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The Ultimate Guide: 12 Things to Do in Chicago During Summer

chicago cityscape

By Zoey Carter

Imagine this. You’re in a city, a stunning architectural masterpiece with skyscrapers kissing the clouds. A rich cultural tapestry is woven through its heart and the smell of deep-dish pizzas and gourmet masterpieces wafting through the air. Welcome to Chicago! But hold on, the real treat starts when summer rolls around, ushering in those long, lazy sun-kissed days and delightfully warm nights.

When summer hits, Chicago cranks up the heat, not just the temperature but also the vibrant energy that spills onto the streets. The city is alive with the pulsating beats of outdoor concerts, the buzz of lively festivals, and the delightful sound of children’s laughter echoing from the lakefront beaches. It’s when the city’s parks and gardens put on a dazzling display of colors, the rooftop bars brim with high-spirited chatter, and Lake Michigan doubles up as a giant mirror, reflecting the summertime revelry. Chicago in summer is a realm of endless fun, a giant playground where every street corner, sandy beach, and river bend serves up a fresh slice of adventure.

Scratching your head, wondering what to do in Chicago in the summer? No worries! We’ve whipped up a handy guide packed with twelve must-do activities for a fun-filled summer in the Windy City. There’s a little bit of everything: leisure, adventure, chill-out spots, and heart-pounding excitement. So, whether you’re a first-timer or a seasoned local, we guarantee a summer in Chicago brimming with memories that’ll last a lifetime. Let’s dive in, shall we?

Chillax on the Chicago Lakefront

First, we’ve got the lakefront, Chicago’s version of beach heaven. It’s got everything a beach bum could ask for sun, sand, and a lot of fun! Favorite spots like North Avenue Beach and Oak Street Beach, two of the best beaches in Chicago, are perfect for soaking up the sun, losing yourself in a good book, or knocking around a volleyball. Just don’t forget the golden rule: Sunscreen is your best friend!

Paddle Out on Lake Michigan

Lake Michigan in Chicago
Lake Michigan on a beautiful day, Chicago, USA.

Fancy a bit of water adventure? Then, it’s time to hit Lake Michigan. Rent a kayak or paddleboard and let the vast, serene waters of the lake or the iconic Chicago River be your playground. It’s not just a workout for your muscles, but your eyes will also get a treat with a unique view of the amazing Chicago skyline. Trust us, it’s a sight to behold!

Enjoy the Great Outdoors with Alfresco Dining

Chicago’s alfresco dining options are as diverse and exciting as the city’s skyline. The city offers a smorgasbord of open-air dining options, from cozy riverside bistros to casual beachfront hangouts, each offering a unique culinary experience.

For a meal with a view, head down to the River Roast on the Chicago River, where you can watch the boats sail by as you savor their signature roast meats. If you’re closer to the lake, The Dock at Montrose Beach offers delicious seafood with the soothing sounds of waves lapping the shore. So, grab an outdoor table, dive into Chicago’s famous dishes, and let the warm summer sun be the perfect seasoning for your meal. And hey, remember, holiday calories don’t count!

Embark on a Memorable Boat Cruise

Immerse yourself in Chicago’s striking beauty with a scenic boat cruise. Whether it’s a romantic dinner cruise under the starlit sky or an enlightening architecture tour during the day, there’s something for everyone. The fresh lake breeze and panoramic city views are sure to leave an indelible mark on your memory.

Dance the Day Away at a Summer Festival

When it comes to summer festivities, Chicago is hard to beat. From the electric atmosphere at Lollapalooza to the soul-stirring melodies at the Grand Park Music Festival, there’s a festival to match every mood. Let the music fill your soul and the city’s energetic vibe carry you away.

Jump into Action with Beach Volleyball

Nothing screams ‘summer fun’ quite like a rousing game of beach volleyball on a Chicago beach. Regardless of your skill level, pick up a volleyball, invite some friends, and experience the thrill of a friendly match on the sands of North Avenue Beach or Oak Street Beach. The sandy courts and inviting water provide the perfect backdrop for an active summer day.

Witness the Skyline Sparkle at Navy Pier

Chicago Navy Pier
Chicago Navy Pier at Night

Navy Pier is a hive of summertime activities, but when dusk falls, the real spectacle begins. Regular fireworks displays paint the night sky in vibrant hues, creating a dreamy setting for an unforgettable night. It’s an enchanting experience that adds a splash of magic to any summer evening in Chicago.

Elevate Your Night at a Rooftop Bar

Chicago’s rooftop bars are the city’s crowning jewels, offering up the best bird’s eye views, and they’re tailor-made for those balmy summer evenings. Here, you can sip on your go-to cocktail while soaking up panoramic views of the city’s glittering skyline. It’s the perfect way to kick back and reflect on your day’s Chicago summer escapades.

Fancy a drink with a view of the Magnificent Mile? Head over to the rooftop lounge at the Peninsula Chicago. For an unmatched view of Millennium Park and Lake Michigan, Cindy’s at the Chicago Athletic Association Hotel is your spot. And then, there’s LondonHouse‘s tri-level rooftop, offering a 360-degree view of the city that’s absolutely breathtaking. So, here’s to summer in the Windy City, and remember, the higher the bar, the better the view!

Experience Fitness and Films at Millennium Park

More than just a scenic spot, Millennium Park brims with activities all summer long. From energizing workout classes that make fitness fun to cozy movie nights under the starry sky, there’s something for everyone. Immerse yourself in this dynamic atmosphere and make the most of your summer in the city.

Discover Chicago on Two Wheels

Travel, summer and couple on bike at beach for date on promenade in Chicago, USA sunshine with smiles

Why not explore Chicago at your own pace? Rent a bike and journey through the city’s diverse neighborhoods, cruise along the gorgeous lakefront, or navigate the bustling downtown streets. It’s a fun, healthy way to see the city and soak up that summer sunshine.

Engage with History and Art at Chicago’s Museums

Beat the summer heat and step into one of Chicago’s premium museums. Visit the Art Institute of Chicago, the Field Museum, or the Museum of Science and Industry for a dose of culture, art, and history. It’s a refreshing break from the summer heat, and who knows, you might even learn something new!

Uncover Architectural Wonders

Known for its architectural innovation, Chicago is a playground for design enthusiasts. Embark on an architecture tour and marvel at the iconic buildings that shape the city’s skyline. Each structure has a story to tell, adding another layer to the rich tapestry of Chicago’s history.

With so many places to visit, a reliable and comfortable ride is essential. That’s where Ideal Charter comes into the picture. With exceptional services and friendly staff, they’ll ensure all your transportation needs are taken care of, leaving you to focus on making unforgettable summer memories.


Closing Thoughts on Chicago

Chicago in summer is an explosion of vibrant colors, enticing aromas, soulful sounds, and unforgettable experiences. With this ultimate guide in hand, your summer in the Windy City is guaranteed to be a whirlwind of excitement. So what’s the hold-up? Jump into the adventure that is summer in Chicago.


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