You are currently viewing Travel to Chicago, Illinois: 18 Awesome Things to Do in the City

Travel to Chicago, Illinois: 18 Awesome Things to Do in the City

Sharing is caring!

Known as the "Windy City", this is a great city to visit in the US. Located on the Michigan Lake, there are plenty of exciting things to do to enjoy this fun place. Here are 18 awesome things to do for when you travel to Chicago, Illinois.

*Please note that this blog post may contain some affiliate links, which we make a small profit on, at zero cost to you. Links are only used on products & services that we've used and believe in, to give you the best buying experience. Purchasing from these links helps us to continue providing free travel guides for you- so thank you for your support!

Things to Do in Chicago, Illinois #1: Take Fun Pictures at the Bean

You can't travel to Chicago, Illinois without a stop at the Bean. This is the most iconic place in Chicago, and is the symbol of the city. Its mirror effect makes it particularly a fun place to photograph, as you can really play around with the effects of it. 

Travel More. Spend Less.

Let us help you plan your dream trip.

Located in Millennium Park, this is the busiest area, and the center of the city. In the wintertime you can go ice skating and visit the Christmas Tree, and in summer you can enjoy the beautiful greenery. If you want to go when no one is there you will have to make it there before 8:00, as that is when it starts to fill up.

The Bean, things to do in Chicago, Illinois
The Bean: Travel to Chicago, Illinois

The bean is the most iconic spot of Chicago.

Things to Do in Chicago, Illinois #2: Check out the Views from the Skydeck

The Skydeck is an absolute must visit for things to do in Chicago. The Willis Tower is one of the highest buildings in the country, and has some spectacular views of the city. The walls are glass from top to bottom, so you can get really great photos.

Preset - before & after

Transform your photos

One click is all it takes to make your photos look stunning. Get our latest package of Lightroom presets, Into The Wild.

There are 4 windows along one wall which are controlled so that people can line up for their pictures. Make sure you are prepared though! For 1-3 people you only get 30 seconds, and for groups of 4 or more you get 60 seconds.

Get ready, as the line can be up to a hour or so long. Tickets are $26 for a one time visit, and $45 if you want to visit twice.

Travel to Chicago, Illinois: Skydeck

Skydeck has glass platforms overlooking the city.

Things to Do in Chicago, Illinois #3: Try Deep Dish Pizza

No travel to Chicago, Illinois is complete without trying their deep dish pizza. As a New Yorker, I can definitely not say that it is better than New York's pizza, but it is still pretty damn good. This pizza has a thick buttery crust, and is full of sauce and cheese, making it more like a pie.

You can get this dish pretty much anywhere in the city, but our personal favorite was at Art of Pizza, which has two different locations. Other popular chains include Lou Malnati's and Giordano's.

Travel to Chicago, Illinois: Deep Dish Pizza

Travel to Chicago, Illinois for the unique deep dish pizza they serve.

Things to Do in Chicago, Illinois #4: Sail Around the Bay

Chicago has a stunning skyline, and what better way to see it than by boat? There are plenty of boat excursions that you can take, some that are booze cruises, some that include dinner, and others that are simply for sightseeing.

For affordable prices you can sail around and see Chicago from unique angles, and have some of the best views of the city.

Travel to Chicago, Illinois: Cruise

Sailing around the bay gives you the best views of Chicago.

Here are a few of our favorite sailings in Chicago:

Things to Do in Chicago, Illinois #5: Stop at Buckingham Fountain

As one of the largest fountains in the world, this is a worth a stop if you travel to Chicago, Illinois. Located in Grant Park, Buckingham Fountain is surrounded by greenery, and situated right near the water.

Buckingham Fountain, Travel to Chicago, Illinois

Buckingham Fountain is one of the biggest fountains in the world.

Things to Do in Chicago, Illinois #6: Walk Along Queen's Landing

You may not travel to Chicago, Illinois for the water, but it is actually a great place to enjoy the lake!

