Boat tour on the Chicago River
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15 Famous Things About Chicago You Must See

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. Find out 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.

The nickname caught on because the politicians 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 and want to find the best spots to photograph, read The Best Locations To Photograph Chicago!

The city skyline and Lake Michigan are a few famous things about Chicago you must see
The city skyline from Lake Michigan

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!

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 Hotel in downtown Chicago.
The front entrance to the elegant Palmer House Hotel
Lavish lobby of the Palmer House Hotel.
Talk about a lavish and fancy lobby!
Elegant staircase in the Palmer House
Elegant staircase in the Palmer House, talk about craftsmanship!

The Palmer House is located in the Loop and is a luxurious hotel filled with so much interesting history. Plus, it is a Hilton hotel which means I got points for staying there! 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 great location are The Westin Michigan Avenue and the Hilton Chicago.

Map Of The Top Chicago Attractions

Use this map to make planning and navigating the best things to do in Chicago easier for you!

This map was made with Wanderlog, a road trip planner

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.

The Bean in Millennium Park.
“The Bean” in Millennium Park

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!

The Crown Fountain in Millennium Park.
Crown Fountain in Millennium Park

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.

Buckingham Fountain in Grant Park of Chicago
Buckingham Fountain in Grant Park

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.

Chicago Riverwalk

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 a great place to walk, run or relax along the Chicago River

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, and 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!

Perfect fall day to enjoy the architecture river & lake tour

There are many tour companies to choose from and I have taken the Wendella Boats Tour and Shoreline Boat Tours.

The tours take you along the Chicago River and some also take you out onto Lake Michigan for a river/lake combo.

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!

Entering the lock system from Lake Michigan to the Chicago River

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!

Oh, and another option is to take a kayaking river tour. I haven’t done this myself but it looks quite fun.

Boat tour on Lake Michigan

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. To book a boat tour visit here.

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!

Chicago Water Tower
Chicago Water Tower

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. A friend and travel blogger introduced me to it and boy am I happy she did. It is incredible, especially if you are a chocolate lover like me! 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.

John Hancock building seen from Milton Lee Olive Park.
Enjoying the view of the John Hancock building from Milton Lee Olive Park

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!

View from the top of the John Hancock Building.
View from the top of the John Hancock Building

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.

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.

View of Willis Tower from street level.
Gazing up at the Willis Tower (formerly the Sears Tower)

On a clear day, you can see four states (Indiana, Wisconsin, Michigan and of course Illinois).

View from the top of Willis Tower.
Birds-eye view of Chicago from the observation deck of the Willis Tower

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 the city then conisder purchasing the Go Chicago Pass where you get discounts on several top attractions. 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.

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.

The Navy Pier in Chicago.
View of the iconic Navy Pier while boating on Lake Michigan

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! Oh and no this isn’t the original Ferris wheel in case you were wondering…

Ferris wheel at Navy Pier.
The Ferris Wheel at Navy Pier seen from Milton Lee Olive Park

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 Rooftop Bar

Hands down a prime way to see the beauty of Chicago is with a birds eye’s view from a rooftop bar. It is a great way to capture some stunning views and paired well with a yummy cocktail!

View of Millennial Park and Lake Michigan from rooftop of Cindy's.
View of Millennial Park and Lake Michigan from the rooftop of Cindy’s

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.

View of Chicago River from rooftop of London House.
View of Chicago River from the rooftop of London House

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.

Ivy covered outfield wall at Wrigley Field.
The famous ivy-covered outfield wall of Wrigley Field
Watching a Chicago Cubs game at Wrigley Field!

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 and movies.

Chicago Theater
The grand marquee of “Chicago” at the Chicago Theater

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.

Biograph Theater where John Dillinger was shot by the FBI.
Biograph Theater where the criminal John Dillinger was shot by the FBI

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.

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.

Walking on the jetty of North Avenue Beach
Walking on the jetty of North Avenue Beach

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 Chicago’s cityscape, especially if you are into photography.

North Avenue Beach
The beautiful sandy North Avenue Beach of Lake Michigan!

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! 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!

A small Pequod's pizza I got to go to take back to my hotel and it was yummy!
A small Pequod’s pizza that I got to go to take back to my hotel, yum!

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? Take this Food Tasting Walking Tour for a fun and delicious few hours!

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.

To Sum it Up

Chicago is one of my favorite U.S. cities as there is so much to do and a little something for everyone.

I didn’t mention any museums because there are many, but if you only have time for one check out the Art Institute of Chicago. It is located between Millennium and Grant Park.

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.

Route 66 sign
Where Route 66 begins heading west out to CA!

Depending on time and the number of attractions you plan to see, look into getting a CityPass Chicago or Go Chicago Card. 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. If visiting only a few, then these passes might not be woth it.

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.

Start planning for your trip to Chicago and explore the best flight deals today!

Getting Around

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.

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Disclaimer: My post may contain affiliate links, which means I may receive a small commission if you click a link and purchase through that link. It won’t cost anything to you to use these links but is very much appreciated. Thank you!

