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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.

best artsy places in chicago

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

Best Artsy Places 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 during your day of the best artsy places 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 perfect hotel anywhere in the world, no matter your taste or budget.

best artsy places in Chicago

Best Artsy Places in Chicago

What to Pack?

  • A cell charger so you can take photos all during your day of the best artsy places in Chicago
  • 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 course.
  • 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 artsy places in Chicago
best artsy places in Chicago

Best Artsy Places in Chicago

Morning: Chicago Architecture Tour

No tour of the best artsy places in Chicago is complete without a 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. Our guide was a hilarious local who told us tons of fun facts about Chicago architecture that I never would have learned otherwise.

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!

APPROXIMATELY TOP 5: CHICAGO ARCHITECTURE TOUR

best artsy places in chicago
1) THE TRIBUNE TOWER

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.

best artsy places in chicago
2) THE MERCHANDISE MART

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.) But it is impressive for other reasons! Most notably, it used to have its own zip code.

Not sure why it had the zip code taken away. Perhaps it was involved in a bribery scandal. I hear that happens a lot in Chicago.

best artsy places in chicago
3) THE WILLIS TOWER

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. Please keep in mind that locals will never call this building the Willis Tower. It’s the Sears Tower forever in their hearts.

best artsy places in chicago
4) 333 WEST WACKER 

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
5) 77 WEST WACKER DRIVE

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.

24 HOUR TIP

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.

Those are just some of my favorite buildings, but I guarantee that wasn’t even half of the amazing structures we saw on the Chicago architecture tour. So if you want to experience its wonders for yourself, go ahead and book the tour here.

best artsy places in chicago

Best Artsy Places in Chicago

Afternoon: Food Tour!

Any old travel itinerary can tell you about a good spot to eat lunch. But how many of them can tell you about an amazing food tour featuring all of Chicago’s most famous and delicious foods? Pretty much just me! Why is this on an itinerary of the best artsy places in Chicago? Because food is an art as great as architecture or painting, IMO. It’s also necessary for life!

That’s why I’m leading you to Chicago Food Planet’s food tour of the Iconic Foods of Chicago. Will there be deep dish and hot dogs? Oh yes, but there will be so much more. Join me for…

Approximately Top 5: Iconic Chicago Foods

best artsy places in chicago
1) Deep Dish

Of course the first stop on any Chicago food tour or any day of the best artsy places in Chicago needs to be for deep dish pizza, and we’re going to Lou Malnati’s which is one of the best. The way you make deep dish is my starting with a butter crust, topping it with a “bed” of cheese, and then putting the tomato sauce on top. In NYC, where I am from, we put tomato sauce first, then cheese, and there’s no butter crust.

New Yorkers are supposed to hate deep dish or something, but I think it’s amazing. There’s room in this world for every kind of pizza style! Jon Stewart famously made fun of deep dish pizza, and then Lou Malnati’s made him try some of their pizza, and he had to admit it was great.

best artsy places in chicago
2) Italian Beef

Our next stop is for a lesser known, but still amazing, Chicago classic called Italian beef. One of the most notorious spots for Italian beef is a joint known as Al’s. This dish was invented to be a cheap dish that people could serve at weddings as part of a celebration. You slice the beef very thin, so a smaller piece of meat goes a long way.

There are several different ways to order Italian beef. You can get it with more or less juice, and you can get it topped with different kinds of peppers like sweet or sour. I like it juicy, but keep in mind that the more juice you get, the more napkins you will need. That’s just science!

Best Artsy Places in Chicago (Approximately Top 10) 2
3) Chicago Hot Dog

As a New Yorker, I have to admit that I prefer Chicago hot dogs to New York hot dogs. They’re just so much fun with all the topping! A proper Chicago hot dog has seven toppings: tomato, mustard, onions, celery salt, a pickle spear, green pickle relish, and a sport pepper. (Yes, I know them all from memory.) And there’s one ingredient you can NEVER put on a Chicago hot dog. Absolutely no ketchup!

We got our Chicago hot dog at Portillo’s, which is a crazy popular spot. And in my opinion, it’s one of the best artsy places in Chicago because the Chicago hot dog is the Windy City’s most beautiful creation.

Our guide said they’re not just popular for their hot dogs, they also make a delicious cake milkshake. We asked very nicely and the restaurant let us sample one. Maybe if you ask nicely, you’ll get to do the same!

best artsy places in chicago
4) Garrett Popcorn

So this might be my favorite stop on the tour. You might be wondering why I am so excited about popcorn, but Garrett’s Popcorn isn’t just any popcorn. It’s breakfast, lunch, dinner, father figure, preacher teacher, whatever you want it to be, so it’s definitely one of the best artsy places in Chicago.

Garrett has lots of flavors, but the only one you need to know about is the Garrett Mix. You are not permitted to try 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 EAT IT! You will thank me later, I promise.

best artsy places in chicago
5) Sweet Mandy B’s

You might be wondering why you are staring at a brownie because brownies can be found anywhere in the United States. But did you know that the ‘umble brownie was invented right here in the Windy City? That’s why we’re stopping at Sweet Mandy B’s to pick up some of this chocolate-y goodness.

