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Chicago is the third largest city in the United States and an awesome place to visit. It is often skipped in favor of more famous cities such as New York or Los Angeles. But it’s a city that should not be missed as there are plenty of cool things to do in Chicago.
Chicago has an amazing skyline to rival New York City and is a city full of history and culture. There are also world-class restaurants, museums, an amazing waterfront, beautiful theaters, and multiple sports stadiums to catch a game.
I was in Chicago only for a few days but absolutely loved my time and will be back soon. So keep reading to find out all the cool things to do in Chicago and you will most likely fall in love with this city too.
1. Start at Chicago’s River Walk (A Cool Thing to do in Chicago for First-timers)
The Chicago River Walk is a 2 kilometers (1.2 miles) long pedestrian walkway beside the Chicago River and is a cool way to start exploring Chicago. The Chicago River snakes its way through downtown Chicago and is lined on either side by towering skyscrapers.
Skyscrapers are one of the defining images of Chicago so you really get a feel for the city along the river. The River Walk was completed in 2016 and cost 110 million USD to complete. But it was well worth the money as it creates an awesome public space to experience downtown Chicago.
The walkway has restaurants, bars, and cafes where you can stop for something to eat and drink. There are also multiple areas to sit and relax or you can hire kayaks and paddle down the river.
The River Walk is very popular with locals going for a run, walking to work, and just enjoying the city. On the weekends there are also lots of boats going up and down the river. Overall there is just an awesome atmosphere on the river and the city has done a fantastic job creating this space.
Taking a free stroll down the riverwalk is in my opinion the best way to start exploring the city. But if you want to have a more in-depth tour of the river you may want to take an architecture boat tour. Which is one of the next cool things to do in Chicago on the list.
2. Go on an Architecture Boat Tour
While you are in Chicago you will see many boats doing tours of the Chicago River. I am usually someone who stays away from tours but the architecture boats tours are really interesting and well worth the money.
Chicago was always been a world leader in Skyscraper trends ever since building the first one in 1885. On the tour along the river, you will see many different styles of skyscrapers from a lot of different eras and angles.
The guide on the boats gives you a lot of interesting facts about the architectural styles and it is also an awesome perspective to seeing the city from the river.
You can book tickets at many locations along the river walk. If you would like you can book your architecture boat tour here.
Save with the GoCity Pass
If you are considering visiting quite a few tourist attractions during your visit to Chicago then you may want to consider buying a Go City Pass starting at 124 USD.
The GoCity pass allows you to visit a selection of tourist attractions such as architecture boat tours, museums, and observation decks. With the pass, you can save up to 48%. This could save you up to 196 USD if you visit all the attractions available on the pass.
3. Check out the Bean in Millennium Park
Millennium Park is a fairly new addition to Chicago but it contains one of its most famous attractions, the Bean. If you google Chicago one of the first images you will see is the Cloud Gate or the Bean as it is more commonly called.
But the Bean is not the only attraction in Millennium Park. The park has multiple outdoor areas, theaters, and public art for people to enjoy.
The park was opened in 2004 and has quickly become its top tourist attraction with over 25 million people visiting per year. Before the park was built the area was filled with parking lots and train tracks.
It is hard to imagine now that the area is full of public art and venues for live music. It has really transformed this part of the city and made it one of the cool and fun things to do in Chicago!
Other attractions to check out
Apart from the Bean one of my favorite parts of Millennium Park is the Crown Fountain. The fountain consists of two large rectangular structures with water cascading down the sides. In the middle people’s faces are projected and every so often water will shoot out of the mouth of the person’s face.
It is a really unique fountain and also super cool to visit at night when you can see the faces reflecting in the pools of water below. If you are visiting Chicago in summer then there is a good chance that you may be able to see some live music in Millennium Park.
The Jay Pritzker Pavilion is located inside Millennium Park and is a creatively designed stage that hosts a lot of free shows in the summer months. But even if there are no free shows on it is still a really cool stage to check out.
4. Enjoy Chicago’s Waterfront (A Cool Thing to do in Chicago for Beach lovers)
Most people would not think of a waterfront and beaches when they think of Chicago. Because of the freezing winters and being so far from the ocean, you would assume there is no waterfront. But you would be dead wrong.
