Historic Route 66 Holidays
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Historic Route 66 Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North
Downtown Chicago
Price was S$6,248, price is now S$6,036 per person
S$6,036
per person
3 Feb - 8 Feb
found 10 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Clean room, beautiful view and friendly staff
Reviewed on 15 Dec, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was S$7,531, price is now S$6,782 per person
S$6,782
per person
3 Feb - 8 Feb
found 10 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on 14 Dec, 2025
Pendry Chicago
Downtown Chicago
Price was S$6,441, price is now S$6,183 per person
S$6,183
per person
3 Feb - 8 Feb
found 10 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man,
Neither would get me a cab, they said to just stand outside
Reviewed on 4 Dec, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was S$6,257, price is now S$6,047 per person
S$6,047
per person
3 Feb - 8 Feb
found 10 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
The staff was outstanding. A great place to stay.
Reviewed on 17 Dec, 2025
Top hotels in Historic Route 66
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$112 per night from 30 Dec to 31 Dec
S$112
30 Dec - 31 Dec
includes taxes & fees
8.6/10 Excellent! (3,315 reviews)
Room and hotel was beautiful. Would have given 5 stars but the check in person was extremely rude. Employee got an attitude because I didn’t call to notify that I would arrive past the check in time. Once he noticed I did not like the way he talked to me, he tried to be nice and say it’s just “standard ...
Reviewed on 15 Dec, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 5 Jan to 6 Jan
S$135
5 Jan - 6 Jan, 2026
includes taxes & fees
8.8/10 Excellent! (3,482 reviews)
Room was clean
Reviewed on 14 Dec, 2025
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,111 reviews)
Walked to Millers Pub for Tom and Jerry’s, went to the Kringle market and rode the train to Wrigley felt very safe in the area. Room was clean and beautiful and you could feel the history of the hotel as soon as you walked in will definitely be staying again!!!!
Reviewed on 10 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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