fbpx Skip to Content

Best Chicago Attractions (Approx Top 10)

This post contains affiliate links. As an Amazon associate, I earn from qualifying purchases.

Greetings Internet Stranger and welcome to the best Chicago attractions. Everyone knows that one of the best things about Chicago is its remarkable skyline. It has some of the most beautiful architecture in the entire country and perhaps the entire world.

And today, we’re going to see many of those famous buildings and places, from the Merchandise Mart to the Bean, up close and personal! Then we’ll dine on some of the best food that the Windy City has to offer. Let’s get started right away! After all, life moves pretty fast. If you don’t slow down and look around once in a while, you could miss it.

best Chicago attractions

Best Chicago Attractions

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 during your day of the top things to see 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.

best Chicago attractions

Best Chicago Attractions

What to Pack?

  • A cell charger so you can take photos all during your day of the best Chicago attractions
  • My favorite travel guide to Chicago.
  • My book Get Lost, that I wrote myself with all my best travel tips. This book will show you exactly how solo travel can take your life from BLAH to amazing!
  • Want to learn how I saved enough money to travel 16 weeks a year? Check out my top secret How to Afford Travel digital system.
  • I always travel with travel insurance from World Nomads. You never know when something might go wrong, especially in this day and age, and you don’t want to get stranded during your trip without help. But with travel insurance, you’re protected even if you’re attacked by the one-armed man during your day of the best Chicago attractions
best chicago attractions

Best Chicago Attractions

Morning: Chicago Architecture Tour

Many architecture tours of Chicago take you on a boat so you can see the buildings from the water. And while that’s great, sometimes you want to get up close and personal with the structures.

That’s why I recommend the Chicago Architecture tour with WeVenture! You’ll learn how to explore the city like a local, get lots of hidden fun facts and gems, and even eat a few delicious treats!

You can book this tour for yourself easily by clicking here. Then get ready for…

Approximately Top 5: Chicago Architecture

best chicago attractions
1) Marshall Fields

OK, so the Marshall Fields department store is now officially Macy’s, but no one calls it that. Chicago has this funny thing about refusing to acknowledge it when buildings change, like how the locals keep calling the Willis Tower the Sears Tower. Marshall Fields/Macys is a gorgeous historic department store that has the largest American flag of any department store. But that’s not all!

best chicago attractions

It also has one of the most beautiful mosaics I have ever seen! This belongs in the Sistine Chapel or something, but really it’s in “Marshall Fields” and you can see it for free any time you’re in Chicago.

best chicago attractions

We also got to sample these Frango chocolates they sell at “Marshall Fields”. They used to be called Franco chocolates but they changed the name so people wouldn’t think of General Franco of Spain. They’re like a very fancy Andes Candy. If I lived in Chicago, I would eat these a lot.

best chicago attractions
2) Public Art

Who do you think made this sculpture? If you said Picasso, you are correct! But our guide, whom I shall call Ferris, said that no one knows exactly what the sculpture is. From some angles it looks like a horse, or a dragon, or a woman. I guess it’s up to you to decide!

best chicago attractions

And speaking of odd-looking things, we stepped inside this contraption, which I never would have known to look for on my own. But that’s the benefit of taking a walking tour. Ferris said that this was just city offices, not Emperor Palpatine’s palace, which is what I would have guessed.

Some people think it’s hideous and want to tear it down and others love it, so for the moment it stays put. Hmmm. That sounds like exactly what Palpatine would want if it were his palace….

best chicago attractions
3) Riverwalk

Of course, you can’t visit Chicago without seeing its famous Riverwalk! The river has existed for jillions of years, but the Riverwalk pathway is fairly new. In fact, it’s modeled after San Antonio’s river walk. Chicago has a very large Irish population, so every year they dye the river green to celebrate St. Patrick’s Day. That’s a lot cleaner than throwing potatoes and cabbages at people like they do in New Orleans.

If you’re looking for tragic history instead of green dye, the Chicago River has that too. Back in 1915, a ship called the Eastland tragically sank on the river, killing over 800 people. It’s probably the second-most famous Chicago disaster after the Great Fire.

best chicago attractions
4) Merchandise Mart

And now we have the Art Deco Merchandise Mart building, which is definitely one of the best Chicago attractions. This building used to belong to the Kennedy family, and it used to have its own zip code, so you know it’s fancy. Now it’s a place for events like bridal expos and things, so it’s not for ordinary people to go shopping. But it’s still delightful to bop around here and peruse the interiors.

best chicago attractions

See! So fancy!

best chicago attractions

Then once you’re inside the Merchandise Mart, you can actually get on the L train, where we will ride it to our next stop. This station is famous because it’s where Tommy Lee Jones almost caught Harrison Ford in the movie The Fugitive. Ferris said people don’t always get that reference anymore, which just goes to show that they don’t teach kids anything useful in schools these days.

best chicago attractions
5) The Bean

There it is! I told you that we couldn’t see the best Chicago attractions without stopping at the Bean. It’s official name is Cloud Gate, but everyone calls it the Bean. I wonder if the sculptor, Anish Kapoor, gets really angry about it. Like, maybe he stays up at night enraged because people have named his beautiful sculpture after something that makes you fart.