The waterfront in Chicago is over 30 kilometers (19 miles) long and is truly amazing. It is full of beaches, parks, museums, and fountains. Because of the location of the city on Lake Michigan, you really feel like you are at the ocean while you walk along the waterfront. Therefore it can’t be missed on the list of cool things to do in Chicago!
In summer the waterfront is full of people exercising and enjoying the sunshine so there is a really nice atmosphere. There is even a huge area with beach volleyball courts at North Avenue Beach if you feel like getting active.
North Avenue Beach and Oak Street Beach were the nicest beaches I visited while in the city. So if you are in Chicago during the summer months I recommend hitting the beach at either one.
As the waterfront is over 30 kilometers (19 miles) long walking the whole way will take a very long time. So you may want to rent a bike to explore. There is a company called Divvybikes that has stations where you can pick up bikes around the city.
You can get a day pass for 15 USD with unlimited 3-hour rides for 24 hours. So every 3 hours you have to return the bike to a designated location then you can take it out again for another 3 hours.
5. Check out the iconic Chicago Theater
The Chicago Theater is a legendary theater located in downtown Chicago. The theater has a very unique old-style marquee that lights up at night and it is one of the iconic and cool things to do in Chicago at night.
The theater was built in 1921 and is a performing arts venue hosting concerts, comedy acts, magic shows, and much more.
The interior of the theater is incredibly beautiful so it is a great place to catch a show while you are in town. To see what events are happening check out the Chicago Theater’s website here. If you don’t feel like a show then it is also worth it just to walk past during the day or at night to see the cool exterior.
6. Have a look at Lincoln Park’s free Zoo
Lincoln Park named after President Abraham Lincoln, is the largest park in Chicago and stretches for more than 11 kilometers (6.8 miles) along the shore of Lake Michigan. It is also located within the popular neighborhood called Lincoln Park.
The park covers a huge area and is full of sports fields, museums, walkways, beaches, lakes, and more. In summer it is a great place to exercise and is very popular amongst locals looking to escape the city.
North Avenue Beach is located right next to Lincoln Park. So I recommend visiting the park before or after visiting the beach.
The Lincoln Park Zoo is also a very popular attraction located within the park. The zoo was established in 1868 and is the fourth oldest zoo in North America.
I am generally against visiting zoos but walked through the zoo as it is totally free. It is also the fast way to get from one side of the park to the other at some points. So you may see people just walking to work or going for a run through the zoo.
It seemed quite well maintained for a zoo and the animals looked like they were cared for well. So if you like zoos then the Lincoln Zoo may be worth a visit.
7. See the Buckingham Fountain (A Cool Thing to do in Chicago for TV fans)
Buckingham Fountain is a famous fountain in Grant Park that was built in 1927 and is one of the largest fountains in the world. It is a really beautiful fountain with water shooting over 40 meters (131 ft) into the sky.
The fountain is located in Grant Park close to the waterfront and attractions such as Millennium Park and the Field Museum.
The fountain operates from mid-April to mid-October so you will not be able to see the water shooting in winter. Also once the sun goes down there are light shows with music at the fountain. The shows happen every hour on the hour until 10:00 pm.
While writing this blog post I had a sudden realization I had seen the fountain on TV before. That’s how I found out that the fountain is featured in the intro to Married with Children! So if you were a fan of that show it could make visiting it one of the cool and fun things to do in Chicago.
8. Visit the Field Museum
The Field Museum is a natural history museum that was established in 1893. It is one of the largest museums of its type in the world and attracts nearly 2 million visitors per year. In the museum, you can find the largest T-Rex skeleton ever discovered and a huge range of other artifacts.
If you are not from Illinois then a general admission ticket will cost you 29 USD and to enter all exhibits it will cost 42 USD. So it is not the cheapest museum but you can save money if you buy the Go City Pass.
If museums do not interest you I still recommend visiting the area around the Field Museum. The museum is located right next to the waterfront and has some of the best views of the Chicago skyline.
