Miles Holidays
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Miles Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was S$1,102, price is now S$943 per person
S$943
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Jasmine was courteous and friendly, made our check in process smooth. Clean rooms and the breakfast was amazing. I definitely recommend staying here.
Reviewed on 31 Dec, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was S$1,118, price is now S$987 per person
S$987
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on 18 Dec, 2025
The Peninsula Chicago
Downtown Chicago
Price was S$1,584, price is now S$1,424 per person
S$1,424
per person
30 Jan - 1 Feb
found 1 day ago
Return flight included
Seattle (SEA) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.
Reviewed on 29 Dec, 2025
Top hotels in Miles
Stoney Creek Inn Galena
940 Galena Square Dr Galena IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,295 reviews)
Loved the check in lady very nice. Room was great beds comfortable. $30 for 2 cardboard pizzas not to great
Reviewed on 25 Dec, 2025
Irish Cottage Inn & Suites
9853 US-20 Galena IL
Fully refundableReserve now, pay when you stay
The price is S$152 per night from 19 Jan to 20 Jan
S$152
19 Jan - 20 Jan, 2026
includes taxes & fees
9.4/10 Exceptional! (1,246 reviews)
Rooms super clean, pub was a blast..Food was great..
Reviewed on 26 Dec, 2025
Chestnut Mountain Resort
8700 W Chestnut Mountain Rd Galena IL
8.4/10 Very Good! (1,004 reviews)
We were staying here for the three nights before Christmas this year and we had an amazing time so convenient for having a lodging with skiing. Also, the restaurant very good. The room was very spacious and very clean. Service good as well. Definitely we will come back and we highly recommend ...
Reviewed on 29 Dec, 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
