Though not as large or notorious as coastal hubs like Los Angeles and New York City, Chicago is undoubtedly one of America’s greatest cities.
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From its historical impact to its modern outlook, there’s something for everyone. I’m talking stunning architecture, delicious eats, music and art scenes you haven’t heard of before, and much more. Underneath it all is a classic Midwestern openness—one that usually portends smiles and easy conversations.
That being said, digging deeper into Chicago’s identity isn’t quite as easy as in other major cities. While we’ve all heard of the Bean monument and the Chicago Cubs, what else is lying beneath the surface? (Cheese magic. That’s what.)
If you’re ready to take on Chicago, I’ve got some of the very best tours in the city. They’ll show you a part of the city you didn’t even know to seek out.
Top 14 Chicago tours that you can’t miss
Architecture River Tour
Let’s start with the crème of the crop. This river cruise cuts through the heart of Chicago, letting you learn about its surprisingly under-discussed architectural impact. Also, who doesn’t love a little relaxing journey by water?
Original Chicago Architecture Interiors Tour
If staring longingly from a river boat isn’t enough for you, dig even deeper into Chicago’s architecture with this entry-included tour. Not only will you learn about the city’s greatest wonders, but you’ll also be invited inside to learn more about the interiors of famous landmarks.
Lake Michigan Sunset Cruise
If you’re a tour-loving traveler (like me), you probably knew to expect a sunset cruise. It’s an unbeatable premise anywhere, but in Chicago, you also get an ice-cold cocktail for the ride. As an added bonus, you also get to see Chicago lit up at night—which is a true spectacle from the water.
Chicago in a Day
Ideally, you’ll have a few days to work your way through Chicago’s coolest spots. If not, get it all done in a day with this highly rated and highly expedited tour. You’ll get to nosh on some classic eats, learn about the city’s wild history, and soak up a few architectural landmarks.
Chicago Favorites Ultimate Food Tour
Speaking of noshing, if you show up to Chicago hungry, then head on this tour. From loaded hot dogs to deep dish pizza to more unexpected delights, you’re in for a full belly and unforgettable tour experience.
Chicago Craft Brewery Barrel
Let this barrel-shaped bus pick you up and ferry you off to Chicago’s most celebrated breweries. I’m not just talking about the most popular tourist breweries—this adventure lets you sample a range of delicious beers at the city’s most celebrated breweries from fanatic hops fans.
Fortune Reading with Cheese
Did you know that Chicago is home to the world’s only cheese psychic? With a short and simple exercise, this clairvoyant takes you closer to the world of cheese magic, offering a fortune reading. Yes, you get to eat the cheese afterwards. I told you—Chicago is home to unexpected surprises.
Delicious Donut Adventure with Underground Donut Tour
If cheese magic doesn’t quite hook you but you’re still interested in a food-based tour, take a closer look at Chicago’s sweeter side. This delicious donut tour covers the city’s top donut shops in the downtown Loop area. Along the way, you’ll get a closer look at the spots locals love.
Pizza City Tour
Personally, I have my sights set on great deep-dish anytime I visit Chicago. If you’re similarly dedicated to finding the best slice, go on one of the Pizza City tours. They offer pizza walks by neighborhood, by bus, and by walking tour. (If you prefer to book on a tour site, you can schedule your pizza adventure on TripAdvisor.)
Chicago Crime and Mob Bus Tour
As with New York City, Chicago has a deeply entrenched history with the mafia. On this tour, you’ll learn how the mob shaped Chicago’s growth throughout the 20th century, along with major events like the St. Valentine’s Day Massacre. Because you’ll cover so much of the city, this one takes place on a bus.
Chicago Murder Mystery Tour
If you want to learn about Chicago’s criminal past while also having fun, book this tour. It combines elements of haunted history and true crime stories from the city into a murder mystery setup. While you learn about the past, you’ll also be trying to go under the radar as the play-murderer or a suspect.
Bikes, Bites, and Brews
Ready to cycle to some of the city’s most delicious restaurants, lounges, and bars? While cycling is too much work for me, I definitely see how breaking up a foodie and boozy tour with short bouts on a bicycle might be a good idea. The more calories you burn, the hungrier you’ll be for the next stop!
2-Hour Guided Segway Tour
Similar to cycling, I can’t be convinced to get on a Segway—on vacation or in daily life. That being said, this Segway tour is highly rated by visitors and comes with an excellent guide. Along with the thrill of Segwaying, you also get to learn about local history and see some of Chicago’s coolest areas.
Neon Paddle
If you like standup paddleboarding and nighttime excursions, book an experience to take one of these neon-lit paddleboards out onto the water. Dubbed the ‘glow and glide’, this adventure lets you explore the city by night from a glowing paddleboard or kayak. If the dark water is too scary, book their Golden Hour tour instead.
