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1 Perfect One Day in Chicago


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Greetings Internet Stranger and welcome to one day in Chicago. I’m a native New Yorker, and people from New York City are supposed to look down their noses at Chicago. “It’s our country cousin!” we might say as we clutch a bagel in one hand and a slice of thin crust pizza in another. “Maybe it’s impressive if you’re in flyover country, but there’s no reason to go there on purpose!” Well, this New Yorker doesn’t agree with those lies! You can have tons of fun with one day in Chicago.

Chicago has amazing food, fabulous comedy, a fascinating and violent history, and outstanding architecture. Join me for One Day in Chicago, and I’ll show you Lincoln Park Zoo and one of Barack Obama’s favorite restaurants. I’ll even admit to liking deep dish! (I just won’t call it pizza. I have to have a little New York pride, after all.)

one day in chicago

One Day 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 for your one day in Chicago.

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.

one day in chicago

One Day in Chicago

What to Pack?

  • A cell charger so you can take photos all during your one day in Chicago
  • An umbrella that is tough enough to last the entire one day 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 a one-armed man during your one day in Chicago
One Day in Chicago

One Day in Chicago

Morning: Secret Food Tours Chicago

I always believe that going on a walking tour of a city is the best way to get acquainted with an unfamiliar environment. Getting off the beaten track is fun, but wandering around helplessly and doing nothing of interest all day when you’ve already sunk so much money into airfare and your hotel room is no fun at all. And walking tours are even better when they’re food tours. You get breakfast, lunch, fun facts, and exercise all rolled into one!

But Chicago is such a foodie town that it’s an actual crime to not go on a food tour when you’re spending one day in Chicago. I believe that there are currently a cool grillion food tours operating in the Windy City, but one of the best has to be Secret Food Tours.

I’ve used this company all around the world, and I’ve always been satisfied with their combination of history and snacks, as well as their local knowledge. You can book this tour easily yourself by clicking here.

I promise if you take this tour, you’ll get more than…

approximately top 5: One day in Chicago food tour edition

one day in chicago
1) Deep Dish

Of course the first thing most people think of when they hear Chicago food is the legendary Deep Dish. The Secret Food Tours Chicago begins at Gino’s Pizzeria so we can take a Deep Dive into Deep Dish. The first restaurant to serve Deep Dish was Pizzeria Uno. Of course, this is now a massive chain and not at all the best place to get Deep Dish in Chicago.

Our guide, whom I shall call Carrie, explained that Deep Dish is made with a rich butter crust. The cheese needs to be on the bottom near the crust when you are cooking Deep Dish, otherwise the crust won’t cook properly. I have to admit, though I do prefer New York style pizza, I like the butter crust on Deep Dish better. It’s so rich and satisfying! I would never throw it away like I sometimes do with my pizza crusts back home.

Here is one more Deep Dish fact I just made up. Eating Deep Dish pizza is actually the only crime in New York State that can get you the death penalty.

one day in chicago
2) Italian Beef

Italian beef is the name for the sandwich in my photo above that looks like a pair of weird meat eyes is staring at you. Not surprisingly, it was the creation of Italian immigrants to Chicago. It’s traditionally meant to be served at weddings, but now it’s an every day food. In fact, I think most brides today would be shocked and annoyed if you demanded that they serve chopped meat sandwiches to their guests on their Special Day.

Carrie told us that there are three main ways to serve Italian beef. You can have it dry, which means without gravy. You can have it wet, which means that the bread is dipped in gravy. Or you can have it soaked, which I guess means that someone comes out and dumps a whole bucket of gravy on top of your head while you’re eating it. That’s the Chicago way!

one day in chicago
3) Chicago Hot Dog

I’ve already admitted that I like New York style pizza better than Deep Dish. But here’s a shocking admission for you: I like Chicago hot dogs better than New York hot dogs. I like my hot dog with a lot of veggie toppings. At home, I always get mine with ketchup, sauerkraut, and relish, a combination literally no other person in the world approves of.

But in Chicago they do me one better by topping their hot dogs with 7 different things. You need mustard, onions, relish, a pickled chili pepper, dill pickled cucumber, a fresh tomato slice (NO KETCHUP!), and some celery salt. Is it a hot dog or a salad? No man can say.

