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Top Pet-friendly vacation packages in Chicago

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

The Royal Sonesta Chicago River North

Downtown Chicago

￥139,018

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (2,241 reviews)

Wonderful customer service, great location!

Reviewed on Dec 8, 2025

Hilton Chicago

Downtown Chicago

￥159,849

per person

Feb 19 - Feb 23

found 10 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.4/10 Very Good! (2,301 reviews)

Love the environment and decorations and very friendly staff.

Reviewed on Dec 8, 2025

L7 Chicago by LOTTE

Downtown Chicago

￥158,916

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.6/10 Exceptional! (3,227 reviews)

Amazing central location to everything Chicago has to offer! Staff greeted us with nothing but smiles and went out of their way to ensure we felt welcomed. The warm lavender towel was an amazing touch, along with the coffee/popcorn station! Everyone that worked here was more than helpful, and it seemed genuine! Checking in and out was a breeze. The rooms were very spacious, clean, and updated. Comfy beds, very hot water, and a thermostat that actually works. Definitely recommend staying here to anyone wanting to be in the heart of Chicago.

Reviewed on Dec 8, 2025

Kinzie Hotel

Downtown Chicago

￥146,684

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,993 reviews)

Very friendly staff. Room was big and bed was very comfy. I would stay here again

Reviewed on Dec 8, 2025

Hotel 55

Downtown Chicago

￥152,307

per person

Feb 19 - Feb 23

found 10 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.8/10 Excellent! (1,577 reviews)

Very friendly staff

Reviewed on Dec 7, 2025

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See all available trips from Tokyo to Chicago

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4 Night Pet-friendly vacations in Chicago

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

Aloft Chicago Downtown River North

Downtown Chicago

￥150,639

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,159 reviews)

Clean room, friendly staff, perfect location

Reviewed on Dec 8, 2025

Hilton Chicago

Downtown Chicago

￥159,849

per person

Feb 19 - Feb 23

found 10 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.4/10 Very Good! (2,301 reviews)

Love the environment and decorations and very friendly staff.

Reviewed on Dec 8, 2025

L7 Chicago by LOTTE

Downtown Chicago

￥158,916

per person

Feb 19 - Feb 23

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.6/10 Exceptional! (3,227 reviews)

Amazing central location to everything Chicago has to offer! Staff greeted us with nothing but smiles and went out of their way to ensure we felt welcomed. The warm lavender towel was an amazing touch, along with the coffee/popcorn station! Everyone that worked here was more than helpful, and it seemed genuine! Checking in and out was a breeze. The rooms were very spacious, clean, and updated. Comfy beds, very hot water, and a thermostat that actually works. Definitely recommend staying here to anyone wanting to be in the heart of Chicago.

Reviewed on Dec 8, 2025

Don't see what you're looking for?

See all available trips from Tokyo to Chicago

View all trips

Top Pet-friendly Chicago Hotels

The Royal Sonesta Chicago River North

505 N State Street Chicago IL

10 min drive from Wrigley Field

Dogs and cats are welcome (fees apply) at this luxury hotel offering pet-friendly amenities, like food and water bowls. If you need a walk during your stay, ...

9/10 Wonderful! (2,295 reviews)

Room and people were nice, no streaming on the TV, the terrace was closed and there was no where to smoke

Reviewed on Dec 2, 2025

Virgin Hotels Chicago

203 N Wabash Ave Chicago IL

11 min drive from Wrigley Field

Four-legged friends stay free at this luxury, city-center hotel, which offers pet-friendly amenities, like food and water bowls. While you're here, visit nearby ...

9/10 Wonderful! (1,418 reviews)

Very clean

Reviewed on Dec 7, 2025

Hilton Chicago

720 S Michigan Ave Chicago IL

13 min drive from Wrigley Field

A city-center getaway awaits at this historic hotel, where pets are welcome (fees apply). Need a walk during your pet-friendly stay? Stretch your legs at nearby ...

8.4/10 Very Good! (2,342 reviews)

It was okay but shops where expensive

Reviewed on Dec 4, 2025

See all 5,610 properties in Chicago

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.