Chicago Travel Guide: Is Chicago Worth the Hype?

As the third-largest city in the United States, you already know Chicago has to be packed with awesome things to do. This city is absolutely loaded with incredible places to visit and things to do, and fitting it all into a week is impossible. From some of the best restaurants in the world to a massive free zoo and the largest coffee roastery on Earth, Chicago has something sure to please everyone.

Best Things To Do In Chicago

Being such a massive city, it’s only natural that Chicago has so much to do. Any city center with five million people is going to be that way. However, Chicago finds a way to actually expand those already high expectations. The Windy City is a place where anyone can have a good time, and you’re bound to find things that interest you. This list includes a bunch of our favorite things to do in Chicago, and we hope that you like them!

1. Visit the Starbucks Reserve Roastery

Full disclosure, I am a huge coffee guy. I worked for years as a barista in college and have had a burning passion for coffee my whole life. As a guy who can appreciate a nice cup of coffee, I will tell you that I truly think Starbucks serves great coffee and is a premier place to go. Some people will disagree, but hey, that’s your right.

Whether you agree with the above or not, though, I 1,000% recommend checking out the Starbucks Reserve Roastery if you are in Chicago. There are actually only six in the world world: Shanghai, New York, Chicago, Seattle, Milan, and Tokyo. I have made it to all of them except for Seattle and Tokyo so far, and I truly think that they are very special places.

Chicago’s location is touted as the largest coffee roastery in the whole world, and I don’t think they’re lying. This facility has five floors, and they serve up an entirely different menu on each floor. From coffee inspired cocktails on the top floor, to iced drinks on another floor, to drip coffees on another floor, this place is massive, fun, and can keep you caffeinated for days. It is located conveniently in the Magnificent Mile, too, so you don’t even need to go out of your way to get there. This is not just any Starbucks, folks; it is the crême du la Bucks.

2. Go on an Architecture Boat Tour

Chicago is renowned for its striking architecture. Honestly, Chicago is one of the most beautiful cities we have seen in the world, let alone the United States. The architecture ranges across all different styles, and the juxtaposition of old and new right alongside one another is really stunning. From old, concrete buildings to new, shard-like fully glass buildings, the Chicago skyline is really something to behold.

In our opinion, the best way to do that is with a sunset boat tour along the Chicago River. There are boats leaving all throughout the day, but we think that the best time to go is around sunset, as you get to catch the buildings while it is light outside and when the sun goes down and all the lights are turned on. The skyline at night is just mesmerizing.

There are several operators that run the tour, and I have heard great things about all of them. We opted for Wendella, and it was a really great experience. While they offer both a 45-minute and a 90-minute tour, we think that the 45-minute tour is plenty of time to really enjoy the experience. If you’re interested in learning about the architecture, sit towards the middle or front of the boat, as the microphone doesn’t really carry well enough to the back when it is windy outside. Also, we were told that the right side of the boat is the better side to sit on, but I think both are equally great, as the ship goes out and comes back the same way.

3. Eat Deep Dish Pizza

Everybody knows that Chicago is famous for its pizza, but I think that it’s easy to just assume that all Chicago pizza is the same. On our most recent trip to Chicago, we decided to dedicate ourselves entirely to trying pizza. We didn’t buy a single dinner that wasn’t pizza! We found out along the way that deep-dish isn’t the only pizza that is famous in Chicago, but it is definitely the one that tourists love to grab the most.

I can’t say that I blame them, either. Chicago deep-dish pizza is a true masterpiece. While some old-school native Chicagoans will tell you that true Chicago pizza is a thin, charred, crispy crust, the truth is that nowadays the city is just dominated by the thick, deep, indulgent stuff that has become world-famous.

We actually wrote a post on the best places to get pizza in Chicago, and you should absolutely check it out if you’re visiting Chicago any time soon. We tried out some of the best places to get pizza in Chicago, and we think we got a pretty good feel for where to go. If you ask me, eating pizza every day is totally one of the best things to do in Chicago.

4. Visit Some World-Class Museums

Any major city is going to have its fair share of museums, but Chicago might actually take that a step further and break the typical expectation. There are a lot of great museums to check out in Chicago, ranging from art, to science, to sports, and beyond.

