West Side Beach Vacations
Book a Beach Hotel + Flight or Car together to unlock savings
Photo by throwingsofas
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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 West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥433,054, price is now ￥359,343 per person
￥359,343
per person
Jul 19 - Jul 23
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,991 reviews)
Great location & breakfast was amazing.
Reviewed on May 11, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥632,616, price is now ￥511,244 per person
￥511,244
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
The hotel is in the best location in the city. The staff is very friendly and rooms are immaculate. Terrace 16 restaurant and bar in the hotel has a great view. Overall experience was wonderful highly recommend and will definitely be back soon.
Reviewed on May 11, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥533,518, price is now ￥448,315 per person
￥448,315
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
London House Hilton Chicago was fabulous. Great location. Wonderful view nice rooms rooftop bar is amazing, make reservations. For a quieter atmosphere the lounge on the second floor is a great place to hang out.. We’ll definitely stay there again.
Reviewed on May 11, 2026
Le Méridien Essex Chicago
Downtown Chicago
Price was ￥466,833, price is now ￥403,255 per person
￥403,255
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,004 reviews)
Staff was attentive and friendly. Atmosphere was welcoming. Restaurant had a great selection food was good and prices reasonable. Rooms were comfy.
Reviewed on Apr 23, 2026
5* Beach vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥425,590, price is now ￥399,524 per person
￥399,524
per person
Jul 27 - Jul 30
found 16 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Loved our suite- gorgeous views! Great service and excellent location
Reviewed on May 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥632,616, price is now ￥511,244 per person
￥511,244
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
The hotel is in the best location in the city. The staff is very friendly and rooms are immaculate. Terrace 16 restaurant and bar in the hotel has a great view. Overall experience was wonderful highly recommend and will definitely be back soon.
Reviewed on May 11, 2026
4 Night Beach vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥433,054, price is now ￥359,343 per person
￥359,343
per person
Jul 19 - Jul 23
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,991 reviews)
Great location & breakfast was amazing.
Reviewed on May 11, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
