Summer In Chicago: 15 Best Things To Do

There’s just something about summer in Chicago that hits differently. I find it rather magical, the whole city seems to come alive,

Yes, it can get hot, but I’m from Florida, so I am used to that.

I’ve rounded up 15 amazing things to do in Chicago, some are iconic, some perhaps unexpected but all will help you enjoy this wonderful city a bot more.

If you’re planning a trip to Chicago in the summer, this list is for you. So grab a drink and let’s dive in!

Summer In Chicago: 15 Best Things To Do

Stroll Navy Pier And Ride The Centennial Wheel

You can’t do summer in Chicago without hitting Navy Pier. It’s a classic for a reason.

Stretching over 3,000 feet into Lake Michigan, it’s full of restaurants, shops, public art, and fun attractions.

I just love spending time here, there is always something different to see.

I always grab some Garrett Popcorn before walking the pier.

And if you’re into boat rides, it’s a perfect place to hop on a lake or river cruise. During the summer every Wednesday and Saturday there are fireworks in the evening which are surprisingly good.

The Centennial Wheel gives you a dreamy 360° panorama of the city skyline and the lake and is absolutely wonderful at sunset.

Book your Navy Pier Centennial Wheel Ticket in advance.

See The City From The Skydeck (And Step Onto The Ledge!)

The Willis Tower Skydeck is one of the top attractions in Chicago, and if you’re not afraid of heights, it’s a thrill.

You’ll take an elevator up to the 103rd floor. The views are spectacular!

Step into The Ledge, which is a glass box that extends out from the building.

It’s an adrenaline rush and an epic photo opportunity, but not for the faint of heart.

If this is something you will enjoy definitely give it a go it’s an incredible way to see the city.

Skip-the-line Skydeck entry with The Ledge experience

Take an Architecture River Cruise

River cruises are among my favorite things to do in a new city as they are such a great way to see the sights.

Architecture river cruises are hands-down one of my favorite activities in Chicago.

Cruising down the Chicago River with a knowledgeable guide pointing out the city’s most famous buildings is both relaxing and fascinating.

Its the best way to spend a morning or an afternoon, in my opinion.

You’ll hear about the Great Chicago Fire, the city’s rebirth, and how its architectural legacy developed.

Whether it’s your first visit or your fifth, this is one of those timeless experiences that never gets old.

If you’re looking for things to do in Chicago in summer that combine sightseeing and storytelling, this is a must.

Book a Chicago Architecture Cruise

Explore Millennium Park & Snap a Selfie with The Bean

This odd tourist attraction in Millennium Park is worth a visit, especially if it is your first visit.

It might be officially known as Cloud Gate, but let’s be honest, it’s The Bean, and that is how most people refer to it.

This giant reflective sculpture is iconic, and yes, it’s always surrounded by people taking selfies (myself included).

However, Millennium Park is so much more than just this sculpture.

You will find public gardens, art installations, free concerts, and plenty of green space to stretch out and relax.

It’s a great spot to take a break from the bustle of downtown.

The Hop-on Hop-off Sightseeing Tour by Open-top Bus can drop you here.

Hit the Beach? Yes, Really

You might not expect beach days in a big city, but Chicago delivers.

On hot summer days, locals and visitors alike head to Lake Michigan’s shoreline.

North Avenue Beach is great for people-watching, playing volleyball, or grabbing a smoothie from the beach café.

Oak Street Beach is smaller and more relaxed, and one of the best places to visit in Chicago for those classic summer-in-the-city vibes.

If you can, go early in the morning or around golden hour.

You will find it less crowded and much more photogenic.

It’s also one of my favorite things to do in the summer when I need a break from the busy city.

Here are some tips on What To Wear in Chicago in the Summer: Chicago Outfit Ideas

Bike (or Walk) the Lakefront Trail

The Lakefront Trail is one of the most beautiful places to visit in Chicago.

This 18-mile path stretches from Edgewater in the north to South Shore in the south and runs right along Lake Michigan.

I love renting a Divvy bike and exploring different parts of the city at my own pace.

There are amazing skyline views, peaceful lake scenes, and plenty of stops for snacks or people-watching.

It’s a great way to see more of Chicago while getting some fresh air.

If you don’t want to go it alone here is a Lakefront Neighborhoods Bike Tour.

Visit the Art Institute of Chicago

Need a break from the heat, or a rainy day plan? The Art Institute is well worth a visit.

It’s home to an incredible collection that includes Monet, Van Gogh, Georgia O’Keeffe, and Grant Wood’s iconic “American Gothic.”

I always find myself drawn to the Impressionist Art wing and the more peaceful Asian galleries.

If you take a visit don’t miss the Thorne Miniature Rooms. They’re like little dollhouses of historical interiors, and weirdly fascinating.

Skip-the-line museum admission

Summer In Chicago: Watch a Cubs Game at Wrigley Field

You don’t have to be a sports fan to appreciate a baseball game at Wrigley Field. If a game isn’t your thing, you can always take a tour.

