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

The Emily Hotel
Downtown Chicago
Price was ¥486,842, price is now ¥420,502 per person
¥420,502
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Convenient location and easy building to deal with. Parking was a little expensive.
Reviewed on Jun 2, 2026


Swissotel - Chicago
Downtown Chicago
Price was ¥520,834, price is now ¥442,672 per person
¥442,672
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,360 reviews)
Location is closer to
Navy pier. Not a lot of nice food options around.
Reviewed on Jun 3, 2026

The Godfrey Hotel Chicago
Downtown Chicago
Price was ¥500,967, price is now ¥427,738 per person
¥427,738
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,242 reviews)
El cuarto es amplio y muy cómodo. El personal es muy atento. La ubicación es céntrica. Alrededor de puede caminar libremente y se siente seguro. Si le agrada dar largas caminatas puedes llegar a los lugares de interés con facilidad. El hotel cuenta con una terraza con lindas vistas y ambiente acogedor. Disfrutamos el hotel y el área. No pierdan la oportunidad de visitar el Instituto de Arte de Chicago, cuenta con una amplia e impresionante colección del arte estadounidense, del impresionismo y de los artistas más importantes del mundo.
Reviewed on May 31, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥565,241, price is now ¥486,931 per person
¥486,931
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great stay and location.
Reviewed on Jun 4, 2026
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View all trips5* All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥565,241, price is now ¥486,931 per person
¥486,931
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great stay and location.
Reviewed on Jun 4, 2026

The Peninsula Chicago
Downtown Chicago
Price was ¥607,556, price is now ¥554,407 per person
¥554,407
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Everyone was so helpful and friendly
Great environment.
Cleaning, room service ,breakfast A+
Reviewed on May 29, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was ¥542,612, price is now ¥507,341 per person
¥507,341
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (854 reviews)
Beautiful room. Well appointed. love the ambiance. Ashley Cartagena was very helpful with reservations!! Great location. Do not eat here, food is not good especially for the price. Rooftop bar view is cute but cocktails not great, I would skip them. There are dozens of cute coffee shops, bakeries, restaurants, bars & shops all steps away. would definitely stay here again.
Reviewed on May 28, 2026
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View all trips3 Night All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago
Downtown Chicago
Price was ¥520,834, price is now ¥442,672 per person
¥442,672
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,360 reviews)
Location is closer to
Navy pier. Not a lot of nice food options around.
Reviewed on Jun 3, 2026


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥565,241, price is now ¥486,931 per person
¥486,931
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great stay and location.
Reviewed on Jun 4, 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.

Chicago Avenue Inn
Humboldt Park
Price was ¥360,055, price is now ¥339,351 per person
¥339,351
per person
Aug 17 - Aug 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7/10 Good! (102 reviews)
Location worked very well for our needs. Location was a bit sketchy but we came across zero issues with the neighborhood. Room wasn’t perfect and could have been a little more clean as there was a dirty rag on the floor and the bed sheets/pillows had some questionable stains. Best New Subs across the street was delicious and worth stopping by. Keep in mind all amenities, bathrooms, kitchen, lounge areas are all shared spaces. Doors to the rooms could have been more secured with deadbolts.
Reviewed on May 21, 2026

Hilton Rosemont Chicago O'Hare
Price was ¥386,452, price is now ¥367,881 per person
¥367,881
per person
Aug 17 - Aug 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Good food in the restaurant and I loved the Starbucks in the lobby.
Reviewed on Jun 2, 2026

Wyndham Garden Elk Grove Village/O'Hare
Price was ¥360,096, price is now ¥343,124 per person
¥343,124
per person
Aug 17 - Aug 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,001 reviews)
Great Staff and hotel. It was a smooth and efficient check in.
Reviewed on Jun 4, 2026
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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.
