South Suburbs Mountain Vacations
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Top Mountain vacation packages in South Suburbs
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥298,195, price is now ￥252,363 per person
￥252,363
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Overall good experience. My room was not cleaned one of the nights because the maid didn’t come until late but we were already in our room. Also, the $25/night resort fee was not properly explained to me, didn’t make much sense at all honestly. Property is nice and in a great location but i wouldn’t stay here again
Reviewed on Dec 19, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥405,962, price is now ￥330,854 per person
￥330,854
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!
Reviewed on Dec 19, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥301,364, price is now ￥253,699 per person
￥253,699
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Amenities, very clean, wonderful buffet service.
Reviewed on Dec 20, 2025
Hilton Chicago
Downtown Chicago
Price was ￥313,682, price is now ￥265,983 per person
￥265,983
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Great stay, lovely hotel. Great staff all around, Hannah upgraded our room to a 2 bathroom 2 bed with no charge after seeing we had a 4 party guest reservation. Definitely will be staying here again
Reviewed on Dec 20, 2025
5* Mountain vacations in South Suburbs
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥405,962, price is now ￥330,854 per person
￥330,854
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!
Reviewed on Dec 19, 2025
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥366,234, price is now ￥333,728 per person
￥333,728
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Very nice amenities and wellness facility. High end shopping within a very short walk.
Reviewed on Dec 16, 2025
4 Night Mountain vacations in South Suburbs
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥293,078, price is now ￥246,075 per person
￥246,075
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (326 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥405,962, price is now ￥330,854 per person
￥330,854
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!
Reviewed on Dec 19, 2025
Hilton Chicago
Downtown Chicago
Price was ￥314,266, price is now ￥267,266 per person
￥267,266
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Great stay, lovely hotel. Great staff all around, Hannah upgraded our room to a 2 bathroom 2 bed with no charge after seeing we had a 4 party guest reservation. Definitely will be staying here again
Reviewed on Dec 20, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
