Miles Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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.
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,256, price is now CA $1,425 per person
CA $1,425
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.
Reviewed on May 14, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,765, price is now CA $1,131 per person
CA $1,131
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.
Reviewed on May 16, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,810, price is now CA $1,190 per person
CA $1,190
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
Great view and room was very clean!
Reviewed on May 17, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,893, price is now CA $1,935 per person
CA $1,935
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (984 reviews)
We loved the view from the 30th floor! The place was near the L, bus stops and walking distance to restaurants.. The bed was comfortable but it would be nice to have a table and lamp on both sides. The room seemed to be geared towards singles rather than couples. The espresso machine was a nice touch but fairly unusable for us. We ended up buying instant coffee and used the electric kettle. Sad that we couldn’t use the hot tub during our trip because it was closed for maintenance. But all in all, we were quite pleased with the apartment! Hubby spent a lot of time on the balcony enjoying the views. Highly recommend!
Reviewed on May 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 $117 per night from May 20 to May 21
CA $117
CA $168 total
May 20 - May 21
includes taxes & fees
9.4/10 Exceptional! (1,339 reviews)
The room was clean but they could update the pillows. Too saoft and lumpy. The chairs in the room are not comfortable; very hard. Breakfast was okay, typical hotel breakfast. The bartenders were great in the pub, live music was good.
Reviewed on May 17, 2026
Stoney Creek Inn Galena
940 Galena Square Dr Galena IL
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from May 19 to May 20
CA $135
CA $150 total
May 19 - May 20
includes taxes & fees
9.2/10 Wonderful! (1,338 reviews)
All Good
Reviewed on May 17, 2026
Hotel Galena
324 Spring St Galena IL
The price is CA $129 per night from May 19 to May 20
CA $129
CA $143 total
May 19 - May 20
includes taxes & fees
9.6/10 Exceptional! (282 reviews)
The room was clean and well stocked with towels, shower items, coffee, generous size fridge. Not enough parking on property but parking lot across the street worked. Breakfast was plentiful.
Reviewed on May 17, 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.