The brownie was invented for the Columbia Exposition (sort of like a World’s Fair) at the famous Palmer House Hotel in Chicago. (This hotel is also famous for being the spot where Dr. Richard Kimble confronted the man responsible for his wife’s murder in the Harrison Ford classic The Fugitive.) But I’d much rather encounter a brownie than a corrupt pharmaceutical company that killed my wife any day.

best artsy places in chicago

Best Artsy Places in Chicago

Late Afternoon: 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. No list of the best artsy places in Chicago is complete without it.

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.

best artsy places in chicago

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.

best artsy places in chicago

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…

APPROXIMATELY TOP 5: THE ART INSTITUTE OF CHICAGO

best artsy places in Chicago
1) AMERICAN GOTHIC BY GRANT WOOD

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
2) SUNDAY IN THE PARK WITH GEORGE BY GEORGES SEURAT

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
3 NIGHTHAWKS BY EDWARD HOPPER

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
4) THE AMERICA WINDOWS BY MARC CHAGALL

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.

best artsy places in chicago
5) Paris Street; Rainy Day by Caillebotte

Every time I visit a museum, I try to find at least one work that I love that’s not quite so famous. At the Art Institute of Chicago, that’s this painting of a rainy day in Paris. It just sucks me right into the painting! I feel as if I’m right there, in Paris with all those stylish Parisians, doing stylish Parisian things.

This isn’t a full on Impressionist painting like a Monet, but there is something impressionistic about the way Caillebotte plays with the light on the cobblestones that gives the painting a dreamy, romantic quality. Dude really nailed the vibes of Paris in the rain, is what I am saying.

best artsy places in chicago

Best Artsy Places in Chicago

Evening: Dinner at Elizabeth

We’ve hit up the classic Chicago street foods today for lunch, so this evening, I’m taking you to one of my favorite fine dining restaurants in Chicago, called Elizabeth. It’s a little out of the way, but I took the L train here for dinner and then an Uber back to my hotel at night, no problem.

Elizabeth is a tasting menu restaurant, which means that you let the chef serve whatever is on the menu and just revel in all the deliciousness. It also means that whatever I ate is sure to NOT be on the menu. But I can give you an idea of what to expect.

best artsy places in chicago

Elizabeth is a fine dining restaurant, but it’s also interactive and tons of fun. I could tell from the very first course, which was Jupiter grapes served with a sour dipping sauce made with fermented raspberry and agave. Got to love a fancy restaurant that kicks things off with finger food!

best artsy places in chicago

Next, we have fluke with elderflower, thai lime, and melon. I was dining out a ton around the time I ate at Elizabeth, and a lot of restaurants were serving melon and elderflower. If it’s in season, it should be on the table, right?

You might be wondering why I included Elizabeth on a list of the best artsy places in Chicago, but this plate is clearly a work of art.

best artsy places in chicago

We’ve got another seafood course coming with kimchi-marinated mussels and squash. The mussels and squash are so light and delicate, which made a delightful contrast with the heat from the kimchi. Also, I’m pretty sure this dish has negative calories, which is always nice to find when you’re dining out.

best artsy places in chicago

Next is one of my favorite types of dishes: mushrooms that are almost meat. This maitake mushroom is served with spruce, cherry, and black garlic. I had never had spruce powder before, but the woodsy flavor is perfect with a mushroom! In fact, I was tempted to ask the waiter if they had actually spilled cocaine on my food, but then I thought better of it.

best artsy places in chicago

Carnivores are super lucky tonight because we get not one, but two meat courses! This is Elizabeth’s glamorous version of steak and potatoes: wagyu beef, potato, and their own housemade “A1” sauce. Isn’t it great when a restaurant takes comfort food like this and makes it just that much more delicious. This is what my grandmother would have made if she hadn’t been such a terrible cook that she could spoil rice.

best artsy places in chicago

And for our final meat course: duck with apricot, mustard, and cashew. I literally would never have thought to put those four ingredients together, but the fact that each ingredient had a different predominant flavor made the dish so much more interesting.

best artsy prices in chicago

This dish was probably my favorite because it was such a creative transition between the savory and sweet courses. We have a mushroom tea served with chocolate cake that has been topped with truffles. (The truffles are a few extra dollars, but just go ahead and add them on when you go to Elizabeth. You’ll thank me later.)

best artsy places in chicago

Our first real dessert is here, and it’s got another ingredient I’ve never heard of! This treat takes full advantage of ripe summer peaches, and then adds tarragon and something called trillium. I had to google trillium and apparently it is a cheese. That makes total sense! So this dish is like the grooviest possible version of a fruit and cheese plate.

best artsy places in chicago

A lot of tasting menu restaurants serve a fruit dessert and then a chocolate dessert, but Elizabeth is a special snowflake, so instead we are getting two fruit desserts. But this dessert was made with fig, honey, coconut, and tonka beans, so it was a richer, sweeter treat than the Trillium we feasted on earlier. (My plan is just to work Trillium into conversation as much as I can, now that I know what it is. Just to show off my knowledge.)

best artsy places in chicago

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.

best artsy places in chicago

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

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 with the best artsy places 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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