Carrie said that the Chicago hot dog was just the result of many different ethnic communities living in close quarters. They each put different things on their hot dogs. Eventually, they started trying each other’s toppings and ended up creating the Chicago-style madness we see today.

root beer
4) root beer at berghoff

You may have heard that Chicago used to have a slight gangster problem back in the day. Of course this was during Prohibition, when bootleggers like Mr. Alphonse Capone made their money selling hooch. And if you’ve got some moonshine to sell, you’re going to need speakeasies at which to sell them. Most places in Chicago did a good business selling bathtub gin when the cops weren’t looking. But not The Berghoff!

one day in chicago

This beauty was founded back in 1898 by a German immigrant. Of course, at the time they served beer. But when alcohol became illegal, The Berghoff decided to be “good” and follow the “rules”. So instead, they started making their own near beer and sodas. You can still taste some of their historic root beer there today!

I think this story is proof that crime doesn’t pay because The Berghoff is still alive and in business, whereas Al Capone is extremely dead. Or maybe the moral of this story is that restaurants live longer than people. I can’t decide!

one day in chicago
5) Garrett Popcorn

I don’t want to be guilty of hyperbole, but Garrett Popcorn is the single greatest thing ever created by humans. I’ve been known to eat nothing but Garrett Popcorn for dinner and be entirely satisfied with my life choices. The pro move here is to get The Garrett Mix, which is cheese popcorn mixed with caramel popcorn.

It’s so good, I believe that if Al Capone had tasted Garrett Popcorn, he never would have turned to a life of crime. There’s even Garrett Popcorn stores in Japan, and if there’s one thing the Japanese know, it’s good popcorn, as my grandmother always used to say. But really nothing beats eating Garrett Popcorn in its hometown, Chicago.

one day in chicago
6) Brownie

No one day in Chicago can be complete without at least two desserts, right? For our last stop of the tour, we went to the restaurant Terzo Piano at the 3rd floor of the prestigious Art Institute. The dessert here was the sweet and salty brownie, with salted caramel ice cream and pieces of pretzel. Sweet and salty is just one of the most satisfying taste combinations there is in this world, isn’t it? Between this brownie and the Garrett Popcorn, I was in flavor contrast heaven.

Carrie told us that the brownie was actually invented in Chicago for the World’s Fair. It was created by the kitchen at the Palmer House Hotel in Chicago, which is still in operation today. My main association with the Chicago World’s Fair is from the novel The Devil in the White City.

It’s all about how America’s first famous serial killer, HH Holmes, went on a rampage in Chicago murdering a whole bunch of ladies, and no one noticed, probably because they were too busy getting ready for the World’s Fair. So it’s nice to know that something delicious came out of the World’s Fair, not just murder.

one day in chicago

One Day in Chicago

Afternoon: Lincoln Park Zoo

Lincoln Park Zoo is the perfect place to spend an afternoon during your one day in Chicago when the weather is nice. (My understanding is that that this happens at least twice a year.) Chicago can be quite a pricey city, so my gentle readers will be happy to hear that the Lincoln Park Zoo is completely without charge. (We’re going to need all that money you saved for dinner tonight, so just keep it in your pocket, Internet Stranger!)

I spent many happy days as a kid at the Bronx Zoo back home learning about animals and their ways, so I always try to seek out high quality zoos when I travel. At each one, I always learn more than…

three fun facts: lincoln park zoo

one day in chicago
1) What kind of Camels do they have?

The type of camels that they house at the Lincoln Park Zoo are Bactrian camels. These come from Asia. One of the ways you can recognize them is because they have two humps instead of one. (The camels I’m more familiar with from my time in Morocco have one humps.

The Bactrian camels at the Lincoln Park Zoo are named Nasan and Scooter, but the camel I really want to introduce you to is their baby. His name is Alexander Camelton, and he was born in 2016. He now lives in Boston, like the patriotic camel that he is. Part of a zoo’s job is to help breed endangered species like the Bactrian camel. And Alexander Camelton is not throwing away his shot! He wants to be in the room where it happens!

one day in chicago
2) Are There More Endangered Species?

Another endangered species with a home at the Lincoln Park Zoo is the Grevy’s Zebra. They come from Eastern Africa. These creatures have become endangered because of human activity, like hunting and destruction of their habitat. The most recent Grevy’s Zebra at the Lincoln Park Zoo was born in 2016, just like Alexander Camelton.

