Things to do in Chicago: 14 Top Activities and Attractions

Things to do in Chicago: 14 Top Activities and Attractions

When planning a vacation or road trip, it’s important to choose a destination, choose your dates, and make your reservations

For upcoming visitors, If you’re traveling to Chicago, there is so much to see and do that it can be challenging to decide on the best activities and attractions to see after you arrive. So, if you’re looking to shop til you drop along the Magnificent Mile, explore the Chicago Riverwalk, check out the Chicago Architecture Center, or simply get a taste of Chicago, we’ve got you covered.

When you land at the airport, you’ll want to hop in your rental car and start your Windy City adventure. You’ll just need to pick a place to start. Here’s your guide to the Windy City that will help you plan your trip and have the most fun.

1 – Laugh Factory 

One of the best parts of a vacation is relaxing and relieving the stress of our day-to-day lives. One great way to relieve stress and relax throughout your whole body is through laughter. For a good laugh while you’re in Chicago, visit the Laugh Factory any night of the week.

2 – The Ribbon 

If you’re headed to Chicago during the winter months, you can go ice skating on The Ribbon at Maggie Daley Park. In the off-season, you can rollerblade, roller skate, or ride a non-motorized scooter for free any day of the week from 6 am – 9 pm.

3 – Outdoor Yoga 

Yoga can be a part of any vacation because you can practice yoga anywhere. There are outdoor yoga classes in Chicago almost every day of the week at either Lincoln Park or Washington Square Park. Chicago is a busy city, so it’s nice to have a way to unwind and recenter yourself. 

4 – Lake Michigan 

Chicago is one of the largest cities in the United States, and there’s so much to see and do that you can forget that it has local beaches on the shores of Lake Michigan. You can even go for a ride on the Tall Ship Windy and take in Chicago’s skyline from the water. Don’t forget to hit the trail and explore the Navy Pier, Chicago’s iconic lakefront destination.

5 – Bad Axe Throwing

One of the most exciting new ways to have a good time with your friends is axe throwing. It’s so popular that even celebrities show up to try their hand at axe throwing so that you can have some food (We recommend Chicago-style deep-dish pizza!), fun, and maybe catch a glimpse of a celebrity at Bad Axe Throwing. 

6 – Lollapalooza 

Lollapalooza is an annual event in Chicago. A four-day music festival with a variety of music genres to enjoy, and it’s been going strong for over thirty years. It’s never too early to start planning for next year’s Lollapalooza. Make sure to grab your concert tickets before they’re sold out.

7 – American Girl Place

Most kids in North America are either about sports like basketball, trips to the local zoos like Lincoln Park Zoo, or the infamous American Girl. If you have a special little reader with you on your trip that enjoys the American Girl series of books and dolls, you may want to plan a visit to American Girl Place. You can have brunch, afternoon tea, dinner, or schedule a trip to the hair salon for your doll and your special little reader. 

8 – Chicago Art Institute

It’s hard to envision enjoying a day of fun in and around Chicago without including the iconic Chicago Art Institute. The art collections on display come from all over the world, and the art exhibits capture centuries of artwork. 

If you want more, you can also visit Chicago’s Art District, and on the second Friday of every month, you can see more than 30 galleries with new exhibits. 

9 – Chicago Botanic Garden

Who can visit the “City in a Garden” without a trip to the city’s outdoor gardens? Besides, there’s something special about being surrounded by natural beauty. Like the Circle Garden, walking through the gardens at the Chicago Botanic Garden is a beautiful way to add memories to your vacation and enjoy just strolling around for a while. You can visit the garden again and again because the beauty there is seasonal and constantly changing.

10 – Von Bergen’s Country Market 

While you’re in the area, you’ll want to use your rental car to visit the Von Bergen’s Country Market in nearby Hebron, IL. The Von Bergen’s Country Market has a sunflower festival with over 30 acres of sunflowers and a sunflower maze. You can capture some gorgeous vacation photos, and how often are you surrounded by 30 acres of beautiful sunflowers?

11 – Twilight Paddle 

Fun happens when the sun goes down, and in Chicago, you can book a guided tour through the main part of the Chicago River to take in the skyline. You can also paddle through the city canyon with the city lights reflecting off the water all around you, creating a beautiful experience complete with a stop just east of the Lake Shore Drive Bridge, where you can view the fireworks show from the water. 

12 – Venteux

You can’t go on vacation without a great dining experience. Venteux Chicago is a French restaurant where you’ll find one of the youngest, most exciting chefs ever to be awarded the coveted Michelin star in the U.S., Donald Young, the Executive Chef and Partner at Venteux. So, before you leave Chicago, make sure you experience Venteux. 

13 – ChiTown Drive-In  

It’s easy to forget that the modern town of Chicago is also full of history. So, while you’re in Chicago, take a step back in time and visit the ChiTown Drive-In for a movie under the stars any night of the week. 

You can order snacks or dinner delivered to your car and enjoy a favorite movie like Harry Potter and the Prisoner of Azkaban, Ferris Bueller’s Day Off, or E.T. It’s also a fun way to show the younger generations the kind of fun people once had in the past.

14 – Catch A Sporting Event

Like many major cities around the United States, Chicago has professional sports teams that fans love to see in person when they have the chance. Depending on the time of year, you can see the Chicago Bears in an American football game at Soldier Field, or you can watch the Chicago Fire FC compete in a Major League Soccer match. 

Baseball fans are lucky because they have two Major League teams to choose from while visiting Chicago. Chicago is home to the Chicago Cubs at Wrigley Field on the North Side and the Chicago White Sox at Guaranteed Rate Field on Chicago’s South Side. During the winter season, there is also an annual skating rink for family and friends to enjoy near Wrigley Building.

Last but certainly not least for any sports fan, Chicago is home to the Chicago Bulls NBA team. Be sure to catch one of their games at the United Center.  If you can’t catch any games, go to the Chicago Sports Museum. The museum is interactive and pays tribute to all of Chicago’s teams. 


Chicago should definitely be on your bucket list of places to see in the United States. It’s one of the largest cities, and it’s right on Lake Michigan. If you’ve got extra time on your hands, don’t hesitate to check out some of the popular tourist attractions like Shedd Aquarium, Adler Planetarium, Millennium Park, Willis Tower Skydeck (formally Sears Tower), and more. 

With its beautiful architecture, art galleries and field museums filled with artifacts from ancient Egypt, food, and fun — you may have a hard time deciding what you want to do on your Illinois vacation. This guide should help you choose some of the top activities and attractions that will make your trip a memorable one for years to come.

Stress relief from laughter? It’s no joke |
Downtown Chicago’s #1 Museum | The Art Institute of Chicago
Circle Garden |

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