Central Chicago Pet-friendly Vacations

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Top Pet-friendly vacation packages in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
￥285,917
per person
Nov 9 - Nov 13
found 23 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥386,152
per person
Dec 26 - Dec 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.

Reviewed on Oct 2, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
￥299,960
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
Ok stay, staff is very inattentive.

Reviewed on Oct 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥298,082
per person
Dec 26 - Dec 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Everything was awesome but there was no microwave and we needed one

Reviewed on Oct 3, 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
￥300,361
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (3,324 reviews)
Don't see what you're looking for?
See all available trips from Osaka to Central Chicago
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5* Pet-friendly vacations in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥386,152
per person
Dec 26 - Dec 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.

Reviewed on Oct 2, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
￥546,593
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class

Reviewed on Oct 1, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
￥431,458
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips

3 Night Pet-friendly vacations in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
￥334,022
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,703 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥374,240
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Everything was awesome but there was no microwave and we needed one

Reviewed on Oct 3, 2026

Arlo Chicago

Arlo Chicago

Downtown Chicago
￥359,916
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,384 reviews)
Clean room and beautiful view! Nice room decor and lighting options that I really appreciated.

Reviewed on Oct 2, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips

4 Night Pet-friendly vacations in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
￥285,917
per person
Nov 9 - Nov 13
found 23 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥361,051
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Room is spacious staff very courteous. i had a memorable stay.

Reviewed on Oct 2, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥354,422
per person
Nov 9 - Nov 13
found 16 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
Don't see what you're looking for?
See all available trips from Osaka to Central Chicago
View all trips

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,853
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Central Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.