Ashton Vacation Packages
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Top Ashton Vacation Deals
Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.
Reviewed on Jan 6, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,469, price is now CA $930 per person
CA $930
per person
Mar 21 - Mar 27
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,282, price is now CA $1,494 per person
CA $1,494
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,424, price is now CA $972 per person
CA $972
per person
Mar 21 - Mar 27
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026
Ashton Hotel Deals
Tru By Hilton Dixon
1806 S. Galena Ave Dixon IL
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Feb 21 to Feb 22
CA $145
CA $161 total
Feb 21 - Feb 22
includes taxes & fees
8.2/10 Very Good! (61 reviews)
Everything was perfect
Reviewed on Jan 26, 2026
Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Feb 15 to Feb 16
CA $133
CA $151 total
Feb 15 - Feb 16
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
The whole facility was great room was clean and roomy. The breakfast was great the biscuits and gravy tasted homemade.
Reviewed on Feb 3, 2026
Home2 Suites by Hilton Dekalb
575 S ANNIE GLIDDEN RD DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Feb 14 to Feb 15
CA $155
CA $176 total
Feb 14 - Feb 15
includes taxes & fees
9.2/10 Wonderful! (417 reviews)
Yes room was clean and spacious. Staff was polite and great
Reviewed on Feb 7, 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.
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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.
