Northwest Side Pet-friendly Holidays

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

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  • Better together

    Save up to £750 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

Top flight + Pet-friendly hotel deals in Northwest Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,353
per person
28 Sept - 4 Oct
found 15 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
Save 100% on your flight
£1,474
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
I loved Chicago but our sink did not drain, the air conditioning made a horrendous noise all night every time it came on and off and to make matters worse, we were close to the elevators which were also extremely noisy. Basically no sleep.

Reviewed on 14 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
£1,632
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Enjoyed the somewhat quiet location at the end of Navy Pier. Highlight was watching the fireworks out on the lake (as well as storms) from our window. Beautiful view. Did not like the mandatory Navy Pier/resort fee but that seems increasingly standard other places as well. Overall wonderful stay.

Reviewed on 14 Aug 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
Save 100% on your flight
£1,931
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,311 reviews)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
£1,645
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (3,779 reviews)
Don't see what you're looking for?
See all available trips from Edinburgh to Northwest Side
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5* Pet-friendly holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,379
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,166
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,445
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Don't see what you're looking for?
See all available trips from Dublin to Northwest Side
View all trips

4 Night Pet-friendly holidays in Northwest Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£1,018
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,096
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Best hotel service in Chicago

Reviewed on 14 Aug 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,379
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Don't see what you're looking for?
See all available trips from Dublin to Northwest Side
View all trips

How to find a pet-friendly holiday in Northwest Side

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

As a pet parent, you want your best bud along for your Northwest 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 Northwest Side pet-friendly holiday?

pet-friendly package holidays start at £1,018, 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 Northwest 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 Northwest Side with hot tubs?

Pet-friendly holidays aren’t just about the animals – you deserve to indulge yourself, too! Filter our Northwest 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 Northwest 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 Northwest Side?

A spontaneous last-minute getaway to Northwest 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 Northwest Side with free cancellation and/or flexible dates?

We offer several places to stay with free cancellation in Northwest 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 Northwest Side pet-friendly travel with Expedia?

Thanks to our dedicated pet-friendly filter, it’s incredibly easy to find accommodation in Northwest 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 Northwest 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.