
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.

Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Price was ¥399,876, price is now ¥332,300 per person
¥332,300
per person
Jun 15 - Jun 19
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Patrick was excellent at check in despite how busy it was. I felt the staff handled the crush of people efficiently and pleasantly. I was pleasantly surprised I received $15 per day towards the bar or snack room. The snack room selections included hot and cold items.
My room was a bit hot for my taste and they took care of it immediately.
Reviewed on May 3, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥445,300, price is now ¥365,962 per person
¥365,962
per person
Jun 15 - Jun 19
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026

Swissotel - Chicago
Downtown Chicago
Price was ¥406,322, price is now ¥337,637 per person
¥337,637
per person
Jun 15 - Jun 19
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026


Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥399,074, price is now ¥332,308 per person
¥332,308
per person
Jun 15 - Jun 19
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Beautiful hotel, very impressed with the cleanliness, space in the room and the breakfast. So pleased we chose this hotel as the location was excellent 👌
Reviewed on May 7, 2026
5* Pet-friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥505,974, price is now ¥428,713 per person
¥428,713
per person
Jun 15 - Jun 19
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Incredible everything
Reviewed on May 8, 2026
4 Night Pet-friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Price was ¥399,876, price is now ¥332,300 per person
¥332,300
per person
Jun 15 - Jun 19
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Patrick was excellent at check in despite how busy it was. I felt the staff handled the crush of people efficiently and pleasantly. I was pleasantly surprised I received $15 per day towards the bar or snack room. The snack room selections included hot and cold items.
My room was a bit hot for my taste and they took care of it immediately.
Reviewed on May 3, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥445,300, price is now ¥365,962 per person
¥365,962
per person
Jun 15 - Jun 19
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026

Swissotel - Chicago
Downtown Chicago
Price was ¥406,322, price is now ¥337,637 per person
¥337,637
per person
Jun 15 - Jun 19
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
