15 Famous Things About Chicago You Must Experience
Chicago, aka, the “Windy City” is located along the shores of Lake Michigan. There are countless famous things about Chicago that should be on every person’s bucket list and are a must to see.
Discover the best things to do in Chicago ranging from incredible architecture, the best pizza, outdoor parks, and entertainment!
Most think Chicago is called the Windy City because of freezing winds that come off the lake during the winter. But that’s not its official origin.
Years ago, the nickname caught on because the politicians apparently blew a lot of hot air…
Come experience Chicago as there is no other city like it with its gorgeous urban vibe that meets outdoor adventure.
Tip: If you are a photography lover, don’t miss out on the top spots to photograph Chicago!
Where To Stay In Chicago
If you want to be near all the downtown attractions with easy walking access, staying around the Chicago Loop or along Magnificent Mile are the best options.
There are many hotels to choose from but my favorite so far might be the Palmer House.
The Palmer House is located in the Loop and is a luxurious hotel filled with so much interesting history.
On this architecture walking tour, you’ll visit The Palmer House too!
Even if you don’t stay there, go visit the lobby and grab a drink at the bar to marvel at the stunning ceilings and décor.
A few other hotels that offer a luxury stay with prime locations near all the top places to visit in Chicago are:
Top 3 Overall Chicago Tours
At the bottom of this post I list my favorite tours in Chicago based on the type of tour.
But overall, these 3 tours are my favorite that I have personally experienced and all uniquely Chicago…
Lake Michigan & Chicago River Architecture Tour – My favorite river architecture tour as it combines both Lake Michigan and the Chicago River with tons of great views!
Classic Chicago Food Walking Tour – Come hungry and sample the best foods that Chicago is famous for!
Chicago Mob & Crime Bus Tour – Learn about the infamous crimes and gangsters in Chicago’s history and visit top sites where these crimes were committed!
Best Things To Do In Chicago
1. Millennium Park
The first stop in exploring Chicago should be Millennium Park especially if the weather is nice.
It is the most visited attraction in the city and a great spot to jumpstart your exploration of famous things about Chicago you don’t want to miss.
Located in the heart of downtown along Michigan Ave, it is nestled between architectural marvels and Lake Michigan.
Wander the beautiful gardens and have fun taking photos of Cloud Gate, better known as “The Bean”.
It’s a sculpture shaped like a bean where you can see a reflection of yourself or the city skyline!
A few steps away is the Crown Fountain featuring two towers merging art with water. It is especially popular with kids as a place to cool off in the summer heat.
Concerts and festivals are frequent in Millennium Park so check out current events to attend during your visit.
Tip: A great way to get a feel for the city while learning about Chicago’s history, culture and architecture is to take this walking tour!
2. Grant Park & Buckingham Fountain
Grant Park is known as “Chicago’s front yard” and a rather impressive one at that! Just a short walk over from Millennium Park, it’s situated along Lake Michigan.
Grant Park is host to gardens, museums (The Field Museum and Art Institute of Chicago), the Shedd Aquarium and views of Chicago’s skyline.
In the heart of Grant Park is Buckingham Fountain. It is a gorgeous fountain and one of the largest in the world.
During warm months, water displays throughout the day running from April to October.
The Buckingham Fountain might seem familiar if you ever have watched Married with Children, an American comedy sitcom. In the opening intro of the show, the fountain is the star.
The four seahorses on each side of the fountain sculpture represent the four states that border Lake Michigan (Illinois, Wisconsin, Indiana, and Michigan).
Tip: The end of every July, the world-famous Lollapalooza music festival is held in Grant Park for 4 days. If you are visiting, it is an awesome event to attend featuring numerous top singers and bands!
3. Explore The Chicago Riverwalk
The Riverwalk is an excellent place to wander as the 1.25 mile path is steps below street level along the Chicago River. You get a glimpse of the busy boating life on the river.
Plus, there are plenty of places to grab a bite to eat or drink. Sit back and take a break from the hustle and bustle of the streets above.
It’s not difficult to enjoy the view of Chicago’s most famous buildings known for their architectural feats.
