Elizabeth Vacation Packages
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Your Elizabeth Vacation
The lively city of Elizabeth is calling. Delve into everything from its highlights to its hidden gems with a Elizabeth vacation package that's tailored to you. Rocky Waters Vineyard and Winery, Fergedaboudit Vineyard & Winery and Apple River Fort are just a few of the attractions you'll want to see during your trip to Elizabeth. Browse Expedia's extensive range of travel options and start planning your perfect vacation to Elizabeth now.
Top Elizabeth Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,753, price is now CA $1,209 per person
CA $1,209
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Staff was amazing and the apartment building was phenomenally clean!
Reviewed on May 28, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,560, price is now CA $1,089 per person
CA $1,089
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes.
Reviewed on May 28, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,024, price is now CA $1,463 per person
CA $1,463
per person
Jul 21 - Jul 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
We had an amazing time, we absolutely loved our stay
Reviewed on May 29, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,318, price is now CA $1,683 per person
CA $1,683
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
10/10 experience! Love this hotel!…the only negative was a less than nice /helpful staff person at the front desk of the spa when I asked about the use of the sauna/steam room and also my neighbors next to my room were quite loud
Reviewed on May 27, 2026
Elizabeth Hotel Deals
Beautiful compound, 10 mile views, on 300 acre ranch, next to Galena Territory
Elizabeth IL
The price is CA $1,647 per night from Jun 21 to Jun 22
CA $1,647
CA $3,076 total
Jun 21 - Jun 22
includes taxes & fees
9.8/10 Exceptional! (50 reviews)
"The property was gorgeous. The houses still kept the farm house feel, while providing modern well kept amenities."
Reviewed on Dec 31, 2025
Luxury Ranch Compound on 300 acres, just outside Galena Territory. 30 bedrms.
Elizabeth IL
10/10 Exceptional! (4 reviews)
Excellent Retreat Experience
"This property offers the luxury of a resort with the down-home experience of a ranch. Peaceful, gorgeous views - especially at sunset from the "Quiet Rock" deck. Or the sunrise from the swing near the Main Lodge. Mark is a gracious host who shared his love of the property by introducing us to Waffles, ..."
Reviewed on Oct 7, 2024
Just rehabbed, amazing views on 300 acre ranch, animals, trails, hottub, pond
Elizabeth IL
9.6/10 Exceptional! (80 reviews)
"The house was great for our size family. We had 14 people and plenty of room. Joe the farm hand was great he met us on arrival and explained everything we needed to know.We would stay here again."
Reviewed on Jan 1, 2026
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.
Discover the most popular places to visit in Elizabeth
Massbach Ridge Winery
You can enjoy a tasting or tour at Massbach Ridge Winery during your travels to Elizabeth. Discover the countryside and spas in this family-friendly area.
What to do in Elizabeth
Downtown Galena Food and Drink Tour
CA $118
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
