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.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Downtown Chicago
¥453,880
per person
Nov 18 - Nov 22
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥626,188
per person
Nov 18 - Nov 22
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago
¥551,993
per person
Nov 18 - Nov 22
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,008 reviews)
Clean room, comfy bed. Loved the bartenders and the menu. Slightly disappointed that the room I chose was not the room I received, and the double queen I booked was not available, leaving me with only a king bed or an accessible queen room without the view. I am not sure if this was due to the hotel or Expedia but I will be confirming from now on.

Reviewed on Sep 11, 2026

AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown

Downtown Chicago
¥554,988
per person
Nov 18 - Nov 22
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,009 reviews)
Accommodations were nice, but there was a little wear on the blackout curtains. Staff was extremely helpful and courteous. I will stay here again

Reviewed on Sep 10, 2026

Hotel EMC2, Autograph Collection

Hotel EMC2, Autograph Collection

Downtown Chicago
¥598,208
per person
Nov 18 - Nov 22
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Great location! Great staff!

Reviewed on Sep 5, 2026

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5* All inclusive vacations in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥461,947
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥626,188
per person
Nov 18 - Nov 22
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥527,227
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
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3 Night All inclusive vacations in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

Downtown Chicago
¥202,462
per person
Nov 19 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,326 reviews)
Everything was smooth and stress-free. The room was exactly what you need after a long travel day. The bed was comfortable and the bathroom was kept in perfect condition.

Reviewed on Sep 11, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥208,225
per person
Nov 19 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥413,536
per person
Nov 29 - Dec 2
found 23 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location and helpful staff! Will stay here again!

Reviewed on Sep 11, 2026

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4 Night All inclusive vacations in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago
¥551,993
per person
Nov 18 - Nov 22
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,008 reviews)
Clean room, comfy bed. Loved the bartenders and the menu. Slightly disappointed that the room I chose was not the room I received, and the double queen I booked was not available, leaving me with only a king bed or an accessible queen room without the view. I am not sure if this was due to the hotel or Expedia but I will be confirming from now on.

Reviewed on Sep 11, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥626,188
per person
Nov 18 - Nov 22
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown

Downtown Chicago
¥554,988
per person
Nov 18 - Nov 22
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,009 reviews)
Accommodations were nice, but there was a little wear on the blackout curtains. Staff was extremely helpful and courteous. I will stay here again

Reviewed on Sep 10, 2026

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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,272
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,453
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

¥6,484
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Northwest Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.