A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.
Photo by throwingsofas
Open Photo by throwingsofas

West Side Pet-friendly Holidays

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Top Pet-friendly holiday packages in West Side

Price found within the past 48 hours. Click for updated prices.
  • 24 Sept - 29 Sept

    Hampton Inn & Suites Chicago Medical District UIC + Flight

    Near West Side
    5 nights
    2.5 star property
    9.6/10 - Exceptional (682 reviews)
    "Staff were wonderful and went above & beyond! Hotel was beautiful. Great location to see a game at the United Center"
    Reviewed July 29, 2026
    Return New York (EWR) - Chicago (ORD)
    EWR - ORDDirect ORD - EWRDirect
    €914
    €761
    per traveller
    found 23 hours ago
    Hampton Inn & Suites Chicago Medical District UIC
  • 6 Sept - 11 Sept

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (542 reviews)
    "Comes with all the comforts of Home."
    Reviewed July 29, 2026
    Return Tirana (TIA) - Chicago (ORD)
    TIA - ORD1 stop ORD - TIA1 stop
    €2,050
    €1,511
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • 8 Oct - 14 Oct

    The Emily Hotel + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,320 reviews)
    "The room was clean, cute and just perfect for the couple of days we stayed. I would definitely stay there again if/when I go back to Chicago. Good location for what we needed about 15-20 away from everything however, with it being a busy weekend (WNBA All Star Weekend), we had to account for more time to get to events on time. Didn't have time to check out the cinema but for sure a cool amenity. It was a great stay! 😎"
    Reviewed July 29, 2026
    Return Athens (ATH) - Chicago (ORD)
    ATH - ORD1 stop ORD - ATH1 stop
    €5,918
    €5,190
    per traveller
    found 1 day ago
    The Emily Hotel
  • 6 Sept - 11 Sept

    Crowne Plaza Chicago West Loop by IHG + Flight

    Downtown Chicago
    5 nights
    3.5 star property
    9.0/10 - Wonderful (2,441 reviews)
    "Very nice room. Could walk to lots of places."
    Reviewed July 30, 2026
    Return Tirana (TIA) - Chicago (ORD)
    TIA - ORD1 stop ORD - TIA1 stop
    €1,422
    €1,302
    per traveller
    found 1 day ago
    Crowne Plaza Chicago West Loop by IHG
  • 10 Oct - 15 Oct

    Nobu Hotel Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.4/10 - Exceptional (892 reviews)
    "Great location, clean, stylish, large rooms. No spa, minimal lobby but excellent rooftop and restaurant of course."
    Reviewed July 29, 2026
    Return Athens (ATH) - Chicago (ORD)
    ATH - ORD1 stop ORD - ATH1 stop
    €5,839
    €5,440
    per traveller
    found 1 day ago
    Nobu Hotel Chicago

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Top Pet-friendly West Side Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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?

West Side pet-friendly package holidays start at €761, 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!