Vacations Close To Skydive Chicago

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Skydive Chicago Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,086, price is now $862 per person
$862
per person
Oct 26 - Oct 30
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,720, price is now $1,168 per person
$1,168
per person
Oct 26 - Oct 30
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $1,465, price is now $1,078 per person
$1,078
per person
Oct 26 - Oct 30
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was $1,847, price is now $1,380 per person
$1,380
per person
Oct 26 - Oct 30
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,154, price is now $1,635 per person
$1,635
per person
Oct 26 - Oct 30
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was $1,673, price is now $1,287 per person
$1,287
per person
Oct 26 - Oct 30
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Lots of fruit flies.. It was bad.. Both sweats...

Reviewed on Sep 12, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,438, price is now $1,129 per person
$1,129
per person
Oct 26 - Oct 30
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was $1,331, price is now $1,056 per person
$1,056
per person
Oct 26 - Oct 30
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Great location, close to everything. Breakfast and 2 drink reception added value to the stay. Went to a cubs game, close to the red line. Would stay again.

Reviewed on Sep 12, 2026

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Best Lodging Options Near Skydive Chicago

Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy

2 out of 5
1879 N 2703rd Rd Ottawa IL
7.78 km from Skydive Chicago
Stay at this cabin in Ottawa. Enjoy free parking, patios, and climate control. Popular attractions Tangled Roots Brewing Company - The Lone Buffalo and Washington ...
Super 8 by Wyndham Ottawa Starved Rock

Super 8 by Wyndham Ottawa Starved Rock

2 out of 5
500 East Etna Rd. Ottawa IL
4.81 km from Skydive Chicago
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms ...
Comfort Inn Ottawa Starved Rock Area

Comfort Inn Ottawa Starved Rock Area

2.5 out of 5
120 W. Stevenson Road Ottawa IL
4.59 km from Skydive Chicago
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Holiday Inn Express & Suites Ottawa by IHG

Holiday Inn Express & Suites Ottawa by IHG

2.5 out of 5
2850 Columbus Street Ottawa IL
4.93 km from Skydive Chicago
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Fairfield Inn & Suites by Marriott Ottawa Starved Rock Area

Fairfield Inn & Suites by Marriott Ottawa Starved Rock Area

3 out of 5
3000 Fairfield Ln Ottawa IL
4.57 km from Skydive Chicago
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn Ottawa (Starved Rock Area)

Hampton Inn Ottawa (Starved Rock Area)

2.5 out of 5
4115 Holiday Ln Ottawa IL
4.47 km from Skydive Chicago
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Quality Inn Ottawa near Starved Rock State Park

Quality Inn Ottawa near Starved Rock State Park

2.5 out of 5
510 E Etna Road Ottawa IL
4.53 km from Skydive Chicago
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Dayton Ridge Golf Club and Reddick ...
Surrey Motel

Surrey Motel

2 out of 5
2750 Columbus St.  Ottawa IL
5.09 km from Skydive Chicago
Stay at this motel in Ottawa. Enjoy free WiFi, free parking, and room service. Popular attractions Dayton Ridge Golf Club and Reddick Mansion are located ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.