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A Perfect 24 Hours in Chicago

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Greetings Internet Stranger and welcome to 24 hours in Chicago! So you want to know what to do with 24 Hours in Chicago? If you’re anything like me, you’ve been dreaming of going to Chicago since you were a little girl for one reason and one reason only: gangsters.

As far back as I can remember I’ve always wanted to be a gangster expert. My favorite movies as a little girl including The Godfather, Goodfellas, and The Untouchables. When the Chicago mass transit system told me I needed to give my subway pass a nickname, I nicknamed it Scarface. Plus, I would never take sides against the family.

24 hours in chicago

Yet Chicago is about so much more than organized crime. A perfect 24 Hours in Chicago starts with a legendary architect, continues with a legendary creature, and finishes with blues by a Legend. The question isn’t what are we going to do, the question is what aren’t we going to do.

24 hours in Chicago

24 Hours 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 24 hours 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.

most quirky chicago things to do

24 Hours in Chicago

What to Pack?

  • A cell charger so you can take photos all during your 24 hours 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 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 24 hours in Chicago.
24 hours in Chicago

24 Hours in Chicago

Morning: The Robie House

The Robie House is one of the most famous and beautiful buildings in all Chicago. (And I think Chicago has the best architecture in the country, so that’s really saying something. This home was built for the wealthy Robie family by the world-renowned architect Frank Lloyd Wright, but they eventually lost possession of the home. Now it’s available for one and all to come explore!

The only way to see the Robie House is on a guided tour, and you need to book your tickets in advance because they sell out fast. Go ahead and do that here. Then get ready for…

Three Fun Facts: The Robie House

24 hours in Chicago
1) What Makes the House Special?

Aside from the fact that Frank Lloyd Wright designed it? It’s an excellent example of his architectural philosophy. He used a combination of small spaces and large spaces to play with the light and give the people in the home a sense of freedom when they passed from one of the small entranceways into the large living room.

I think the Robie House should lean into this by having the speakers blast Freedom by George Michael when you enter the living room.

24 hours in chicago

The Robie House isn’t furnished now, so you can’t really see what it would have been like for the Robie family when they lived there. But you can see the original Frank Lloyd Wright fireplaces, which remain stunning. It must have been so cool to entertain guests around this awesome geometric fireplace, having everyone admire your original FLW.

You know that the Robies were big at keeping up with the Joneses because, most unusually for the time period, they had a garage full of cars. In fact, one of the reasons Frank Lloyd took the job is that he was eager to design a garage that fit in seamlessly with the rest of the house.

24 hours in Chicago
2) So How Long Did the Robies Enjoy the Robie House?

Sadly, it wasn’t that long. The Robies got divorced not too long after they moved in, and then the family didn’t need this house anymore. In fact, there wasn’t a market for such a famous, expensive house, so the house has only been occupied for about 16 years of its existence. It’s had a much longer and more popular life as a Frank Lloyd Wright Museum.

Our docent kept saying that there was no hex on the house, but you know what? I didn’t believe him. The fastest way to get someone to believe that there’s no hex on a house is to repeatedly tell them that there is NO HEX on the house.

24 hours in chicago
3) What’s the Coolest Looking Thing in the House?

I’d have to say that it’s the windows. You can see one of Frank Lloyd Wright’s signature design patterns made of colored glass and set in the windows. There are similar patterns on the rugs as well; I liked them so much that I bought a pair of earrings in the same shape at the Robie House’s excellent gift shop.

Another interesting feature of the house is the large number of light fixtures. Our docent explained that this was because the house was built over 100 years ago, and back then light fixtures weren’t as strong. Just another reason I am so glad to be alive today and not a century ago!

Well, that’s three fun facts, but you’ll learn a lot more if you just go here and take the tour for yourself. I promise that my photos don’t do the beauty of the house justice.

24 hours in chicago

24 Hours in Chicago

Afternoon: Field Museum

The Field Museum is the best natural history museum I have ever been to, and I say this as someone who went to the American Museum of Natural History in NYC about two times a year as a child. Whether you are a child who loves dinosaurs, an actual dinosaur, or just a dinosaur at heart, there will be something for you here.

It’s pretty easy to get to from Hyde Park and the Robie House, just hop on a Chicago city bus and you are there! Then dive straight in to…

Approximately Top 5: Field Museum

24 hours in chicago
1) Lunch Time!

We won’t have time on this itinerary for a massive lunch, but fortunately there’s a great Chicago hot dog stand right outside the Field Museum called Kim and Carlos. It’s popular, so if the weather is nice there will be a line, but it’s worth it to get to experience their amazing and authentic Chicago hot dogs.