The Field Museum is one of the classic Chicago places to check out, as it is one of the largest museums of natural history in the world. It has almost 500,000 square feet of space showing absurd things, like dinosaurs and mummies. If ancient animal skeletons aren’t your thing, think about heading to either the Lincoln Park Zoo or the Shedd Aquarium to see some living ones! The Lincoln Park Zoo is completely free to visit, while the Shedd Aquarium tickets are more like $40.

Apart from animals and natural history, Chicago is a major city for art, human history, and niche scientific fields, like medicine. The Art Institute of Chicago is a common place to visit, and we also opted for a visit to the International Museum of Surgical Science. Whatever your interest, you’re bound to find a museum that you’ll like in this city, which makes visiting museums one of the best things to do in Chicago. For a more in-depth look at the best museums to visit in Chicago, check out this post from TimeOut.

5. Go Kayaking on the Chicago River or Lake Michigan

While Chicago is very much so a concrete jungle, it also has its fair share of natural escapes. Being located on a river and one of the Great Lakes definitely helps with that, too! A common Chicago pastime is going to the beaches of Lake Michigan to relax and bask in the sun. As the weather is only beach-worthy for a couple months of the year, you’d better believe that the beaches get packed!

If you’re craving a bit more physical activity, though, consider renting a kayak to take out on the water. Kayakers are allowed on parts of both the Chicago River and Lake Michigan, and seeing the massive buildings from a tiny kayak offers a really unique perspective of the city. If you’re interested in doing this, I highly recommend checking out Urban Kayaks. Urban Kayaks is a kayak-tour agency located right at the meeting point of the lake and the river, and they offer kayaks to be used conveniently and affordably.

6. Get a Breath of Fresh Air at the Morton Arboretum

While some people love the hustle and bustle of being downtown in a major city, others need a bit of a break. If this is you, or if you are simply craving a unique, relaxing thing to do in Chicago, I recommend making the trip out to the Morton Arboretum. This place is located a bit outside of the city, but it is a beautiful (and increasingly iconic) escape from the skyscrapers. This location is famous for its large sculptures, and they remind me a lot of the iconic “Ven a la Luz” sculpture in Tulum, Mexico. Maybe that is because they were made by the same guy, Daniel Popper!

This outdoor garden space offers rotating art exhibitions, several miles of hiking trails, and very much tranquility. Tickets to enter are just $16, which is pretty affordable compared to a lot of other things to do in Chicago. While the Morton Arboretum is only a 30-minute drive from downtown Chicago, it takes a bit longer with public transportation as there is no direct route. However, even if you need to take a blend of buses, metros, and potentially even Ubers, most people will tell you that it is worth the trek.

If you want to escape the city but the Morton Arboretum doesn’t sound like your kind of thing, check out my post on the best day trips from Chicago. Maybe one of those will be more up your alley!

7. Go for a Stroll Through the Magnificent Mile

Sometimes the bests attractions aren’t attractions at all. I am a big walker, and I find that walking around with no real plan is often the best way to explore a city. While Chicago is too big (and in some areas too dangerous) to just walk aimlessly forever, there are some areas I think deserve some time to just walk around and explore without a specific destination in mind. The Magnificent Mile is one of those.

This part of the city is a mile-long strip of luxury. From restaurants to stores to offices, this strip feels like the cushy, luxurious “downtown” vibe that many people dream of. This is where the Starbucks Reserve Roastery is located, too. Whether you have cash to spend or not, going for a walk through this area and admiring the architecture, the storefronts, and the beautiful backdrops is a must-do thing while in Chicago.

Additionally, not too far south from here is the famous bean sculpture that everyone loves to take pictures at. Taking a picture at the bean is often considered one of the iconic things to do in Chicago, and visiting the bean before or after walking through the Magnificent Mile is an easy walk.

