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Most Quirky Chicago Things (Approx Best 10)


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Greetings, Internet Stranger, and welcome to the most quirky Chicago things to do! Chicago is the third largest city in the United States, and for a large city, it’s got quite a lot of quirks. And today, we’re going to get up close and personal with some of the quirkiest Chicago quirks of all.

How would you like to take a food tour that’s…entirely donuts? Or meet the country’s most rabid sports fans? How about taking in some quirky improvisational comedy? What about dining at a restaurant that has its own garden planted in your table? All these and more await on this day of the most quirky Chicago things to do.

most quirky chicago things to do

Most Quirky Chicago Things to Do

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 exploring the most quirky Chicago things to do.

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

Most Quirky Chicago Things to Do

What to Pack?

  • A cell charger so you can take photos all while looking for the most quirky Chicago things to do
  • 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 while you look for the most quirky Chicago things to do
most quirky chicago things to do

Most Quirky Chicago Things to Do

Morning: Chicago Underground Donut Tour

Any city can have an ordinary food tour, but it takes a special city like Chicago to have its own donut only tour. The first time I visited Chicago, almost a decade ago, I noticed that they seemed to have an unusual amount of gourmet donut places, and we’re going to visit four of them on this tour. It’s definitely one of the most quirky Chicago things to do.

If you wanted to try this donut tour on your own, you’d have to eat eight donuts by yourself and probably get very sick. So instead, on the donut tour, we’ll get to have a quarter of eight different donuts, adding up to two whole donuts. That’s a perfectly reasonable breakfast!

You can book this quirky and delicious tour for yourself by clicking here. I don’t want to spoil the whole thing, but I do want to share…

Approximately Top 5: Chicago Donuts

most quirky chicago things to do
1) Doughnut Vault

Our first stop is at Doughnut Vault, which was literally built in a bank vault. The funny guide, who kept saying he knows people think he is too skinny to be a doughnut guide, had selected the best flavors for us before the tour got started, so all we needed to do was dig in as he explained.

The two flavors at Doughnut Vault were the crumbly raspberry old-fashioned doughnut and the chestnut-glazed yeast doughnut. The old-fashioned doughnuts are the richest kind of doughnut, while the yeast doughnuts are the lightest, so it was delightful to have the two as a contrast. (The third kind of doughnut, in the middle, is the cake doughnut, which we will try at other stops.)

quirky chicago things to do
2) Firecakes Donuts

Ah, here we finally get to try the cake donut. (I’m using the doughnut/donut spellings kind of interchangeably in this blog post because it’s my blog and I CAN.) Our next stop is at Firecakes, a local chain that is famous for its glamorous Tahitian vanilla donut, which we will definitely try on this tour. They’re also famous for their birthday cake donut, which we will not try on this tour. However, you are welcome to come back and try it another time.

Along with the Tahitian vanilla, we were given a seasonal cake donut with lemon and blueberry. This tasted like the perfect donut to bring along on a summer picnic. It tasted like a perfect picnic with your favorite people and absolutely no ants. (Also, no aunts, if your aunts are especially annoying.)

most quirky chicago things
3) Stan’s Donuts

OK, these are definitely the least beautiful donuts we’ll see on the tour, but they are still absolutely delicious. I’m talking about Stan’s Donuts, which is actually a chain that started in Los Angeles but was later imported to Chicago. Now they’re an Illinois only operation.

The first donuts we tried here were the pistachio-lemon old fashioneds, and I supposed that the pistachio-lemon combo is what gives them that chartreuse color. I mostly tasted the lemon instead of the pistachio, but out of all the donuts on the tour, these were the ones I most wanted to eat for breakfast.

most quirky chicago things to do

And what would a donut tour be without a filled option? These babies I like to call Delta Donuts because they are filled with a paste made from those Biscoff cookies you get on all Delta flights. Just one mouthful of these, and I was transported back to a coach seat with somebody’s toddler kicking my back while I try to watch an old episode of How I Met Your Mother.

most quirky chicago things
4) Do-Rite Donuts

For the final stop of the tour, we’ve got Do-Rite Donuts, which are the very first donuts I ever ate in Chicago, many moons ago. They specialize in old-fashioned donuts, so do rite and pick one up if you come here.

On the donut tour, we tried their buttermilk old-fashioned, which is pure and magical and almost dissolves on the tip of your tongue. Along with the pistachio-lemon, this would be my choice for a breakfast donut, as opposed to a dessert or snacktime donut.