A Chicago hot dog comes with yellow mustard, white onions, pickle relish, tomato slices, a sport pepper, celery salt, and a dill pickle. (Yes, you need all seven things. It’s sometimes called being dragged through the garden.) Kim and Carlos will literally make you dance if you ask for ketchup, so don’t do it! The hot dog doesn’t need any.

24 hours in chicago
2) Dinosaurs

Basically every exhibit is worth exploring, but you should start your 24 hours in Chicago with the Field Museum’s specialty, the dinosaurs. There are dinosaurs in the lobby, dinosaurs hanging from the ceiling, and dinosaurs in their very own special exhibit.

24 hours in chicago

The Field Museum’s T-Rex is one of the largest T-Rexes ever found, which is about as large as a thing can be. She’s so impressive that she has her own name (Sue) and her own Wikipedia entry here. I’d like to point out that I still don’t have my own Wikipedia-entry, faithful readers!

24 hours in chicago
3) Animals

Don’t worry! It looks like that mean bird is going to steal the baby birds away and eat them, but in fact all these birds are already dead. Like many natural history museums, the Field Museum has a staggering collection of stuffed animals. You can see birds…

24 hours in chicago

Just a whole bunch of dead and taxidermized puffins.

24 hours in chicago

Still vaguely pink flamingos…

24 hours in chicago

Creatures of the snow…and more! Seriously, if stuffed animals of any kind are your jam, the Field Museum is the place for you!

24 hours in Chicago
4) Africa Exhibition

Like many natural history museums, the Field Museum also contains exhibits on human cultures, and their most impressive exhibit on humankind is their Africa exhibition. Here you can learn about African communities ranging from the French-speaking population of Senegal to the nomadic peoples of Morocco known as the Touareg.

24 hours in chicago

You’ll also learn about how the European colonial powers carved up Africa in many nonsensical ways, obliterating the pre-existing communities and taking away their leaders. It’s amazing to see how many African arts and traditions survived this period of violence and upheaval.

For example, we learned about how the Oba was considered to be a divine king by the Edo people, and in fact there is still an Oba ruling in Nigeria today. However, the current Oba doesn’t have the same kind of power that the Oba did before colonists arrived.

24 hours in chicago
5) Gemstones

And here we have my favorite part of any natural history museum, the gems and minerals. No, it’s not quite as impressive as the legendary collection at the Natural History Museum in New York City, but it’s still quite nice to look at. They have an especially impressive selection of both pearls and emeralds.

24 hours in chicago

In fact, it was here that I learned that top-quality emeralds are rarer than diamonds. This pleased me, since emeralds are my birthstone.

24 hours in chicago
24 Hour Tip

If you’re going to see other things in Chicago, I really recommend the Chicago City Pass. It will save you money if you’re going to check out other major attractions like the Shedd or the Art Institute. But if all you’re seeing is the Field Museum, it isn’t worth the money. You can buy the City Pass by clicking here.

24 hours in chicago

24 Hours in Chicago

Evening: Dinner at Boka

Chicago is one of the top 5 fine dining cities in the United States, and you can spend your entire time here feasting on Michelin-starred restaurants, which is basically what I did. I recommend Boka because the food is amazing, it’s near a lot of theaters, so you can have dinner before a show, and it’s open on Mondays, which is not the case for a lot of nice restaurants in Chicago.

Boka has both a tasting menu and an a la carte menu, but I always go for the tasting menu because you get to try more amazing dishes. What’s not to love?

24 hours in chicago

Up first is a kind of sashimi salad with kampachi sashimi, green apple, green strawberry, and kohlrabi.
One thing I really liked about the look of this dish is that the green strawberries sort of look as much like fish as the kampachi does.

This was a refreshing dish, and I loved the contrasting flavors. Kampachi is one of my favorite sashimi fishes because it doesn’t taste “fishy”, so you can do a lot of things with it.

24 hours in chicago

For our next appetizer, we have heirloom tomatoes in a tomato consommé. This tastes like the first moments of being released into school for summer vacation. Sometimes it’s better to have a dish with just one pure flavor, instead of a whole bunch of different flavors, when that one flavor is this pure and intense.

24 hours in chicago

Easing into our main courses, we start with the fish course. This was arctic char with yellow beans and nori sabayon. Arctic char is my favorite cooked fish because it’s so rich and decadent, almost like eating a steak, but healthier. The nori sabayon just added even more creamy sinfulness. I was glad for the yellow beans to add some texture because we needed a little snap and crackle with the soft fish and sauce.

