Best Guided Tours in Chicago 2024 1
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Best Guided Tours in Chicago 2024

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Greetings, Internet Stranger! I’m Stella Jane, author of the travel memoir Get Lost, and welcome to the best guided tours in Chicago! Chicago is the third largest city in the United States, and it’s full of fascinating history. If you love food, architecture, movies, gangsters, and shiny sculptures that are shaped like beans, you’ll want to find a tour here.

That’s why I’ve put together this list of the best guided tours in Chicago. I’m not from the Windy City, but I’ve been there many times, and I’ve actually taken all these tours myself. Join me and hopefully you’ll agree that these are the best guided tours in Chicago…and you’ll want to take one of your own!

Stella’s Top 3 Picks: Best Guided Tours in Chicago

#1 TOP PICK

Best Guided Tours in Chicago 2024 2

⭐️⭐️⭐️⭐️⭐️
CHICAGO FOOD TOUR
✔️ Delicious and fun!
✔️ Expert local guide

#2 PICK

Best Guided Tours in Chicago 2024 3

GANGSTER AND GHOST TOUR
✔️ Tons of fun
✔️ Surprisingly affordable

#3 PICK

Best Guided Tours in Chicago 2024 4

ALL OTHER CHICAGO TOURS
✔️ Find your favorite!
✔️ Get the best deals

Best Guided Tours in Chicago

best guided tours in Chicago

1) Chicago Doughnut Tour

There are all kinds of tours in this world: history tours, architecture tours, food tours, movie tours, and street art tours. However, did you know that there can also be Doughnut tours?

That’s right, everyone loves doughnuts! And just a few cities out there are lucky enough to have their own doughnut tours. Fortunately, Chicago happens to be one of them.

Chicago has an excellent number of high end doughnut shops, and we’re going to meet a few of them on this excursion.

This tour illustrates why I like food tours so much. If I wanted to try all eight of the doughnuts on the tour by myself, I’d have to eat eight doughnuts. Yikes! But on this tour, you get to eat a quarter of eight different doughnuts, which adds up to only two doughnuts. In my opinion, that’s the perfect way to start the day.

You can book this quirky and delicious tour for yourself by clicking here.

best guided tours in Chicago

So we went to four different doughnut shops, and at each shop we got to try two different doughnuts. The first stop was at a store located in a former bank vault. I guess all those baked goods need a lot of protection!

The flavors here were raspberry old-fashioned and a yeast doughnut with a chestnut glaze. Our guide taught us all about the three different kinds of doughnuts: old-fashioned, yeast, and cake. (Technically old fashioned is a type of cake doughnut.) The old fashioneds are the richest and the yeast are the lightest. You probably know which kind is your fave already!

best guided tours in Chicago

At our next stop, we experienced the third kind of doughnut, and of course I am talking about the cake. The most famous doughnut at this place is their decadent Tahitian vanilla, though I was kind of tempted to come back and try the birthday cake flavor another time.

They also do different flavors with the seasons, and like this beautiful blueberry lemon flavor. It was positively bursting with a hot girl summer attitude.

best guided tours in Chicago

Our next stop featured these luridly colored pistachio and lemon old fashioned doughnuts. They might have been a strange color, but they were rich and yummy, especially if you like natural lemon flavor.

best guided tours in Chicago

But my favorites were the stuffed doughnuts filled with Biscoff cookie paste. Those are the cookies you get on every Delta flight, so in my mind, these are going to be dubbed Delta Doughnuts. I fly Delta a LOT and I like Biscoff cookies just fine, but these doughnuts are way better.

best guided tours in Chicago

This is the last stop of the tour, and by a strange coincidence, it’s the very first place where I ever ate doughnuts in Chicago, on my first trip to the Windy City many moons ago. I was quite broke back then, and doughnuts were my lunch.

They specialize in old fashioned doughnuts, so we had the plain buttermilk old fashioned, which would make a terrific breakfast by itself. For a fancier choice, we had chocolate doughnuts that were covered in Valhrona chocolate. Delicious! And it was the perfect end to one of the best guided tours in Chicago.

I hope I have intrigued you and made you want to eat these doughnuts yourself.

