Best Artsy Places in Chicago (Approximately Top 10)

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Greetings Internet Stranger and welcome to the best artsy places in Chicago! Are you interested in experiencing Chicago’s fine art scene? Of course you are, my cultured World Traveler! You want to follow in the footsteps of Ferris Bueller and make out with your sweetie in front of a Chagall stained glass window at the Art Institute.

But even for those of you who are not a fan of John Hughes’s greatest achievement, I promise this 24 Hour itinerary will hit all of the best artsy places in Chicago. If this is your first time in Chicago, this day is most ideal for you.

If it is not your first time in Chicago, I’m sure you haven’t exhausted the wonders of American Gothic, postmodern architecture, and the Garrett Mix. So enjoy spending a beautiful day enjoying all that the Windy City and the best artsy places in Chicago have to offer!

Best Artsy Places in Chicago

How To Get There

Now, I wish I knew where you lived, Internet Stranger, because I could send you a beautiful bag of Chicago hot dogs. But sadly, I do not, and so I can’t tell you exactly how to get from your home to Chicago.

But I can tell you that I used a lovely airplane to get from my hometown NYC to Chicago, and I recommend Expedia for the best way to find the cheapest flight to Chicago at the best time of day. O’Hare Airport in Chicago is a major hub, so it’s pretty easy to find direct flights. You can even use Expedia to rent a car so you’ll be all set when you arrive at your destination. (I can’t drive, but if you can, this must be helpful.)

Just click here to start looking for the best possible deals on your flight, so you can head out to the best artsy places in Chicago ASAP.

Best Artsy Places in Chicago

Where to Stay?

Many of the best artsy places in Chicago are located in the famous Chicago Loop. So when we’re choosing a hotel, we’ll want to stay someplace conveniently located near said Loop.

That’s why I recommend the Hampton Inn Chicago West Loop. It’s got large, comfy, immaculate rooms, the gentleman at the front desk couldn’t have been more helpful, and there’s a complimentary breakfast spread every morning so you can get your yogurt and cereal on before tackling the best artsy places in Chicago.

If you want to find a great deal on this hotel, click here. If you don’t trust my wisdom in hotels, and would rather go it alone for great deals on hundreds of hotels in Chicago, just click here.

Best Artsy Places in Chicago

What to Pack?

  • In the cold-weather months (which are many months in Chicago), you’ll want to bring along a sturdy coat. I recommend this one because it’s beautiful and stylish as well as warm, and it comes in a ton of colors.
  • In warmer months, it’s more likely to rain than snow, so bring along cute rain boots that would be cool enough for Ferris Bueller’s girlfriend Sloane.
  • A cell charger so you can take photos of the Marc Chagall blue windows without worrying your battery will die a hideous death.
  • A light jacket with a hood because it’s windy in Chi-town!
  • An umbrella strong enough to stand up to the Chicago winds or Mr. Rooney
  • My favorite guidebook to Chicago
  • The Devil in the White City, which is one of the best narrative nonfiction books ever written. It’s all about the Chicago World’s Fair, Chicago architecture…and a deranged serial killer. You’ll love it.
  • The saddest, most powerful novel set in Chicago, Native Son by Richard Wright. Every American should read this book.
  • 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 in a foreign country without help. Even if you live in the US, you never know when extreme weather will strike or some other emergency. But with travel insurance, you’re protected even if you’re attacked by the ghost of Al Capone while you’re looking for the best artsy places in Chicago.

Best Artsy Places in Chicago

Morning: Art Institute of Chicago

Are you a museum loving fool like I am? I hope so, but if not I just plan to bully you until you learn to love museums. If you’re nervous about getting started with the wide world of ArtLovin’, the Art Institute of Chicago is an excellent place to start.

The entrance fee is quite pricey, so I suggest getting the Chicago City Pass if you’ll be in Chicago for a few days and want to see other big attractions like the Field Museum. You’ll save money.

For most of us outside the Chicago area, our first peek inside the Art Institute of Chicago was during the film Ferris Bueller’s Day Off. But the AIOC is so much more than a background for Ferris, Cameron, and Sloane’s hijinks.

