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The Top Things To See In Chicago (Approx Best 10)


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Greetings Internet Stranger and welcome to the top things to see in Chicago, which is full of amazing Chicago history. 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 the top things to see in Chicago, learning our way through the Chicago History Museum, and then dining our way through Chicago’s best restaurants. By the end of this itinerary of the top things to see in Chicago, you’ll be a true expert on the Chicago Way!

top things to see in chicago

Top Things to See 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 day of the top things to see 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.

top things to see in chicago

Top Things to See in Chicago

What to Pack?

  • A cell charger so you can take photos all during your day of the top things to see 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 day of the top things to see in Chicago.
Chicago History Museum

Top Things to See in Chicago

Morning: 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. We can’t say we’ve seen the top things to see in Chicago without stopping here.

top things to see in Chicago

I suggest starting with the film The Great Chicago Adventure, which is the Citizen Kane of cheesy educational movies. 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

top things to see in Chicago
1) What is 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.

top things to see in chicago

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.

The Top Things To See In Chicago (Approx Best 10) 2
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2) Whose Head Is That?

Don’t be alarmed! This isn’t a real animal head. It’s a bronze calf head that used to sit perched above the Union Stock Yard gate in Chicago. After all, Chicago used to be the capital city of US meatpacking during the 19th century. I guess that’s why they’re so good at making hot dogs!

You can find this cow head in the main exhibit at the Chicago History Museum, called Chicago: Crossroads of America. You can learn about the many innovations that thrived in Chicago, from trains to Blues, to mail order shopping. Chicagoans are full of pride for their city, and here you’ll understand why!

top things to see in Chicago

In fact, Chicagoans love their city so much that they fly their city’s flag proudly at every opportunity. The stars stand for four major events in Chicago history: two tragedies and two celebrations. Will a fifth star ever be added?

top things to see in chicago
3) What About Gangsters?

“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.

best things to do in Chicago Old Town

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!

top things to see in chicago

Top Things to See In Chicago

Afternoon: Explore!

When I said we were going to explore the top things to see in Chicago, I meant that quite literally. I’ll be taking you to the top of the “Willis” Tower, which will give you the highest views in the city. Just keep in mind that its real name is the Sears Tower, even if that’s no longer its legal name. Even The Great Chicago Adventure acknowledges this, and that’s a movie for children.

But there are plenty of other things to explore rather than just the “Willis” Tower, so let’s kick things off with some lunch! That way you’ll have the right amount of energy for…

Approximately Top 5: Top Things to See in Chicago

The Top Things To See In Chicago (Approx Best 10) 3
1) Lunch at Small Cheval

Small Cheval is a great place to go for a quick and tasty lunch after the Chicago History Museum and before the “Willis” Tower. There are two locations, but for the purposes of this itinerary, you want to go to the one on N. Wells Street. It’s as yummy as a Shake Shack burger, but without all the lines and with much better fries.

I also liked that the burger was served with Dijonnaise and absolutely no ketchup. At a certain point, you have to admire Chicago’s commitment to living that ketchup-free life. Even one of these dense cheeseburgers will keep you totally full up until it’s time for our delicious dinner.

top things to see in chicago
2) “Willis” Tower “Museum”

I recommend getting your tickets to Willis Tower in advance online because the lines can sometimes get crazy. Just show up at your appointed time and enter the “museum”.

You might be surprised to find that the “Willis” Tower has a museum, but it’s actually a super fun interactive experience in the passages leading up to the top of the tower. I think more skyscrapers should have something like this because it makes paying the money to get the amazing views seem more worthwhile.

At this museum, you’ll learn more about the top things to see in Chicago and even get to take fun photo-ops. Here’s me doing a bit of stand up at Second City.

top things to see in chicago

And have you always want to take a photo of Chicago’s famous Bean without a billion tourists around? Now you can!

The Top Things To See In Chicago (Approx Best 10) 4

OK, it’s not the real Bean, but it’s pretty close!

top things to see in chicago
3) “Willis” Tower Views

Next, get ready to enjoy the amazing views from the top of “Willis” Tower. This is really the reason to come up here. The glass is so clean and clear that you really do feel as if you’re suspended in space, floating above the Windy City like a…gust of wind!

top things to see in chicago

If you’re very brave, step out into one of the glass boxes known as The Ledge. The “Willis” Tower had these boxes installed because people kept putting their foreheads on the glass windows to mimic the scene from Ferris Bueller’s Day Off. Now you can wait on line for a few minutes and then step out onto the ledge to get a similar experience. (If you are deathly afraid of heights, skip this.)

top things to see in chicago
4) Big Bus Tour

If you’re looking for the most efficient way to see the top things to see in Chicago, take a Big Bus tour of the city. This way you’ll be able to see some of Chicago’s attractions that you wouldn’t be able to get to otherwise.