If you walk from the Field Museum to the Adler Planetarium there is an amazing view of the Chicago skyline and some nice grassed areas to take in the view.
9. Check out the Art Institute of Chicago
The Art Institute of Chicago was founded in 1879 and is one of the most important cultural attractions in the city. It is home to over 300,000 paintings from all over the world and has many famous paintings by artists such as Picasso and Van Gogh.
There is art from a wide range of countries, styles, and eras. So no matter what art you are interested in there should be something for you inside. Tickets cost 25 USD but it is also available on the Go City Pass if you would like to save some money.
10. Go inside the Oriental Institute Museum (A Cool Thing to do in Chicago for Free)
The Oriental Institute Museum is a small museum dedicated to the Middle East at the University of Chicago. Inside you will find mummies, statues, and many other interesting artifacts. A big benefit is that it is free to enter, although a donation is encouraged.
During the early 1900s, the Oriental Institute from Chicago University carried out many excavations in Egypt, Israel, Syria, Turkey, Iraq, and Iran. The museum was founded in 1919 to display the discoveries of the institute.
So most of the artifacts you see have been discovered by researchers from the University. The institute still carries out active research, primarily in the Middle East. So there are some interesting displays from more recent discoveries.
Visiting will probably only take up 1 hour of your time or less. But if you are interested in history it is well worth the visit. Another benefit of visiting is that it is located on the beautiful University of Chicago campus which is the next cool thing to do in Chicago on my list.
11. Wander around the University of Chicago
The University of Chicago is consistently ranked as one of the best universities in the United States. But it also happens to have one of the country’s most beautiful campuses.
The University was established in 1890 and is full of amazing Gothic buildings. It really feels like you are in a different city when you walk around the campus with vines creeping up the walls of the grand old buildings.
The campus is very nice to walk around but I recommend combining it with a visit to the Oriental Institute Museum as it is located within the University. The Museum of Science and Industry is also located close by so it is also worth checking out while you are in the area.
12. Visit the Museum of Science and Industry
The Museum of Science and Industry is a science museum located in the South of Chicago close to the University of Chicago. It contains a wide range of exhibits such as a mirror maze, tornado simulator, trains, space crafts, and World War 2 airplanes.
Inside the museum is a German submarine captured by the Americans during World War 2 and Apollo 8 the first spacecraft to travel around the moon. So if you are into machines and history there is definitely something for you inside.
Tickets to enter are 22 USD but you can also visit the museum as part of your Go City Pass if you choose to buy one.
See the Garden of the Phoenix
While you are at the Museum of Science and Industry I would recommend visiting the Garden of the Phoenix. It is a Japanese Garden located in Jackson Park behind the museum. It is a really pretty garden and you get a really nice view of the museum over the lake.
13. Check out the National Museum of Mexican Art (A Cool Thing to do in Chicago for Free)
A surprising fact I learned once I was in Chicago is that there are over 670,000 Mexican-born residents living in the city. Because of this you will see signs in Spanish all over the city and Mexican food everywhere which is great!
The National Museum of Mexican Art is a free museum dedicated to displaying artwork by Mexican artists. It is a colorful Museum with lots of interesting artwork.
Through the descriptions of the art, you can also learn a lot about the history of Mexico and the history of Mexicans living in the United States. It is a small museum so will probably only take up 30 – 60 minutes of your time. But considering it is free it is very well done and well worth the visit.
The museum is also located in Pilsen which is a predominately Mexican neighborhood. Where you can find lots of authentic Mexican food and is well worth a visit after the museum and the next cool thing to do in Chicago on the list.
14. Grab some Mexican Food in Pilsen
Pilsen is a neighborhood that historically had a large Mexican community. Because of this, the streets are covered in colorful Mexican murals and there are Mexican restaurants everywhere.
So if you are interested in eating some authentic Mexican food then you will find plenty of options in Pilsen!
There is a highly-rated Mexican restaurant 5 Rabanitos Restaurante & Taqueria located right around the corner from the National Museum of Mexican Art. So you can combine the two to have a truly Mexican day while in Chicago.