In fact, TripAdvisor customers voted it the number one museum in the world in 2014! However, it has since been dethroned by the Met, the World War II Museum in New Orleans, and the Musee d’Orsay, and it now sits at #4.

Is that like the Bronze medal for museums? Does the Art Institute have to stand on a podium and grit its teeth while it watches two American flags and one French flag being raised and plots to kneecap the Musee d’Orsay so it can win the Gold medal next year? I sure hope so!

But enough about the revenge of the museum! You’re here to hear my mildly confused comments about the best artsy places in Chicago! So I present the…


best artsy places in Chicago

This painting is one of the most famous works in the Art Institute, which definitely makes this one of the best artsy places in Chicago. People argue over whether or not Wood meant to satirize Middle Americans with this portrait or depict them lovingly. (Fun Fact: the model for the woman in the portrait was Wood’s sister Nan.)

I come firmly down on the side of satire because these people do not look fun to spend time with at all. In fact, I’m pretty sure this guy is planning to murder you in your sleep with that pitchfork.

best artsy places in chicago

OK, that’s not actually the title of this painting, but I always think of it as Sunday in the Park With George because of the Sondheim musical, so let’s just go with that. This masterpiece of Pointillism depicts stylish yet faceless Parisians out for a stroll in the park, to see and be seen.

I like to think Seurat’s attitude toward the urban and chic is similar to Wood’s attitude toward the rural and simple. IF ONLY WE COULD REALLY KNOW WHAT THAT ATTITUDE IS! Are Wood and Seurat condescending and critical or supportive and affirming? Say it with words, painters! They’re a lot clearer than a bunch of colorful tiny dots.

best artsy places in chicago

A great work of art raises a million questions in the viewer’s mind, and it’s easy to see how Nighthawks succeeds on that level. We have so many questions when we look at this painting. Who are these people? Why are they at the diner? Is there no one outside the diner? Was this after the Zombie Apocalypse Why is the woman so dressed up? Why does she look like Jessica Rabbit? What are the people eating? Is it any good? Who do those mysterious shadows belong to?

Oh, actually I think those shadows are really reflections of museum-goers. All our other questions still stand, though.

best artsy places in chicago

Look at these babies. They are so choice. When you stand near them, you are bathed in a peaceful blue light. It is almost as if you become part of the artwork. Also they are by Chagall and he is my favorite 20th century artist.

Old Marckie Marc created these beautiful windows for America’s bicentennial celebration, and it is fun to look through the different panels for as many monuments and symbols of America as you can possibly find. It’s like a really classy version of Where’s Waldo.


You have to leave the Art Institute to do this one, but it is worth it. Ordinarily you do not need to be told that popcorn is not lunch. But Garrett’s Popcorn is breakfast, lunch, dinner, father figure, preacher teacher, whatever you want it to be.

That’s why when you’re done with the Art Institute, you should just bop over to the Garrett Popcorn store and buy a small bag to nosh on the go for your lunch. This is going to be a busy day, and we have more of the best artsy places in Chicago to see!


Garrett has lots of flavors, but the only one you need to know about is the Garrett Mix. You are not permitted to order anything else. The Garrett Mix combines CheeseCorn with the CaramelCrisp flavor of popcorn.

It is the perfect marriage of salty, sweet, and sticky fingers. Even if it doesn’t sound appealing to you, JUST ORDER IT! You will thank me later, I promise.

Best Artsy Places in Chicago

Afternoon: Chicago Architecture Tour

No tour of the best artsy places in Chicago is complete without the famous Chicago Architecture Tour. On this tour, you will explore and learn about Chicago’s justly famous skyline from the high seas! Well, actually it’s the Chicago River, not the high seas, but l think I can take a little poetic license.

