Far Southwest Side Beach Vacations
Book a Beach 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 Beach vacation packages in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥382,948, price is now ￥314,808 per person
￥314,808
per person
May 13 - May 16
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great location! Excellent customer service! My only one complaint is that there are no microwaves at this property.
Reviewed on Mar 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥507,936, price is now ￥368,246 per person
￥368,246
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
The Wade
Downtown Chicago
Price was ￥442,434, price is now ￥337,288 per person
￥337,288
per person
May 13 - May 18
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,719 reviews)
Enjoyed our stay. Views were amazing and location convenient.
Reviewed on Mar 26, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥695,660, price is now ￥574,362 per person
￥574,362
per person
May 13 - May 18
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
Don't see what you're looking for?
See all available trips from Osaka to Far Southwest Side
View all trips5* Beach vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥695,660, price is now ￥574,362 per person
￥574,362
per person
May 13 - May 18
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Great place to stay . The staff was friendly and helpful !!!
Reviewed on Mar 22, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥555,302, price is now ￥474,136 per person
￥474,136
per person
May 18 - May 22
found 22 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Wonderful, from the property to the staff, the food and the amenities. Will be staying again any time I travel to Chicago.
Reviewed on Mar 25, 2026
Don't see what you're looking for?
See all available trips from Osaka to Far Southwest Side
View all trips3 Night Beach vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥331,962, price is now ￥288,802 per person
￥288,802
per person
Jun 8 - Jun 11
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Good staff, clean room,m. I didn’t like that the bathroom was almost see through from the other side of the room, you can’t see the person inside the bathroom but you can see the cilhouette
Reviewed on Mar 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥430,412, price is now ￥342,638 per person
￥342,638
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great location! Excellent customer service! My only one complaint is that there are no microwaves at this property.
Reviewed on Mar 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥434,357, price is now ￥350,134 per person
￥350,134
per person
May 14 - May 17
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Elegant and beautiful
Reviewed on Mar 26, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Far Southwest Side
View all trips4 Night Beach vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥320,278, price is now ￥272,523 per person
￥272,523
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent.
Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value
Reviewed on Mar 24, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥393,128, price is now ￥296,468 per person
￥296,468
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great location! Excellent customer service! My only one complaint is that there are no microwaves at this property.
Reviewed on Mar 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥471,077, price is now ￥378,208 per person
￥378,208
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Elegant and beautiful
Reviewed on Mar 26, 2026
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.
