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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥378,473, price is now ￥286,400 per person
￥286,400
per person
Jun 8 - Jun 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Clean room , staff are friendly , breakfast is amazing just the rooftop bar was closed due to the winter season
Reviewed on Mar 31, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥454,488, price is now ￥361,036 per person
￥361,036
per person
May 1 - May 6
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon
Reviewed on Mar 29, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥408,952, price is now ￥326,052 per person
￥326,052
per person
Jun 8 - Jun 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing
Reviewed on Mar 27, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥491,402, price is now ￥394,486 per person
￥394,486
per person
Jun 4 - Jun 8
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Super clean, super friendly staff.
Reviewed on Mar 29, 2026
5* Mountain vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥483,150, price is now ￥395,209 per person
￥395,209
per person
Jun 8 - Jun 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Quality staff and the property was well appointed
Reviewed on Mar 30, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥458,142, price is now ￥430,439 per person
￥430,439
per person
Jun 8 - Jun 12
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!
Reviewed on Mar 27, 2026
3 Night Mountain vacations in West Side
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥395,386, price is now ￥337,268 per person
￥337,268
per person
May 13 - May 16
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Breakfast was delish! Staff was nice..great location.
Reviewed on Mar 31, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥430,486, price is now ￥354,482 per person
￥354,482
per person
May 13 - May 16
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Clean room , staff are friendly , breakfast is amazing just the rooftop bar was closed due to the winter season
Reviewed on Mar 31, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥513,756, price is now ￥438,043 per person
￥438,043
per person
May 13 - May 16
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Quality staff and the property was well appointed
Reviewed on Mar 30, 2026
4 Night Mountain vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Ohio House Motel
Downtown Chicago
Price was ￥394,776, price is now ￥354,113 per person
￥354,113
per person
Jun 11 - Jun 15
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,080 reviews)
Finding this place felt like a bit of an anomaly. Easiest and cheapest parking possible, and in walking distance of tons of stuff to do. The staff was incredibly courteous and helpful with any questions I had. The room was very spacious, even compared to the big name hotel chains. My single and only issue is that you can hear basically everything that happens outside of the immediate area of your room. I understand that its Chicago but hearing every door slam and conversation in and around the hotel was a bit much when trying to sleep (luckily I remembered to pack earplugs). That said, I'd still absolutely come back and stay again. This place was exceptional, especially for the price.
Reviewed on Mar 30, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥491,402, price is now ￥394,486 per person
￥394,486
per person
Jun 4 - Jun 8
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Super clean, super friendly staff.
Reviewed on Mar 29, 2026
The Buckingham Hotel
Downtown Chicago
Price was ￥425,648, price is now ￥380,130 per person
￥380,130
per person
Jun 4 - Jun 8
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Price was great. Room was huge with such a beautiful view of the city. Also a safe location within walking distance of things to see and do
Reviewed on Mar 5, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
