Rush Street All inclusive Vacations
Book a All inclusive 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
5* All inclusive vacations in Rush Street
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 21 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 7 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
4 Night All inclusive vacations in Rush Street
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was ￥289,694, price is now ￥234,962 per person
￥234,962
per person
Mar 26 - Mar 30
found 21 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
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 21 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 20 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.
