Cool Destinations
Top Chicago activities
Top Chicago landmarks
Beyond Chicago
Chicago trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by the numbers
  • Top Chicago landmark tours
  • Tours in nearby places
  • Explore USA tours
  • Chicago travel guides
  • Chicago travel calendar
Language $Currency
Login / Sign up
Bookings
Bookings
Cool Rewards Rewards
$0.00
Cool Rewards Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Top Chicago Outdoor Activities

11 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
10
6
6
Duration Clear
2
6
4
0
0
Price Clear
$0 $500+
Rating Clear
6
7
8
Specials Clear
10
3
0
3
3
Features Clear
2
4
10
0
9
0
Accessibility Clear
1
4
9
Families Clear
4
7
1

Chicago Tours

Attractions

Guides

Calendar

Flyover in Chicago
4.8 (686)

Flyover in Chicago

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover...

30 minutes • Free Cancellation
4.8 (686)
from
$28
Chicago-Rosemont Indoor Skydiving with Two Flights
4.7 (32)

Chicago-Rosemont Indoor Skydiving with Two Flights

Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Chicago in Rosemont, a premier indoor skydiving facility powered...

1 hour 15 minutes • Free Cancellation
4.7 (32)
from
$126
Lincoln Park Zoo & Nature Museum Private Tour
5.0 (21)

Lincoln Park Zoo & Nature Museum Private Tour

Discover the wild heart of Chicago on our guided walking tour through Lincoln Park, where nature and history meet in one unforgettable experience. What sets...

2 hours • Free Cancellation
5.0 (21)
from
$275
Chicago Shoreline Adventure Boat Tour
5.0 (39)

Chicago Shoreline Adventure Boat Tour

This tour is the perfect way to experience the shoreline of Chicago in a new and exciting way! Our tour vessel is a former military...

1 hour 30 minutes • Free Cancellation
5.0 (39)
from
$90
Bird Tours across Chicago
5.0 (1)

Bird Tours across Chicago

With over 10 years of birding, Wayne can not only identify birds out in the wild through sight, but also through their many calls! Interested...

2 to 5 hours • Free Cancellation
5.0 (1)
from
$60
Golden Hour Motorized Paddleboard Tours w/ Mobile DJ
5.0 (2)

Golden Hour Motorized Paddleboard Tours w/ Mobile DJ

One of a kind experience you can only find in Chicago. Motorized paddle boards take the stress out of paddling. LED-lights make the boards illuminate...

1 hour • Free Cancellation
5.0 (2)
from
$105
Electric Bike Tours in Lincoln Park
5.0 (2)

Electric Bike Tours in Lincoln Park

Discover the streets of Lincoln Park, Chicago, and the Magnificent Lake Front on a high-quality electric bike rental from E-Z Rider Bike Shop. Our e-bikes...

2 hours 30 minutes • Free Cancellation
5.0 (2)
from
$85
One Day Galena and Dubuque Tour from Chicago
3.0 (2)

One Day Galena and Dubuque Tour from Chicago

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque,...

9 to 10 hours • Hotel pickup offered • Free Cancellation
3.0 (2)
from
$315
Chicago Highlights Running Tour
Likely to Sell Out
Likely to Sell Out

Chicago Highlights Running Tour

Join us for the most memorable experience you will have while visiting Chicago! For runners from around the world, this is definitely a “bucket list”...

1 hour 15 minutes • Free Cancellation
from
$44
Chicago Exotic Auto Experience
Likely to Sell Out
Likely to Sell Out

Chicago Exotic Auto Experience

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride...

3 to 7 hours
from
$1,800
Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenient...

