West Side Pet-friendly Holidays

Book a Pet-friendly Hotel + Flight or Car together to unlock savings

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Top flight + Pet-friendly hotel deals in West Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£899
per person
30 Oct - 3 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,212
per person
25 Nov - 29 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£938
per person
30 Oct - 3 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£1,064
per person
30 Oct - 3 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,681 reviews)
We were so excited about spending the time at Sable hotel however, when we arrived, it was the House of horrors. It was very filthy. Went to go grab an extra blanket and a butt plug fell out of it. Asked for them to please come clean the room they said housekeeping was not there and would take care of it tomorrow so we spent the first night in a filthy dirty room as they had no extra room rooms due to multiple concerts being held that weekend. My advice the location is great, but there’s other options that are more affordable.

Reviewed on 14 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£920
per person
30 Oct - 3 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Comfortable room with a great view and luxuriously soft bed!

Reviewed on 13 Sept 2026

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5* Pet-friendly holidays in West Side

Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,171
per person
19 Nov - 22 Nov
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,212
per person
25 Nov - 29 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£1,971
per person
16 Nov - 20 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
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3 Night Pet-friendly holidays in West Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£813
per person
19 Nov - 22 Nov
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,044
per person
19 Nov - 22 Nov
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
£905
per person
19 Nov - 22 Nov
found 23 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
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4 Night Pet-friendly holidays in West Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£938
per person
30 Oct - 3 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,212
per person
25 Nov - 29 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,155
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Terrific location, wonderful views and little to complain about!

Reviewed on 14 Sept 2026

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How to find a pet-friendly holiday in West Side

How can I book the best pet-friendly holidays in West Side?

As a pet parent, you want your best bud along for your West Side holiday, right? So use our pet-friendly filter to find all the places that are purr-fect for cats, dogs or even well-trained rabbits. Think stacks of outside space, welcome treats and maybe something lovely that keeps the travel time to a minimum.

Can I book a cheap West Side pet-friendly holiday?

pet-friendly package holidays start at £813, but prices and availability are subject to change, and additional terms may apply. To narrow down the best deals, sort by price and use the filters to find cheap places with tail-wag-worthy amenities.

How can I book holiday lets in West Side that are pet friendly?

The space and seclusion of a holiday let is great for holidaying as a family or bigger group, and if your furry friends are with you, even better. Use both the private holiday home and pet-friendly filters to find all the options that tick both boxes.

How can I find pet-friendly holidays in West Side with hot tubs?

Pet-friendly holidays aren’t just about the animals – you deserve to indulge yourself, too! Filter our West Side properties using the hot-tub and pet-friendly holiday options and find somewhere you can relax while the pooches snooze.

Can I book a pet-friendly holiday in West Side with a car?

For hassle-free pet-friendly travel, a car is a no-brainer. Book both your car hire and accommodation with Expedia and you’ll sniff out some great savings.

How can I book last-minute pet-friendly holidays in West Side?

A spontaneous last-minute getaway to West Side with your pet is what holiday dreams are made of. You might even dig up discounted rates on some hotels by booking close to the date.

Can I book a pet-friendly holiday in West Side with free cancellation and/or flexible dates?

We offer several places to stay with free cancellation in West Side, just use the fully refundable filter to find the ones available on your dates. Make sure you read the terms and conditions, too.

Why should I book West Side pet-friendly travel with Expedia?

Thanks to our dedicated pet-friendly filter, it’s incredibly easy to find accommodation in West Side that welcomes fur babies. Search, choose and book in just a few clicks. Purr-fect!

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
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

£35
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

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in West Side

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.