Check rates and availability of the tour for yourself by going here.

best guided tours in Chicago
2) Big Bus Tour

Chicago is a pretty big city, and the best way to see all the main attractions in one day is to take a Big Bus tour of the city. The narration is entertaining, and when the weather is good, it’s great fun to sit on the top deck.

Once you buy your ticket, which you really should in advance, you can get on and off the bus all day. I personally like to do one loop in the morning, and then get off again at whatever stops look the most interesting to me.

Just keep in mind that Chicago traffic can be awful, so you can’t necessarily guarantee that you’ll get to the next stop at a specific time.

Just buy your ticket for the Big Bus tour by going here.

best guided tours in Chicago

As I said, the audio guide is lots of fun. It’s jammed full of entertaining facts about Chicago, and they use tons of great Chicago movie quotes from classics like The Untouchables and Ferris Bueller’s Day Off.

My personal favorite was when they told us to go on “a hard target search of every gas station, residence, warehouse, farmhouse, henhouse, outhouse and doghouse in that area”, which is a reference to The Fugitive, one of the best Chicago movies.

best guided tours in Chicago

Above, you can see Soldier Field, home of the Chicago Bears.

best guided tours in Chicago

You will also be able to see Chicago’s famous skyscrapers.

best guided tours in Chicago

My favorite fun fact was about the neighborhood Streeterville. It was given this name in honor of a very weird guy named George Streeter who tried to take over the neighborhood using “an army of hobos”.

This happened back in the 19th century, and it seems like Streeter was never really punished, which baffles me. I feel like there would be consequences if I tried to take over my neighborhood with an army of hobos.

And those are just a few of the fun facts you can expect to find on the tour!

Check rates and availability for yourself right here!

best guided tours in Chicago

3) Chicago Architecture Tour

One of the most famous things about Chicago is its architecture. After all, some say that Chicago invented the skyscraper. And as a native New Yorker, even I have to admit that Chicago’s architecture is amazing. That’s why I suggest taking the Chicago Architecture Tour.

This isn’t a walking tour–you’ll actually get to see Chicago’s buildings in the most relaxing way possible–from a boat! That’s why it’s one of the best guided tours in Chicago. Your live local guide will teach you all about the fabulous history of the buildings.

Just click this link to check rates and availability!

You’ll learn all about the different periods of architecture in the most fun way possible. That way you’ll develop knowledge that you can impress your friends with back home.

best guided tours in Chicago

For example, this building that you can see in my photo above is called Gothic Revival because it uses the style of Gothic Cathedrals. Of course, it isn’t a religious building at all, but at least it has some cool twists and curlicues for decoration.

best guided tours in Chicago

Above, you can see the Merchandise Mart, which is one of the most famous buildings in Chicago. It is so large that is used to have its own zip code, and it was featured in the movie The Fugitive.

It’s also one of the only major Art Deco buildings in Chicago. This surprised me because in New York City we have a ton of Art Deco skyscrapers. Why are there so few in Chicago? I assume it has something to do with putting sport peppers and no ketchup on their hot dogs.

best guided tours in Chicago

You can probably recognize this building above, which is one of the most famous in the city. It is officially called the Willis Tower, but its first and most popular name is the Sears Tower. If you ask a local about Willis Tower, they’ll just chuckle.

The style of the Willis Tower is Mid-Century Modern, which I think is German for sleek and imposing.

best guided tours in Chicago

The final style we’ll talk about today is postmodern. If you see a building that kind of makes you chuckle, that’s a good sign that it’s postmodern.

For example, you can see that the building in my photo above is curved like the Chicago River. It’s a similar color too, right? So it’s a little way of making all the glass and chrome seem more natural.

We also saw a building made with very modern materials, but in the classical Greek style. Very clever!

My one final tip for the tour is that you should check the weather in advance and bring layers. Even on a warm day, it can get windy on the boat, or it can start to rain.

I haven’t even shown you half of the amazing buildings that we saw on the tour.

So if you want to experience its wonders for yourself, go ahead and book the tour right over here.

best guided tours in Chicago

4) Chicago Architecture Walking Tour

So we’ve tried one of Chicago’s famous boat architecture tours, but there are so many interesting buildings and places in Chicago that you can’t see from the water.

That’s why I recommend the Chicago Architecture walking tour, which is definitely one of, if not the best guided tours in Chicago! On this tour, we’ll go inside some of the most unique buildings in Chicago, and we’ll even snack on a couple of tasty treats!

