By Meredith Lyons

Conquering the skies has always been a fervent desire of land-bound man. And now there are at least three ways to get a taste of flight. Now that the weather is warming up, perhaps you’d like to try a sky-high adventure. There are several places near Chicago to get your flight on.



Skydive Midwest
13851 56th Road
Sturtevant, WI 53177
(262) 886-3480

Skydive Midwest is just over the Wisconsin state border and right off I-94 at the Sylvania Airport. Each group of jumpers generally goes through a 20-minute training, the staff loads your equipment and suits you up. The staff consists of knowledgeable divers and airline crew. If you can get in the first dive group just after sunrise on a clear summer day, you may see the sun coming up and sparkling over the lake. Some tandem instructors will turn their divers so they can see Milwaukee to the north and the Chicago skyline to the south. Your instructor will ask if want to do flips during the jump, no obligation. They’ll make you feel safe throughout your ride. Also, tandem jumpers get a longer free fall and have the option to pull their own chute.

Skydive Chicago

3215 E. 1969th Road
Ottawa, IL 61350
(815) 433-0000

Skydive Chicago is a friendly group who isn’t going to push you into getting all of the extras on your first jump, although you probably will want the video and photos anyway. Skydive Chicago also offers skydiving lessons for those who get the bug and decide that one dive isn’t enough. It offers several packages for first-time jumpers, including a couples jump if you really want to impress that date. The packages are all inclusive and sometimes include a picnic or gift shop vouchers. Skydive Chicago also offers both normal and expedited student options. Choose the expedited if you’re itching to get your license in one week.



Skydive Milwaukee
W1341 Highway L
East Troy, WI 53120
(800) 382-4883

Also known as the Sky Knights, Skydive Milwaukee will take you through a lengthy five-hour class before your jump with equipment talks, hanging out in classroom harnesses, practice landings and what-if scenarios so you’ll feel fully prepared. If you opt for the static line jump (where your chute is attached to the plane), it’s a solo jump, but as you’re attached, the free fall experience will be a bit shorter. Classroom practice will make the nerves easy once you step out onto the wing and you will be able to steer it to the landing zone guided by radio instructions from the ground.

A Great American Balloon Company

935 Highway 22
Fox River Grove, IL 60021
(877) 933-6359

A Great American Balloon Company has many balloon ports around the country (click here for a list of all of them). The Fox River Grove port is near Chicago, and you can book both sunrise and sunset rides. All company pilots are hot air balloon certified and are able to navigate the landscape at various altitudes to ensure that your flight is picturesque. A post-flight celebration is included in your flight featuring a ceremonial champagne toast and regional hors d’oeuvres. Be aware that the weather will affect your flight and too much wind or inclement conditions can cause cancellation. Morning flights are the safest to book. Be sure to bring your camera.

Chicagoland Skydiving Center
1207 W. Gurler Road
Rochelle, IL 61068
(815) 561-3663

The folks at Chicagoland Skydiving Center not only offer the general tandem skydives, they’ll also offer a unique marriage proposal (complete with champagne and complimentary stemware post dive) that one couldn’t possibly say no to. General group outings are also offered as well as corporate outings. What better way to build team relationships than a tandem free fall? Also on the premises is the Flight Deck Bar and Grill. Once you and your friends have experienced the adrenaline rush of a free fall, you’ll most likely all want to go out and celebrate post dive!

Meredith Lyons is an actor, competitive fighter and fitness instructor in Chicago who also owns an amazing cat named Jake. Meredith has been writing on Examiner as the Chicago Martial Arts Examiner since 2008. Her work can be found at