Just click this link to book the tour right away! Then follow me as I give you a preview of some of the highlights.

best artsy places in chicago

The tour is more fun if you keep an eye out for examples of different periods of architecture history. Allow me to give you a few pointers as a head start. Then you can impress the guide with your stealthily acquired knowledge!


best artsy places in chicago

This building is considered Gothic Revival because it has elements taken from cathedrals, even though it is a commercial building. I’m sure this says something sad about the state of religion and commerce in the modern world, but I don’t feel up to fully thinking through a position today. All I had for lunch was popcorn.

best artsy places in chicago

The M and M is one of the few Art Deco buildings on the tour. Unlike NYC, Chicago is not as known for Art Deco skyscrapers. Suck it, Chi-Town! (This is your daily reminder that your friendly neighborhood travel blogger, aka me, is a Native New Yorker.)

best artsy places in chicago

The Willis Tower is that Mid-Century Modern building with devil horns. I don’t know exactly what Mid-Century Modern means, but I assume it has something to do with Don Draper.

best artsy places in chicago

This is considered a postmodern building in part because it features playful design elements. Here, the green curves of the skyscraper reflect the curves of the river below. This kind of creativity definitely makes it one of the best artsy places in Chicago.

best artsy places in chicago

This is also a postmodern building. I guess a building is postmodern if you look at it for a minute and then say out loud, “Oh, I get the joke!” It’s a nifty building to look at because the design elements look classical, but it’s made with very modern materials. See, you get the joke too, right? Also, it’s shiny.


Bundle up! It gets really cold and windy on the water. Also the tour runs rain or shine, so be prepared! Like with an umbrella, but also just be mentally prepared for bad weather any time you are in Chicago.

Best Artsy Places in Chicago

Late Afternoon: Millennium Park

Chicago itinerary

After a busy afternoon of sitting on on boat, you will want to spend the rest of the afternoon sitting in the park! If you are here in the summer, there will be plenty of enjoyable events at the spidery Jay Pritzker Pavilion, which looks like a missing set piece from a Terry Gilliam science fiction movie. If not, why are you visiting Chicago at another time of the year? Don’t you know it gets cold?


The greatest thing to do in Millennium Park is to chill out at the embarrassingly named AT&T Plaza and glory in the wonders of this sculpture by Anish Kapoor. No list of the best artsy places in Chicago is complete without this, arguably Chicago’s most famous work of art.

Its official name is Cloud Gate, but the whole wide world knows it as The Bean. I imagine that is because it looks like a big, shiny silver bean. Isn’t it adorable? Isn’t it tempting/illegal to sit on it?

best artsy places in chicago

Suddenly I wonder if Boston gets mad that Chicago has a sculpture called the Bean when Boston’s nickname is Beantown. Maybe Boston cursed Chicago for the sculpture and that’s why it look so long for the Cubs to win the World Series…

Best Artsy Places in Chicago

Evening: Pizanos Pizza

What would a list of the best artsy places in Chicago be without a mention of deep dish pizza? A sad, lonely thing, that’s what. After all, deep dish is possibly Chicago’s greatest artistic creation, even more so than the Bean.

Unlike some New Yorkers, I love deep dish pizza. I love a good NYC slice more, but deep dish pizza is an intriguing mutant beast, and I’ll be damned if there’s anything to hate about adding more crust, more cheese, and more sauce to the already perfect creation that is the pizza pie.

There might be a bit of a line at Pizano’s because the place is so popular, but I got around that by taking an odd seat at the bar. Keep in mind that if you are a single lady sitting at the bar, you may get asked a lot what you are doing alone.

Also probably at least one man will call you Princess in a tone that implies he thinks it is your first name and you two are on a first name basis. But Pizano’s is a friendly place, so probably no one’s going to harass you.

I especially recommend Pizano’s for the solo diner because they serve individual pizzas! So there’s no wasting food. I got the individual cheese, which had the perfect balance of dough to sauce to mozz.

I personally do not like it when the dough on a deep dish is so thick that you feel like you’re just eating a loaf of bread covered with essence of tomato. Fortunately Pizano’s does not make this mistake. Two thumbs up from this New Yorker!

Those are the Best Artsy Places in Chicago!

What do you think are the best artsy places in Chicago? Are you ready to start booking your hotel room in Chicago? And did Boston put the ultimate curse on Chicago for stealing the mighty Bean? 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 spend 24 hours in Chicago.

If you’d like to visit the Chicago History Museum, add this itinerary. If you want to see the Field Museum, try this one. And if you’d like to a Chicago itinerary with the Lincoln Park Zoo, here you go.

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