The Big Bus tour is a hop-on hop-off tour, which means that you can get on and off at any of the stops all day, as long as you have a ticket. But I don’t really like to use hop-on hop-off buses that way. Because of urban traffic, you can’t always rely on them to be at the stop at the appointed time and public transportation in Chicago is faster. Better to use them like a fun guided tour of the city and you’ll have a much better time!

Just buy your ticket for the Big Bus tour by clicking here and I’ll tell you what we’re going to see!

top things to see in chicago

The best thing about the Big Bus tour was the audio portion because it was full of fun trivia about the Windy City as well as tons of Chicago movie references. If you’ve ever wanted a Chicago tour that instructed you to go on a “a hard target search of every gas station, residence, warehouse, farmhouse, henhouse, outhouse and doghouse in that area” in search of Dr. Richard Kimball, this is the tour for you.

top things to see in chicago

This tour is also the easiest way to see Soldier Field where Da Bears play.

top things to see in chicago

You’ll get the best views of Chicago’s amazing architecture.

The Top Things To See In Chicago (Approx Best 10) 5

Plus, you’ll learn about the neighborhood Streeterville, which was named after a guy named George Streeter. In the 19th century, Streeter declared that this neighborhood was rightfully his and tried to take it over with “an army of hobos”. (That phrase is a direct quote from the audio guide.) Why hasn’t anyone made a movie about this dude yet? It sounds like a perfect project for the Coen Brothers.

top things to see in chicago

Anyway, that’s just a few of the amazing facts and sights on the Big Bus tour. You’ll have to book it yourself right here if you want to learn the rest!

top things to see in chicago

Top Things to See in Chicago

Evening: Dinner at Sepia

Chicago has one of the best fine dining restaurant scenes in the United States, which is proven by the fact that it’s one of the few American cities where the Michelin guide operates. And Sepia is one of the best restaurants in the city.

Unlike many Chicago fine dining restaurants, it offers a choice of dishes over four courses, instead of a fixed tasting menu. So if you’re a picky eater or you have dietary restrictions, it’s easy to accommodate them.

top things to see in chicago

For my appetizer, I selected the foie gras tart with rose gelee, peach, and aged balsamic. I love foie gras with a passion, but I had never eaten it inside a tart before. But of course, it makes as much sense as serving foie gras on bread.

Foie gras is often served with something sweet, so the peach made sense, but it was interesting and creative to try it with flowers and rose gelee as well. This was like eating the world’s fanciest meat garden.

top things to see in chicago

For my second appetizer course, I selected the sablefish misoyaki with charred cabbage, grapes, and beurre blanc. I loved the combination of umami, sweet, and bitter tastes in this dish, and the sablefish and beurre blanc are both such rich tastes that this small portion was extremely satisfying. And of course, we still need to save room for the main course!

top things to see in chicago

And here we’re going to take a little jaunt to Argentina and try the striploin with spring onion, bone marrow chimichurri and a braised beef empanada. I enjoyed this method of serving beef two different ways, and I was especially glad to see an empanada on the menu.

Empanadas are often not sufficiently appreciated in fine dining restaurants. Do people think they too closely resemble Hot Pockets? I assure this empanada tasted a jillion times better than even the finest of Hot Pockets.

top things to see in chicago

As far as I’m concerned, nothing goes better after a fine piece of red meat than chocolate. That’s why I ordered the whole fruit chocolate ice cream with brown butter cake, preserved lemon, and blackberry.

Whole fruit chocolate uses the entire cacaofruit, which is mostly wasted during traditional chocolate making processes. The flavor was extremely rich without any added bitterness, which is exactly what I am looking for in a chocolate! And the flavor paired perfectly with the other fruits in the dish, so it was win-win!

top things to see in chicago

Top Things to See in Chicago

How to Get There?

By Car: This is an easy way to get to 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.

top things to see in chicago

By Plane: You can absolutely fly into Chicago if you are coming from far away. 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.

top things to see in chicago

That’s the Top Things to See in Chicago!

What do you think are the top things to see in Chicago? Would you be scared to get out on the Ledge, or are you dying to imitate Ferris Bueller? And is The Great Chicago Adventure really almost as good as Citizen Kane? Are you ready to start booking your hotel in Chicago right now? 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 enjoy one day of the top things to see in Chicago.

If you have time for more of the top things to see in Chicago, add this itinerary with the Field Museum. If you want a day in Chicago with the Art Institute, click here. And if you want to see Chicago with the Lincoln Park Zoo click here.

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