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Top Miles Vacation Deals
Price found within the past 48 hours. Click for updated prices.

The Emily Hotel
Downtown Chicago
per person
Oct 23 - Oct 26
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,149 reviews)
Moments after arriving the hotel room, I took a shower and when I got out, there was a cockroach on my floor near the bed.
Reviewed on Aug. 7, 2025

Level Chicago - River North
Downtown Chicago
per person
Oct 17 - Oct 22
just found
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on Jul. 27, 2025


Hotel Riu Plaza Chicago
Downtown Chicago
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
The Breakfast Buffet ( included with your stay ) was a real surprise. Reminded us of the ones when we stay at all inclusive resorts when it comes to breafast options. The food was fantastic and the staff was very attentive cleaning and seating everyone quickly. Rooms were really nice, comfortable bed, bathroom was laid out really well. Super clean hotel that we would definitely recommend & stay at again when returning to Chicago
Reviewed on Aug. 7, 2025
Miles Hotel Deals

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 Aug 24 to Aug 25
CA $135
CA $150 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (1,206 reviews)
"Clean, friendly staff."
Reviewed on Aug. 5, 2025

Irish Cottage Inn & Suites
9853 US-20, Galena, IL
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Aug 11 to Aug 12
CA $117
CA $169 total
Aug 11 - Aug 12
includes taxes & fees
9.4/10 Exceptional! (1,157 reviews)
"Live music and atmosphere of pub and character of building"
Reviewed on Aug. 5, 2025

Country Inn & Suites by Radisson, Galena, IL
11334 Oldenburg Ln, Galena, IL
Fully refundable
The price is CA $138 per night from Aug 25 to Aug 26
CA $138
CA $154 total
Aug 25 - Aug 26
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"The kids really enjoyed the pool area."
Reviewed on Aug. 4, 2025
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.