A Perfect Chicago in a Day

This post contains affiliate links. As an Amazon associate, I earn from qualifying purchases.

Greetings Internet Stranger and welcome to a Perfect Chicago in a Day. For any readers short on time, I’m happy to present the Cliffs Notes Version of the history of Chicago: Shikaakwa, Checagou, Lincoln-Douglas, Great Fire, World’s Fair, Al Capone, “Your fugitive’s name is Dr. Richard Kimball”, Da Bears!

But for those of you who are still confused, join me for a day of dining our way through Chicago’s Old Town, learning our way through the Chicago History Museum, and then jaw-dropping our way through the most award-winning restaurant in Chicago: Alinea. By the end of this Chicago in a day tour, you’ll be a true expert on the Chicago Way!

Chicago in a Day

Where to Stay?

Chicago is the third largest city in the United States, so there’s no shortage of places to stay here for your Chicago in a Day tour. 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.

Chicago in a Day

What to Pack?

A Perfect Chicago in a Day 2

You’ll need comfy shoes for all the walking we’re going to do. If it’s summertime, I love my special pink Birkenstocks. These aren’t your grandpappy’s Birkenstocks anymore. They come in every shade, and I always get compliments on my electric magenta shoes.

A Perfect Chicago in a Day 3

If the weather is rainy or snowy, which can happen 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.

A Perfect Chicago in a Day 4

Finally, since we’re going to be out all day, you’ll want a battery for your cell phone. I always use the Anker charger. It’s light enough to fit in even a small purse. Plus the Anker lasts for several full charges of a phone, so I’ll never run out of juice!

Chicago in a Day

Chicago in a Day

Morning: Second City Classic Food Tour

There are so many food tours in Chicago, it was hard for me to know where to start. But of course a city that’s synonymous with so many different styles of cuisine is going to be a popular destination for foodies. On my previous Chicago in a Day tour, I had spent the morning taking a food tour of the famous Loop neighborhood.

So this Chicago in a Day tour, I decided to take a tour of the more residential Gold Coast/Old Town part of Chicago. Fortunately, the Chicago Food Planet company had just what I was looking for with their Second City Classic Food Tour! A good time was had by all the guests on the tour with…

Approximately top 5: old town/gold coast food

lou malnatti's
1) Lou Malnatti’s

Our first stop on the food tour was for that Chicago classic, Deep Dish. As I’ve mentioned in my other posts on Chicago, even though I’m from New York City, I like Deep Dish. I just don’t call it pizza. We got our deep dish at Lou Malnati’s which is a family run restaurant. In fact the late Lou Malnati used to manage Pizzeria Uno, the restaurant where Deep Dish was first invented.

If you’re looking for a rich butter crust, topped with a thick schmear of melted cheese, sitting underneath the world’s largest mound of tomato sauce (and who among us is not?) Lou Malnati’s is definitely for you.

Our guide, whom I shall call Sela, said that Lou Malnati’s is a favorite restaurant of the Chicago Cubs baseball team. That’s all the recommendation I need because professional athletes are definitely the first people I look to for food reviews. (Do the Cubs ever get resentful that the football team gets to be The Bears and they have to be the baby bears? Couldn’t they have been the Grizzlies or something?)

2) Tea Gschwender

This food tour had an unusual number of food shop stops. I’ve definitely been on food tours that have a food shop stop, but this one had three. However, I liked the inclusion of these stores because there was no pressure to buy. Also we got samples at the food stores, so it added a little extra value to the tour.

The first food shop was TeaGschwender. We sampled some of their iced tea while they explained the proper way to brew loose leaf tea. Apparently you shouldn’t steep your tea for more than two minutes or bitterness will set it. Who knew? I’ve always been steeping mine for about half an hour because I like it when my tea is strong enough to slap me in the face.

the spice house
3) The Spice House

Up next was The Spice House, which has its own lovely back garden. We were able to sit here and watch a demonstration of how some of their spice blends are prepared. The Spice House is also a family run business. Its owners are Tom and Patty Erd. If you’re looking to be educated further, check out Tom Erd’s YouTube channel, called The Spice Boss. If you’ve ever wanted to hear a grown man with a Midwestern accent tell you about a salt that will “rip your face off”, this YouTube Channel is for you.

