Far Southwest Side Pet-friendly Holidays

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

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    Packages with flights are ATOL protected

Top flight + Pet-friendly hotel deals in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£795
per person
1 Oct - 6 Oct
found 14 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (2,079 reviews)
Perfect location

Reviewed on 7 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,055
per person
1 Oct - 6 Oct
found 14 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Awesome breakfast. Clean and beautiful room. Amazing shower. Perfect location to walk to a lot

Reviewed on 7 Aug 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,406
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£992
per person
1 Oct - 6 Oct
found 14 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Great staff, great place!

Reviewed on 5 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
£1,780
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Family friendly, beautiful views. Easy public transportation available.

Reviewed on 7 Aug 2026

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5* Pet-friendly holidays in Far Southwest Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,278
per person
8 Sept - 11 Sept
found 13 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Great experience!

Reviewed on 7 Aug 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,406
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£2,523
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
Don't see what you're looking for?
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3 Night Pet-friendly holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£795
per person
10 Sept - 13 Sept
found 17 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.2/10 Very good! (2,879 reviews)
Pas très loin de la rivière Chicago

Reviewed on 7 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,034
per person
10 Sept - 13 Sept
found 17 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Awesome breakfast. Clean and beautiful room. Amazing shower. Perfect location to walk to a lot

Reviewed on 7 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£929
per person
10 Sept - 13 Sept
found 17 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Don't see what you're looking for?
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4 Night Pet-friendly holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,054
per person
9 Sept - 13 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,127
per person
25 Sept - 29 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Awesome breakfast. Clean and beautiful room. Amazing shower. Perfect location to walk to a lot

Reviewed on 7 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£1,514
per person
8 Oct - 12 Oct
found 11 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Family friendly, beautiful views. Easy public transportation available.

Reviewed on 7 Aug 2026

Don't see what you're looking for?
See all available trips from London to Far Southwest Side
View all trips

How to find a pet-friendly holiday in Far Southwest Side

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

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

pet-friendly package holidays start at £795, 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 Far Southwest 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 Far Southwest Side with hot tubs?

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

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

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

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