Get ready for an unforgettable summer in the Windy City! With summer just around the corner, I want to share my ultimate Chicago Summer Bucket List with you. Being a proud Chicago native, my favorite part about living in this city is the endless activities to explore.

Whether you're a local seeking fresh inspiration or a visitor ready to dive into the city's vibrant outdoor scene, my summer bucket list will help you make the most of Chicago’s summertime charm! From outdoor activities to live music, read along to see what I’ll be up to this summer.

Cruse the River via Donut Boat

Spend a day on the Chicago River with your friends! You can rent an 8-passenger circular donut boat that’s perfect for floating around the lake and enjoying drinks, food & Chicago sunshine.

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Break a Sweat

Let’s sweat it out in the heart of Chicago! Join me for a series of free 45-minute workouts at Millennium Park. From Pilates and Yoga to Cardio Kickboxing and Zumba, there are so many fun classes I want to try.

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P.S. Chicago is home to a wide variety of fantastic workout studios just waiting to be discovered. Use my ClassPass link to try one for free!

Go Berry Picking

Looking for something fresh to do (and snack on) this summer? Chicago has multiple nearby farms to pick your own berries- perfect for a tasty snack or picnic!

Where to pick your own berries near Chicago »

Bike the Lakefront Trail

If you’re looking for a leisurely bike ride, Chicago’s Lakefront Trail is the perfect place! This scenic 18-mile path winds its way alongside the shores of Lake Michigan, offering stunning views and a refreshing breeze.

P.S. Bike Lake Shore Drive on Sunday, September 3, 2023 Learn more »

Root, Root, Root for the Home Team

Whether you're a diehard fan or just there for the mouthwatering hotdogs, a trip to one of Chicago's iconic MLB stadiums is a must. Historic Wrigley Field and the modern Guaranteed Rate Field provide the perfect atmosphere for spending time with family and friends!

Jazzin’ at the Shedd

Experience a mix of live jazz, breathtaking city views, and incredible marine life at the Shedd Aquarium's Jazzin' at the Shedd series this June—a night out that highlights the best of Chicago's skyline and vibrant music scene!

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Visit Salt Shed

After years of passing by this old warehouse along the expressway, it's exciting to see the building’s transformation into a stunning new outdoor venue! Check out some of the events and concerts lined up for this summer:

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Discover Chicago’s Past

A little random, but the Gangsters & Ghosts Tour has been on my Chicago bucket list for YEARS! Located in the Loop, this 2 hour, 1.5 mile tour is the perfect way to learn about the ghosts & gangsters of historic Old Chicago.

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For something a bit more lighthearted and sweet, the Donut Tour is one of my go-to recommendations for visitors.

Attend a Neighborhood Festival

Did you know, Chicago has 77 distinct communities? Explore the diverse neighborhoods this summer, each offering a unique blend of cultures and experiences! Below is a list of some local events and festivals to attend to learn more about the people who make each community unique.

Festivals and events happening in Chicago this summer »

Ravinia Concert

Ravinia Festival, the oldest music festival in North America, offers a diverse lineup of concerts and events throughout the summer, featuring renowned artists like John Legend and Yo Yo Ma and the annual summer residency of the Chicago Symphony Orchestra. Resting on a 36-acre park you can pack a picnic and relax with friends or eat at one of the park’s restaurants!
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P.S. If you’re coming from the City or the North Shore, take the Metra! The train drops you right off at Ravinia’s entrance.

Day Trip Adventure

Looking to get out of the city for a day/weekend? Here are a few places surrounding Chicago that could be a refreshing experience for you and some friends! Check out the list below for a quick

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Explore Chinatown

Chicago's lively Chinatown is a vibrant neighborhood filled with Chinese-inspired architecture with delicious dining, teahouses and shopping experiences. I’ve never actually been, but so many people have said it makes for a great afternoon adventure! If you’re in the Loop or River North area, you can actually get to Chinatown via Water Taxi.

Jump in the Lake

Have you heard about the Friday Swim Club? Each week at 7 am during Chicago’s summer months, locals gather for a swim in the lake before work! It’s a refreshing way to start off your weekend, enjoy the water and share some coffee before heading into work.

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Attend a Garden Walk

From front yards to backyards and rooftops to parkways, neighborhoods, such as Bucktown and North Center, host annual Garden Walks to showcase the many unique gardens and green spaces they have to offer.

Can’t make it to a Garden Walk? Stroll through the 385-acre Chicago Botanic Garden in Glencoe.

Catch a Movie Under the Stars

Looking to catch a box-office hit? From Wrigley’s Gallager Way to the Rooftop Cinema Club in West Loop and even in Millenium Park, you’re sure to find your favorite movie on the big screen.

Host a Summer Event

Save the date — Thursday, August 10! An exciting event is in the works. Join my email list below to be on the invite list!