It’s basically impossible to take a photo of the Bean without other tourists around. Like maybe you could if you came here at 2 AM on a Tuesday in February, but that sounds like a terrible experience. But you can get up close to the Bean and take as many wacky selfies as you want.

best chicago attractions

Where am I in this picture? I’ll never tell!

best chicago attractions
6) Garrett’s Popcorn

You might wonder why popcorn is special enough to be included on a tour of the best Chicago attractions, and all I can say is that must mean you’ve never had Garrett Popcorn, which is the most delicious popcorn in the world. That’s especially true if you get their Garrett mix, which is caramel and cheese popcorn blended together. Eat as much as you can when you are in Chicago. You’ll thank me later.

That’s where our tour ended, but I promise I didn’t share even half of the fun secrets and stories that I learned or the gorgeous buildings I saw. You’ll just have to book the tour by going here if you want to learn about them for yourself!

best chicago attractions

Best Chicago Attractions

Afternoon: Museum of Contemporary Art

Everyone and their cousin is aware that Chicago’s museums are some of the best Chicago attractions. Chicago’s Art Institute is famous, and we’ll definitely be going there another day. But if you want to see funky art without the crowds, head on over to the Museum of Contemporary Art, which has all the cutting-edge wackiness any art lover could want.

I would be delighted to introduce you to this museum and its ways, but first…

Three Fun Facts: Museum of Contemporary Art

best chicago attractions
1) Can You Feed Me?

Sure! I recognize that popcorn isn’t lunch. Ferris suggested that I get food at the Dearborn Tavern, which was just down the street from where the tour ended. I ordered their fish and chips because apparently they beat Bobby Flay with them in a cooking contest, and I always like to see Bobby Flay lose.

The fish was full of flavor, not soggy and bland like fried fish can be. Plus, I appreciated that they gave me ketchup with my fries, since from what I can tell, the city of Chicago hates ketchup.

best chicago attractions

And if you feel like a cocktail, go for it! Contemporary art is always better with a drink, and the Dearborn’s cocktails are yummy. I had a drink with ice wine, which I had only ever had for dessert before. I just love finding new ways to drink!

best chicago attractions
2) So What Kind of Art Does This Museum Have?

Well, it’s contemporary art, which means it’s as recent as possible. (Modern art often means art from the late-19th to mid-20th centuries. You won’t really see any of that at the Museum of Contemporary Art., so don’t come here looking for some Jackson Pollocks or Monets or whatnot.)

The art at the MoCA is often surprising or odd, but that’s just part of the adventure. You’ll probably always be discovering a new artist every time you go here. For example, when I went, I saw the works of Christina Quarles, who paints images of bodies merging in ways I have never seen a body do in real life. I found her work fascinating because it was often difficult to look at, but minus points to her because she is younger than I am and that makes me feel like I haven’t accomplished anything in life.

best chicago attractions
3) Are There Special Exhibits?

Oh, of course! When I was there, they were featuring an exhibit on comic book art in Chicago. Some of the comics were extremely famous, like Dick Tracy. It hadn’t occurred to me that Dick Tracy was set in Chicago, but then he was fighting gangsters all the time, so that totally makes sense.

best chicago attractions

But the exhibit was mostly dedicated to indie comic book artists who worked in Chicago, like the feminist artist Nicole Hollander. You can see a blow-up of one of her panels above. (And to answer that shirt’s question, no there aren’t any. Give me a good satin dress any day.)

I was glad that MoCa was treating comic artists like serious creators worthy of being featured in a museum. After all, what medium requires more of a constant outpouring of creativity? I can’t think of one!

best chicago attractions

Best Chicago Attractions

Evening: Dinner at Topolobampo

Ah! Here we definitely have one of the best Chicago attractions, and it happens to be a Mexican restaurant. Topolobampo, Rick Bayless’s fine dining restaurant, has a Michelin star, and it’s supposedly President Obama’s favorite restaurant in Chicago. You know it’s good because I feel like President Obama can get a table in Chicago at any restaurant that he wants!