8. Visit One of Chicago’s Observation Decks

Seeing the city from below on a kayak or a boat is a really unique perspective. Seeing it from way above is the complete opposite perspective. The fact that you can gain both perspectives of this massive city while visiting is a really cool concept! There are two main observation decks in Chicago, and both offer really striking views of the city. The two decks are called 360 Chicago and Skydeck Chicago, and many people say that visiting one of them is one of the best things to do in Chicago.

Which Chicago Observation Deck is Best?

Chicago has one of the most beautiful skylines in the United States, so it definitely makes sense if you want to check it out from high up! There are two towers in Chicago with observation decks, and many people wonder which Chicago observation deck is better. Frankly, we wish we would have known this before we visited, because we felt like we wasted $30.

There are two sky-high observation decks in Chicago: 360 Chicago and Skydeck Chicago. We were very excited for this, because we had seen the Instagram-famous glass floor that everyone loves to visit. How cool, to walk out onto a glass floor above the city of Chicago! We naturally headed to 360 Chicago excited for this experience.

This wound up being quite the costly error. While the views at 360 Chicago are fine, the glass floor is in a whole different building. The glass floor in Chicago is located at Skydeck Chicago, which is high up – 103 floors, in fact – in the Willis Tower. We wish we had known this, as the Willis Tower is the tallest building in the Western Hemisphere, and it is so much more worth visiting even without a glass floor. Add the glass floor, and there is simply no reason to choose 360 Chicago over Skydeck Chicago.

If you are looking for the Insta-famous, epic glass floor, head to Skydeck Chicago in Willis Tower. Skydeck Chicago is only $5 more expensive than 360 Chicago, making it very worth the money in comparison. If you’re looking for a little more thrill, though, 360 Chicago does offer its TILT attraction, which leans a glass panel out over the city. This is a lot of fun, but costs more money and is not safe for children.

What is the Chicago Bean Actually Called?

One of the most iconic things to do in Chicago is visit the giant statue of a bean and take a picture. However, if you are not familiar with Chicago’s geography, you might not have an easy time finding the bean! While it is commonly referred to as the Bean, searching for the Bean on Google Maps doesn’t come up with any direct matches. If you search for the Chicago Bean on Google Maps, it tries to take you to the “Cloud Gate,” whatever that is.

Well, the Cloud Gate is actually the formal name for the sculpture that everyone calls the Bean, and it is located in Millennium park. This is not far from the Magnificent Mile at all, either, which makes it very easy to visit both iconic areas at the same time. If you’re in Chicago wondering where the Bean is, Google Maps is not wrong; head to the Cloud Gate.

How to Get to Chicago

As one of the biggest cities in the United States, you’d be correct to assume that Chicago is well-endowed when it comes to airports. In fact, much like New York City, Chicago has two major, popular airports at its disposal. O’Hare International Airport (ORD) is the city’s flagship airport, and it is actually one of the busiest airports in the entire country. Chicago Midway International Airport (MDW) is the city’s secondary airport, but it is still a major people-mover.

If you’ve read my post on finding cheap airfare, you know that the biggest airports tend to yield the cheapest ticket prices, and that is very much so the case with O’Hare. However, Midway has also recently shot up the ranks of U.S. airports, as it has become a major budget airline hub. Southwest Airlines uses Midway Airport heavily, and they have direct flights running from all over the United States. If you’re a bit wary of flying on budget airlines, check out my budget airline guide to help alleviate some fears and avoid hidden costs. I highly recommend looking up flights into both airports before buying any tickets, as there is a great chance that either one could offer fantastic rates.

Both airports are directly connected to the city by the metro, which I recommend using to get downtown. In my opinion, the metro is the best way from the airport to Chicago in both cases. Midway Airport is the last stop on the orange line, and it takes you right into the heart of Chicago in just about 30 minutes. O’Hare, on the other hand, is the last stop on the blue line, and takes about 35-40 minutes to get downtown. This makes Chicago a great candidate for a stretched-out layover, too, as you can easily get from the airport to the city and back during a long layover.

How to Get Around Chicago

METRO | BUS | REGIONAL RAIL

I am an avid hater of American public transportation, as I think that it is among the worst in the western world. The fact that the U.S. only has a handful of cities with metro systems blows my mind, and the fact that most of them are as bad as New York and Philadelphia’s subway systems is even more shocking. In Chicago, the metro system is called the “L” and it is actually a smidge better than the typical American metro system.

