Cool Destinations
Top Illinois activities
Top Illinois landmarks
Beyond Illinois
Illinois trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by the numbers
  • Top Illinois landmark tours
  • Tours in nearby places
  • Explore USA tours
  • Illinois travel guides
  • Illinois 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 Illinois Outdoor Activities

17 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
15
11
10
Duration Clear
3
12
6
0
0
Price Clear
$0 $500+
Rating Clear
9
12
14
Specials Clear
15
5
0
5
3
Features Clear
2
4
15
0
12
0
Accessibility Clear
1
6
13
Families Clear
6
9
2

Illinois Tours

Attractions

Guides

Calendar

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 …More

Chicago, USA
4.8 (704)

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 (704)
from
$28
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 …More

Chicago, USA
4.7 (33)

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 (33)
from
$126
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 …More

Chicago, USA
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

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 …More

Chicago, USA
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
Zipline Adventure in Galena, Illinois

Treetop thrills await, where a zipline adventure in Galena, Illinois promises a unique outdoor experience. The 2 to 2.5-hour tour kicks off with an exhilarating …More

5.0 (10)

Zipline Adventure in Galena, Illinois

Treetop thrills await, where a zipline adventure in Galena, Illinois promises a unique outdoor experience. The 2 to 2.5-hour tour kicks off with an exhilarating...

2 hours 30 minutes • Free Cancellation
5.0 (10)
from
$119
Chicago-Naperville Indoor Skydiving with 2 Flights & Personalized Certificate

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

4.6 (10)

Chicago-Naperville Indoor Skydiving with 2 Flights & Personalized Certificate

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

1 hour 15 minutes • Free Cancellation
4.6 (10)
from
$120
Skip the Line: Miller Park Zoo General Admission Ticket

Miller Park Zoo offers many exhibits and Zookeeper interaction opportunities that are enjoyed by the whole family. Some highlights include: reindeer, Sumatran tiger, greater flamingos, …More

4.5 (20)

Skip the Line: Miller Park Zoo General Admission Ticket

Miller Park Zoo offers many exhibits and Zookeeper interaction opportunities that are enjoyed by the whole family. Some highlights include: reindeer, Sumatran tiger, greater flamingos,...

2 to 4 hours • Free Cancellation
4.5 (20)
from
$8
Horseback Rides, Interactions, and Petting Zoo

We provide a controlled environment for safe horseback riding for kids and beginners, and a petting zoo. We have a 24,440 sqft equestrian center with …More

5.0 (7)

Horseback Rides, Interactions, and Petting Zoo

We provide a controlled environment for safe horseback riding for kids and beginners, and a petting zoo. We have a 24,440 sqft equestrian center with...

1 hour • Free Cancellation
5.0 (7)
from
$27
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 …More

Chicago, USA
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

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 …More

Chicago, USA
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
Guided Seasonal Hike

Discover Starved Rock’s canyons, bluffs and seasonal waterfalls on this 3-mile (round trip) guided hike. Listen as the guide tells stories of how Starved Rock …More

5.0 (1)

Guided Seasonal Hike

Discover Starved Rock’s canyons, bluffs and seasonal waterfalls on this 3-mile (round trip) guided hike. Listen as the guide tells stories of how Starved Rock...

4 hours • Free Cancellation
5.0 (1)
from
$33
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 …More

Chicago, USA
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
Chicago Bulls Basketball Game at United Center

Whether this your last dance or your first dance when it comes to going to NBA games, watching the Chicago Bulls live at the United …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA
3.0 (1)

Chicago Bulls Basketball Game at United Center

Whether this your last dance or your first dance when it comes to going to NBA games, watching the Chicago Bulls live at the United...

2 hours
3.0 (1)
from
$90
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, …More

Chicago, USA
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

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” …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

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

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 …More

Likely to Sell Out
Likely to Sell Out
Chicago, USA

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

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 …More

Chicago, USA

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
Flying rollercoaster of fun around downtown Chicago
New York City
Flyover in Chicago
Angela_S, Sep 2026
Flying rollercoaster of fun around downtown Chicago
If you’re good with heights and motion, it is an AMAZING experience and way to see downtown Chicago. I recommend doing Flyover after you’ve been around downtown. day or two so you recognize some of the buildings as you fly. The one thing that would make it better is if they had a little better customer service and communicated about the number of stairs or even verbally offered an elevator option instead of just ushering everyone to the stairs. There are already a lot of stairs in Chicago so taking what seemed like 2-3 flights of stairs (as in going down to the L) was a surprise. The ride made up for this. It was so cool to fly all around the riverfront and downtown area. At one point, I put my hands in the air because it felt like we were on a rollercoaster drop. So much fun!
Read more
Book it !
New York City
Flyover in Chicago
Sheena_T, Sep 2026
Book it !
BOOK IT!! It was so fun! My husband and I enjoyed it. The most realistic experience ever. I would definitely book again.
Read more
Perfect experience. Luis...
New York City
Chicago-Rosemont Indoor Skydiving with Two Flights
47g7xwwhzw, Sep 2026
Perfect experience. Luis...
Perfect experience. Luis is fantastic!! The whole process was professional yet relaxed. The experience was exhilarating.
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
Miller Park Zoo
New York City
Skip the Line: Miller Park Zoo General Admission Ticket
Sunshine_F, Sep 2026
Miller Park Zoo
Admission was super simple and the zoo was a lovely time for my family. The tickets were for my son and my grandkids and they had such a great time. They're excited to go back again!
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
Fun ride through the forest.
New York City
Zipline Adventure in Galena, Illinois
AmandaL263, Aug 2026
Fun ride through the forest.
Experience was great. Amanda and Gracie were skillful guides who were safe, knowledgeable and considerate. And, funny. Thoroughly enjoyed my experience and would do it again.
Read more
Best experience ever!
New York City
Zipline Adventure in Galena, Illinois
maggiehP7562NO, Aug 2026
Best experience ever!
Extremely kind, patient, and professional guides! Made our experience so much more fun. Just loved the experience and would definitely do it again!
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
Jam & iFly...An Awesome Experience!
New York City
Chicago-Naperville Indoor Skydiving with 2 Flights & Personalized Certificate
shaunalynb, Aug 2026
Jam & iFly...An Awesome Experience!
Jam our guide was so personable, so attentive to the needs of every person in the group from the youngest to the oldest, and a great couch! We could not have asked for a better leader over our group! We will be back Jam! Blessings, Shaunalyn
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
Illinois Tours
Attractions
Guides
Calendar
View more
View more