Topolobampo is a tasting menu restaurant, which means that you get what you get and you don’t get upset. But if you’re an adventurous eater who loves amazing food, you’ll love it here. The menu changes all the time, so you definitely won’t be served what I ate. But I’ll show you my meal so you have an idea about what to expect.

best chicago attractions

The theme of the night was other countries that have influenced Mexican cuisine, so we start with Germany and beer! Of course, beer is incredibly popular in Mexico, so this dish featured a broth made with a Michelada, which is a spicy Mexican beer cocktail. This was a great way to start the meal because it was a light dish, but it still had a ton of flavor and heat.

best chicago attractions

The next dish demonstrated West African influence on Mexican cuisine, so it was halibut served with coconut and plantain. Of course, I knew that coconuts and plantains were popular in both African and Mexican dishes, but I never put two and two together and made this connection.

This dish reminded me of black cod with miso because of the sweetness and firm texture, only this time the sweetness was coming from the coconut. It was an intriguing variation.

best chicago attractions

At any proper tasting menu restaurant, there will be a few tricks and surprises. This snack was fried angel hair pasta with avocado, chile, and blue corn tortilla. Fried angel hair pasta is a popular snack in Mexico, but I never would have thought to try it if I hadn’t happened on Topolobampo that night.

best chicago attractions

Our next influence was China, and it’s time for the vegetarian main course. This was tamal colado served with eggplant, salsa macha, and pak choy. It reminded me of spicy Chinese noodle dishes because the tamal colado almost ended up resembling a thick noodle in texture.

Apparently this is a special kind of tamal from the Yucatan that is served strained, which does make it like noodles. I’m not sure I’ve ever eaten a meal before where I was trying so many new items in one dish.

best chicago attractions

And for our meat course, we have the Spanish influenced dish, which was pata negra pork served with mole poblano. Obviously nothing can be more Mexican than the mole poblano, which is made with 25 different special ingredients. But that top-quality Spanish pork just melts in your mouth like butter. Honestly, this is the only type of pig meat dish that’s more delicious to me than bacon.

best chicago attractions

And here we have one of the most unusual cheese courses I’ve ever seen. It’s bringing the Dutch influence, and it’s based on the Marquesita, which is a popular dessert in the Yucatan that’s often filled with Edam cheese. Ah, there’s the Dutch influence! The Dutch certainly are tops when it comes to cheesemaking. That’s where the phrase “Blessed are the cheesemakers” comes from.

Flavor-wise, this dish was an excellent segue in between the savory and final sweet dishes. But our big dessert is still up ahead.

best chicago attractions.

Just look at this beauty! You could almost hang it in the Museum of Contemporary Art, except I think it’s a little too pretty to pass as contemporary art. This is based on the Mexican dessert mil hojas, which in turn is based on the French dessert mille feuille.

This baby contains tons of layers of puffed pastry, prickly pear cactus, Bavarian cream made with Mexican vanilla, and Tabasco chocolate made at Topolobampo’s sister restaurant Xoco. Honestly, you had me at Tabasco chocolate. So many fine dining restaurants seem afraid of spicy food. Thank goodness Topolobampo doesn’t make that mistake. And it’s the perfect way to end our day of the best Chicago attractions.

best Chicago attractions

Best Chicago attractions

How to Get There?

By Car: This is an easy way to get to the best Chicago attractions if you’re coming from elsewhere in Illinois or a neighboring state. However, I don’t know how to drive and traffic can get nasty in Chicago, so I was pleased to explore the city without a car.

Fortunately, pretty much everything in Chicago is within reach of their excellent public transportation, and Uber is widely available in Chicago, if you are traveling at night. If you need to rent a car, you can use the search engine Expedia to find the best price from the available car rental companies.

best Chicago attractions

By Plane: You can absolutely fly into Chicago if you are coming from far away. Chicago has two airports, and both of them have public transportation that goes into the city. (Again, I recommend using a search engine like Expedia to search for the best prices on flights.)

Just keep in mind that O’Hare is one of the busiest airports in the entire country, and some people find flying in and out of it overwhelming. Midway mostly handles Southwest flights, though I did take a Delta flight out of Midway once.

By Bus or Train: I’ve taken both the bus and the train to and from Chicago to nearby cities like Milwaukee and Detroit. If you’re using the bus, I suggest going with Megabus, and if you’re using the train, it’s gotta be Amtrak. Chicago has a beautiful train station that seemed to play a lot of Frank Sinatra, so check that out if you can.

best Chicago attractions

That’s the Best Chicago Attractions!

What do you think are the best Chicago attractions? Did I have you at Tabasco chocolate? Is Anish Kapoor really mad at The Bean? Are you ready to start booking your hotel in Chicago right now? Please leave your thoughts below!

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 enjoy one day of best Chicago attractions

If you have time for more of the best Chicago attractions, add this itinerary with the Field Museum. If you want the best Chicago attractions with the Art Institute, click here. And if you want to see the best Chicago attractions with the Lincoln Park Zoo click here.