Old Town Oil
4) Old Town Oil

The final store on the tour was Old Town Oil. If there’s anything I’ve concluded in all my travels, it’s that every town in America with a decent amount of yuppie residents has a Fancy Oil and Vinegar Shop. I’ve been in Fancy Oil and Vinegar Shops everywhere from Cold Spring, New York to Palm Springs, California. I definitely don’t hate on the trend because Fancy Oil and Vinegar is delicious, and it’s the easiest way to make a simple worknight meal something I’m excited to eat.

At Oil Town Oil, we got all the bread we wanted and we were able to try the various flavor combinations the store recommends, like Lemon Olive Oil with Blueberry Balsamic Vinegar. But I prefer to try random, unappealing combinations and then yell, “Don’t tell me what to do, Fancy Oil and Vinegar Store!” Usually at that point someone calls security.

Old Jerusalem
5) Old Jerusalem

OK, now the shopping is over and the restauranting can begin! (The three stores weren’t actually presented back to back on the food tour. I just wanted to be thematic.) Our next snack was at another family-run business: Old Jerusalem. The owner’s name is Ahmed Ali Awad. He is from Lebanon originally, but he has lived and cooked in Chicago since the 1970s.

We each got a falafel on half a fresh pita bread. Everyone in my tour group commented on how fresh and flavorful the falafel and pita were. This was the favorite stop for most people on the tour.

the fudge pot
6) The Fudge Pot

I think my favorite spot on the tour, however, might have been The Fudge Pot. I am absolutely a registered chocoholic. Also I need to appreciate any store that can make so many different dogs out of chocolate and also have a chocolate cassette tape with the title Debbie Does Chocolate printed on it.

fudge pot

The Fudge Pot has been in operation since 1963. It’s another family-run business, and they make their decadent sweets in the store. Our tour sampled their chocolate covered butter toffee. I could basically hear my dentist crying in the background as I ate it, but it was worth every bite. They make each batch of butter toffee by hand, dip it in chocolate, and then cover the whole thing in almonds. I could easily have eaten a whole box of these, but it’s rich enough for me to be satisfied with one.

la fournette
7) La Fournette

The final stop on the tour was La Fournette. It’s also one final family-run business! La Fournette was founded by Frenchman Pierre Zimmerman and his wife Michele. They’ve won awards for their classic French bread and pastries. On this tour, we tried the croque monsieur and macarons. Croque Monsieurs are a sandwich made with ham, Gruyere cheese, and a rich bechamel cream sauce. You need a good quality bread to stand up to all that fat, and La Fournette’s definitely did the job.

Macarons are the tres trendy French almond sandwich cookie. You can now get them all over the world in different flavors like red velvet and unicorn. But I prefer the French classics like salted caramel and pistachio. Eating one always makes me feel like Audrey Hepburn studying in Paris in the movie Sabrina. So on this food tour we had gone from Italy to Germany to Lebanon to Spice Boss Town to France. Not bad for a few hours work!

Chicago History Museum

Chicago in a Day

Afternoon: Chicago History Museum

For far too many people, their knowledge of Chicago’s history stops and ends with gangsters and a cow starting a fire. Please rectify this situation immediately by heading with me to The Chicago History Museum. I suggest starting with the film The Great Chicago Adventure. We can’t spend a Chicago in a Day tour without stopping here.

It’s definitely kid friendly, but you’ll get a kick out of it even if you’re an “adult” like me. What to say about a history film for kids that quotes Ferris Bueller’s Day Off and references The Untouchables? That’s my kind of film, Chicago. Once the movie is over, you’ll be able to explore the Chicago History Museum at your leisure. I’m sure you’ll learn much more than…

three fun facts: chicago history museum edition

chicago history museum great fire
1) The Great Fire of 1871

One of my favorite parts of the Chicago History Museum is the dioramas dedicated to different periods of Chicago History. One of the most famous events was the Great Fire of 1871 that took down a massive portion of the Windy City. One third of the city was left without a home. (In fact, Chicago’s famous wind might have helped contribute to the spread of the fire.)