The Riverwalk is divided into six sections or coves that all feature their own unique activities.
Moving from State Street to Lake Street, they are:
- The Marina
- The Cove
- The River Theater
- The Water Plaza
- The Jetty
- The Riverbank.
Whether you are looking for a great place to get in a run or a drink (or both!), the Riverwalk has plenty to keep you occupied.
4. Take An Architecture River Tour
No visit to Chicago is complete without taking an architectural riverboat tour. It is a great way to get a grasp of how downtown Chicago is laid out.
It gives you the opportunity to learn about Chicago’s history through the various architectural periods and the buildings themselves.
This tour is one of the best things to do in Chicago weather permitting!
Over the years, I have taken a handful of the river architecture tours are my two favorites are:
Chicago River Architecture Cruise
Lake Michigan & Chicago River Architecture Cruise (combo)
Both are excellent tours but I like the combo of going out onto the lake and the river as you get incredible views.
I recommend this as Lake Michigan is gorgeous with killer views of the Chicago skyline.
Another plus is that you get to go through the lochs moving to and from the Chicago River to Lake Michigan. That in itself is quite an experience!
Did you know that the Chicago River is the only river in the world that runs backward?
Naturally, the river would flow into Lake Michigan but to prevent sewage and pollution from going into the lake, they reversed engineered it in the opposite direction.
Tip: Boat tours start along the Riverwalk, so in planning your time best, do these two activities back to back. All tours run 75 – 90 minutes.
Book A River Architecture Boat Tour
Book A Lake & River Combo Architecture Boat Tour
5. Stroll Along Magnificent Mile
Magnificent Mile (Mag Mile) is a 13 block stretch along North Michigan Ave that begins at the Chicago River and runs north up to Oak Street.
It is referred to as “magnificent” because of its high-end shopping, luxury hotels, and fine dining.
Some might say that it is similar to 5th Ave in New York City. It is definitely a great excuse to get in some walking and do some serious shopping!
While strolling the mile, don’t miss the Chicago Water Tower which stands out with its unique architecture from 1869.
The tower was built to pull water from Lake Michigan and is one of the oldest in the U.S.
It now hosts a visitor center and the City Gallery with various photography exhibits throughout the year.
Tip: If you are looking to take a break from all that shopping and are craving a little decadence, hop into the Grand Lux Café on the Magnificent Mile and order the Molten Chocolate Cake. It is incredible, especially if you are a chocolate lover. It goes well with one of their many yummy cocktails…
6. John Hancock Building
The John Hancock Building is one of two famous towers in Chicago (see below for the other one) and located along the Magnificent Mile about a block north of the Chicago Water Tower.
As of 2018, the name “John Hancock” has been removed and as of this post doesn’t have a name, just referred to by its address of 875 N Michigan Ave.
But I have a feeling we will all still refer to it as the John Hancock building…
It stands an impressive 100 stories tall and has an observation deck up on the 94th floor called 360 Chicago that offers breathtaking views of Chicago’s skyline and Lake Michigan.
If you are feeling adventurous, opt to purchase a ticket for Tilt in combination with your general admission ticket.
Hence its name, visitors grip a window pane as it “tilts” 30 degrees out 1,000 feet high over Magnificent Mile!
Tip: On the 95th floor, the Signature Room offers up fine dining with a view but it is a bit pricey.
I suggest heading up to the Signature Lounge on the 96th floor to enjoy a cocktail and stunning views galore.
Get Your 360 Chicago Ticket Today!
7. Willis Tower (Sears Tower)
The Willis Tower or otherwise known as the former Sears Tower (and what most still call it today) rises at 110 stories and is the tallest building in Chicago.
You may wonder if it is worth visiting both the John Hancock building and the Willis Tower and I say yes!
Both offer up such amazing views and quite different perspectives of Chicago.
On a clear day, you can see four states (Indiana, Wisconsin, Michigan and of course Illinois).
In more recent years, the draw to the Willis Tower is the Skydeck up on the 103rd floor that has two ledge glass balconies that extend four feet outside of the tower.
It looks more like a glass box and is terrifying to see the street 1,353 ft below but can’t be missed!