Check rates and availability for yourself easily by clicking here.

best guided tours in Chicago

Our first stop is at the famous Marshall Fields department store. It is now called Macy’s but much like people still call the Willis Tower the Sears Tower, locals still call this Marshall Fields.

One reason this store is famous is that it has the biggest American flag of any department store in the world. How do you even measure something like that?

best guided tours in Chicago

It also has a stunning mosaic ceiling that you get to see up close on the tour.

best guided tours in Chicago

And our final treat are Frango mint chocolates, which taste like Andes Candies, but classier. One of the reasons it was nice to take the tour is that we got to sample just one chocolate box and didn’t need to eat the whole thing ourselves.

best guided tours in Chicago

You can probably tell which famous artist made this sculpture, no? It looks exactly like a Picasso, and that’s because it is. Unfortunately he didn’t tell anyone what it is supposed to be. Some say a lady, some say a dragon, and some say it is a horse. I say it is a sculpture of ME because Picasso is dead and can’t say that it isn’t.

best guided tours in Chicago

This looks like a rocket ship, right? Like I’m going to rocket you to space. But this is actual just some offices for city workers. These are probably the coolest offices for public officials I have ever seen. Our guide said people are always wanting to tear this building down, but thank goodness they haven’t yet.

best guided tours in Chicago

Onto the Riverwalk! For some reason, I thought the Riverwalk had been around for ages, but that’s not true. The Chicago River has been around for ages, but the Chicago Riverwalk is relatively new and patterned after the San Antonio Riverwalk, which is quite nice. Probably the most famous time of year to visit the Riverwalk is during St. Patrick’s Day, when they dye the river green.

The river is also famous because of a disaster that happened here in 1915. There was a boat carrying hundreds of people that sank on the river, and more than 800 people drowned. But it’s highly unlikely that anyone could drown in this river today with all the people around.

best guided tours in Chicago

We saw the Merchandise Mart on one of the boat tours, but on this tour, we get to go inside. That’s one of the reasons I say this is one of the best guided tours in Chicago.

You’d think there’d be an awesome mall inside here or something, but no. They use it to host large commercial events like bridal expos. It’s still need to see the interior, though!

best guided tours in Chicago

Oooh! Aaah! Pretty!

best guided tours in Chicago

The Merchandise Mart is also where we caught the famous L train and went to our next destination. This L stop was a major plot point in the movie The Fugitive. My guide said some people don’t get that reference anymore, which makes me sad. It’s a great movie!

best guided tours in Chicago

And finally, you can’t spend time with the best guided tours in Chicago without seeing The Bean! This piece of public art was done by the sculptor Anish Kapoor, and its official name is Cloud Gate. However, no one calls it that. It’s like calling Willis Tower Sears Tower or something. Just call it the Bean and everyone will know what you mean.

You’ll have some time on the tour to take fun selfies at the Bean.

best guided tours in Chicago

And a good time was had by me!

best guided tours in Chicago

And here we have our second tasty treat of the tour, popcorn! this is actually Garrett Popcorn, which is my favorite popcorn in the world, and I love popcorn. On the tour, you’ll get their best flavor, which is the Garrett Mix, a blend of cheese and caramel. Yum-tastic!

Interested in going on this tour? Think it might be one of the best guided tours in Chicago?

Check rates and availability by going here!

best guided tours in Chicago

5) Chicago Food Tour

OK, we had a few snacks on our last walking tour, but now we’re actually going on an official Chicago food tour. On this Food Tour, you’ll experience some of the best food that Chicago has to offer.

You’ll also learn a bunch about Chicago history and have a ton of fun while doing it! That’s what makes it one of the best guided tours in Chicago.

You can check rates and availability by clicking here.

best guided tours in Chicago

What’s the first thing you think of when you think of what to eat in Chicago? If you said deep dish pizza, you’re in luck! Deep dish was invented in Chicago, and of course you are going to want to try some when you’re here.

I’m from New York City, so naturally I prefer our style of pizza, but even I have to admit that deep dish is delicious. What makes it special is that it has a butter crust, then you put the cheese on the bottom so it melts into the crust, and then you top it with tomato sauce. Dig in!

best guided tours in Chicago

This next Chicago food creation is called Italian beef. It was invented by Italian immigrants as a way to celebrate weddings without spending too much money. There are three ways to eat it, and they all depend on how much gravy you want on the sandwich.

