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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥255,736
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,839 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥382,516
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
¥271,338
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,269 reviews)
Arlo Chicago

Arlo Chicago

Downtown Chicago
¥271,918
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) 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

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago
¥270,461
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,008 reviews)
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5* Pet-friendly vacations in Northwest Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
¥382,516
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
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)
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 Pet-friendly vacations in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

Downtown Chicago
¥308,552
per person
Nov 30 - Dec 3
found 16 hours ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥413,536
per person
Nov 29 - Dec 2
found 16 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
¥394,806
per person
Nov 29 - Dec 2
found 16 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
Property was very clean. The rooms were nice and spacious offered me a upgrade where my key didn’t work to the room the first time close to the Willis Tower with a lot of food. Options would stay again.

Reviewed on Sep 11, 2026

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4 Night Pet-friendly vacations in Northwest Side

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 11 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
¥625,391
per person
Nov 18 - Nov 22
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Hotel EMC2, Autograph Collection

Hotel EMC2, Autograph Collection

Downtown Chicago
¥598,208
per person
Nov 18 - Nov 22
found 11 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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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.