West Side Pet-friendly Vacations

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Top Pet-friendly vacation packages in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥284,448
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
.

Reviewed on Oct 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥372,880
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hands down the best hotel in Chicago!

Reviewed on Oct 5, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥305,278
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
¥314,167
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (3,324 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
¥301,820
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
8.8/10 Excellent! (2,309 reviews)
Fantastic hotel! Really nice, clean, staff was incredibly friendly. We got the Fairmont gold room edition and it was totally worth it having food and drinks available during the day. We ate breakfast there each morning and it was great! Would definitely stay here again Next time we come to visit.

Reviewed on Oct 5, 2026

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5* Pet-friendly vacations in West Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
¥372,880
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hands down the best hotel in Chicago!

Reviewed on Oct 5, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥480,806
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Was amazing experience we want to go back

Reviewed on Oct 5, 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
¥577,532
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.

Reviewed on Sep 24, 2026

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3 Night Pet-friendly vacations in West Side

Price found within the past 48 hours. Click for updated prices.
L7 Chicago by LOTTE

L7 Chicago by LOTTE

Downtown Chicago
¥502,922
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.6/10 Exceptional! (4,918 reviews)
I loved this hotel! It was very clean, chic, updated, and modern. I stayed here for a solo trip, and the room was extremely spacious, definitely more than enough room for just me. The location was one of my favorite things about the hotel. It was very central, and so much was within walking distance, including Millennium Park, restaurants, and many of the attractions I wanted to visit. It made exploring the city really convenient because I could simply walk to most places. The staff was also very nice and helpful throughout my stay. I had a late flight on my last day, and they allowed me to store my luggage at the hotel after checkout, which made things so much easier. My only small complaint was that the only full-length mirror was in the bathroom. Other than that, I had a great experience and would absolutely stay here again!

Reviewed on Oct 6, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥506,220
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
.

Reviewed on Oct 5, 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

Downtown Chicago
¥512,146
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
The rooms are very small ,the pictures and videos is what sells the hotel for sure. Disappointed with the stay and the amount I was charged

Reviewed on Oct 4, 2026

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4 Night Pet-friendly vacations in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥284,448
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
.

Reviewed on Oct 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥372,880
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hands down the best hotel in Chicago!

Reviewed on Oct 5, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥303,208
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
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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
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

¥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in West Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.