I think I prefer mine wet, which is the medium amount of gravy. Dry, without gravy, seems kind of weird, and I honestly don’t think I could handle a sandwich that was soaked in gravy. Could you?

best guided tours in Chicago

And now we’re on to the other most famous Chicago food–the hot dog! The Chicago hot dog is actually my favorite food in Chicago. To get it proper Chicago styles, you need seven toppings exactly. There’s mustard, relish, onions, a sport pepper, a dill pickled cucumber, a slice of tomato, and celery salt. Also there is ABSOLUTELY no ketchup. You’ve been warned.

best guided tours in Chicago

Hmm, what’s this root beer doing here? Well, this was a pleasant non alcoholic tribute to the days of Prohibition in Chicago. Of course the most famous Chicago bootlegger was Al Capone, who was actually from Brooklyn.

Many bars turned into illegal bars or speakeasies, but we stopped by a historic bar that actually decided to obey the law and follow Prohibition. They made their own non alcoholic beverages, like this delicious root beer, which you can drink today.

best guided tours in Chicago

And what would a Chicago food tour be without Garrett Popcorn? Literally absolutely nothing. No list of the best guided tours in Chicago can be complete without this magic.

In case you didn’t read my earlier comments on Garrett Popcorn, just remember that you’ll be getting the famous Garrett Mix, which combines cheese and caramel popcorns in a most glorious way.

best guided tours in Chicago

Why are we having a brownie on a Chicago food tour? Well, the brownie was actually invented in Chicago at the famous Palmer House Hotel for the famous Chicago World’s Fair. (This fair was also the occasion for inventing the Ferris wheel, so it’s quite historically important.)

The Palmer House Hotel was also featured in the movie The Fugitive, like the green river for St. Patrick’s Day and basically every other good Chicago thing.

I hope I’ve explained to you why this is one of the best guided tours in Chicago.

Check rates and availability of the tour by clicking here to find out the rest!

Stella’s Top 3 Picks: Best Guided Tours in Chicago

#1 TOP PICK

Best Guided Tours in Chicago 2024 2

⭐️⭐️⭐️⭐️⭐️
CHICAGO FOOD TOUR
✔️ Delicious and fun!
✔️ Expert local guide

#2 PICK

Best Guided Tours in Chicago 2024 3

GANGSTER AND GHOST TOUR
✔️ Tons of fun
✔️ Surprisingly affordable

#3 PICK

Best Guided Tours in Chicago 2024 4

ALL OTHER CHICAGO TOURS
✔️ Find your favorite!
✔️ Get the best deals

best guided tours in Chicago

Best guided tours in Chicago

Where to Stay?

Chicago is the third largest city in the United States, so there’s no shortage of places to stay here. But you want something that’s in a safe, convenient neighborhood. And if you’re anything like me, you want something within your price range for exploring the best guided tours in Chicago

So I recommend staying at Aloft Chicago Downtown. It’s near many trendy restaurants like Topolobampo, the staff is friendly and helpful. Plus, it’s attached to a restaurant that serves a mean croissant and coffee in the morning! What more could you want?

If you want to find a great deal on this hotel, click here.

If you’re looking for great deals on hundreds of hotels in Chicago, just click here.

This search engine will help you find the most affordable and convenient hotel during your day of the best guided tours in Chicago. With hundreds of options to choose from, I’m sure you’ll find something for your schedule and budget.

best guided tours in Chicago

That’s the best guided tours in Chicago!

What do you think are the best guided tours in Chicago? Please email me at stellajane@aroundtheworldin24hours.com and let me know!

Note: If you want to know how I put my travel itineraries together, just click here. Keep in mind that while each article is about how to spend 24 hours in a place, that doesn’t mean you should ONLY have a day with the best guided tours in Chicago.

You should also try 24 hours in Chicago. Add on a Chicago doughnut tour. Experience the most fun stuff to do in Chicago Illinois. Go for the best architecture tour in Chicago. Get to know the top Chicago attractions for tourists. Enjoy a good food in Chicago IL day.

Best Guided Tours in Chicago 2024 8

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