You might have heard that Mrs. O’Leary’s cow is responsible for the fire, but no one knows exactly how the fire got started. However it’s definitely true that the fire started near the O’Leary barn. I personally don’t think the cow was responsible. If Chick Fil-A ads have taught me anything, it’s that chickens were probably responsible and then blamed the cows so people would eat less chicken.

As tragic as the Great Fire was, some good came out of it. If it weren’t for the fact that basically the entire city needed to be rebuilt, we wouldn’t have the gorgeous Chicago skyline full of modern skyscrapers that we see today.

hugh hefner little black book
2) Little Black Book

The Chicago History Museum is home to many objects that hold an important place in Chicago’s history. (Although a lot of those objects are just Things That Got Real Melted in the Great Fire.) But what could be so fascinating about a little black book? Well, it’s not just any little black book. This book belonged to the founder of Playboy, Hugh Hefner.

Hefner was originally from Chicago, after all. In fact, the original Playboy Mansion is right near the Chicago History Museum in the Gold Coast neighborhood. (It has a doorbell outside that says, “If you don’t swing, don’t ring,” in Latin. That’s not even one of my ridiculous jokes.)

gangster comics
3) Gang Wars

“Blah, blah, blah,” I can hear some of you Internet Strangers out there saying. “Nobody cares about fires and nudie mags. We just want to hear about Al Capone.” Ask and ye shall receive! One of the exhibits at the Chicago History Museum shows a map of the North Side of Chicago during Capone’s heyday. You can see how many gangs there were in Chicago at the time, their territory boundaries, and how the various gangs used to come into conflict. One of Capone’s big rivals was an Irish mobster named Dean O’Banion who had a day job…as a florist.

I was also interested in the Chicago History Museum’s collection of gangster-themed comic books. It’s hard to understand that during Prohibition, a gangster like Al Capone would have been a national celebrity. The Mafia nowadays has lost much of its glamour and prominence. Here in New York City, a mob boss was just murdered in Staten Island, and no one really cares that much.

…I hope no mob bosses out there are reading this and have become offended by my lack of respect. I meant no offense, Don Corleone, on this, the day of your daughter’s wedding!

Chicago in a Day

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.

If you’re a solo diner like me, you only have one option when it comes to Alinea. They have one table for a solo diner at every 8PM seating. So you need to be very prepared if you’re looking to eat at Alinea. For me it was a one of a kind experience, which means obviously that I need to eat here every time I am in Chicago. And now, without further ado…

approximately top 10: alinea edition

A Perfect Chicago in a Day 5
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.

alinea course
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.

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.

A Perfect Chicago in a Day 6
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.

glass alinea
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).

alinea stella jane
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.

alinea potato

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.

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.

Course Seven
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.

A Perfect Chicago in a Day 7
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!

A Perfect Chicago in a Day 8
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! And a waiter setting fire to your table! This ain’t your grandma’s Chicago in a Day tour!

alinea balloon
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. And the perfect end to a Chicago in a Day tour!

That’s a Perfect Chicago in a Day Tour!

What would you do on a Chicago in a Day tour? Are you ready to start booking your hotel in Chicago right now? Has a waiter ever set fire to your table? And do I need to go into witness protection now that I’ve insulted the Staten Island Mafia? 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 see Chicago in a Day. If you have time for another Chicago in a Day tour, add this itinerary with the Field Museum. If you want a Chicago in a Day tour with the Art Institute, click here. And if you want a Chicago in a Day tour with the Lincoln Park Zoo click here.

Want to Stop Misplacing Your Travel Plans?

Sign up to get a Free Travel Planner!

    I'll never share your email! It's off the record, on the QT, and very hush hush!

    This post contains affiliate links. That means if you purchase something using one of the links on this post, I may earn a small commission. But I would never recommend anything unless I loved it, dahlink!

    Recent Posts