences!
I am obsessed about architecture so your suggestion of multiple walking tours sold me. I need to buy a ticket to Chicago! It would be heaven. I also want to visit Oak Park to see homes designed by Frank Lloyd Wright.
These tours all sound awesome! That’s actually pretty cool that they have a pizza tour — what a fun way to learn about the deep-dish life!
These all sound great! We visit Chicago often but have never thought to do a tour! Saving this for next time!
I am obsessed about architecture so your suggestion of multiple walking tours sold me. I need to buy a ticket to Chicago! It would be heaven. I also want to visit Oak Park to see homes designed by Frank Lloyd Wright.
What a great list! We’d be all about the speakeasy and pizza tours. Thanks for sharing!