Miles Vacation Packages
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Top Miles Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Price was CA $1,296, price is now CA $921 per person
CA $921
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
We stayed at this hotel for a small wedding venue. I booked the larger room and was glad I did. The hotel was close for walking to restaurants and some bars. The front desk was very friendly and helpful.
Reviewed on Jun 19, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
I loved how simple and easy it was to access everything.
Reviewed on Jun 16, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,315, price is now CA $1,667 per person
CA $1,667
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun
Reviewed on Jun 17, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,541, price is now CA $1,138 per person
CA $1,138
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!
Reviewed on Jun 18, 2026
Miles Hotel Deals
Irish Cottage Inn & Suites
9853 US-20 Galena IL
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Jun 21 to Jun 22
CA $114
CA $165 total
Jun 21 - Jun 22
includes taxes & fees
9.4/10 Exceptional! (1,363 reviews)
"Breakfast menu was fresh but pancakes were not hot. Tea was a pleasant bonus. Dinner was good and entertainment was nice surprise. Overall very pleasant stay and would book again."
Reviewed on Jun 16, 2026
Stoney Creek Inn Galena
940 Galena Square Dr Galena IL
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Jun 25 to Jun 26
CA $139
CA $154 total
Jun 25 - Jun 26
includes taxes & fees
9.4/10 Exceptional! (1,338 reviews)
"We chose this hotel because we had stayed at Stoney Creek in KC. This hotel did not live up to previous standards. The room was small in size with not even a closet. The hotel offered a pool but it was quite small as well. We did enjoy the hot tub and the fact the area was adults only after 10. The ..."
Reviewed on Jun 17, 2026
Country Inn & Suites by Radisson, Galena, IL
11334 Oldenburg Ln Galena IL
Fully refundable
The price is CA $150 per night from Jun 29 to Jun 30
CA $150
CA $166 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Clean room.Staff wonderful. All property looks little bit older. Swimming pool. It's it's smaller than I expected. Everything it was okay. We have affordable good stay"
Reviewed on Jun 16, 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.
