Far Southwest Side Mountain Vacations
Book a Mountain Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Mountain vacation packages in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥247,175, price is now ￥190,223 per person
￥190,223
per person
Mar 7 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on Dec 8, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥263,905, price is now ￥203,427 per person
￥203,427
per person
Mar 7 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on Dec 14, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥393,998, price is now ￥304,081 per person
￥304,081
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Excellent stay.
Loved everything about this hotel. Definitely coming back.
Reviewed on Dec 18, 2025
The Emily Hotel
Downtown Chicago
Price was ￥275,574, price is now ￥215,922 per person
￥215,922
per person
Mar 7 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Love staying at the Emily. Very helpful friendly Staff & ccool architecture. Also love the front Patio in Summer☀️
Reviewed on Dec 16, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥420,340, price is now ￥330,843 per person
￥330,843
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
Don't see what you're looking for?
See all available trips from Osaka to Far Southwest Side
View all trips5* Mountain vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥393,998, price is now ￥304,081 per person
￥304,081
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Excellent stay.
Loved everything about this hotel. Definitely coming back.
Reviewed on Dec 18, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥420,340, price is now ￥330,843 per person
￥330,843
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Far Southwest Side
View all trips4 Night Mountain vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥292,616, price is now ￥245,230 per person
￥245,230
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was nice. Service was good.
Reviewed on Dec 17, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥393,998, price is now ￥304,081 per person
￥304,081
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Excellent stay.
Loved everything about this hotel. Definitely coming back.
Reviewed on Dec 18, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥420,340, price is now ￥330,843 per person
￥330,843
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Far Southwest Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
