2025 Guide to Best Outdoor Activities in Chicago

Whether you’re a lifelong resident or a first-time visitor, Chicago offers a wealth of opportunities to embrace the great outdoors.

From picturesque parks to vibrant waterfronts, I have carefully curated a list of twelve activities that showcase the city's unique charm and beauty.

Whether you’re seeking adventure, relaxation, or a way to connect with nature, there’s something for everyone.

Join me as we explore the best spots to enjoy the fresh air and make the most of your time in the Windy City!

Riverwalk

Highlights
Stunning architectural views
Peaceful walking experience
Various seating options
Water taxis and guided tours
Perfect for photography

Riverwalk: A Stroll by the Stream of Chicago

During my recent escapades in Chicago, the Riverwalk truly called out to me. As I ambled along the picturesque waterfront, I was mesmerized by the stunning architectural views that framed the skyline. Each step felt like a new adventure, offering a unique blend of art, nature, and urban life.

What I adored most was the peaceful walking experience—a delightful escape from the city's hustle and bustle. The gently flowing river created a relaxing backdrop, making my stroll feel almost meditative. With plenty of seating options, I found cozy spots to soak in the scenery while watching boats glide by, touching the surface like dancing sprites.

For those seeking a bit more thrill, the water taxis and guided tours offered vibrant modes to explore the city from a different perspective. My camera was thrilled to capture the lively dynamics of the Riverwalk, as it proved to be a haven for photography enthusiasts.

In essence, the Riverwalk is a must-visit for anyone looking to embrace Chicago's charm, blending culture and relaxation effortlessly. I left the Riverwalk revitalized, already daydreaming about my next visit!

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Grant Park

Highlights
Central location
Beautiful green space
Home to iconic attractions
Easy public transit access
Great food options nearby

Grant Park: A Green Oasis in the Heart of Chicago

When I strolled into Grant Park, I couldn’t help but feel enveloped by its vibrant energy and sprawling green spaces. Nestled in the heart of the city, this park offers a stunning escape from the urban hustle. As I walked along the pathways, the sight of the iconic Buckingham Fountain dancing to the rhythm of classic tunes was simply enchanting.

Being centrally located, it’s a breeze to hop on public transit and find yourself amidst lush lawns that beckon you to lounge or enjoy a casual picnic. The park is not only beautiful; it’s also home to various cultural attractions—like the Art Institute—just a stone’s throw away. If you find yourself feeling a bit peckish, there are plenty of delightful food options nearby to satisfy any craving.

Whether you’re seeking a serene spot to unwind, a picturesque venue for a leisurely stroll, or a vibrant pace to enjoy outdoor events, Grant Park has it all. This gem of Chicago truly embodies the essence of outdoor relaxation while remaining infused with the city’s artistic spirit. Don’t miss the chance to soak in its charm!

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Maggie Daley Park

Highlights
Lots of things to do
Different parks for different ages
Signs with age ranges provided
Security keeps the area safe
Open until 9pm during the week

First off, this park is not just your typical run-of-the-mill park. It's got a variety of different sections for different age groups, so whether you're a kid or an adult, there's something for everyone. And speaking of kids, the signs around the park make it easy to find which areas are best suited for their age range. As someone who values safety and security, I was pleased to see that this park had plenty of security personnel keeping an eye on things.

But let's get to the fun stuff. There are lots of things to do at Maggie Daley Park. From rock climbing to mini golf to skating in the winter months, you'll never be bored here. And if you're feeling competitive, challenge your friends to a game of tennis or basketball.

One thing I love about this park is that it stays open until 9pm during the week, so even if you're working late or just want some fresh air after dinner, this is the perfect spot.

Overall, I highly recommend checking out Maggie Daley Park if you're looking for a fun outdoor activity in Chicago. It's safe, it's diverse, and it's full of adventure!

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Riverwalk - East End - Gateway - 500 E

Highlights
Playground
Dog-friendly
Picnic area
Geodesic domes

First of all, let's talk about the playground. As a kid-at-heart, I had a blast trying out all the equipment myself. The monkey bars were a bit of a challenge for me, but I persevered and felt like a champion when I finally made it across!

If you're a pet owner, you'll be happy to know that this location is dog-friendly! My furry friend was able to join me on my adventure and even made some new doggie pals at the park.

