Historic Route 66 Romantic Vacations
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Top Romantic vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
￥58,476
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
The staff was extremely accommodating, it was marathon week so I understand things can be tough, my issues were with the room as a whole. The shower would leak into the bathroom and completely cover the floor and when I informed staff I was having flooding problems they said oh it’s the shower curtain as if it’s a common issue. The wall paper in the bathroom was peeling off the wall. Tv guide didn’t work so you get to play channel roulette. On the plus side staff was great and they provided cold drinks in the morning, ac works really well
Reviewed on Oct 14, 2026
Swissotel - Chicago
Downtown Chicago
￥66,276
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Beautiful location by Chicago river. We used parking with spot hero app and valet was very helpful,in showing us how to get to our parking location. Room was spacious and clean. Beds were comfortable. Staff was helpful
Reviewed on Oct 14, 2026
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View all trips5* Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
The Langham, Chicago
Downtown Chicago
￥379,986
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,014 reviews)
We stayed in The Langham beautiful suite with the club access to celebrate our 35th wedding anniversary. Excellent location, wonderful staff. We would enjoy the stay so much more if we could have our favorite drinks.
Neither the club lounge or restaurant had Pinot Grigio wine or any type of scotch.
This is our third time we have stayed in this Chicago hotel and believe previously the club lounge had much more to offer as far as variety of food and drinks.
Reviewed on Oct 14, 2026
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View all trips3 Night Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
￥66,276
per person
Nov 24 - Nov 27
found 13 hours ago
Roundtrip flight included
Louisville (SDF) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Beautiful location by Chicago river. We used parking with spot hero app and valet was very helpful,in showing us how to get to our parking location. Room was spacious and clean. Beds were comfortable. Staff was helpful
Reviewed on Oct 14, 2026
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View all trips4 Night Romantic vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
￥236,203
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
The room was very small. The espresso machine had no counter top to set it on. The toilet had a long red streak on it. The beds were fine but squeaky. Could hear noise from other rooms and the street, even on the 14th floor.
Reviewed on Oct 14, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