If you are planning to visit many attractions in Chicago then consider purchasing the Go Chicago Pass where you get huge discounts. The Wills Tower is included in this pass too!
Tip: If traveling with someone, have them go into the opposite glass box to capture a side shot of you. It gives a different perspective of you hanging out over the city.
Get Your Sky Deck Ticket Here!
8. Take In The Fun At Navy Pier
The Navy Pier is the most visited attraction in Chicago and it has an assortment of activities ranging from museums, a Ferris wheel, theatre, fun house and of course places to eat.
I personally like to walk out on it to experience the incredible vantage point of the Chicago skyline.
Built in 1916, it is considered the longest public pier in the world.
Over the years it has been home to the U.S. Navy, the University of Illinois first Chicago campus and now it’s present-day entertainment spot.
Did you know that the Ferris Wheel was actually invented in Chicago for the 1893 World’s Fair?
It clearly stands out against all the high-rises in the background and adds a little something to photos.
If you are wondering, this isn’t the original Ferris wheel but one built at a later date.
Tips: If you are visiting in the summer months, catch the firework show on Wednesdays and Saturdays.
If you aren’t up for walking to Navy Pier hop on the free trolley that loops around downtown Chicago and has a stop at the pier.
9. Enjoy A Cocktail On A Chicago Rooftop Bar
Hands down a prime way to see the beauty of the city is with a birds eye’s view from a Chicago rooftop.
It is a great way to capture some stunning views and paired well with a yummy cocktail!
There are many to choose from but one that I love is Cindy’s which is located up top of the Chicago Athletic Association Hotel.
It provides views of Millennium Park, Lake Michigan, Grant Park and more.
For a view of life on the Chicago River, head over to the London House rooftop bar.
You can view famous high-rises, beautiful architecture and boating action along the Chicago River.
10. Watch The Cubs Play At Wrigley Field
If its baseball season, jump at the chance to catch a Chicago Cubs game at the iconic Wrigley Field which is over 100 years old and probably the most famous thing about Chicago!
It’s one of the last old school ballparks in the U.S. (Fenway in Boston is the oldest) that has so much nostalgia and history.
Watching the Cubs play in this ballpark is one of my favorite things to do in Chicago when I visit.
Two features that make Wrigley stand out and original is the ivy-covered outfield walls and the hand turned scoreboard.
It is quite interesting to see someone behind the scoreboard changing the numbers by hand, especially in such a digital world.
11. See The Chicago Theater
Even if you have never visited Chicago, you most likely will recognize the theater’s marquee with “Chicago” lit up in lights.
It has been featured in many shows, movies, and commercials being one of the most photographed sights in Chicago.
Whether you see it by day or night, it is appealing to see from the exterior and even better if you are lucky enough to catch a concert or show.
The theater opened up in 1921 and its design is very much influenced by France’s Palace of Versailles, Paris Opera House and the Arc de Triomphe throughout.
Tip: If you purchase the Go Chicago Pass, it includes a tour of the Chicago Theatre!
12. Hop On The Crime And Mob Tour
Chicago has a notorious history when it comes to crimes and the mob.
The Crime and Mob Tour highlights a visit giving a glimpse into Chicago’s darker history.
Visiting several crime-related spots in Chicago by jumping on and off a bus, you get to see the sites up close and personal.
Hearing about famous mobsters and criminals such as Al Capone, John Dillinger, Hymie Weiss and many more will have you on the edge of your seat with intrigue.
Expect to spend about 2 hours on this awesome tour.
Tip: Another great gangster tour option is the gangster & ghost walking tour!
13. North Ave Beach
Whether you are looking to hit the beach (yes, it is technically the shores of Lake Michigan) or enjoy a run along the waterfront, North Avenue Beach is a destination must.
Other than the two reasons mentioned above, it is one of the best places to view the city skyline especially an early morning sunrise.
I recommend walking out to the end of the jetty for a spectacular panorama of the cityscape, especially if you are into photographing Chicago.
You can catch a bus to North Avenue beach or because I wanted to get there right at sunrise, I took a Lyft to get there quicker.