The “L” is pretty well connected, as it links most major parts of the city to both airports. It isn’t immaculately clean, but it is cleaner than a typical New York subway. We had a fine experience with the “L” and definitely recommend it as your main way of getting around the city.

Beyond just the metro, Chicago has a very great network of buses and regional rail lines. Between all three modes of transportation, you can definitely get anywhere within the city that you want to go. You do not need a car in Chicago, and I would actually recommend opting for public transportation over driving because of parking reasons. Rental cars, gas, and parking are expensive, and the metro isn’t.

To pay for the metro and the buses, you can buy a Ventra card at any station or many convenience stores and news stands around the city. This card can be linked to the Ventra app on your phone, which makes tapping into the public transportation network very easy. You can reload its value at the stations or directly on your phone.

The Best Time to Visit Chicago

Chicago is a city of extremes in many ways, and the weather is just another example of that. Chicago winters are absolutely horrid, and unless you have a good reason, visiting Chicago during the winter is not a good idea. Visiting Chicago in July and August is also not a great idea, as the summers a blazing hot and the streets are packed with tourists.

The best time of the year to visit Chicago is usually April through early June and September through early October, as the temperatures are manageable, the crowds are not as large, and the lines to get into museums, restaurants, and attractions are not out the door due to high tourist season.

Is Chicago Safe to Visit?

You will often hear people say that Chicago is more dangerous than anywhere else in the country. People even draw comparisons between Chicago and war-torn countries, like Iraq. Frankly, the numbers don’t lie…according to the numbers, Chicago is just as dangerous as some of those places. Tijuana, Mexico, for example, often has similar crime rates as Chicago, depending where you look.

This is extremely misleading in so many ways, though, for both of these cities. Tijuana is often referenced as one of the most dangerous cities in the world, and Chicago is often referenced as the most dangerous city in the United States. The fact is that in both of them, as long as you are in touristy areas, the threat of violent crimes happening to you is very low. Things can happen – there was actually a mass shooting in the Magnificent Mile while we were 5 blocks away, and a gang execution 3 blocks from us when were in Tijuana – but the chances that you will get caught in something like that are very low, especially during the day.

If you venture out into other neighborhoods, things are very different. Parts of southern Chicago are absolutely horrible. Chicago is, indeed, overrun with gang violence, and anyone that says otherwise is wearing a blindfold. However, that gang violence is largely contained to the rough parts of the city, and visiting places like the Loop, the Magnificent Mile, the Riverfront, the Lakeshore, and Lincoln Park is as safe as any other major city. It has its inherent risks, like any city, but that is about it.

Don’t go out too late at night, don’t venture too far out from the touristy parts, and take basic safety precautions like not carrying much cash on you and keeping you phone in your front pockets. Other than that, just relax and have a great time. You should be just fine.

Is Chicago Worth The Hype?

Chicago is a really hyped-up city, and talking to Chicagoans will only amplify that. Most Chicagoans love their city, and they’ll be quick to tell you that it’s the best city in the country. While I don’t think I’d take it quite that far, it is indeed a beautiful, enjoyable city with endless things to do. It definitely falls in my top-5, at least!

From stunning architecture to Michelin star restaurants, and from a beautiful lake to incredible museums, this city has a lot to see and do, and you will not regret visiting. Chicago has a strong reputation, and I truly think that it backs it up when you visit. Take a bit of extra caution when visiting due to the higher danger level, but don’t let the worries distract you from having a good time. Chicago is marvelous, and it is definitely worth the hype.

That’s all we have for you about Chicago! Hopefully this post is helpful as you start planning your journey to the Windy City. I really do think that Chicago is worth visiting, and as long as you stay in main touristy areas, the odds of anything bad happening to you are slim. Chicago is one of the all-around greatest cities we have visited, and we can’t wait to go back.

If you’re planning a trip to Chicago, comment your plans below! We’d love to chat ahead of time and answer any questions you have. Otherwise, have a wonderful day and stay present!