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.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
￥310,036
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (518 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥326,482
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Beautiful hotel and nice staff. Will definitely return.

Reviewed on Aug 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥318,029
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Best hotel stay ever. Excellent location wonderful staff and delicious bread spread

Reviewed on Aug 23, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥461,172
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Everything was outstanding!

Reviewed on Aug 23, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
￥586,192
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
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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
￥461,172
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Everything was outstanding!

Reviewed on Aug 23, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
￥488,550
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
First time staying at this Property and we absolutely loved it! Will definitely go back and recommend

Reviewed on Aug 23, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

Downtown Chicago
￥736,678
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Had the best time ,Staff was excellent! Accommodating and friendly!

Reviewed on Aug 21, 2026

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3 Night Pet-friendly vacations in West Side

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
￥269,536
per person
Sep 26 - Sep 29
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Front desk staff where very unprofessional - friends of theirs hanging out at the desk and when asked for assistance it was as if we were bothering them. housekeeping staff was excellent and attentive when we had to ask for extra bedding and towels since we were 4 not 2pp - these extra items should have been in the room at check in. Pool deck, hot tub, exercise room and sauna/steam area are all top notch. We really loved the concept but would have liked more of a customer service oriented stay.

Reviewed on Aug 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥308,025
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Best hotel stay ever. Excellent location wonderful staff and delicious bread spread

Reviewed on Aug 23, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥274,372
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Beautiful hotel and nice staff. Will definitely return.

Reviewed on Aug 23, 2026

Don't see what you're looking for?
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

￥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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.