
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.

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
Price was ¥356,266, price is now ¥288,236 per person
¥288,236
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.8/10 Good! (1,034 reviews)
The hotel was clean and well-maintained, with excellent exterior lighting that made me feel secure. The staff were exceptionally friendly and helpful throughout our entire stay, making for a very positive experience.
Reviewed on Jun 17, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was ¥501,650, price is now ¥364,000 per person
¥364,000
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views
Reviewed on Jun 22, 2026


DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
Price was ¥368,772, price is now ¥297,485 per person
¥297,485
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,016 reviews)
Booked a King size bed. Got up to our room and it was smaller than the standard King size everyone expects when booking that size. Asked the front desk staff and they insisted it was King size. Did some quick measuring and it is in fact a Queen size for every other person in the country and would have been a deciding factor on where I stayed had I known they were truly a Queen being touted as a King. Very disappointed with the bed size and was able to make do but there are plenty of people out there that require that size bed to sleep comfortably, and the foldout couch bed would still not have been sufficient to compensate for the smaller bed depending on their physical needs. Location was great and access to food was also fantastic although very pricey, especially for the morning breakfast that is normally free in other hotels. I would personally look around at other comparable hotels if I go back to the same area since there are plenty to choose from.
Reviewed on Jun 21, 2026

Embassy Suites by Hilton Chicago O'Hare Rosemont
Price was ¥384,910, price is now ¥310,787 per person
¥310,787
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,429 reviews)
I chose the business suite which was roomie well equipped, and clean. The evening social is nice where they offer two free drinks per evening and light appetizers. The breakfast is top-notch! I love that they will freshly make an omelette for you and everything else is very well stocked. The breakfast staff were very nice and seemed happy to help people. I love that they have airport shuttle as well. I’ll definitely stay there again. Next time I visit Chicago as Rosemont is a very clean, beautiful part of town
Reviewed on Jun 22, 2026
5* Pet-friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Park Hyatt Chicago
Downtown Chicago
Price was ¥375,831, price is now ¥346,797 per person
¥346,797
per person
Sep 15 - Sep 17
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
The entire experience was incredible! The only place I will stay at while in Chicago from now on!
Reviewed on Jun 10, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥739,152, price is now ¥584,323 per person
¥584,323
per person
Jul 30 - Aug 5
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
hotel was immaculate and the people were amazing.
Reviewed on Jun 20, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was ¥493,418, price is now ¥414,756 per person
¥414,756
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (869 reviews)
My stay was remarkable! Staff was extremely friendly, room clean, in room dining food was delicious!
Reviewed on Jun 21, 2026
3 Night Pet-friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Omni Chicago Hotel
Downtown Chicago
Price was ¥381,100, price is now ¥333,296 per person
¥333,296
per person
Aug 26 - Aug 29
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
The facility is beautiful and perfectly located on Michigan Ave. The staff are friendly and quick to respond to requests. Use the valet for easy use of your vehicle with in and out privileges. I traveled with my family of 5 and service dog. The room was clean and comfortable.
Reviewed on Jun 22, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥433,683, price is now ¥362,435 per person
¥362,435
per person
Aug 26 - Aug 29
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,464 reviews)
Excellent Hotel! Great location on Magnificent Mile. Delicious breakfast. Big rooms with Queen beds. Early checkin available.
Reviewed on Jun 22, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥467,203, price is now ¥405,796 per person
¥405,796
per person
Aug 26 - Aug 29
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
hotel was immaculate and the people were amazing.
Reviewed on Jun 20, 2026
4 Night Pet-friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.


Level Chicago Fulton Market
Downtown Chicago
Price was ¥501,650, price is now ¥364,000 per person
¥364,000
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views
Reviewed on Jun 22, 2026

Hilton Chicago O'Hare Airport
O'Hare
Price was ¥425,496, price is now ¥330,543 per person
¥330,543
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,349 reviews)
I love how convenient this hotel is. However they should FIRE their designer. Whoever thought shag carpets work with rolling luggage has never been a guest at the hotel. The room hallways have a lower profile carpet but still difficult. Even the maintenance people joke about it; not really funny when you have multiple bags.
Reviewed on Jun 22, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