And if you are up for getting in a workout at the same time, rent a bike and cruise along the Lakefront Trail (19-mile path).
You can hop on the Lakefront Trail anywhere as far south as Jackson Park. You can easily rent a “Divvy” bike at various locations in the city.
14. Indulge In Deep Dish Pizza
Chicago is home to some incredible food and top restaurants which would require a post on its own. Maybe a later date but here we will focus on pizza…
A visit to Chicago will involve a lot of eating and is incomplete if you haven’t tried deep-dish pizza.
I’m sure many will debate who has the best deep dish, but my favorites are Lou Malnati’s and Pequod’s.
Because Chicago deep dish is much heavier to eat, be prepared to do some eating.
I can usually only eat one slice whereas I can normally put away 2-3 slices of a regular crust pizza.
There are several locations for Lou Malnati’s throughout the Chicago downtown area. Whereas Pequod’s is a little further out about 5 miles or so, easily accessed by getting a Lyft.
Tip: Interested in learning more about the best foodie places in Chicago?
Book This Food Tasting Walking Tour!
15. Wander Along The 606
The 606 is fairly new to Chicago as a 2.7-mile stretch of multi-use trail where you can walk, run or bike on an old abandoned elevated railway.
It’s a green space that shares some similarity to NYC’s Highline.
The 606 has been in use now since 2015 and is named after the zip code where it resides. Scattered along the trail, you can see various art and places to grab some food.
There are 17 different ramps or entry points onto the 606. If you want to go end to end, it runs along Bloomingdale Ave between Ashland Ave and Ridgeway Ave.
The 606 is open from 6am to 11pm so a great way to start or end the day with a bit of exercise.
More Chicago Experiences & Activities
Chicago is one of my favorite U.S. cities as there is so much to do and a little something for everyone.
I have visited Chicago in all seasons but my favorite is summer and fall. It offers the ability to do more activities and spend more time outdoors in the parks, river, and lake.
If you have more time and are looking for additional Chicago activities beyond this post, here are my top picks:
- Art Institute of Chicago
- Field Museum
- Shedd Aquarium
- Adler Planetarium
- Catch A Comedy Show at The Second City or Laugh Factory
- Lincoln Park Zoo
Depending on time and the number of attractions you plan to see, look into getting a CityPass Chicago.
You can get big discounts rather than paying for individual attraction fees. You get huge savings if you plan to visit most or all of the attractions.
Top Chicago Food Tours
Classic Chicago Food Walking Tour – Come hungry and sample the best foods that Chicago is famous for!
Best Donuts Food Tour – If you have a sweet tooth and love donuts then this walking tour of Chicago’s best donuts is for you!
Taste of Chinatown Food Tour – Visit Chicago’s Chinatown and enjoy delicious and traditional Chinese dishes!
Best Walking Tours In Chicago
Chicago History, Architecture & Culture Walking Tour – Explore the top attractions in Chicago and learn all about their history and architecture!
Gangsters & Ghosts Walking Tour – Learn all about Chicago’s darker and more spookier side as you walk the Chicago Loop District
History & Chicago Architecture Tours
Lake Michigan & Chicago River Architecture Tour – This is my favorite river architecture tour as it combines both going onto Lake Michigan and along the Chicago River with tons of great views!
Chicago River Architecture – A top favorite architecture tour along the Chicago River learning all about the famous and impressive buildings making up Chicago’s skyline!
Treasures Of A Gilded Age Architecture Tour – This walking tour is amazing for seeing some of the most beautiful architecture in Chicago!
Chicago Mob & Crime Bus Tour – Learn all about the infamous crimes and gangsters in Chicago’s history and visit top sites where these crimes were committed!
Chicago Hop-On Hop-Off Bus Tour – Want to give your legs a break? This open-top, double-decker bus tour makes stops at all the top Chicago attractions!
Map Of The Top Chicago Attractions
Use this map to make planning and navigating the best places to visit in Chicago easier for you!
Where Is Chicago?
Chicago is located in the state of Illinois and the third-largest city in the U.S. after New York and Los Angeles.
