
Historic Route 66 Ski Vacations
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Top Ski vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.


Hotel Riu Plaza Chicago
Downtown Chicago
Price was NT$24,563, price is now NT$17,225 per person
NT$17,225
per person
Apr 28 - May 1
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Good breakfast, excellent service, unfortunately, they don't have microwave service to heat food
Reviewed on 2026/3/13

The Emily Hotel
Downtown Chicago
Price was NT$32,671, price is now NT$25,681 per person
NT$25,681
per person
Apr 28 - May 1
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again.
Reviewed on 2026/3/7

Arlo Chicago
Downtown Chicago
Price was NT$23,315, price is now NT$18,434 per person
NT$18,434
per person
Apr 28 - May 1
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (2,002 reviews)
Friendly staff, very helpful and approachable. The rooms were clean and I pay attention to these things, the room was immaculate upon checkin. I appreciated the lovely in-room espresso machine too. Good breakfast from the onsite restaurant. There’s also coffee, donuts and bubble tea cafes right across Michigan ave. Close to the art institute, the orange and red lines, and more I am sure. Highly recommend the Arlo for your stay in downtown Chicago.
Reviewed on 2026/3/9

Eurostars Magnificent Mile
Downtown Chicago
Price was NT$22,978, price is now NT$18,760 per person
NT$18,760
per person
Apr 28 - May 1
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on 2026/3/12
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View all trips3 Night Ski vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was NT$24,563, price is now NT$17,225 per person
NT$17,225
per person
Apr 28 - May 1
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Good breakfast, excellent service, unfortunately, they don't have microwave service to heat food
Reviewed on 2026/3/13

The Emily Hotel
Downtown Chicago
Price was NT$32,671, price is now NT$25,681 per person
NT$25,681
per person
Apr 28 - May 1
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again.
Reviewed on 2026/3/7

Arlo Chicago
Downtown Chicago
Price was NT$23,315, price is now NT$18,434 per person
NT$18,434
per person
Apr 28 - May 1
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.4/10 Exceptional! (2,002 reviews)
Friendly staff, very helpful and approachable. The rooms were clean and I pay attention to these things, the room was immaculate upon checkin. I appreciated the lovely in-room espresso machine too. Good breakfast from the onsite restaurant. There’s also coffee, donuts and bubble tea cafes right across Michigan ave. Close to the art institute, the orange and red lines, and more I am sure. Highly recommend the Arlo for your stay in downtown Chicago.
Reviewed on 2026/3/9
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See all available trips from Columbus 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.
