12 Popular Things to Do in Chicago, Illinois While on Vacation

It’s an exciting place to be! A city with over 2.6 million people and rich history, there are many different places to visit and things to do in Chicago.

Things to Do in the Windy City

Chicago is an exciting place to be! A city with over 2.6 million people and rich history, there are many different places to visit and things to do in Chicago while on vacation. From architecture and river tours to jazz music and deep dish pizza, the local culture is definitely worth exploring. Below we’ve recommended some of the more popular things to do while visiting the windy city.

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1. Willis Tower SkyDeck

12 Popular Things to Do in Chicago, Illinois While on Vacation

Formerly known as the Sears Tower, the Willis Tower should definitely be on everyone’s list of things to do in Chicago. At 1451 feet, this incredible skyscraper is the 3rd tallest building in North America and is home to the highest observation deck in the U.S.

Located just a 20-minute walk from Millenium Park, the Willis Tower is where you will find several attractions including an interactive Chicago experience, the SkyDeck, and The Ledge.

The interactive Chicago experience is a brand-new exhibit that takes you through the Windy City’s rich history, famous foods, incredible architecture, popular events, and homegrown celebrities. The exhibit is a fun way for the whole family to learn a little something about Chicago, before heading up to the SkyDeck.

Next, take the elevator up 103 floors to the fully-enclosed SkyDeck where you will experience some of the best views of Chicago and beyond. In fact, on a clear day, you can see approximately 50 miles and four states (Illinois, Indiana, Michigan, and Wisconsin)!

Lastly, don’t forget to head out onto The Ledge. The Ledge is a glassed-in box that extends 4.3 feet out from the SkyDeck. At 1353 feet up, the views from inside are incredible. But if you have a fear of heights, The Ledge (which has a glass floor) is probably not for you!

General Admission is approximately $30 and includes access to the interactive Chicago experience, the elevator ride to the Skydeck, and The Ledge. All tickets are for timed entries, so you will need to plan your visit accordingly.

Recommended by Marianne of Pasta Pretzels and Passports.


2. Architecture Tour

12 Popular Things to Do in Chicago, Illinois While on Vacation

Instead of a walking tour, one of the best ways to learn about and see Chicago is from the water on an architectural tour! Chicago is home to various gorgeous buildings that tell the story of the city’s boom from the Age of Skyscrapers to the present day.

On the tour, visitors get the opportunity to cruise down the beautiful Chicago River and admire Art Deco, Modern, Gothic Revival, and Postmodern, along with interesting facts like the Marina Bay Towers (affectionately known as the corn cob buildings) were built to be a city within a city. Also, depending on the guide, as they cruise down the river, they will share other fun spots in Chicago that you should check out!

On average, the tours last approximately 1 hour 15 minutes and cruise by more than 40 famous buildings and places like the famed Navy Pier, the John Hancock Building, the Willis Tower, and many more. Another bonus, these tours are offered frequently throughout the day, especially during the summer, so you can easily fit one into your packed sightseeing itinerary. Many of the tours start from either Michigan Ave. or the Navy Pier, depending on the company.

After the tour, check out the vast assortment of excellent vegan restaurants in Chicago. From fried mac-n-cheese balls and donuts to perfectly styled plates of pasta, you won’t leave Chicago hungry!

Recommended by Rebecca from Veggies Abroad.


3. Chicago River Walk

12 Popular Things to Do in Chicago, Illinois While on Vacation

Looking for one of the best things to do in Chicago? If so then why not go for a picturesque stroll along the Riverwalk on the Chicago River? Not only does it make for a great date night in Chicago, but it’s an amazing attraction on the south bank that was recently completed in 2016.

In fact, this amazing attraction consists of a series of multi-use walking paths that were created in an effort to make the city more sustainable and the waterfront more accessible to locals and tourists alike. 

So, enjoy a beautiful fusion of urban architecture with natural beauty as you walk past floating gardens, take in awesome permanent art displays, and try a truly unique Chicago cycleboat tour. 