24 hours in chicago

It’s not enough for Boka to give me my favorite fish, they also gave me my favorite option for a poultry course: duck! This was served with plum jam, which is appropriate because duck is often served with a sweet sauce. But I appreciated the celery puree on the side for a little surprise and contrast.

24 hours in chicago

And here we have one of the earthiest dishes imaginable: lamb with chanterelle mushrooms and eggplant. I felt myself turning into a goblin as I ate this dish, literally sinking deep underground with hobbits and Smeagol and my hordes of gold and enchanted swords and things.

24 hours in chicago

Any proper tasting menu has two desserts: one light and fruity, and one more rich and chocolatey. (There are a few exceptions, such as some restaurants do cheese courses instead of one dessert, but mostly these are the rules.)

At Boka, we had a yuzu pudding for our first dessert, which was light and refreshing. I also liked that the pudding included freeze-dried mandarin, so we got to try more than one type of citrus and more than one type of texture.

24 hours in chicago

And here we have the grand finale: chocolate with sesame and puffed wheat. I think of chocolate and peanut butter as being the classic combo, but I’ve noticed more restaurants experimenting with ingredients like sesame replacing the peanut butter, and I approve of this experimentation.

24 hours in chicago

24 Hours in Chicago

Late Evening: Buddy Guy’s Legends

Spending 24 hours in Chicago without hearing a blues performance is like going to New Orleans and not listening to jazz or visiting Nashville and screaming, “LA LA I CAN’T HEAR YOU!” any time you hear a country song. It’s just sick and wrong.

Buddy Guy’s bills itself as the greatest blues club in the country, and it just might be true. That’s because the joint is run by blues legend Buddy Guy himself. He plays the club regularly every January, but he shows up and plays on other nights randomly when he feels like it. If you get lucky, maybe he will show up and play for you!

Buddy Guy was ranked 30th in Rolling Stone’s list of greatest guitarists of all time. Eric Clapton once called him the greatest living guitar player. I’m not sure which of those is a bigger compliment, but I’m going to go with Clapton’s remark. You should buy your ticket in advance online.

24 hours in Chicago
24 Hour Tip

 Please go to the bathroom when you are at Buddy Guy’s because it is beautifully appointed and there is a friendly attendant who will ply you with hand lotions and whatnot. Be sure to bring a dollar and tip her! If you don’t have cash, Venmo her. I’m really serious! She deserves everything she gets.

24 hours in chicago

I can’t predict who’ll be playing when you go to Buddy Guy’s, but I was there to see a terrific singer named Sheryl Youngblood. She had that kind of spontaneity in her style that makes the blues so exciting, as if she were singing straight from the heart. But the most exciting part of the evening was when Buddy Guy himself stepped out to join her!

Sadly he did not have his guitar with him, but he sang for us some old blues songs and some songs that he improvised on the spot that were definitely not safe for work because they were mostly about sex and drugs. The evening was a complete thrill for me because how often do you get to see a living legend perform? (And I only paid ten dollars for my ticket!)

When you are ready to go home, just step outside because there will be plenty of cabs waiting to take you to your hotel. The perfect end to a perfect 24 hours in Chicago!

24 hours in Chicago

24 Hours in Chicago

How to Get There?

By Car: This is an easy way to get to your 24 hours in Chicago 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.

24 hours in Chicago

By Plane: You can absolutely fly into Chicago if you are coming from far away for your 24 hours in Chicago. 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.

24 hours in Chicago

That’s a Perfect 24 Hours in Chicago!

What would you do with 24 hours in Chicago? Have you ever seen a blues legend perform live? And would you be willing to dance for ketchup? Please email me at [email protected]dtheworldin24hours.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 spend 24 hours in Chicago.

If you’d like to visit the Chicago History Museum, add this itinerary. If you want to try 24 hours in Chicago with the Art Institute, try this one. And if you’d like to spend 24 hours in Chicago at the Lincoln Park Zoo, here you go.

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Bob Lambert

Tuesday 6th of August 2019

Not bad. I live near Chicago and go all the time. I was surprised you did not take one of the many Gangster tours available. Where the Field museum is is close to the old Leeve area of Chicago where all the Brothels were. The history is amazing. I am glad you had a good time in Chicago. I hope you try it again. This was my first story from you, but it won't be my last. Amazing Adventures!.

Stella Jane

Tuesday 6th of August 2019

Thanks for commenting! Remember, this is only one Chicago itinerary. It's not possible to do everything in Chicago on one day! That's why I recommend combining several itineraries in one trip.