How to Fit Skydiving Into Your Chicago Vacation Itinerary

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The Chicago area is packed with tons of things to do, places to go, and people to see. That’s why it’s one of the country’s top vacation destinations. 

Still, one of the most exhilarating options is always skydiving. A skydiving experience is unforgettable — there’s no question about that. 

The challenge is in scheduling your skydive so that it fits into your Chicago vacation!

Here’s how you can work a jump into your vacation. 

1. Book Accommodations Outside Downtown

To ensure you can experience your entire vacation, it’s smart to book your Chicago accommodations outside of downtown

There are a couple of advantages to this. The first is that areas like Downers Grove and Naperville tend to have lower accommodation rates because they’re not in the middle of downtown. 

The second is that it’s not possible to go skydiving over the city of Chicago. All of the Chicago skydiving centers are located on the outskirts of the city, and some are actually closer to other cities like Rochelle

When you stay outside of downtown Chicago, you’re still close enough to the city to make day trips and soak in the city’s cultural landmarks. You’ll also be closer to your skydiving destination so that you won’t have to block out a whole day just to do it. 

Instead, you can set aside an afternoon and still have plenty of time to pick up dinner after your jump.

2. Choose the Right Dropzone

When it comes to skydiving in Chicago, you have a few different dropzones to choose from. But how do you narrow down your options? 

There are a lot of factors to consider, but generally speaking, you can vet any dropzone by looking at five major factors: 

  1. The dropzone’s safety record
  2. The dropzone’s staff experience
  3. The dropzone’s pricing
  4. The dropzone’s resources for first-timers
  5. The dropzone’s online reviews

A good dropzone will have a stellar safety record, plenty of experienced staff, reasonable pricing (but not too “cheap”), information for first-time jumpers, and lots of positive online reviews. 

It’s also important to note that some dropzones will go above and beyond to make sure you can make your scheduled jump. 

Services like private shuttles can make a big difference when you want to take a vacation, but you don’t want to navigate an unfamiliar city. 

When you find a few dropzones that meet these criteria, you have your pick of the litter! 

3. Set Aside at Least Half a Day to Jump

Most first-time freefallers will need to go through training prior to their jump, which includes watching instructional videos and learning how to operate their gear. 

These safety lessons can vary based on the dropzone, but you can bet on this class taking up a decent portion of your day. 

After all, it’s essential to your safety!

Your skydiving experience can be longer or shorter based on the altitude from which you jump, but generally, you can expect the plane to take about 30 minutes to climb to exit altitude. 

Some dropzones may have fast-turbine aircraft, which only take about 15 minutes to climb to exit altitude, but that varies depending on your skydiving center. 

Once you’ve climbed to exit altitude, you’ll spend time in freefall and parachuting. Here’s what you can expect from each altitude: 

  • 9,000 foot jump = 30 seconds of freefall
  • 14,000 foot jump = 60 seconds of freefall
  • 18,000 foot jump = 90 seconds of freefall

After you jump, you can expect anywhere from 5-7 minutes parachuting until you reach your destination. 

All in all, you can expect a single jump to take about an hour from the time you step on the plane to the time you touch the ground. 

When you add orientation time, most skydiving experiences end up being 2-hour events.

Your travel time will add more to that as well. For those traveling to reach the skydiving center, you may need half of a day for your skydive adventure.

4. Keep an Eye on Weather

For safety reasons, a dropzone may choose to cancel jump appointments on days with inclement weather. Wind, rain, cloud coverage, and more can all affect flying conditions and ruin your skydiving plans.

That’s why it’s important to adjust your trip itinerary based on the weather. If you see a sunny day on the forecast, arrange your jump for that day. 

This is also why it’s smart to schedule your skydiving experience as early as possible into your Chicago vacation– so you can still do it in the event of a cancellation.

Schedule Your Skydive for Your Chicago Vacation

Skydiving can be a thrilling experience, but it can also be a little nerve-racking for first-timers. 

If you’re feeling the first-time jitters, you’re not alone! 

More importantly, we’ve got you covered. 

Prepare for your exciting vacation freefall with our tandem skydiving guide!



Douglas Smith is CEO/President, and Guest Relations Associate at Chicagoland Skydiving Center. He has owned and operated the business since 2000. He has been skydiving since 1994, and in addition to leading the CSC Team, is currently an instructor, videographer and pilot for CSC.

Topics: Skydiving Industry, Chicago