Because as the name suggests, you and everyone else aboard this unique boat will be using bike power to pedal yourselves down the river. 

Just don’t leave the river without grabbing a sweet treat from Sweet Home Gelato first – especially on a hot summer evening. 

You can also grab a cup of coffee – or something a little stronger – at Tiny Tapp and then relax, with a drink in hand, at River Theater.

Other fun things to do along the Chicago Riverwalk include paying your respects at the Vietnam Veterans Memorial Plaza before embracing the island vibes and partying like a rockstar at the Island Party Hut Tiki Bar & Grill. 

In fact, they even have this awesome Island Party Boat that will take you, and the tiki bar, on a 75-minute, scenic cruise along the river for $30 per person.

Recommended by Linda of Midwest Explored.


4. Green Mill Jazz Club

12 Popular Things to Do in Chicago, Illinois While on Vacation

More than 100 years old, the Green Mill jazz club is a Chicago institution. It’s the kind of place you go to soak in the atmosphere, even if you’re not a jazz music fan. The cozy club has an old-time vibe with big band music and swing dancing several nights of the week.

Being at the Green Mill truly feels like being transported back in time to the 1930s or ‘40s. Though it’s not required, some folks even dress up in vintage clothing as they dance to the vibrant music created several decades before they were born

There’s so much history in this club. Legends like Billie Holiday and Louis Armstrong took the stage here years ago, and the club has been featured in more than a dozen mainstream movies. But more than that, the business played a major role in Chicago’s infamous gangster history.
The Green Mill was used to smuggle alcohol during Prohibition, and mobster Al Capone used to frequent the establishment. You can still sit in his favorite booth today. He chose it because the booth has views of both exits, allowing him an easy escape in case his enemies or the police came looking for him.

Spending an evening at the Green Mill is an experience all visitors to the Windy City should have once. Arrive by subway, since street parking in the Uptown neighborhood is scarce. Visitors must be age 21 and older, and there’s usually a cover charge, so set aside $10-20 for the entry fee.

Recommended by Scott of the Quirky Travel Guy.


5. Breakfast on Route 66

12 Popular Things to Do in Chicago, Illinois While on Vacation

Chicago has so many wonderful things to do that it can be difficult to choose the right ones to fill your itinerary. However, eating breakfast at the beginning of Historic Route 66, at Lou Mitchell’s diner, is an easy addition. 

Many people don’t know that the starting point of Route 66 in Chicago changed a few times since the highway started in 1926. The sign currently says Route 66 started on Jackson Blvd and Michigan Avenue. However, the historic highway originally began on Jackson Boulevard right in front of Lou Mitchell’s. The diner opened three years before the highway began.

Lou Mitchell’s is well known for having some of the best breakfast food in Chicago. On weekends, visitors who arrive after 10 am will find themselves waiting in a line that can wind around the block. Don’t worry if you do have to wait in line, though. The restaurant serves homemade donut holes to the diners who are waiting in line. 

Note: The restaurant is cash only but there’s an ATM at the entrance.

Lou Mitchell’s opens at 6 am on weekdays and at 7 am on weekends. It closes at 2 pm daily. Get there early to ensure you don’t have to waste valuable sightseeing time waiting in line at this historic Windy City diner.

Recommended by Brodi of Our Offbeat Life.


6. Chicago Deep Dish Pizza

12 Popular Things to Do in Chicago, Illinois While on Vacation

If you’re visiting the Windy City, you must indulge in Chicago deep-dish pizza. This is the opposite of NY or Italian style pizza, which are both thin crusted. And if you think you’ve had deep-dish pizza, you haven’t had the real deal if you haven’t had it in Chicago!

