Historic Route 66 Luxury Vacations
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Top Luxury vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was ₩1,203,789, price is now ₩847,524 per person
₩847,524
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very Good! (2,054 reviews)
The location is great, but the room is kind of small.
Reviewed on Jul 29, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,086,853, price is now ₩1,229,825 per person
₩1,229,825
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Loved the breakfast. The room was nice and clean. However there are very little amenities here like no ice machines. No grab and go. No pool. My room got hot a few times but hotel maintenance was quick to respond. Other staff members appeared confused when asked a question about amenities. Check in was confusing as well. Staff had trouble finding reservations as well.
Reviewed on Jul 29, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,876,989, price is now ₩1,300,118 per person
₩1,300,118
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,144 reviews)
The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District.
Reviewed on Jul 28, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ₩1,526,662, price is now ₩1,064,725 per person
₩1,064,725
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
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See all available trips from Newark Liberty Intl. Airport to Historic Route 66
View all trips5* Luxury vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,290,935, price is now ₩1,623,642 per person
₩1,623,642
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,945 reviews)
5 star hotel need to offer free gig on arrival like wine bottle fancy water
Reviewed on Jul 29, 2026
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See all available trips from Newark Liberty Intl. Airport to Historic Route 66
View all trips3 Night Luxury vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,086,853, price is now ₩1,229,825 per person
₩1,229,825
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Loved the breakfast. The room was nice and clean. However there are very little amenities here like no ice machines. No grab and go. No pool. My room got hot a few times but hotel maintenance was quick to respond. Other staff members appeared confused when asked a question about amenities. Check in was confusing as well. Staff had trouble finding reservations as well.
Reviewed on Jul 29, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,876,989, price is now ₩1,300,118 per person
₩1,300,118
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,144 reviews)
The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District.
Reviewed on Jul 28, 2026
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