9 to 10 hours • Hotel pickup offered • Free Cancellation
from
$1,200

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Fabulous for Chicagoans and Visitors.
New York City
Flyover in Chicago
X7291ITdavidg, Sep 2026
Fabulous for Chicagoans and Visitors.
As a 30+ year Chicagoan, this is fantastic for visitors and residents.
Read more
Big Fun
New York City
Flyover in Chicago
Yvette_H, Sep 2026
Big Fun
I didn't know what to expect but I was surprised with the technology and excitement of the Flyover Chicago excursion. It's worth every penny.
Read more
Great tour!
New York City
Lincoln Park Zoo & Nature Museum Private Tour
Y3892OVharryg, Sep 2026
Great tour!
I went with my 10-year old daughter, and we both had a blast. The butterfly garden, seeing the baby zebra and rhino at the zoo, it was all awesome. The tour guide was funny and engaging for adults and kids. Highly recommend!!!
Read more
Zoo review
New York City
Lincoln Park Zoo & Nature Museum Private Tour
Linda_M, Sep 2026
Zoo review
Our guide Scout, was extremely well versed in all aspects of the Museum and Zoo. We had plenty of time, and she took great care in explaining the plants, butterflies, reptiles, and animals. I would highly recommend this tour and do ask for Scout as your guide. Exceptional.
Read more
Go yachti ⛴️
New York City
Chicago Shoreline Adventure Boat Tour
sharea2025, Aug 2026
Go yachti ⛴️
Adventurous & knowledgeable • very well worth it‼️#GoYachti
Read more
Chicago in two hours
New York City
Electric Bike Tours in Lincoln Park
Amir_I, Aug 2026
Chicago in two hours
Jackson was a great guide and very down to earth. Thanks a million! I think it's the best bike tour I've been on and the weather was perfect.
Read more
E-bike fun!
New York City
Electric Bike Tours in Lincoln Park
Ambassador593837, Jul 2026
E-bike fun!
Cole, the owner, called the day before to ask specifics on what we would like to do. He made some suggestions and we decided to go with a guide since we are not from Chicago. He was very informative of all we needed to do. When we arrived, the bikes and Cole were ready to go. He was our personal guide and was fabulous. We had a blast! One of our top 5 things to do on our 2 week long adventure!!
Read more
10/10 Experience
New York City
Golden Hour Motorized Paddleboard Tours w/ Mobile DJ
J7432PXmaryc, Jun 2026
10/10 Experience
This is the best way to see the city at night. I haven’t really gotten into watersports but saw this and thought I would give it a try. My partner loved it and we barely got wet. The floating DJ made it a vibe
Read more
Best Tour On Chicago River
New York City
Golden Hour Motorized Paddleboard Tours w/ Mobile DJ
johnsumm24, Jun 2026
Best Tour On Chicago River
This experience was a 10/10. The tour was super cool and the paddleboards are so easy to manuever with the motors. It really is no paddling required. You can chill, take in the skyline views, as the floating DJ sets the vibes behind the tour. The staff is super friendly and knowledgable on river safety. This is my girlfriends second time on a watercraft of any kind and she actually said she wants to come back again before the summer ends. We have to check out one their floating DJ sets on Sundays that features a local Chicago DJ.
Read more
Fun but expensive!
New York City
Chicago-Rosemont Indoor Skydiving with Two Flights
Sherri T, May 2026
Fun but expensive!
Super fun experience! It was easy enough to learn and do right away. It is quite an expensive activity, even with any discounts, and especially since you only get two 1 minute flights, but I'm glad we did it. I also paid extra for high flights, the media, and a last minute extra flight for my son. My son and I had a lot of fun.
Read more
Very pleased!
New York City
Bird Tours across Chicago
R908PWdaniloa, May 2026
Very pleased!
A phenomenal introduction to birding! Coordinating with Wayne was so easy — would highly recommend
Read more
Flying high on our trip to Chicago!
New York City
Chicago-Rosemont Indoor Skydiving with Two Flights
Emily_E, Mar 2026
Flying high on our trip to Chicago!
It was our first time doing a flight experience and I was nervous. They were so patient with all of us and really explained the activity well. They made sure we all understood the hand signals and reviewed them often. The pictures and videos we received afterward were great and very reasonably priced. My 12 year old son LOVED it!
Read more
Part of the city
New York City
Flyover in Chicago
LaKendra_E, Sep 2026
Part of the city
I went with a group of friends and we all enjoyed the flyover experience of Chicago. It shows you a different side of the city that you never hear people talk about. 10/10
Read more
Awesome
New York City
Flyover in Chicago
markwS7969XS, Sep 2026
Awesome
We went on a Thursday around noon and there was no line. Good experience. Enjoyed the experience
Read more
Friendly and knowledgeable tour guide.
New York City
Lincoln Park Zoo & Nature Museum Private Tour
498vatsalp, Sep 2026
Friendly and knowledgeable tour guide.
Bernie, our tour guide was amazing. A few minutes in, it felt like we were all old friends hanging out with each other. He led the pace of the tour very well, and very helpful and pro active with sharing information.
Read more
Fantastic trip with really professional and kind tour guide
New York City
Lincoln Park Zoo & Nature Museum Private Tour
182siweic, Aug 2026
Fantastic trip with really professional and kind tour guide
It’s a fantastic trip about 2.5 hours. We visit the nature museum, the botanical gardens and the zoo, see a lot of tropical plants, butterflies and animals. Chicago is known for its skyscrapers but the trip let me see how Chicago tries to coexist with nature and maintain the biodiversity. And I really appreciate my tour guide Bernie, he is really professional and kind, told me details about these plants and animals, which impress me greatly.
Read more
Chicago Tours
Attractions
Guides
Calendar
View more
View more