Exclusive Skydive Chicago Vacation Deals

Skydive Chicago vacation package deals

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,227, price is now CA $687 per person
CA $687
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,289, price is now CA $707 per person
CA $707
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $3,192, price is now CA $1,902 per person
CA $1,902
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,576, price is now CA $1,543 per person
CA $1,543
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,378, price is now CA $841 per person
CA $841
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,294, price is now CA $808 per person
CA $808
per person
Jan 31 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Frequently asked questions

How much are vacation packages to Skydive Chicago?
A fantastic CA $687 package deal can be booked for your journey to Skydive Chicago. Why not let Travelocity take all the stress out of sorting out your travel plans? The good thing about combining your hotel and flights is that it'll save you a tidy sum. And who wouldn't love a little extra cash to play with?
Where can I get the best vacation package deals for Skydive Chicago?
There's no need to look any further than Travelocity. With no less than 400 air carriers and 665,000 properties around the world, it's easy to put together a Skydive Chicago package deal that ticks all your boxes.
Why should I book my Skydive Chicago vacation package with Travelocity?
With first-rate service, support available 24/7 and some of the most perfect getaways on offer, you'll never wander alone. And if you find a lower price, we'll match it. That's our Price Match Guarantee.
Can I go on vacation to Skydive Chicago at this time?
Learn all the info you should know about quarantine policies and travel restrictions before you head for Skydive Chicago. Our Covid-19 Travel Advisor is full of advice to help make your trip relaxed and stress-free.

Top Skydive Chicago hotel deals

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
The price is CA $129 per night
CA $129
CA $143 total
Jan 11 - Jan 12, 2026
includes taxes & fees
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. Popular attractions Dayton Ridge Golf Club and Reddick Mansion are located nearby.
Pool
Hot tub
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
The price is CA $97 per night
CA $97
CA $108 total
Dec 23 - Dec 24
includes taxes & fees
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 in our reviews. Popular attractions Dayton Ridge Golf Club and Reddick Mansion are located nearby.
Breakfast included
Parking included
Holiday Inn Express & Suites Ottawa by IHG

Holiday Inn Express & Suites Ottawa by IHG

2.5 out of 5
2850 Columbus Street Ottawa IL
Free cancellation
The price is CA $184 per night
CA $184
CA $205 total
Dec 21 - Dec 22
includes taxes & fees
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 in our reviews. Popular attractions Dayton Ridge Golf Club and Reddick Mansion are located nearby.
Pool
Breakfast included
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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.