While it may not have a sandy beach, it still has direct access to the water that you can take advantage of. This makes the city much more enjoyable, especially in the summer time. Walk along Queen's Landing to enjoy the view of all of the boats, or dip your toes in to cool off.

Queen's Landing, travel to Chicago, Illinois

Head to the lake to enjoy the views or cool off in the summer.

Things to Do in Chicago, Illinois #7: Marvel at the BAPS Shri Swaminrayan Mandir Temple

Sounds like a mouthful right? This temple is located just an hour outside of the city, and is one of Chicago's hidden gems.

Although it's not really intended as a touristic attraction, the BAPS Shri Swaminrayan Mandir Temple is a really cool place to check out, and was one of our favorite places we saw on our travel to Chicago, Illinois.

temple in Chicago
BAPS Shri Swaminrayan, travel to Chicago, Illinois

This temple is a true hidden gem of Chicago.

There are free guided tours here, and you are able to make donations. You must take your shoes off and cover your legs while here, and refrain from taking any photos on the inside (which is extremely hard to do considering how magnificent it is).

There is no public transportation here, so we rented a car to get to the temple, which was cheap and easy!

Don't have time to read the whole article and want to save it for later? Just pin it!

travel to Chicago Illinois Pin
travel to Chicago Illinois Pin
travel to Chicago Illinois Pin

Things to Do in Chicago, Illinois #8: Have a Wild Night out in Boystown

Boystown is the gay neighborhood in Chicago and it is one of the most fun areas to go out. 

Although a few of us went for a bachelorette party, it really makes for a fun night out! Our personal favorite was a bar called Hydrate, which started with a drag show and champagne, and finished off turning into a night club with male dancers on the bars.

Boystown Chicago

Boystown is one of the most fun neighborhoods to go out in when you travel to Chicago, Illinois. 

Things to Do in Chicago, Illinois #10: Have a Picnic at Lincoln Park

Lincoln Park is an affluent neighborhood in Chicago, and has the biggest park in the city. Although we are not fans of zoos, that is where the famous honeycomb (shown above) lies. Enjoy the lakes and greenery, or have a picnic is the park when the weather is nice.

How To Travel Cheaper and Better in 15 minutes!

How much more would you travel, if it costed you less resources?

With our Free eBook, you will learn how to save money and time on your future trips. Plus, you'll see the exact system we use.

Grab your copy for free when you sign up for our newsletter 👇

Book cover 2021

Things to Do in Chicago, Illinois #11: Have a Drink at the Signature Lounge

Also known as Chicago 360, the Signature Room is one of the the must do things in Chicago. The restaurant and bar is located 95 stories high, and has some really spectacular views of the city.

Even the women's restroom have windows from top to bottom! (sorry men). Make sure you go when the weather is clear so you can enjoy the views while sipping on a cocktail.

Preset - before & after

Transform your photos

One click is all it takes to make your photos look stunning. Get our latest package of Lightroom presets, Into The Wild.

Classic American cuisine is served here, but pretty pricey. We suggest coming for sunset, before dinner for an appetizer, or after dinner for just a drink to enjoy the views and feel like a rock star.

Signature Lounge, 360 Chicago


Things to Do in Chicago, Illinois #11: Take a Stroll down the Riverwalk

This is pretty much just how it sounds, an area to walk along the river. Nonetheless, this area is pretty beautiful, and is lined with restaurants, shops, and skyscrapers. Want one of the best things to do in Chicago once it gets warm out? You can rent a kayak or take a boat down the river to enjoy the views even more!

Riverwalk- travel to Chicago Illinois

The riverwalk is a great area to go kayaking when the weather is warm.

Things to Do in Chicago, Illinois #12: Stop at the Historic Water Tower

The Historic Water Tower looks like a stunning European Cathedral on the outside, but is actually the Chicago Office of Tourism art gallery. Known as the City Gallery in the Historic Water Tower, it features the work of local photographers, artists, and filmmakers, and looks incredible on the outside when lit up at night.