I don’t think it has as cute a name though. What would we call a zebra we were naming after a famous American? I got it! Zebraham Lincoln! You’re welcome, WORLD!

one day in chicago
3) What about this amazing gorilla?

I found the Western Lowland Gorillas to be the most impressive creatures at the Lincoln Park Zoo. Like the other animals I’ve introduced you to today, the Western Lowland Gorilla is critically endangered. One of the reasons is that there’s a mineral called coltan that is widely used in the manufacture of cell phones.

Unfortunately, the areas in the Democratic Republic of the Congo where coltan is mined are also where the gorilla habitats are located. So one small thing you can do for gorilla conservation is to recycle your cell phone.

My favorite memory from visiting the gorillas here was watching a boy, about six years old, approach the glass and stare at the gorilla, with eyes as wide as UFOs. His father (or possibly kidnapper? I didn’t ask) stood close behind him.

After about a minute, the boy ran away from the gorilla back to his father and screamed, “HE’S GOING TO KILL ME!” pointing at the gorilla. The father threw back his head and laughed. Smooth move, Dad! Now that kid’s going to be in therapy for years because you didn’t take his gorilla phobia seriously.

One Day in Chicago

Evening: Dinner at Alinea

If you consider yourself a foodie, and I hope you don’t because I hate that word, you’ve heard of Alinea. If you watch the Netflix show, Chef’s Table, you’ve seen the episode dedicated to the mastermind behind Alinea, Grant Achatz. How to describe Alinea? It’s like going to a performance of Sleep No More, if Sleep No More had three Michelin stars and were in Chicago.

You don’t get to make any choices; you just sit down and eat what the chef serves you. The waiter might set your table on fire! Sometimes you eat balloons! The menu is a crossword puzzle! Up is Down! Day is Night! If that description doesn’t intrigue you, you’re reading the wrong blog, Internet Stranger! There was no way I was spending a Chicago in a Day tour without stopping at Alinea.

approximately top 10: alinea edition

best things to do in Chicago Old Town
Course One

The first course was this little spear made out of avocado and coriander. It was delicately balanced on a lime when I arrived at my seat. I waited for a bit, but nobody came by to explain the dish, so I ate it. Then a waiter appeared out of thin air to tell me about what I had just eaten and pour me some champagne.

I feel like this was a test to see if I was adventurous enough to eat a dish with no explanation and I passed. Or it was a test of my patience, and I failed. Maybe an even better meal would have been waiting for me if only I’d waited for the waiter to explain this lime spear to me.

best things to do in Chicago Old Town
Course Two

This next course on the menu was described as Crunch and Paper. (Remember, the menu I was given was a crossword puzzle, so each course was represented by a different, vaguely associated word.) This course was kind of like a deconstructed, Japanese-influenced bouillabaisse.

You have a piece of fried nori wrapped around a garlicky rouille in the background. Then up front, there is langoustine in bouillabaisse, except the langoustine has been turned into a kind of noodle. Two courses in, and already my mind has been blown two times.

best things to do in Chicago Old Town
Course Three

Now we get a Spanish vibe with a course labeled GARDEN. It’s a golden-orange soup served with heirloom tomatoes and sherry. Achatz is famous for his molecular gastronomy techniques, using ingredients like foam and air. The steam you can see in the background is actually orange scented air that wafted over the soup as I ate it. The whole thing really did temporarily transport me to some garden in Seville, and I have never even been to Seville.

best things to do in Chicago Old Town
Course Four

Now we’re off to a tropical island! This is black bass, shellfish and kuzu, which is a kind of starch like arrowroot. It is served with kaffir lime and tropical fruit. The fish tasted so fresh, I was almost convinced that I had caught it myself and was enjoying it with my invisible lover on this nonexistent tropical island.

However, I didn’t understand the purpose of the fire that the waiter started in the background except that it made me feel I was participating in some insane ritual. But all would become clear in a short amount of time.

best things to do in Chicago Old Town
Course Five

I don’t normally suggest eating glass, but that’s how this course was listed on the menu. I think the “glass” is actually made out of blueberries using one of those molecular gastronomic processes that only Achatz and a couple of Spanish chefs understand.

