The best places to go skydiving near Chicago

3215 E. 1969th Road, Ottawa, IL
Driving time from Chicago: One hour and 15 minutes

When 104-year-old skydiver Dorothy Hoffman became the oldest person to ever go skydiving, she did it at Skydive Chicago in Ottawa, IL. The center has options for licensed skydivers, as well as beginners. The company’s tandem flights consist of a 60-second free fall, and a five-to-seven minute canopy flight, all while strapped to a professional. More experienced skydivers can purchase one of the skydiving company’s passes, including the unlimited jump pass, which starts at $2,120 and allows experienced skydivers to jump as many times as they want throughout the year. 

Skydiving itself might be thrilling enough for some, but Skydive Chicago also offers a drop zone that’s packed with amenities, including a swimming pond, gym and a cafe. 

1207 E. Gurler Road, Rochelle, IL
Driving time from Chicago: One hour and 10 minutes

For more than 50 years, Chicagoland Skydiving Center in Rochelle, IL has been flying passengers up for tandem and individual skydiving experiences. While the company is beginner-friendly, they also offer an opportunity to attend Freefall University—a skydiving “school,” where passionate skydivers train to become licensed. The best part for anyone who’s a little nervous? Freefall University has a perfect student safety record.

Although continuously sending planes into the sky isn’t the most eco-friendly activity, Chicagoland Skydiving Center has found numerous ways to make its business more green. The decades-old skydiving company has invested approximately $600,000 in solar panels, and has switched over to more eco-conscious aircraft, which consume 30% less fuel per passenger.

800 W. Scott Street, Chicago

Skydiving isn’t for everyone, especially for anyone who has a fear of heights. But there is a way to capture the rush of floating throughout the year, without the frightening heights and intense free fall—indoor skydiving. Rather than jumping out of a plane, skydivers are blown into the air in an indoor wind tunnel. At iFly Indoor Skydiving, which has a location in Chicago’s Lincoln Park neighborhood, each flight lasts for approximately 60 seconds. 

In addition to the Lincoln Park indoor skydiving center, iFly also has nearby suburban locations in Naperville and Rosemont.

1300 IN-212, Michigan City, IN
Driving time from Chicago: One hour

Many skydiving facilities are in rural areas, to ensure that there’s a safe drop zone for skydivers. Skydive Windy City Chicago can claim bragging rights of having the city’s skyline be visible on most of the company’s jumps. As one of the closest skydiving destinations to Chicago, the facility's dropzone is also located next to Lake Michigan.

Skydive Windy City Chicago flies passengers up 14,000 feet and offers tandem jumps at four different price points, depending on if skydivers want to include a photo and video package with their experience.

4046 WI-67 Hangar 1, Beloit, WI
Driving time from Chicago: One hour and 20 minutes

One of the best parts of skydiving is the sights, and skydivers at Skydive The Rock in Beloit, WI don’t just get a view of one state—instead they can see both Wisconsin and Illinois during the free fall, which takes place near the border seperating the two states.

Another perk of skydiving with Skydive The Rock? Its King Air aircraft is fast. The company’s plane gets passengers up to 14,000 feet in the sky in under 15 minutes. While jumping out of a plane can be terrifying, the most frightening part of the whole experience is arguably sitting in the plane, waiting to jump, as it reaches elevation. It helps that Skydive The Rock gives skydivers less time to get nervous and potentially back out.

13851 56th Road, Sturtevant, WI
Driving time from Chicago: One hour

While skydiving companies try to get customers in the air as quickly as possible, there are a number of factors that can result in delays, like bad weather or a high number of bookings. Because of this, Skydive Midwest recommends that skydivers plan on spending the day at the facility—but that doesn’t mean they’ll be stuck in a waiting room.

The skydiving facility offers an 80-foot elevated observation deck at the drop zone, where visitors can stop by and watch jumps as they’re happening. That’s not the only amenity offered at the company’s drop zone: There’s also a sand volleyball court, cornhole boards, a charcoal grill for community use and an on-site food truck. Skydive Midwest offers tandem jumps, as well as lessons for anyone looking to get certified.

W1341 County Highway L, East Troy, WI
Driving time from Chicago: One hour and 30 minutes

Rather than being operated by a company, Skydive Milwaukee, located in East Troy, WI, is run by the Sky Knights—a parachuting club that’s been training skydiving students for more than 60 years. Tandem jumps range in cost depending on whether it’s a weekday ($259) or a weekend ($279). The club also offers several jump packages for licensed skydivers, like a 25-jump package ($825), a 50-jump package ($1,600) and a 100-jump package ($3,100).

N3407 County Road K, Jefferson, WI
Driving time from Chicago: Two hours

The Wisconsin Skydiving Center is owned by husband and wife Bo Babovic and Alex Kolacio. The married couple has gone skydiving throughout the world, and collectively have jumped more than 25,000 times. They’ve used their expertise to put together the Jefferson, WI-based skydiving company.

The company offers tandem jumps, as well as skydiving lessons for anyone interested in becoming certified. It also offers the Rise Above Program—targeted specifically for people who are scared to skydive and want to overcome the fear. The program, which costs $390, includes a facilitated workshop focused on acknowledging and understanding the fears that arise around skydiving, while also working to conquer them. It’s followed up by a tandem skydive, as well as a post-skydiving reflection.

7530 WI-73, Marshall, WI
Driving time from Chicago: Two hours and 20 minutes

At Seven Hills Skydivers of Madison, located in Marshall, WI, they say that skydiving is their passion, not their job. That’s entirely true. The skydiving company operates as a nonprofit, so all of its staff are volunteer workers, and it’s been that way for decades.

The long-running skydiving company, which first started operating in 1962, offers solo and tandem flights. For solo jumpers, planes travel up to 4,000 feet, and for tandem skydivers, they reach a height of 10,000 feet. 

16448 Cornstock Street, Grand Haven, MI
Driving time from Chicago: Two hours and 40 minutes

For Tony Gwinn, the owner of Skydive Grand Haven, skydiving is a family affair. The business is family owned and operated, and all of Gwinn’s five kids have made solo jumps—two of them are even certified skydivers. 

The skydiving company was originally based out of Wayland, MI, 55 miles away from Grand Haven. It moved to its current home as business grew, and with the new location came new views—the drop zone is less than two miles from Lake Michigan, offering skydivers unbeatable sights of the water on each jump.