
Northwest Chicago All inclusive Vacations
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Top All inclusive vacation packages in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥233,615, price is now ¥189,692 per person
¥189,692
per person
Nov 21 - Nov 25
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
We stayed in a deluxe king. Extremely small only one desk chair. Absolutely no space to relax. Interior doors were very beat up. Would not recommend or stay at this property again.
Reviewed on Sep 13, 2025


Pendry Chicago
Downtown Chicago
Price was ¥256,500, price is now ¥211,142 per person
¥211,142
per person
Nov 21 - Nov 25
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!
Reviewed on Sep 12, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥518,452, price is now ¥428,637 per person
¥428,637
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
You were being taken care of felt like home away from home good job to the staff at the Trump tower Chicago
Reviewed on Sep 12, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥243,274, price is now ¥204,282 per person
¥204,282
per person
Nov 21 - Nov 25
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on Sep 9, 2025
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View all trips5* All inclusive vacations in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥518,452, price is now ¥428,637 per person
¥428,637
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
You were being taken care of felt like home away from home good job to the staff at the Trump tower Chicago
Reviewed on Sep 12, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Chicago
View all trips4 Night All inclusive vacations in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥233,615, price is now ¥189,692 per person
¥189,692
per person
Nov 21 - Nov 25
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
We stayed in a deluxe king. Extremely small only one desk chair. Absolutely no space to relax. Interior doors were very beat up. Would not recommend or stay at this property again.
Reviewed on Sep 13, 2025


Pendry Chicago
Downtown Chicago
Price was ¥256,500, price is now ¥211,142 per person
¥211,142
per person
Nov 21 - Nov 25
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!
Reviewed on Sep 12, 2025
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.