Traveling to Chicago soon? I’ve put together the top things to do in the Windy City that you don’t want to miss. Explore the Chicago River, the best pizza, where to capture downtown’s skyline and Lake Michigan to name a few! #chicago #chicagotravel #usatravel #bestofchicago #chicagoguide

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34 Comments

  1. Really liked this article. Lots of good information, I even took notes lol. Hoping to go to Chicago in early September and will def check out the places you suggested. Thanks for sharing!!!

  2. Chicago looks like such a beautiful city! I’ve always wanted to visit. I had no idea they could reverse engineer a river, that’s crazy! And that pizza looks epic. Will be saving this post for my future visit!

    1. Yes, Chicago is such a great city with so much to do. I highly recommend visiting! Haha yes, I had no idea they could change the direction of a river either but it works. So glad that you found it useful for the future! 🙂

    1. The U.S. is so big that it’s hard to see everything in one trip. But yes definitely go to Chicago on your next trip to the U.S., it really is a wonderful city with so much to do! 🙂 My goal is to start doing more road trips too. You get to see so much more!

    1. You’re welcome! I’m so glad you found the info helpful. It will be cold but so beautiful in December, have a great time! 🙂

  3. One of my favorite cities! My cousin is supposed to get married there next July, hopefully covid goes away by then so the wedding takes place. I’m so ready to visit Chicago again!

    1. You have great taste! Chicago is a pretty great place for so many reasons. What a beautiful destination for a wedding. I hope you get to go for the wedding and to see the city again! 🙂

  4. I agree that the architectural river tour is one of the best things to do in Chicago! So many fun things to see and do. And Chicago’s food scene definitely deserves a post of its own!

    1. The architecture tour should be a must for all first-time visitors for sure! Such a great way to see the city, rest your feet, and admire incredible architecture. There are so many yummy places to eat in Chicago and yes deserves a whole post to that! 🙂

  5. There’s so much to do in Chicago. I always thought it was named Windy City due to the wind too, not the politicians, although that makes sense!
    The riverwalk looks beautiful and I’d have to have a photo taken with the bean and visit the Willis Towers for those views. Hope to use all this wonderful info one day.

    1. I think everyone thinks the name is because of the gusty winds off Lake Michigan, so you are not alone! Chicago has a little of everything and when it’s nice out the Riverwalk is an incredible spot. The views from Willis Tower are pretty epic and if you are brave enough to stand on the glass ledge! 🙂

  6. Really enjoyed this. I think Chicago is such an under-rated city, and definitely a place to visit for anyone interested in architecture. It’s a while since I’ve been but I still remember the delicious Lake Michigan Whitefish I had in one of the many lovely restaurants 🙂

    1. Thank you for the kind words Carole! I agree, Chicago doesn’t get as much attention as some other cities but really is an amazing place to explore. I have yet to try Lake Michigan Whitefish but I imagine I would love it. Thanks for the tip, I’ll definitely try it on my next trip! 🙂

  7. I love this post!! Lived in Chicago for almost 7 years in the past and you captured everything! Don’t forget to visit Sue the dinosaur at the field museum 🙂

    PS I just read a few months ago the Palmer house is set to close due to financial issues. I don’t know what the status is now but that would be a tragedy!!

    1. That is so exciting that you lived in Chicago! I know I would enjoy living there as I’ve visited enough to fall in love with it. Maybe one day… Oh no! I really hope the Palmer House doesn’t close down for good. I love that hotel as there is so much history and nostalgia there. Hopefully, they can figure something out and turn it around! 🙂

    1. Taking the architecture tour is by far one of the coolest things to do in Chicago! Plus you get to rest your feet from tons of walking. 🙂

  8. I have family in Chicago and they are huge Cubs fans and we always talk about going to see a game! This is such a great comprehensive guide for when I finally do visit!

    1. Oh that is so cool that you have family there which makes for a great excuse to visit! Cub games are so fun plus the park has so much nostalgia. 🙂

  9. Actually I did quite ok on your list. I’m surprised. I don’t know if Millennium park existed in 2000. But should have. Btw cocktails were expensive in the Signature lounge back then too. You’ve given me some great ideas for when I go back. I would love to do the mob tour. I didn’t see a show in the Chicago theatre either.

    1. It sounds like you have seen the most important sights to see in Chicago! I’m not sure when Millenium Park came about. I know it was there in about 2006 when I first visited. Something to see next time! Omg yes, drinks will likely always be expensive as you are paying for the epic view! I found the mob tour so fascinating and relearned a lot of history I had forgotten. 🙂

    1. Ah that’s such a bummer. I had it booked for May and it was hard having to cancel. Now we both have something to look forward to next year! 🙂

    1. What a great name! 🙂 Thank you, I’m glad you enjoyed reading about all the cool things to do in Chicago. There is a lot to see and is a city that has something to offer everyone!

  10. I didn’t know that the city was actually dubbed after politicians. I miss Navy Pier! It was my favourite spot in Chicago when I visited as a teen.

    1. Haha yes, it is funny how names originate and then take on another life of their own. The Navy Pier is so fun and I imagine as a teenager even more so! 🙂

    1. Yes, a great location to visit next year and it’s one of those cities you can’t help but love! 🙂

  11. I lived in the US for over three years but never visited Chicago. Your photos inspired me to definitely check it out next time I’m in the country!

    1. There are so many great cities to visit in the U.S. and it takes some time to cover them all. Now you have a great reason to go back and spend some time in Chicago! 🙂

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