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Greetings Internet Stranger and welcome to a perfect Chicago itinerary! 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 if you’re not a fan of John Hughes’s greatest achievement, I promise this 24 Hour itinerary will hit all of Chicago’s main points. 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 Art Institute have to offer!

Chicago Itinerary

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 your Chicago itinerary.

So I recommend the Hampton Inn Chicago West Loop. It’s near many trendy restaurants like The Girl and the Goat, the staff is friendly and helpful. Plus breakfast is included! 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.

Chicago Itinerary

What to Pack?

If the weather is rainy or snowy, which happens quite often in Chicago, I recommend the Asgard Rain Boots. They are comfy/cozy and keep my feet dry all day. Plus they’re cute enough that I can wear them out without feeling like some gauche tourist with gross feet.

The other thing you need when it rains is an umbrella. I hope you don’t need me to tell you that, Internet Stranger! My favorite travel umbrella is the Repel Teflon Waterproof Umbrella. It is strong enough to stand up to the sometimes-quite-strong winds of Chicago. I hear they’re strong enough to beat up Al Capone with a baseball bat.

And if it gets chilly during your Chicago itinerary, which is likely every month that’s not called July or August, you’ll want a good coat. Here in NYC, the chic coat of the season is the Orolay Down Jacket. The camouflage color is the most popular, but I get oodles of compliments on this shiny wine color.

Chicago Itinerary

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.

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 famous works of art! So I present the…


Art Institute Chicago American Gothic

This painting is one of the most famous works in the Art Institute. People argue over whether or not Wood meant to satirize Middle Americans with this portrait. (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 me in my sleep with that pitchfork.

Art Institute Chicago 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 chic is similar to Wood’s attitude toward the rural and simple. IF ONLY I 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.

Art Institute Chicago Nighthawks 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. I have so many questions when I 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 my other questions still stand, though.

Art Institute Chicago Marc Chagall Windows

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, 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 I 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. 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!


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.

24 Hours: Chicago Itinerary

Afternoon: Chicago Architecture Tour

The Chicago Architecture Foundation gives several different tours, but the one I recommend is the First Lady river cruise. 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.

Chicago Architecture

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!


Chicago Architecture Tribune Tower

This 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.

Chicago Architecture 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 blogger is a Native New Yorker.)

Chicago Architecture 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.

Chicago Architecture 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.

Chicago Architecture Tour 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!” I like this building because the design elements look classical but it’s made with very modern materials. See, you get the joke too, right? Also I like shiny things.


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 I shouldn’t really have to specify that.

24 Hours: Chicago Itinerary

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. 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?

Chicago The Bean

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…

24 Hours: Chicago Itinerary

Evening: Pizanos Pizza

What would a Chicago itinerary be without a mention of deep dish pizza? A sad, lonely thing, that’s what. 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 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 no one’s going to harass you.

I 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!


Are you ready to start booking your hotel room in Chicago? Let me help you out with some further reading. I always use Lonely Planet’s guide to Chicago. They divide the book into chapters based on neighborhoods, which is very convenient.

My favorite nonfiction book about Chicago is The Devil in the White City. It’s about architect Daniel Burnham’s quest to create the perfect city for the World’s Fair, while at the same time serial killer JJ Holmes was operating his murder house in Chicago.

Tons of American classics have been set in Chicago. But perhaps none is so classic as Richard Wright’s tragedy, Native Son. This book makes The Devil in the White City look like Biscuit Goes to School, but you can’t be an educated American without reading it.

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.

Stella Jane
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