The other flavor we tried here was the Valhrona chocolate covered chocolate donut. This was probably the most decadent chocolate donut I have ever eaten, thanks to the chocolate sinful covering. I almost wanted to take a nap after downing this baby, but no time! We’ve still got way more of the most quirky Chicago things to see.

That’s all for the doughnuts, but there were a whole bunch of fun facts about Chicago and secret doughnut info I didn’t share with you. If you want to learn those and actually get to eat the doughnuts, you’ve got to book the tour for yourself here.

most quirky chicago things

Most Quirky Chicago Things to Do

Afternoon: Chicago Culture

Some of you snarksters out there might tell me that Chicago doesn’t really have culture. It has hot dogs and Da Bears, but no culture. And those people would be wrong. Dead wrong. Chicago has tons of fantastic cultural attractions that stand as some of the most quirky Chicago things to do.

I’m going to tell you about my favorites, but there are plenty more I could just as easily have put on this list. Allow me to prove it to you with…

Three Fun Facts: Quirky Chicago Things to Do

most quirky chicago things to do
1) What’s the Most Chicago Sports Venue?

Opinions differ, but I certainly vote for Wrigley Field, which is where the Chicago Cubs play. Chicago does have another baseball team called the White Sox, which actually did better than the Cubs last season. But the Cubs get more attendance, even if they don’t play well, and the ballpark is historic. Even if the game isn’t that exciting, you’ll have fun wiggling back and forth in the wonky chairs.

You might be wondering why a baseball field is one of the most quirky Chicago things to do. After all, don’t about 25 other American cities have ballparks. First of all, do we really want to call Anaheim a city? And second of all, Wrigley Field is the oldest ballpark in the National League, which is enough to make it a unique national treasure.

most quirky chicago things to do

Plus, Cubs fans’s devotion to their team is definitely one of Chicago’s most notable quirks. I had an Uber driver in Chicago who told me that on the night Chicago finally won the World Series, grown men were in the streets of the Windy City openly weeping.

Pro tip: If you ever get your hands on something called a Grays Sports Almanac and a time machine, use it to go back in time and put some money on the Cubbies to win the World Series.

most quirky chicago things to do
24 Hour Treat: Italian Beef

I know we had two donuts for breakfast, but at some point during the game, you’ll probably want to eat something with protein. Head over to the Buona Beef stand at Wrigley Field and pick up a juicy Italian beef sandwich and a local beer. If you like spicy food, get the beef/Italian sausage combo. It’s nice and perky on a warm Chicago summer day. (And Italian beef is definitely a Chicago specialty.)

most quirky chicago things
2) What’s the Most Chicago Performance Venue?

Again, lots to choose from, but my vote is for the legendary comedy venue The Second City. So many comedians have gotten their start here: John Belushi, John Candy, Bill Murray, Dan Ackroyd, Eugene Levy, Gilda Radner, Shelley Long, Mike Myers, Chris Farley, Tim Meadows, Bob Odenkirk, Steve Carell, Amy Sedaris, Stephen Colbert, Tina Fey…the list goes on and on. And there are a whole bunch I didn’t mention.

most quirky chicago things to do

It actually can be possible to see a Cubs game and a comedy show at Second City on the same day. I know because I did it. Unfortunately, I was supposed to go to the Second City for the 6 o’clock show and then to a 9 PM dinner reservation, but it turned out the show got moved to 7 o’clock instead. So I only got to see the first half of the show, and they nicely gave me a full refund as an apology.

most quirky chicago things

If you’re hungry or thirsty, the friendly staff will gladly bring you something to your seat. I got a cucumber gimlet, which was quite refreshing, if a little pricey.

The Second City show isn’t completely improvisational. They have some material that they prepare in advance, but they do use a little audience participation. For example, one audience member called out the suggestion to do a sketch around acid rain, so one of the comics pretended he had just taken some acid and was now sitting out in the rain. Comics are a tricky bunch; they never take you literally.

most quirky chicago things to do
3) What’s the Most Chicago Thing to Do Before Dinner?

Drink, I guess? And we should have time to get one more drink before I take you to one of my favorite, very quirky restaurants in Chicago, Temporis. So let’s head to a bar that’s just a few blocks away from Temporis; it’s called Beatnik West Town.

Their drinks change with the seasons, so I can’t guarantee that you’ll see what I saw on the menu. But I can guarantee that what you see will be funky and creative, like my fig zaatar old fashioned that managed to be a little spicy and not too sweet at all. It will put you right in the mood for our most unusual dinner.

most quirky chicago things to do

Most Quirky Chicago Things to Do

Evening: Dinner at Temporis

Here it is, Internet Stranger! The restaurant with the garden in the table. I’ve eaten at a lot of places, but never before have I had an herb garden in my own table before. And Temporis allows you to pick the herbs and snack on them whenever you wish.

