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Greetings Internet Stranger! 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. When the Chicago mass transit system told me I needed to give my subway pass a nickname, I nicknamed it Scarface.

Yet Chicago is about so much more than organized crime. A perfect 24 Hours in Chicago starts with some natural history, continues with Great Lakes and exploding tapioca, and finishes with blues by a Legend.

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. 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.

24 Hours in Chicago

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 in Chicago, 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.

24 Hours in Chicago

Morning: 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. Basically every exhibit is worth exploring, but you should start your 24 hours in Chicago with the Field Museum’s specialty, the dinosaurs.

Field Museum Chicago Mammoth

The Field Museum’s T-Rex is the largest T-Rex ever found. 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!

Field Museum Chicago dinosaur
24 Hour Tip

Because the museum is expensive, it’s only worth a visit if you spend a large part of the day there. I recommend arriving around nine and staying until at least 2. Having said that, you’re going to want to get lunch at the museum. The Field Bistro is a perfectly adequate place to get a soup/half sandwich combo before jumping back into the museum. If that sounds like I am damning with faint praise, I kind of am. But you’re not at the Field Museum for the food. You’re there for the dinosaur bones.

Field Museum Chicago Pterodactyl
24 Hour Treasure

Ordinarily, I do not recommend that a first time visitor to a museum see the special exhibitions unless the museum is really small. But I make an exception for the Field Museum because their special exhibitions are truly specialriffic.

The two exhibitions I saw (one on Vikings, the other on Vodou) completely changed my perception on the two subjects. Did you know that the Vikings were mostly peaceful farmers? Did you know that if you can read French, you can read Haitian Creole even though the spelling is totally different? These are just two of the fun facts I learned at the exhibits. But that is truly the best thing about the exhibits at the Field Museum; they spark that kind of child-like wonder that makes you want to learn all of the fun facts that you can.

If you want to see one special exhibit, the museum ticket costs 31 dollars. If you want to see all the special exhibitions and a 3D movie, it will set you back 38 Dollars. So think very carefully about what the special exhibition is and if it will change your life, like it did mine. If it won’t, the price might not be worth it.

24 Hours in Chicago

Afternoon: Explore!

Provided it is not too cold (and that is not always provided) Chicago is a wonderful city for walking. It has decades worth of wonderful architecture, but more importantly it is on a Great Lake. There are a million things to see and do during your 24 hours in Chicago, but here are…

Approximately top 5: 24 Hours in Chicago

Water Taxi lake michigan
1) walk around lake michigan

When you step out of the Field Museum, that is Lake Michigan you are stepping out on to! You should definitely spend at least an hour walking along the wall-less Lake Michigan. The views of the Chicago skyline are just dazzling.

Chicago Skyline
2) explore the chicago skyline

If you get tired (doubtful) or if it gets windy (doubtless), head inland and do some exploring there. You will definitely encounter a melange of gorgeous skyscrapers.

South Loop of Chicago 24 hours in Chicago
3) walk to Paris

Just kidding! This is actually the entrance to the Van Buren subway Station. But I fooled you for a second, didn’t I?

If you get really bored, you can check out the Adler Planetarium or the Shedd Aquarium, which are right by the Field Museum, but I’m not sure I could do one of those and the Field Museum on the same day. My brain does not have an infinite capacity.

4) See Chinatown 

It’s pretty easy to get to Chinatown from the Field Museum. Just take the Red Line two stops to Cermac-Chinatown and presto! You are there. I of course walked because I am the original walking fool.

Chicago’s Chinatown is not that impressive next to the Chinatowns in New York, San Francisco, Los Angeles, Vancouver, Philadelphia, Montreal…basically any other Chinatown I’ve ever been to. But what it does have is some amazing boba tea.

5) drink boba tea

Boba tea, for those who don’t boba, is a delightful concoction from Taiwan consisting of some combination of tea + fruit + milk + tapioca balls (boba). The fruit and milk are optional, but the tea and boba are not, else how could it deserve the name boba tea?

I went to a delightful palace of boba called Joy Yee. They have every kind of tea and boba you could want. They even have a kind of slushy base for the tea called a freeze. I got a pineapple freeze with strawberry popping boba. These were boba that exploded in my mouth, but in a gentle way. I can’t wait to go back to Joy Yee and try another demented flavor of boba tea that I can’t get here in NYC.

24 Hours in Chicago

Evening: Buddy Guy’s Legends

Buddy Guy Legends

Going to 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!

Fun Fact!

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. The show will probably start at 9:30 but you can arrive at 8 and order dinner. I thought the food was good! Buddy Guy is from Louisiana, so the food is Southern-influenced. I enjoyed the BBQ chicken with homemade sauce and spicy fries. Buddy also makes his own beer called Buddy Brew, which is tasty and cheap! My two favorite words in the English language!

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!

Buddy Guy Sheryl Youngblood

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.

Related Reading: 24 Hours in Chicago Way!

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 absolute favorite book about Chicago gangsters is Get Capone. You’ll be endlessly entertained while reading about the US Government’s efforts to stop Capone and his efforts to evade them. It’s nonfiction that reads like fiction.

And I know this is listening and not reading, but please listen to Buddy Guy’s wonderful album, Buddy’s Baddest. If you can’t hear him in person in Chicago, this is the next best thing.

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 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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