Package deals near Skydive Chicago

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Top Skydive Chicago vacation deals

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
4.0-star property

La Banque Hotel

9.4/10 Exceptional! (431 reviews)

Sep 19 - Sep 22

3 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 11 hours ago
Beautiful boutique hotel with great staff!

Reviewed on Sep 16, 2022

The Emily Hotel
4.0-star property

The Emily Hotel

Downtown Chicago
9.2/10 Wonderful! (1,159 reviews)

Oct 26 - Nov 2

7 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
per person
found 1 day ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.

Reviewed on Jul 26, 2025

The Langham, Chicago
5.0-star property

The Langham, Chicago

Downtown Chicago
9.8/10 Exceptional! (1,004 reviews)

Oct 26 - Nov 2

7 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Just an absolutely beautiful hotel with spectacular service. Highly recommend.

Reviewed on Mar 29, 2024

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0-star property

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago
8.2/10 Very Good! (2,727 reviews)

Oct 26 - Nov 2

7 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Breakfast was amazing

Reviewed on Aug 11, 2025

Holiday Inn Express Chicago - Magnificent Mile by IHG
2.5-star property

Holiday Inn Express Chicago - Magnificent Mile by IHG

Downtown Chicago
8.4/10 Very Good! (1,012 reviews)

Oct 26 - Nov 2

7 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
the location was perfect, the building with just to small elevators that took forever to be available and always full. The bedroom, extremely small. The bed, too high, impossible to just sit on the bed, very uncomfortable.

Reviewed on Aug 11, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Downtown Chicago
9.4/10 Exceptional! (1,679 reviews)

Oct 23 - Oct 26

3 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
I recently stayed at the Trump International Hotel & Tower Chicago, and it exceeded every expectation. From the moment I arrived, I was impressed by the warmth and professionalism of the staff. Check-in was smooth and welcoming, and I was personally escorted to my room—which turned out to be nothing short of spectacular. The room itself was spacious, immaculately clean, and beautifully designed with modern touches and classic elegance. Floor-to-ceiling windows offered breathtaking views of the Chicago River and city skyline. The kitchenette was a nice bonus and made the room feel more like a luxury apartment than a typical hotel room. The service throughout my stay was consistently excellent—attentive without being overbearing. Every request was handled promptly and with a smile, and it was clear that the staff genuinely cared about making my stay enjoyable. I also had the chance to dine at Rebar, and the food and views were equally impressive. The atmosphere was relaxed yet refined, and it made for a perfect evening. The location is ideal—walking distance to the Magnificent Mile, Millennium Park, and plenty of restaurants and shops. Despite being in the heart of downtown, the hotel felt like a peaceful retreat above the city. Whether you're visiting Chicago for business or pleasure, I highly recommend the Trump International Hotel. It’s a standout experience in every way—luxury, location, service, and comfort all rolled into one.

Reviewed on Aug 14, 2025

Hotel deals near Skydive Chicago

Super 8 by Wyndham Ottawa Starved Rock

Super 8 by Wyndham Ottawa Starved Rock

2 out of 5
500 East Etna Rd., Ottawa, IL
Free Cancellation
Reserve now, pay when you stay
2.91 mi from Skydive Chicago
$73 nightly
The price is $81 total per night
$81 total
Sep 1 - Sep 2
Total includes taxes and fees
At Super 8 by Wyndham Ottawa Starved Rock, guests have access to free WiFi in public areas, a computer station, and free newspapers. Free parking is included with your stay. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and securing valuables. Additional amenities include laundry facilities, a TV in a common area, and an ATM.
Breakfast included
Parking included
Comfort Inn Ottawa Starved Rock Area

Comfort Inn Ottawa Starved Rock Area

2.5 out of 5
120 W. Stevenson Road, Ottawa, IL
Free Cancellation
Reserve now, pay when you stay
2.78 mi from Skydive Chicago
$103 nightly
The price is $114 total per night
$114 total
Aug 24 - Aug 25
Total includes taxes and fees
Guests staying at Comfort Inn Ottawa Starved Rock Area enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, take advantage of free parking. The 24-hour front desk has staff standing by to help with securing valuables and dry cleaning/laundry. Additional amenities include a hot tub, a 24-hour business center, and coffee/tea in a common area.
Pool
Hot Tub
Ottawa Cabin: Hot Tub, Wraparound Deck, Games

Ottawa Cabin: Hot Tub, Wraparound Deck, Games

0.3 mi from Skydive Chicago
Get rates
Guests staying at this cabin enjoy a sauna, a hot tub, and a garden. This smoke-free cabin also has barbecue grills.
Pool
Hot Tub
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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.

Book a Skydive Chicago vacation package

Stop dreaming and start traveling. If you’ve always wanted to see Skydive Chicago, now is the perfect time. Book your getaway to Ottawa with Orbitz and get ready to tick this attraction off your bucket list. Plus when you lock in your package with us, you’ll have plenty of cash leftover to splash out on other amazing Ottawa sights. Because travel is all about investing in experiences, not things!

If you’re hoping to stay close to Skydive Chicago, we’ve got you covered. Choose from a great range of hotels not far from this attraction. Roll out of bed, slip on your walking shoes and you’ll be there within moments. What could be more convenient than that? You won’t just be close to all the action — you’ll save money on transportation, and a hot shower and cozy bed will be within reach after a big day of exploring. Now that’s what we call a stress- free, full-of-fun getaway.

Orbitz has your ticket to a rewarding Skydive Chicago vacation. Book your Ottawa package with us and you’ll be able to access Orbitz Rewards. Earn Orbucks when you reserve your flights, hotels and activities with Orbitz and redeem them at over 385,000 hotels worldwide. $1 Orbuck = $1 off your next hotel. Join, earn, redeem — just like that! When you join Orbitz Rewards, you’ll also instantly unlock exclusive deals and save on thousands of properties with Insider Pricing.

We believe the best reward that you can give to yourself or others is the gift of travel. So, don’t put off exploring Skydive Chicago any longer. Save a bundle and book your Ottawa escape with Orbitz today.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.