After playing around, I decided to relax and have a bite to eat at the picnic area. The scenery was picturesque and provided an ideal setting for an outdoor lunch with friends or family.

One of the most unique features of this park are the geodesic domes. They're visually stunning and provide shelter from any unexpected rain showers - which can happen in Chicago!

Overall, I had a fantastic time at Riverwalk - East End - Gateway - 500 E. With its diverse range of activities including playgrounds, picnic areas, and geodesic domes; it's definitely worth checking out!

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Ping Tom Memorial Park

Highlights
Waterfront view
Playground
Beautiful walls
City skyline

Firstly, let me tell you that this park is a hidden gem! As soon as you enter the park, you'll be amazed by the waterfront view of Chicago River. The view is so breathtaking, it will make you feel like you're on vacation in a tropical paradise!

The park has an excellent playground area for kids - with slides, swings, and climbing structures. While your kids are playing, you can relax and enjoy the beautiful walls that surround the playground. They are adorned with bright and colorful murals that add to the vibrancy of the park.

And if that's not enough to convince you to visit Ping Tom Memorial Park, then consider this - while enjoying all these activities, you can also take in a breathtaking view of Chicago's city skyline. It's like having all three attractions in one place!

Overall, I had a fantastic time at Ping Tom Memorial Park. Whether you're looking for some relaxation or an exciting adventure with your family, this park has got it all! Don't miss out on this opportunity to experience one of the best outdoor activities in Chicago!

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Chicago Riverwalk - West End

Highlights
Beautiful views
Restaurants and bars
Relaxing atmosphere
Incredible architecture

First of all, let me just say that the views are absolutely gorgeous! The riverwalk offers a unique perspective of the city with its incredible architecture and stunning skyline. I felt like I was in a movie as I walked along the water's edge.

But wait, it gets even better! The restaurants and bars along the way are top-notch. From delicious seafood to mouth-watering cocktails, there is something for everyone. And let's not forget about the relaxing atmosphere. It was so peaceful strolling down the riverwalk, taking in all the sights and sounds of Chicago.

I have to say that my favorite part of this outdoor activity in Chicago was simply taking a break on one of the many benches and watching people go by. It was such a great spot for people-watching!

All in all, Chicago Riverwalk - West End is definitely one of my top picks for outdoor activities in Chicago. Whether you're looking for beautiful views or a relaxing afternoon with friends, this location has it all.

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Wild Mile Chicago

Highlights
Scenic paddle spot
Free river view
Abundant wildlife

First of all, let me just say that the paddle spot at Wild Mile Chicago is nothing short of scenic. From the moment I started paddling, I was surrounded by beautiful views of the city and nature. And what's even better? It's completely free! That's right folks, you can get a stunning river view without paying a dime.

But what really made this outdoor activity stand out for me was the abundant wildlife. As someone who loves animals, I was in heaven! From turtles to birds to fish, there was so much to see and appreciate. And it wasn't just your typical wildlife either - there were some unique species that I had never seen before.

Overall, I highly recommend checking out Wild Mile Chicago if you're looking for an enjoyable and unique outdoor activity in Chicago. With its scenic paddle spot and abundant wildlife, it's truly one-of-a-kind. Plus, did I mention it's free? So grab your paddles and get ready for a wild ride on Wild Mile Chicago!

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The Wild Mile

Highlights
Free parking
Beautiful views
Public kayak launch
Safe and well-lit
Quick access to Downtown

The Wild Mile is the perfect spot for anyone looking to escape the hustle and bustle of city life. With its stunning views of Chicago's skyline and serene surroundings, it's no wonder why this hidden gem has become a popular destination for locals and tourists alike.

One thing that really impressed me was the public kayak launch. As an avid kayaker, I'm always searching for new places to paddle, and The Wild Mile did not disappoint. It was so easy to launch my kayak from their dock and start exploring the Chicago River.

I also appreciated how safe and well-lit the area was, making it a comfortable environment for everyone to enjoy. Plus, with free parking available, it was super convenient to get there.

Lastly, The Wild Mile's location provides quick access to downtown Chicago, making it a great option for those who want to enjoy outdoor activities while still being close to all the action.

Overall, I would highly recommend visiting The Wild Mile if you're looking for a peaceful retreat in the heart of Chicago. Don't miss out on this amazing outdoor activity!