Temporis is a Michelin-starred restaurant that changes its menu with the seasons, so your tasting menu probably will feature different ingredients. But it would still be my pleasure to give you an idea of what to expect. There will be a ton of herbs and flowers, for one thing.

quirky chicago things to do

Our first snack was a wagyu beef dumpling that was bursting with tender flavor, like a meat flower.

quirky chicago things to do

Next was foie gras with green strawberry and elderflower. I’m used to having foie gras with fruit, but it’s usually something sweeter than green strawberry, so this was a delightful little surprise. And look at that presentation! Hang it in the Louvre! (Actually, it would probably be more appropriate to hang it in MOMA.)

quirky chicago things to do

Many tasting menu restaurants have courses that you can add on for a little extra money, so I opted for the special caviar course. It was quite a good price for caviar and added that special touch of decadence every fancy lady dinner so needs.

quirky chicago things to do

And speaking of fancy ladies, Temporis gave me this special Dungeness crab custard with grapefruit granita and avocado just because I was a solo diner. The flavor of the crab was beautiful and delicate, but I also enjoyed trying all the different textures and temperatures in one tiny bowl.

quirky chicago things to do

Up next we have some beautiful flowers sitting on top a “play on gazpacho”. Really, it was all the ingredients you’d find in a gazpacho, but separated out. The flawless summer tomatoes were the star of the show here; my photo doesn’t really do them justice.

quirky chicago things to do

Now we’re moving on to some warmer courses. This was a lobster bucatini with uni that tasted exactly like that level of Super Mario Bros. where you are just underwater and hanging out with the fish the whole time. I loved how the deceptively simple preparations and small portions of these dishes really allowed you to just concentrate on the quality of the ingredients.

quirky chicago things to do

This corn covered with truffle might have been my favorite dish of the night. You actually eat the entire corn and it is like eating corn that has died and gone to the field of dreams. The waiter said that they have to put this dish on the menu every summer or their guests get mad.

quirky chicago things to do

And now we roll out the meats. In the previous dish, the corn was the main attraction, and now it’s a side for a squab and polenta with blueberry and corn. The squab and the polenta were almost what you would expect from an earthy peasant dish, but the blueberry and corn added that pleasant ray of summer.

quirky chicago things to do

Aha! They teased us with that wagyu dumpling at the beginning, but now we get the whole thing. This wagyu was served with coffee, orange, and bacon, which is a combination I had never thought to try. I’d say that this dish alone was one of the most quirky Chicago things I saw. But it doesn’t get more decadent than a flawless piece of steak served with bacon, does it?

quirky chicago things to do

And now we get our first of three dessert courses. Here’s something of a palate cleanser: yuzu custard with cardamom sorbet. I think of cardamom as going with baked goods, so it was intriguing to try it in a frosty sorbet form with a light citrus custard.

quirky chicago things to do

Our desserts get a little more intense with lemon, huckleberry, and goats milk along with an earl grey gelee. As you can see, the flavors here are quite tart and not so sweet, though it was certainly a more substantial dessert than the previous one. But we are still easing our way into dessert mode.

quirky chicago things to do

Finally! A purely decadent dessert has arrived! I’m used to eating and loving chocolate with peanut butter, but this is chocolate, tahini, and red wine, which is basically all the flavors I’m looking for in a dessert fit for a king. (Abe Froman, the sausage king of Chicago, perhaps.) It was the perfect end to a day of the most quirky Chicago things to do.

most quirky chicago things to do

Most Quirky Chicago Things To Do

How to Get There?

By Car: This is an easy way to get to the most quirky Chicago things to do 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.

most quirky chicago things to do

By Plane: You can absolutely fly into Chicago if you are coming from far away for your day of the most quirky Chicago things to do. 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.)

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.

most quirky chicago things to do

That’s the Most Quirky Chicago Things to Do!

What do you think are the most quirky Chicago things to do? Have you ever eaten your table before? And where can I get my hands on a Grays Sports Almanac so I can go back to 2015 and put some money on the Cubbies? Please email me at [email protected] 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 see the most quirky Chicago things to do.

If you have time for another day, add this itinerary with the Field Museum. If you want a day with the Art Institute, click here. And if you want a day with the Lincoln Park Zoo click here.

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