Miles Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Miles Vacation Deals
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - Alsip
Price was CA $1,526, price is now CA $1,082 per person
CA $1,082
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (MDW)
8.4/10 Very Good! (1,015 reviews)
Didn't eat breakfast..parking was fine.
Reviewed on Apr 12, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,344, price is now CA $1,668 per person
CA $1,668
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,434, price is now CA $1,746 per person
CA $1,746
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Was lovely but remember it being better experience
Reviewed on Apr 16, 2026
Miles Hotel Deals
Irish Cottage Inn & Suites
9853 US-20 Galena IL
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Apr 21 to Apr 22
CA $121
CA $172 total
Apr 21 - Apr 22
includes taxes & fees
9.4/10 Exceptional! (1,322 reviews)
Nice large king bed. Staff was helpful, especially the shuttle driver. Nice restaurant for dinner with great music!
Reviewed on Apr 15, 2026
Stoney Creek Inn Galena
940 Galena Square Dr Galena IL
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from May 18 to May 19
CA $134
CA $149 total
May 18 - May 19
includes taxes & fees
9.2/10 Wonderful! (1,333 reviews)
Great staff and hospitality.
Reviewed on Apr 16, 2026
Country Inn & Suites by Radisson, Galena, IL
11334 Oldenburg Ln Galena IL
Fully refundable
The price is CA $142 per night from May 6 to May 7
CA $142
CA $157 total
May 6 - May 7
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Very nice hotel, rooms were good and the pool area was great!
Reviewed on Apr 13, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