Chicago-style pizza is thick all over and built upside-down compared to most pizzas so that the sauce is on top. A thick-crust layered with toppings, tons of mozzarella cheese, and a layer of tomato sauce,

Many Chicago pizzerias advertise deep-dish pizza, but if you’re visiting for the first time, you’ll want to try one of the classics. Pizzeria Uno is the original Chicago deep-dish pizza maker. There are now multiple locations, but the original can be found at 29 E Ohio St. Check out this historic landmark or Lou Malnati’s Pizzeria which also may be considered original. Some say Lou Malnati who was the head chef at Pizzeria Uno was the actual creator of deep-dish pizza. There are now also multiple locations of this pizza dynasty.

If you try the classics and want to keep going with creative pizza’s, Gino’s East should also be on your list of pizzerias. The Chicago Fire is probably their most famous with spicy sausage, roasted peppers and onions. Other popular pizza choices are the Italian Beef with giardinera and the Burger and Fries—yes, these are pizzas, not different dishes.

Recommended by Denise of Chef Denise.


7. Art Institute of Chicago

12 Popular Things to Do in Chicago, Illinois While on Vacation

The Art Institute of Chicago is one of the major attractions of the Windy City, and one of the premier art museums in the world. It was founded in 1879, making it one of the oldest art museums in the world.

The institute features major works dating back to ancient Egypt, as well as works from the Renaissance, Baroque, Classical, Romantic, and Modern eras.

One of the best-known works at The Art Institute is A Sunday Afternoon on the Island of La Grande Jatte, the monumental painting by Georges Seurat. The painting was designed in the pointillist style, using tiny points of color that combine to form a unified tableau. 

Other masterpieces at The Art Institute include American Gothic by Grant Wood, The Old Guitarist by Pablo Picasso, The Bedroom by Vincent Van Gogh, and Water Lilies by Claude Monet. The museum also includes sculptures by Rodin, Degas, and much more. Special exhibitions have ranged from subjects as diverse as Ancient Egyptian art to Cezanne. 

The Art Institute is not just a museum. It is also dedicated to educational programs and art scholarship. They also offer 30-minute guided tours of the museum’s collection, as well as “Gallery Talk” lectures.

The museum is conveniently close to the Chicago Lakefront Trail, near Millenium Park and Grant Park, and within a 15-minute walk to Willis Tower. It is open every day except Tuesdays and Wednesdays.

With such a rich collection of some of the best art in the world, the Art Institute is a can’t-miss destination for any trip to Chicago. If you’re an art lover, take a private Art Institute of Chicago tour!

Recommended by Merry Allison Virginia Vacation Guide.


8. Chicago Hop On/Hop Off City Tour

12 Popular Things to Do in Chicago, Illinois While on Vacation

Chicago has a series of buses and trains stretching across the city and beyond for local public transportation. It’s hard to pass up a ride on the Windy City’s famous above-ground L trains, and, if you want to extend your vacation, you can even hop on a bus from Chicago to New York

But for tourists looking to see all the culture, activities, art, and more that Chicago has to offer, the best option is to grab a ticket for a hop-on-hop-off bus. These buses have travelers in mind and are the perfect way to navigate the city, hit all the main attractions, and learn a little about the city’s history as you go along.

You can choose to simply sit on the bus for a panoramic view of Chicago, or get on and off at whichever stops you choose. The majority of hop-on buses are double-decker, some with an open-top, which gives an unparalleled and unobscured view of the city as you drive along.

Most hop-on-hop-off services go to major landmarks, including John Hancock Center, Adler Planetarium, Soldier Field, Grant Park, Magnificent Mile, Navy Pier, and more. The majority of companies use color coding to show which routes stop where, very similar to typical public transportation and subway lines (but with much less hassle).

Some companies also with various restaurants, tours, and attractions, so you may get a discount with your ticket! There are multiple hop-on-hop-off bus companies in Chicago, like BigBus Chicago, so try to check for one with a route that picks up near your hotel or accommodations.

Recommended by Rachel of Buck List Places.