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The 606

Highlights
Elevated walking trail
Amazing views of city
Beautiful and well-maintained landscaping
Adjacent parks with accessible access

Let me start by saying that The 606 is not your average walking trail. This elevated trail takes you on a journey above the city and grants you amazing views of Chicago's beautiful skyline. As I was walking, I couldn't help but admire the well-maintained landscaping surrounding the trail. It truly adds to the ambiance and makes for a peaceful walk.

What's great about The 606 is that there are adjacent parks with accessible access for those who want to take a break from walking or enjoy some greenery. You can choose to continue your walk or take a pit stop at one of these parks, making it a versatile option for all types of outdoor enthusiasts.

I especially recommend visiting during sunrise or sunset because watching the sun hit the buildings just right is breathtaking. Plus, if you're feeling adventurous, try running or biking along the trail! It's a great workout with an even better view.

Overall, The 606 is definitely worth checking out if you're looking for a unique outdoor activity in Chicago. Trust me, it'll have you feeling like you're on top of the world!

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Navy Pier

Highlights
Ferris wheel
Boat tours
Great food
Light up event
Beautiful view

First of all, I have to mention the Ferris wheel. It's not just any Ferris wheel - it's a giant one with enclosed pods, providing an aerial view of Chicago's skyline that is simply breathtaking. If you're afraid of heights, don't worry! The ride is smooth and safe.

Next, I went on one of the boat tours available at Navy Pier. With knowledgeable guides and incredible views, this tour took me around Lake Michigan and gave me a unique perspective of Chicago from the water.

While exploring Navy Pier, I couldn't resist trying some of the great food options available there. From classic Chicago-style hot dogs to delicious deep-dish pizza, there was something for everyone.

I also had the opportunity to attend a light up event in the evening which illuminated Navy Pier in a beautiful display of colors. It was a magical experience and definitely worth checking out if you're in town.

Lastly, I have to mention the beautiful view from Navy Pier. The pier extends far into Lake Michigan and offers stunning views of both the lake and the city skyline. It's a perfect spot for taking photos or just enjoying a relaxing stroll by the water.

Overall, I highly recommend visiting Navy Pier as it has so much to offer for all ages. Plus, with its various attractions and events throughout the year, you'll always find something new and exciting to do here!

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Spirit of Music Garden in Grant Park

Highlights
Stunning sculpture and engravings
Great atmosphere for SummerDance
Adequate dance floor for dancing
Nice places to sit and relax
Reasonable food prices

First of all, let me tell you that the garden is a treat for the eyes. The stunning sculptures and engravings are sure to leave you in awe. I was impressed with the attention to detail and creativity put into each piece.

But what really makes this garden stand out is its atmosphere during SummerDance. It's no surprise that it's become one of the city's most beloved summer traditions. The music, lights, and lively atmosphere create an unforgettable experience.

The dance floor is adequate for dancing and there's plenty of space to move around. Whether you're a seasoned dancer or just starting out, you'll find yourself tapping your feet and swaying to the rhythm.

If dancing isn't your thing, there are plenty of nice places to sit and relax while enjoying the music. You can grab a bite to eat from one of the food vendors at reasonable prices.

Overall, I highly recommend visiting Spirit of Music Garden in Grant Park. It's truly a gem in Chicago's outdoor activities scene.

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Northerly Island Park

Highlights
Great views
Eastern beach
Southern shore
Aquarium nearby
Planetarium near

First of all, let me tell you that the views are absolutely stunning! From the great views of the Chicago skyline to the calming waters of Lake Michigan, this park has it all. But let's get down to business and talk about what this park has to offer.

If you're craving some sand between your toes, then you'll definitely want to check out the Eastern beach. It's perfect for a summer day spent lounging on the shore with friends or family.

For those who prefer a more rugged shoreline, head over to the Southern shore where you can explore natural rock formations and enjoy some peace and quiet away from the hustle and bustle of city life.

Oh, did I mention that there's an aquarium nearby? The Shedd Aquarium is just a short walk away and it's definitely worth checking out. And if you're in the mood for some stargazing, then make sure to visit the Adler Planetarium which is also conveniently located nearby.

Overall, Northerly Island Park is a great place to escape from the city without actually having to leave it. So pack a picnic basket, grab your sunscreen and head on over for a day filled with outdoor fun!

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