Not many can resist the historic stadium, the buzz in the stands, the chance to sing “Take Me Out to the Ball Game” with thousands of strangers and a Chicago-style hot dog.

If it isn’t your thing, even just wandering around Wrigleyville before or after the game is fun.

The area is full of lively bars and a strong sense of community.

Catch a Sunset from a Rooftop Bar

Chicago in summer means rooftop season. There are plenty of stunning spots, all with incredible views.

My favorites are Cindy’s Rooftop (above the Chicago Athletic Association Hotel) with views over Millennium Park.

The LondonHouse rooftop that overlooks the Chicago River.

It’s perfect for sipping a cocktail, enjoying the breeze, and watching the sky change colours as the sun sets behind the skyscrapers.

Cruise on Lake Michigan

Want to level up your Chicago experience? Take a cruise on Lake Michigan.

Whether it’s a laid-back daytime sightseeing cruise or a dinner cruise with live music, I know you will love it.

Being out on the lake gives you a different perspective of the city.

On Saturday nights, you can even time your cruise with the Navy Pier fireworks for an extra bit of magic.

This is one of the best things to do in Chicago in July and August to take advantage of the lakefront.

Lake Michigan dinner or fireworks cruise

Snap Photos at the Chicago Riverwalk

The Riverwalk is one of those beautiful places in Chicago that blends city energy with a relaxed vibe.

There are public art installations, floating gardens, cafés, and even kayak rentals.

It’s a great place to stop, sit, and watch the boats go by or to walk along and discover something new around every bend.

If you’re there in the evening, the city lights reflecting on the river are truly something else.

Try going right before sunset for the golden hour glow.

Read my reviews of the 15 best Tours in Chicago.

Attend A Summer Festival During Summer In Chicago

No matter when you visit in June, July, or August, there will be something going on.

From Taste of Chicago and Lollapalooza to neighborhood art fairs and food truck festivals, the city knows how to celebrate summer.

Many events are free, and it’s one of the best ways to experience the culture, music, and creativity of Chicago all at once.

It’s also one of the most popular things to do in Chicago in summer.

What’s Chicago without pizza? Here are the best places in Chicago to get pizza!

Summer In Chicago: Take a Street Art or Food Tour

Want to explore Chicago’s creative side?

Book a tour in a neighbourhood like Pilsen, Wicker Park, or Logan Square.

These areas are full of colourful murals, independent shops, and some of the city’s best food.

I’m always the person who explores the back streets and goes looking for the locals and food delights.

Nothing helps you understand a city as much as the food it offers and the people who live there.

It’s one of my favorite things to do.

Here are 15 Best Restaurants In Chicago You Must Try.

The Ultimate Foodie Walking Tour with Tasty Stops.

BYOB Spray Paint and Sip Workshop

Experience Chicago at Night

From rooftop lounges to historic jazz clubs, Chicago has a rich nightlife scene.

If you’re visiting in the summer, your evenings can include anything from a candlelit architecture cruise to a walking ghost tour through the Loop.

I’ve also done a few nighttime photography walks, and the city truly sparkles after dark.

If you’re looking for things to do in Chicago in June, July, or August that feel a little special, start here. Honestly, it’s one of the most memorable things to do in the summer.

Here is my post about the 15 Best Things To Do In Chicago At Night.

Ghosts & Hauntings of the Windy City Walking Tour

Dummer In Chicago: Play Like A Kid At The Museum Of Ice Cream

Okay, if you’re looking for something totally whimsical (and super Instagrammable), you have to check out the Museum of Ice Cream.

I went with a friend not expecting much, and we ended up having so much fun.

It’s part museum, part interactive experience, and part candy-coloured dream world.

You get to wander through different themed rooms, think giant sprinkle pools, a retro diner, tunnels of pink bananas, and more.

And yes, you get to eat ice cream along the way.

It’s one of those places that makes you feel like a kid again, whether you’re visiting solo, with your partner, or bringing kids along.

I’d recommend booking ahead, especially in the summer, as it’s a popular spot.

And wear something fun or bright, because this is a place where you’ll want to take a million photos.

Museum of Ice Cream Entry Ticket

Packing List Suggestions When Visiting Chicago In The Summer

No matter if you fly or drive to Chicago, read my tips on how to pack lightly in a carry-on.

This unisex RFID blocking concealed travel pouch is lightweight and comes in several colors.

These RFID Sleeves D sleeves are another perfect solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday.

It has Bluetooth connectivity and is a breeze to use for taking selfies.

I never leave home on a trip without my Bobble filtration bottle. 

The replaceable carbon filter ensures fresh water whenever you need it.

This foldable water-resistant backpack would be great.

Not all beaches are created equally and these quick dry slip-on Aqua shoes will come in handy for the beaches in Chicago.

These men’s quick-drying trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in a lot of lens colors and frame designs and are extremely affordable too.

If you are fond of aviator-style sunglasses, these polarized aviators may interest you.

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