9. Navy Pier

12 Popular Things to Do in Chicago, Illinois While on Vacation

Located on Lake Michigan, the Navy Pier is one of the top things to do in Chicago. It’s actually one of the top attractions in the Midwest and sees more than nine million visitors each year. You’ll find parks and gardens, shopping, restaurants, and lots of other options for things to do.

Take a ride on the Centennial Wheel and take in beautiful views of the city and Lake Michigan. Then head over to Polk Bros Park green space and enjoy live music and time outdoors. Then take a walk over to the East End Plaza where you will find public art and gorgeous views of the lake.

If you’re looking for a little retail therapy, you can check out the Fifth Third Bank Family Pavilion where you’ll find shopping and restaurants. There is also the Navy Pier Beer Garden where you can enjoy local craft beer, food, and live outdoor performances.

Lastly, check out your options for cruises! You can take architecture tours, speed boat tours, sunset cruises, and more.


10. Millennium Park

things to do in chicago millennium park

A public park managed by the Chicago Department of Cultural Affairs, Millennium Park is filled with permanent rotating art exhibits. The most notable sculpture is called the Cloud Gate, or more lovingly known as The Bean by locals.

Another popular piece of art is the Crown Fountain. The fountain consists of two 50-foot glass blocks at each end of a reflection pool. The blocks are interactive videos featuring Chicago citizens. It really is very unique.

Then visit the Lurie Garden which is a beautiful botanical garden located at the park. Take a guided tour through the ever changing plant life featured each season or even a scavenger hunt through the grounds.


11. Shedd Aquarium

12 Popular Things to Do in Chicago, Illinois While on Vacation

If you’re looking for fun things to do in Chicago with kids, you can’t go wrong with the Shedd Aquarium. Filled with aquatic wonders, touch experiences, and 4-D experiences, you’re sure to have a good time.

Put your eyes on a giant Pacific octopus, beluga whales, sharks, seahorses, California sea lions, dolphins and more. You can take shark feeding tours, learn all about belugas, and touch stingrays, sea stars, and sturgeon.

Check out the 90,000 gallon Caribbean Reef tank, get a diver’s eye view of 540 underwater species at the Wildlife Reef, and then check out dolphins at the Abbott Oceanarium.


12. St. Patrick’s Day

12 Popular Things to Do in Chicago, Illinois While on Vacation

Chicago goes all out and holds true to their reputation as one of the top St. Patty’s day celebrations outside of Ireland. Each year, a quick dye job leaves the Chicago River running green!
Here’s what you need to know to get the most out of the day’s festivities:

On the Saturday of Chicago’s St. Patrick’s Day celebration, you can watch boats dye the river bright emerald at 10:00 am from the River Walk. The spectacle lasts about 45 minutes. If you want to surround yourself in the brilliant shade of green, consider taking one of the river cruises that same day.

In 2022, the famous parade returned to the city for its 67th year running. To view the downtown parade, arrive at least 45 minutes before its scheduled start if you want to be anywhere near a street on the parade route.

Stock up on traditional Irish foods, beverages, and treats at an Irish imports store, especially if you’re visiting Chicago with kids and won’t be partying at the pubs. Pat and Jack’s Old Fashioned Store, Winston’s Market, and Gaelic Imports each have a large variety of Irish brands.

These are also excellent stores to explore if you’re in Chicago any other time of year! There’s a massive population of Irish immigrants and expats in the city so you’re sure to find authentic goods in these shops.

Recommended by Catherine of Postcard Narrative.


Things to Do in Chicago, IL on Vacation
Things to Do in Chicago, IL on Vacation
A city with over 2.6 million people and rich history, there are many different places to visit and things to do in Chicago while on vacation.

ABOUT THE AUTHOR
Alexandrea Sumuel

Alexandrea Sumuel is the founder of Wander With Alex, where she provides vacationers and travel enthusiasts with trip ideas, travel guides, news, and itineraries. She travels to experience, eat, and explore-- and, on occasion, escape! Alex’s mission is to help people travel better.

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Things to Do in Chicago, IL on Vacation