
Rush Street Ski Vacations
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Top Ski vacation packages in Rush Street
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥379,770, price is now ¥295,940 per person
¥295,940
per person
Jul 9 - Jul 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,914 reviews)
It was great property, amazing location and the breakfast was fantastic.
Reviewed on Apr 25, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥480,293, price is now ¥375,986 per person
¥375,986
per person
Jul 9 - Jul 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
The Trump Hotel was located in the best center place possible in the heart of Downtown Chicago, walkable distance to literally everything, bars, restaurants, tourist attractions, walk by the river and boat tours, magnificent mile, millennium park and the bean, the willis skydeck... it's also Super clean! Fresh nice smell in the hallways and the rooms. Lake view room had the entire Downtown and the lake view covered. Super amazing!!!! Amenities top notch. Very polite and friendly staff. Terrace 16 was a little slow but amazing food and ambiance. Highly recommended!
Reviewed on Apr 24, 2026


Pendry Chicago
Downtown Chicago
Price was ¥405,438, price is now ¥330,630 per person
¥330,630
per person
Jul 9 - Jul 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,137 reviews)
Great hotel! Very central location, helpful staff. The speak easy was a great surprise
Reviewed on Apr 20, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was ¥394,981, price is now ¥332,408 per person
¥332,408
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place
Reviewed on Apr 25, 2026
5* Ski vacations in Rush Street
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥480,293, price is now ¥375,986 per person
¥375,986
per person
Jul 9 - Jul 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
The Trump Hotel was located in the best center place possible in the heart of Downtown Chicago, walkable distance to literally everything, bars, restaurants, tourist attractions, walk by the river and boat tours, magnificent mile, millennium park and the bean, the willis skydeck... it's also Super clean! Fresh nice smell in the hallways and the rooms. Lake view room had the entire Downtown and the lake view covered. Super amazing!!!! Amenities top notch. Very polite and friendly staff. Terrace 16 was a little slow but amazing food and ambiance. Highly recommended!
Reviewed on Apr 24, 2026


Park Hyatt Chicago
Downtown Chicago
Price was ¥458,498, price is now ¥393,096 per person
¥393,096
per person
Jul 9 - Jul 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
I truly enjoyed my 5 night stay at this hotel. Everyone was helpful, friendly, and accommodating. I love its location, near the Michael mile.
When I return to Chicago I will definitely stay at the Park Hyatt.
Reviewed on Apr 4, 2026
3 Night Ski vacations in Rush Street
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥365,342, price is now ¥331,545 per person
¥331,545
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Great location and value
Reviewed on Apr 25, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥427,049, price is now ¥362,143 per person
¥362,143
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,914 reviews)
It was great property, amazing location and the breakfast was fantastic.
Reviewed on Apr 25, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥451,470, price is now ¥384,474 per person
¥384,474
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
The Trump Hotel was located in the best center place possible in the heart of Downtown Chicago, walkable distance to literally everything, bars, restaurants, tourist attractions, walk by the river and boat tours, magnificent mile, millennium park and the bean, the willis skydeck... it's also Super clean! Fresh nice smell in the hallways and the rooms. Lake view room had the entire Downtown and the lake view covered. Super amazing!!!! Amenities top notch. Very polite and friendly staff. Terrace 16 was a little slow but amazing food and ambiance. Highly recommended!
Reviewed on Apr 24, 2026
4 Night Ski vacations in Rush Street
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥379,770, price is now ¥295,940 per person
¥295,940
per person
Jul 9 - Jul 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,914 reviews)
It was great property, amazing location and the breakfast was fantastic.
Reviewed on Apr 25, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥480,293, price is now ¥375,986 per person
¥375,986
per person
Jul 9 - Jul 13
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
The Trump Hotel was located in the best center place possible in the heart of Downtown Chicago, walkable distance to literally everything, bars, restaurants, tourist attractions, walk by the river and boat tours, magnificent mile, millennium park and the bean, the willis skydeck... it's also Super clean! Fresh nice smell in the hallways and the rooms. Lake view room had the entire Downtown and the lake view covered. Super amazing!!!! Amenities top notch. Very polite and friendly staff. Terrace 16 was a little slow but amazing food and ambiance. Highly recommended!
Reviewed on Apr 24, 2026

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