15. See the Chicago Board of Trade Building (A Cool Thing to do in Chicago for Batman fans)
The Chicago Board of Trade Building is an Art Deco skyscraper that was built in 1930 and was the tallest building in Chicago until 1965. It is still a very striking building despite its age and is surrounded by many other historical skyscrapers.
It is a beautiful building to have a look at but it is especially interesting if you are a Batman fan. In ‘Batman Begins’ the Board of Trade Building was used as the headquarters of Wayne Enterprises. The building and surrounding area were also featured in The Dark Knight.
What is really cool is that the streets around the Board of Trade Building really give you the feeling of Gotham so you can see why they chose the location for the movie. So if you are a Batman fan you may recognize the area which makes it a really cool and fun thing to do in Chicago!
16. Admire Chicago’s, Street Art
There are multiple areas in Chicago where you can find some cool street art. If you want to go out and explore on your own then some good areas to check out are:
- The Beta Project (Hubbard Street Murals)
- The Wabash Art Corridor
- Pilsen neighborhood
- Logan Square
- Fulton Market area
But as it can be a bit tricky to navigate around some areas to find all the good murals it can also be a good idea to do a street art tour. Viator has some good street art tours with local guides that can tell you all about the artists and the meaning behind the artwork.
Getting Around Chicago
One of my favorite things about Chicago is that it is very easy to get around by public transport. In many American cities, it can be quite difficult to get around without a car. But in Chicago, public transport is very affordable and covers a large proportion of the city.
The public transport system in Chicago is made up of buses and trains. The trains are all above ground on raised tracks so you can get some good views of the city while you ride around the city. The buses are just standard buses but when I used them they were on time and easy to figure out.
A day pass for the entire public transport system only costs 5 USD. A single trip will cost you 3 USD so if you are planning to take more than one trip in a day then you should get the day pass.
Or if you are in town for a week then a weekly pass is only 20 USD which is crazy cheap! It has to be one of the most affordable public transport systems that I have ever used.
Train from the Airport
If you decide to take the train from the airport you will have to pay 5 USD for the ride into the city. This is just a one-off fee charged for all rides from the airport. But if you are catching the train to the airport from the city you can simply use your day or weekly pass to get there.
🚃 Tip: if you are trying to pay for your subway ticket with a card that is not from the U.S. you will be asked to enter your zip code which you obviously cannot do if you are from another country. So to fix this problem you can just press 0 and then enter and the machine will accept your card.
Where to Stay? How much will it cost?
Hostels
If you are looking at saving money then a hostel bed in Chicago will cost you around 30 USD per night. I stayed at Chicago Getaway Hostel which was great with free breakfast and nice common rooms.
It is also located in Lincoln Park which is a nice neighborhood north of the city center. I really enjoyed the hostel so I can highly recommend it.
Hotels & Airbnb
Otherwise, if you are looking for an Airbnb you can find rooms for around 110 USD per night. Hotels will be quite a bit more pricey setting you back around 150+ USD.
Pet Sitting
We are big fans of petsitting and have done many pet sits around the world using Trusted House Sitters. It is a great way to save money while traveling and get to hang out with super cute pets.
We haven’t done a pet sit in Chicago but there are lots available. So it is a good idea to sign up if you are a pet lover who wants to go to Chicago.
Read here: How Trusted House Sitters works & our experience
If you would like to sign up to Trusted House Sitters use our link and enter HAPPYHEALTHYNOMADS at checkout for a 25% discount.
Now you know all the Cool Things to do in Chicago
That brings us to the end of my list of cool things to do in Chicago. I can’t wait to get back to Chicago and do some more exploring. It is truly one of the most underrated cities I have ever visited and amazing to explore in the summertime.
I hope you find this blog post helpful while planning your trip to Chicago. If you have any questions or any suggestions of things to add to this list then let me know in the comments below!
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Hi Allan,
I am very impressed with your report from Chicago – so many references to history and places of interest! And so many details about this town – that must have been an immense amount of work!
Congratulation!!!👏👏👏Herbie
Thank you! It was quite a bit of work but fun to write. I really enjoyed my time in the city so it was fun to learn the history and write about it.