But rest assured I didn’t cut my mouth when I was eating this, even if it does look like there’s blood on the plate. The blueberry glass covered some exquisite maitake mushrooms, which are also sometimes known as hen of the woods. It’s clever to have a meatless dish look so bloody (and taste so delicious).

best things to do in Chicago Old Town
Course Six

Now I finally got to learn why the waiter set my table on fire! Hiding in the bowl was a potato that had been submerged in salt. At this point in the meal, the potato was cooked, and the waiter came out to create what I can only describe as the greatest mashed potato the world has ever known.

(He also took my picture with the ingredients, which was very kind. The service at Alinea is the opposite of pretentious. I know this because I showed up in an inexpensive dress (not out of disrespect, but because I don’t own any expensive clothes) and kind of dripping wet because I got caught in a tiny Chicago rainstorm, but they still treated me like a princess.

best things to do in Chicago Old Town

So here’s everything you need to make the world’s greatest mashed potato. We have a potato you’ve set on fire at the dinner table. You also need two giant bowls of cream and butter, a whole bunch of black truffles, and for some reason I cannot figure out, pumpernickel. There! Now it will be easy for you to replicate this experience at home.

best things to do in Chicago Old Town
Course Seven

And now for a little snack in between the main courses (and a finger bowl for your digits, you classy Internet Stranger). This black blob is a bocadillo made with jamon and manchego. I enjoy that it is savory but it looks kind of like an artisanal Oreo cookie. Things that are not what they seem is kind of a theme of this evening.

best things to do in Chicago Old Town
Course Eight

Finally the meat course! Of course, it looks nothing like any meat course I have ever seen. It looks more like a modern art painting. But here we have an impossibly tender veal cheek served with pineapple and hearts of palm.

The surprising part of that dish is the bean in the jar in the background. It looks like a vanilla bean, but it’s actually made with tenderloin that’s been infused with vanilla. It’s rather a shocking experience to bite into something you expect to taste like one thing and have it be another. Almost as shocking as having your waiter set your table on fire.

best things to do in Chicago Old Town
Course Nine

Our first dessert course was called Rock on the menu, which didn’t sound appetizing. But it is when the rock is actually made out of chocolate! The crunchy shell gave way very satisfyingly to a soft, sweet interior. I think the purple comes from a Japanese sweet potato, but I’m not 100 percent sure.

I’ve seen purple sweet potatoes used in Japanese desserts before. What I’ve never seen before is a delicious dessert that also looks like a rock garden, so my hat’s off to you once more, Alinea!

best things to do in Chicago Old Town
Course Ten

Our final course of the meal is called Nostalgia. The flavors here are birthday cake and bubblegum. I usually hate the taste of birthday cake. It’s just sad, plain white cake! Who wants it? But biting into this actually did make me feel like a child, only a happy child, instead of an oddball who used to lock herself into a pillow-lined box so she could read for hours without anyone bothering her. Alinea! It’s not just a restaurant, it’s also therapy!

best things to do in Chicago Old Town
Course Eleven

One of Alinea’s specialties is its flavored balloons. Mine came in grape, and you have to eat it by biting it and just sucking the whole thing into your mouth. It actually tasted like real grape, not like Artificial Purple No. 2. Unbeknownst to me, the balloon was really filled with helium, so when the waiter came by to ask me how I liked the meal, I answered him back sounding exactly like Minnie Mouse. It was the perfectly bizarre ending to one of the weirdest and best meals of my life.

one day in chicago

One Day in Chicago

How To Get There

Now, I wish I knew where you lived, Internet Stranger, because I could send you a reservation to Chez Qui. But sadly, I do not, and so I can’t tell you exactly how to get from your home to your one day in Chicago.

However, if you need to take a plane or car to get to Chicago, I recommend Expedia for the best way to find the cheapest flight or car rental, depending on how you want to get around. Just click here to start looking for the best possible deals on your flight or car rental, so you can head out to your one day in Chicago.

That’s a Perfect One Day in Chicago!

What would you do with one day in Chicago? Are you ready to start booking your hotel in Chicago right now? What are some other Politician-Zoo Animal names we could come up with? (Ben-chimapanzee Franklin? John Elephant Adams?) And is Deep Dish a type of pizza or is it a concoction sent by extra-terrestrials to start a war between New York City and Chicago? 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 One Day in Chicago.

If you have another One Day in Chicago, add this itinerary with the Field Museum. If you want a One Day in Chicago itinerary with the Art Institute, click here. Finally if you want a one day in Chicago itinerary with the Chicago History Museum, click here!

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