Top 10 Outdoor Activities In Chicago, Illinois - Updated 2021

outdoor activities in chicago

Chicago is the most populated city in Illinois and is nestled on the banks of the stunning Lake Michigan, which is the fifth largest body of freshwater in the world. It is a great base for those of you who are looking for all the benefits of a city break without the stress. Each of the four main districts has something special to offer tourists, and we think that the best way to explore Chicago is to head outdoors. You can explore the city by bike or segway or take to the water or even the skies. There is so much to see and do al fresco. Here’s a list of the top outdoor activities in Chicago, Illinois.

1. Enjoy the great outdoors with hula hoops at Wicker Park (from USD 28.0)

You may recall your days hula-hooping as a child, well this incredibly fun day out, which lasts for two hours has taken it up a level. Not only will you be able to explore the peaceful area of Wicker Park, but you’ll also learn the fundamental form of this unique dancing form. The equipment is all provided and the instructor will guide you on multiple trick movements. You’ll soon be ready to join the circus, or at the very least be infatuated with a new hobby. Hula hooping is a great way to enjoy the outdoors, stay fit, and make new friends.

Exploring & Hula Hooping Wicker Park

Duration: 2 hours

8 reviews

2. Discover the true heart of Chicago on bike (from USD 90.0)

This custom-designed bike ride will take you on a guided tour to all the best sites in the area. You’ll have the chance to stop off and try local food and, if you want, discover the craft beer scene, too. This five-hour tour will introduce you to the backstreets of Chicago, where you can see 1920s gangster related sites, high skyscrapers, and everything in between. You might even spot some scenes that you recognize from movies. This tour will show you the true ‘locals’ view of Chicago.

Chicago Bike Adventures

Duration: 4 hours

130 reviews

3. Explore Chicago from the water (from USD 160.0)

From bikes to boats, you can feel the breeze in your hair. This tour will let you explore Chicago’s lakeside by boat. Wednesday and Saturday night sails are particularly special as you can also enjoy the fireworks overhead. You’ll also see some of the major sights from the water and be expertly sailed by your captain. You can even become the captain of your own boat. Soft drinks, food, and all necessary equipment are provided.

Sailing Chicago's Gorgeous Lakefront

Duration: 3 hours

43 reviews

4. Ride around the city on a Segway and watch fountain light shows and fireworks (from USD 75.0)

You’ll get excellent value for money with this small-group segway tour, which finishes with watching the fireworks at night. You’ll make a number of stops at important landmarks as you weave your way through this vibrant city. You’ll also witness the beautiful Buckingham Fountain evening light show, which is an absolute must-see. If it’s your first time on a segway, don’t worry you’ll be given a training course on how to use it safely.

2-Hour Chicago Fireworks Segway Tour

Duration: 2 hours

5. Discover all of Chicago's secrets on this unique scavenger hunt tour (from USD 13.0)

Chicago is full of secrets and unique facts, you will discover them all on this unique scavenger hunt tour along the Magnificent Mile. Ever wondered how a skyscraper can be made of gum, or how the Tribune Tower really takes people around the world? Well, you’ll find the answer to these questions, and many more. With 16 stops over a 2-hour period, you’ll have plenty of opportunities for photos and will feel like you know everything about Chicago, all while having fun.

Chicago Scavenger Hunt: Chicago's Magnificent Mile

Duration: 2 hours

6. Go kayaking along the Chicago River (from USD 66.0)

This leisurely and fun kayak tour along the Chicago River will float you past the iconic skyscrapers, to the Civic Opera Building and Marina City Towers. This tour is suitable for both experienced and novices alike. All of the equipment is provided by the host and they’ll carefully show you how to safely kayak. Both single and double kayaks are available, so it’s a fun couple activity.

Chicago River Kayak Tour

Duration: 2 hours 30 minutes

2 reviews

7. Explore Chicago in a stylish Jeep Wrangler (from USD 60.0)

Explore a predetermined route and visit some of the best sights of Chicago in a private Jeep Wrangler. Take the roof off and let the cool breeze blow through your hair as you travel the roads and stop at eight different iconic Chicago landmarks. This tour is ideal for a group of up to four people. The Jeep Wrangler can either be picked up or dropped off at select hotels, so you can start your tour in absolute comfort.

Private Tour of Chicago in Open Air Jeep

Duration: 1 hour 30 minutes

8. Zip along the streets and learn about life in the city from the most knowledgeable guides (from USD 75.0)

zip along the streets and learn about life in the city from the most knowledgeable guides

Have you ever ridden a segway? Well, now is your chance, by joining this two and a half hour tour of the best sites of Chicago. Riding a segway is a fun way to explore this unique city. Your experienced guide will show you the hotspots of Chicago and give you an informal and friendly insight into what life is like living in the area. Stop for a photo in front of the beautiful Buckingham Fountain before heading to Museum Campus and revel in the beautiful views.

Amazing Lakefront Segway Tour of Chicago

Duration: 2.5 hour

28 reviews

9. Cruise along the Chicago River and take in the beautiful sights and sounds (from USD 297.0)

cruise along the chicago river and take in the beautiful sights and sounds

Feel like a celebrity in this extra-special self-guided, private pontoon trip. You can set your own course along the Chicago River and captain your pontoon that can fit up up to eight people. We love that the hosts provide grills and pizzas so when you want to enjoy lunch, you can do so on the river at your own pace. You can rent the boat for two hours, and see some of the major landmarks of the city while cruising along the river.

Private Pontoon Boat Rental with Pizza Included

Duration: 2 hours

1 review

10. Get a bird's-eye view of the Windy City through a helicopter ride (from USD 408.0)

This once-in-a-lifetime opportunity should not be missed. It’s time to take to the skies and fly high above Chicago for a birds’-eye view of this beautiful urbanscape. This 15-minute tour in a helicopter will allow you to communicate with your own pilot. You can see all the classic landmarks, such as Lincoln Park, Willis Tower, and the John Hancock Building. This helicopter tour is the perfect way to capture unique aerial shots of Chicago. Maximum of two people are allowed on this tour, thus making it ideal for a special romantic trip. You’ll make lifelong memories together.

Chicago City Sights Private 2-Person Helicopter Tour

Duration: 30 minutes

10 reviews

See Chicago in all its glory

All of these tours and experiences offer a unique and special way to explore Chicago. You’ll hear first-hand about life in this creative and bustling city. Discover a whole new side of Chicago with the help of the locals. Book these best outdoor activities in Chicago, Illinois, today.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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A full-time global wanderer and volunteer. Strong compass leading to random and remote pockets of Earth; exploring jungles, abandoned villages and the open seas. Passionate about documenting on my...Read more

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