Diamond Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$134 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
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Diamond 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 24 hours 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 24 hours 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 24 hours 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 Diamond
Wingate by Wyndham - Joliet
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
The price is S$120 per night from 6 Jan to 7 Jan
S$120
6 Jan - 7 Jan, 2026
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
Staff is always friendly.
Reviewed on 23 Dec, 2025
Super 8 by Wyndham Joliet
1806 McDonough St Joliet IL
Fully refundableReserve now, pay when you stay
The price is S$120 per night from 7 Jan to 8 Jan
S$120
7 Jan - 8 Jan, 2026
includes taxes & fees
8/10 Very Good! (729 reviews)
The only issue was the condition of the bathroom ceiling: water damage has not been repaired.
Reviewed on 21 Nov, 2025
La Quinta Inn & Suites by Wyndham Shorewood
19715 NE Frontage Rd Joliet IL
Fully refundableReserve now, pay when you stay
The price is S$145 per night from 8 Jan to 9 Jan
S$145
8 Jan - 9 Jan, 2026
includes taxes & fees
9/10 Wonderful! (886 reviews)
Staff, amenities, everything very clean! The only suggestion we have is that you have a shower mat for the bottom of the bathtub. The surface is very slick and, even with the bars, easy to fall.
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.