It is smack in the middle between the two in the area known as the Midwest.
The top portion of the city is bordered by Lake Michigan, which is one of the “Great Lakes”. It is a city that has it all as there are so many Chicago attractions to see both indoors and outdoors!
Best Time To Visit Chicago
If it is your first time visiting Chicago, I would recommend visiting Chicago in the spring through fall months which is May through October.
That is when you will have the best weather and have more things to do in Chicago than if you visited in the winter.
If I had to pick one season to visit it would be the fall as the weather is fantastic and not as crowded as the summer months.
The summer can lead to high temperatures and humidity so prepare for some hot and sticky days. In contrast, the winter can be extremely cold and several days of snow.
Having said, Chicago is worth visiting any time of the year, and plenty to do year-round.
Plan to do a lot of walking as you explore the downtown area, parks, and waterfront which means wearing comfortable shoes like these!
How To Travel To Chicago
If you are visiting Chicago, you are likely staying in the downtown area around the “Loop” which is the most central region of downtown.
There is a debate on why it is called the Loop. It’s said that the “L” CTA Train (elevated train/subway) travels in a loop around the central downtown with eight stops.
There are many options to reaching downtown such as hailing a taxi or scheduling an Uber/Lyft.
But if you don’t have a ton of luggage, I recommend taking the L train (subway) as it is much cheaper and quicker.
You can catch the L train from both Midway International (MDW) and O’Hare International (ORD) airports.
Take the Orange Line CTA train from Midway International Airport to downtown Chicago. The fare costs $2.50 (one way) with a 20-25 minute travel time.
Or take the Blue Line CTA train from O’Hare International Airport costing $5.00 (one way) with a 45 minute ride.
I have only taken the L CTA train from Midway, so here is step by step directions: Once you get your bags, look for signs that say, “CTA trains” or “Trains to the City” and head that way.
To make it easier, follow the painted “orange” line that will lead you to automated vending machines to buy a Ventra ticket. I purchased a round trip ticket for $5.00.
Hop on the train heading to downtown and exit on one of the 8 stops on the Loop.
They are Harold Washington Library-State/ Van Buren, La Salle/Van Buren, Quincy, Washington/Wells, Clark/Lake, State/Lake, Washington/Wabash or Adams/Wabash.
Book Your Flight To Chicago Today!
Getting Around Chicago
Hands down the best way to get around Chicago is to walk! You will get a better sense of the city and stumble upon hidden gems you won’t discover any other way.
I always try to walk as much as possible but if it is super hot (and I don’t feel like sweating buckets). But if it is raining, I am all about taking the L train or getting an Uber/Lyft ride share.
Another great option is to rent a Divvy bike as there are stations all over Chicago for easy access.
For destinations that are further out, I found using an Uber/Lyft rideshare to be the most convenient.
Got Travel Insurance?
Don’t leave home without travel insurance as you never know what might happen on a trip! It is always when you least expect it that something can go wrong like getting sick, in an accident or cancellation of some sort.
Get a no-obligation quote from two trusted travel insurance companies for peace of mind on your next trip!
Looking For More Travel Inspiration?
The Best Locations to Photograph Chicago
23 Cool And Fun Oklahoma City Attractions That Are A Must To See
11 Best Wineries In Fredericksburg, Texas That Are A Must To Try
Boston Itinerary: How To Spend 3 Awesome Days
19 Cool Things To Do On A Weekend In Memphis, Tennessee
Ultimate New Orleans Bucket List: 35 Fun Things To Do In NOLA
25 Best Things To Do In Birmingham, Alabama You Don’t Want To Miss
10 Best Things To Do In South Dakota
How To Spend The Best Weekend In Albuquerque
17 Best Things To Do In Santa Fe, New Mexico Not To Miss
The Ultimate Guide To The Albuquerque Balloon Festival
15 Best Things To Do In San Diego
The Best Places To See In Jaipur The Pink City
Vanessa Shields
Vanessa Shields is the founder of Traveling Ness helping people with trip ideas, itineraries, travel planning, and boosting confidence for female travelers to take a solo trip. She has been a travel writer and content creator since 2019.