Chicago Skydiving
The closest skydiving to Chicago is Skydive Midwest in Sturtevant, Wisconsin — about 60 minutes north on I-94. Tandem jumps launch from 14,500 feet, cost $229 weekday / $259 weekend, and include 60+ seconds of freefall with Lake Michigan and Chicago skyline views. No weight surcharge up to 250 lbs. Season runs April through October.
Chicago is about 60 miles from the closest real skydiving operation. That's us. Skydive Midwest sits right off I-94 in Sturtevant, Wisconsin. That's about an hour from the Loop and 50 minutes from O'Hare. On a clear day, you can see the Chicago skyline, the Milwaukee skyline, and Lake Michigan all at once from 14,500 feet.
We've been here since 2004. We operate a fleet of aircraft that get to 14,500 feet fast. On top of that, we don't charge weight surcharges at any weight. And we don't make you drive two hours into central Illinois to find a runway in a cornfield.
If you're looking for tandem skydiving near Chicago, here's everything you need to know.
What to Expect on Your Tandem Skydive
Your tandem skydive starts with a ground training session. That's about 15-20 minutes where your instructor walks you through body position, the jump sequence, and what to expect. No prior experience needed. Your instructor handles everything that matters.
After training, you gear up and board the aircraft. The ride to 14,500 feet takes about 15 minutes. The views on the way up are half the experience. Lake Michigan stretches north, the Chicago skyline sits to the south, and farmland rolls out in every direction.
At altitude, you and your instructor move to the door. Three seconds later, you're in freefall.
Freefall — 60 Seconds at 120 MPH
Freefall lasts about 60 seconds. It doesn't feel like falling. There's no stomach drop. The aircraft is already moving at speed when you exit, so you don't feel any sudden acceleration. Instead, it feels more like floating on a column of wind at 120 mph. It's loud, it's intense, and it's over way too fast.
At around 5,500 feet, your instructor deploys the parachute.
Canopy Ride — 5-7 Minutes
The canopy ride lasts 5-7 minutes. Catch your breath, take in the view, and your instructor may let you steer. Under canopy, it's quiet enough to have a conversation. Then you come in for a smooth landing on the grass.
The Full Day
The whole process — check-in to landing — takes about 4-6 hours. Most of that is wait time, not jump time. Weekday and early morning bookings have the shortest waits. Plan to spend the day. We've got plenty to do while you wait (more on that below).
Tandem Skydiving Pricing
We keep it simple.
- $229 — Weekday (with reservation)
- $259 — Weekend (with reservation)
- $299 — Walk-in (any day)
A $20 deposit reserves your spot. The deposit applies to your remaining balance on jump day.
No hidden fees. No weight surcharges at any weight up to our 250 lb limit. In other words, you pay the same whether you're 130 lbs or 250 lbs. That's not how it works at most dropzones, but it's how it should work. Read more about our weight limit policy →
Video Packages
Three options. All include 3 fully edited videos — a social media short, a highlight reel, and a full-length edit from ground interview to landing. Plus photos. We deliver everything same-day.
- Hand Cam — $99
Your instructor wears a wrist-mounted camera and captures the entire jump — exit, freefall, canopy, landing — all from their perspective. - Premium — $136.50 (most popular)
A separate outside videographer jumps alongside you with a dedicated helmet camera. You get angles of yourself in freefall that hand cam can't capture. - Extreme — $189
Both hand cam and outside videographer combined. Every angle, every moment. Maximum coverage.
If you're doing this once, get the video. Book your media package when you make your reservation.
Group Rates
Planning a bachelor party, birthday, corporate outing, or just getting a crew together? Group pricing:
- 3-5 people: $229/person
- 6-10 people: $219/person (organizer jumps for $199)
- 11+ people: $209/person (organizer jumps for $189)
All group rates work for weekday and weekend jumps. Call us at (262) 886-3480 to set up your group booking.
Getting Here from Chicago
Skydive Midwest is in Sturtevant, Wisconsin — right off I-94 at Exit 333 (Highway 11). From downtown Chicago, it's about 60-70 minutes depending on traffic.
Directions
- Take I-90/94 north into Wisconsin
- Continue on I-94 past Kenosha and Racine
- Take Exit 333 (Highway 11 / Durand Ave) — head west
- Turn right on 56th Road
- We're at 13851 56th Road, Sturtevant, WI 53177
From O'Hare: About 50-60 minutes north on I-94.
While You're Here
Skydiving takes time. Plan to spend the day. We've built a place worth hanging out — before your jump and after.
- 80-foot observation deck — Watch skydivers land from the best seat in the house. Bring your friends and family, even if they're not jumping.
- 14K Kitchen — Our on-site food truck with solid options for pre- and post-jump meals.
- Full-service bar — For after you jump. Not before.
- Sand volleyball court — Because you might have a few hours to kill.
- Cornhole and yard games
- Lockers — Leave your phone, wallet, and keys on the ground while you jump.
- Picnic tables and community grills
Bring your crew. The non-jumpers have a great time too.
Reserve Your Jump — Just $20 Deposit →
Questions? Call us at (262) 886-3480. Closer to Milwaukee?
FREQUENTLY ASKED QUESTIONS
Understandably, you might have some questions about throwing yourself out of an airplane! We’ve answered many of them below. If you don’t find what you’re looking for, please send us a message. We’d love to hear from you.
About 60-70 minutes from downtown Chicago, straight up I-94 to Exit 333. We're the closest skydiving center to the city. From O'Hare, it's about 50 minutes. From the south suburbs, even less. Every other option is farther out — most are 80+ miles from downtown in central Illinois.
Yes — three packages: Hand Cam ($99), Premium ($136.50, most popular), and Extreme ($189). Every package includes 3 professionally edited videos plus photos, all delivered same-day. The Premium package gives you a dedicated outside videographer jumping alongside you for the best angles. Book your media package when you make your reservation.
Last updated: February 2026