Northwest Side Pet-friendly Vacations

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Top Pet-friendly vacation packages in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Ivy Boutique Hotel

Ivy Boutique Hotel

Downtown Chicago
¥438,505
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,431 reviews)
Nice location. Only concern was my bed seemed very old and really should be replaced.

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 13 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 13 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 13 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

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Downtown Chicago
¥453,880
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
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5* Pet-friendly vacations in Northwest Side

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

The Peninsula Chicago

Downtown Chicago
¥425,000
per person
Nov 18 - Nov 22
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥626,188
per person
Nov 18 - Nov 22
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
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3 Night Pet-friendly vacations in Northwest Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥208,225
per person
Nov 19 - Nov 22
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
¥227,166
per person
Nov 19 - Nov 22
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥413,536
per person
Nov 29 - Dec 2
found 1 day 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

Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
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4 Night Pet-friendly vacations in Northwest Side

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 13 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 13 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 13 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

Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
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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
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,886
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Northwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.