Historic Water Tower, Chicago


Things to Do in Chicago, Illinois #13: Visit the Bahaai House of Worship

The Bahaai House of Worship is another beautiful religious building that is worth checking out while in the area. Located just 45 minutes away in car, this place has beautiful architecture, and is welcoming of all religions and backgrounds, making it a truly unique House of Worship.

Bahaai House of Worship: travel to Chicago, Illinois

This house of worship is open to everyone in the world.

Things to Do in Chicago, Illinois #14: Walk Along the Magnificent Mile

The Magnificent Mile is Chicago’s premier commercial district. This vibrant, bustling area is home to premium shops, upscale fashion outlets, trendy restaurants and fancy hotels.

Some great landmarks here include the historic Chicago Water Tower, the neo-Gothic Tribune Tower, Wrigley Building, and the 100-story John Hancock Center. (also known as Chicago 360)

Magnificent Mile Chicago


The Magnificent Mile is a great place to walk around, and take in all of the Metropolitan vibes that this city has to offer, making it one of our favorite things to do when we travel to Chicago, Illinois.

road to Zabljak Montenegro

Stay Up To Date📫

We have a non-spammy weekly newsletter, where we give travel tips, and exclusive content and discounts.

Things to Do in Chicago, Illinois #15: Check out the Art Institute of Chicago

Located in Chicago's Grant Park, The Art Institute is one of the oldest and largest art museums in the United States. Tickets are $25 for adults, and $19 for seniors, students, and teens, with reduced rates for locals.

Institute of Art, Chicago

The Art Institute is one of the best museums in Chicago,

Things to Do in Chicago, Illinois #16: Visit the Wrigley Building

While you're on the Magnificent Miles, you can also check out The Wrigley Building, which is located at 400–410 North Michigan Avenue on Chicago's Near North Side. This skyscraper is great for a photo stop, one of of the quick things to do in Chicago to check off your list.

All Your Travels

in One Book

Transform your travel memories into a unique book, with personalized pages, country by country.

Things to Do in Chicago, Illinois #17: Try a Ben & Jerry at Miller's Pub

This classic winter cocktail is perfect for the holidays! Tom & Jerry is a creamy spiced batter swirled with Cognac, rum, and hot milk, making it perfect to warm you up in the cold Chicago weather. Miller's pub is famous for this particular drink, so if you are visiting in the winter, make a stop here for a nice Tom & Jerry drink!

Tom & Jerry Drink

Miller's Pub serves the best Tom & Jerry Drinks.

Things to Do in Chicago, Illinois #18: Bike Along the Lakefront Trail

The Chicago Lakefront Trail is an 18.5 mile stretch along the water, with beautiful views of the skyline. The trail is separated for pedestrians, cyclists, and skateboarders, making it the perfect place to get in some exercise while taking in some nice views.

Pink Dot Thessaloniki Greece

Will You Buy Us A Coffee? ☕

As coffee lovers, we always enjoy the energy of caffeine. It helps us get the best free travel guides out there for you! 😄

Chicago is one of the most popular cities in the US, and definitely a great city to check out. Flights here are fairly cheap, so take a trip over to the windy city and see all that it has to offer! Let us know if you plan to travel to Chicago, Illinois, and what you look forward to the most!

Traveling within the US? We have plenty of other US travel guides throughout the states to check out.

Need help planning your trip? Well, we're here to help you! Now with Scratch Your Mapa Travel Planning Services we're working hard to find you the best deals, and all of the hidden gems out there. Want to learn more? Take a look at some of our travel planning packages.

Here are some other articles you'll love:

Like the article? Pin it!

Like this article? Please share it with your family and friends, so that we can continue to keep creating free travel guides for you! It takes just a second, and would mean the world to us. Thanks for being here!

Sharing is caring!