Central Chicago All inclusive Vacations
Book a All inclusive Hotel + Flight or Car together to unlock savings
Photo by Phil Ostroff
- 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 All inclusive vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was ￥501,650, price is now ￥364,000 per person
￥364,000
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views
Reviewed on Jun 22, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥625,471, price is now ￥488,656 per person
￥488,656
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,744 reviews)
Excelente, ubicación perfecta cerca de todo
Reviewed on Jun 23, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥739,152, price is now ￥584,323 per person
￥584,323
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great customer service! Let us in in the morning even our check in time was afternoon. Views were incredible!
Reviewed on Jun 23, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ￥661,388, price is now ￥532,911 per person
￥532,911
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
The hotel is beautiful with so many bars and restaurants nearby. About 4 -5 blocks from Millenium Park. The seating areas are so peaceful and the design is amazing. They let me store my bike box the day before my stay which was so convenient. Staff are friendly and professional.
Reviewed on Jun 17, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips5* All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Price was ￥375,831, price is now ￥346,797 per person
￥346,797
per person
Sep 15 - Sep 17
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
Excellent hotel and location. 1 min away from Michigan avenue
Reviewed on Jun 23, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥739,152, price is now ￥584,323 per person
￥584,323
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great customer service! Let us in in the morning even our check in time was afternoon. Views were incredible!
Reviewed on Jun 23, 2026
Nobu Hotel Chicago
Downtown Chicago
Price was ￥480,282, price is now ￥426,559 per person
￥426,559
per person
Aug 9 - Aug 13
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (869 reviews)
My stay was remarkable! Staff was extremely friendly, room clean, in room dining food was delicious!
Reviewed on Jun 21, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips3 Night All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was ￥381,100, price is now ￥333,296 per person
￥333,296
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable
Reviewed on Jun 23, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥433,683, price is now ￥362,435 per person
￥362,435
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,464 reviews)
Excelente hotel para quedarse en chicago
Reviewed on Jun 23, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥467,203, price is now ￥405,796 per person
￥405,796
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Great customer service! Let us in in the morning even our check in time was afternoon. Views were incredible!
Reviewed on Jun 23, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips4 Night All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was ￥501,650, price is now ￥364,000 per person
￥364,000
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views
Reviewed on Jun 22, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥425,496, price is now ￥330,543 per person
￥330,543
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,349 reviews)
I love how convenient this hotel is. However they should FIRE their designer. Whoever thought shag carpets work with rolling luggage has never been a guest at the hotel. The room hallways have a lower profile carpet but still difficult. Even the maintenance people joke about it; not really funny when you have multiple bags.
Reviewed on Jun 22, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all tripsThings to do
Wendella's 90-min Chicago River Architecture Tour
￥6,478
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
