West Side Mountain Vacations
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Top Mountain vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥274,580, price is now ￥221,432 per person
￥221,432
per person
Mar 16 - Mar 20
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥471,930, price is now ￥365,182 per person
￥365,182
per person
Feb 20 - Feb 23
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥395,658, price is now ￥312,870 per person
￥312,870
per person
Mar 26 - Mar 30
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!
Reviewed on Jan 6, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥290,986, price is now ￥236,196 per person
￥236,196
per person
Mar 16 - Mar 20
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥266,600, price is now ￥221,508 per person
￥221,508
per person
Mar 16 - Mar 20
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The staff and hotel were great. The rooms were spacious and bathrooms were very well thought out to accommodate multiple people. The staff were friendly and helpful. The breakfast every morning was wonderful. The breakfast has everything you can imagine. Will definitely stay there again.
Reviewed on Jan 7, 2026
5* Mountain vacations in West Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥395,658, price is now ￥312,870 per person
￥312,870
per person
Mar 26 - Mar 30
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!
Reviewed on Jan 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥471,930, price is now ￥365,182 per person
￥365,182
per person
Feb 20 - Feb 23
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
3 Night Mountain vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Suites O'Hare
Price was ￥384,612, price is now ￥321,928 per person
￥321,928
per person
Feb 20 - Feb 23
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The staff were friendly and professional. The room was clean and as expected. Only drawback was the lack of amenities. Coffee was out of a machine in lobby and cost $4 - WiFi was not free and $15 a day.
Reviewed on Dec 28, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥471,930, price is now ￥365,182 per person
￥365,182
per person
Feb 20 - Feb 23
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥414,480, price is now ￥338,803 per person
￥338,803
per person
Feb 20 - Feb 23
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
We noticed the plumbing was very noisy in adjoining rooms. Woke us up at 4 am
Reviewed on Jan 5, 2026
4 Night Mountain vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥310,730, price is now ￥249,464 per person
￥249,464
per person
Mar 16 - Mar 20
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 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 ￥395,658, price is now ￥312,870 per person
￥312,870
per person
Mar 26 - Mar 30
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!
Reviewed on Jan 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥428,324, price is now ￥339,200 per person
￥339,200
per person
Mar 28 - Apr 1
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
