Chicago Pet-friendly Holidays

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    Packages with flights are ATOL protected

Top flight + Pet-friendly hotel deals in Chicago

Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was £1,718, price is now £1,368 per person
£1,368
per person
22 Jun - 28 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Wonderful restaurant, amazing food.

Reviewed on 18 Apr 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was £2,526, price is now £1,912 per person
£1,912
per person
28 May - 1 Jun
found 20 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,727 reviews)
Always a great stay! Love this hotel. Great area with great restaurants and fun things to do close by.

Reviewed on 11 Apr 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was £1,843, price is now £1,478 per person
£1,478
per person
22 Jun - 28 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (2,090 reviews)
Really enjoyed our stay and will be our "go to" when visiting Chicago!

Reviewed on 18 Apr 2026

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was £2,214, price is now £1,823 per person
£1,823
per person
24 May - 29 May
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
I truly enjoyed my 5 night stay at this hotel. Everyone was helpful, friendly, and accommodating. I love its location, near the Michael mile. When I return to Chicago I will definitely stay at the Park Hyatt.

Reviewed on 4 Apr 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £1,919, price is now £1,618 per person
£1,618
per person
1 Jul - 8 Jul
found 14 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
It was ok. Nothing special. Hunting for coffee in the morning was annoying. The advertised “apertivo”

Reviewed on 14 Apr 2026

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5* Pet-friendly holidays in Chicago

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was £2,214, price is now £1,823 per person
£1,823
per person
24 May - 29 May
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
I truly enjoyed my 5 night stay at this hotel. Everyone was helpful, friendly, and accommodating. I love its location, near the Michael mile. When I return to Chicago I will definitely stay at the Park Hyatt.

Reviewed on 4 Apr 2026

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3 Night Pet-friendly holidays in Chicago

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was £1,373, price is now £1,209 per person
£1,209
per person
16 Jun - 19 Jun
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.2/10 Wonderful! (2,090 reviews)
Really enjoyed our stay and will be our "go to" when visiting Chicago!

Reviewed on 18 Apr 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Price was £1,493, price is now £1,312 per person
£1,312
per person
16 Jun - 19 Jun
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.6/10 Exceptional! (3,910 reviews)
Nice large room. Unique Korean breakfast was excellent. Very friendly and helpful staff.

Reviewed on 18 Apr 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was £1,463, price is now £1,291 per person
£1,291
per person
16 Jun - 19 Jun
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.6/10 Excellent! (2,727 reviews)
Always a great stay! Love this hotel. Great area with great restaurants and fun things to do close by.

Reviewed on 11 Apr 2026

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4 Night Pet-friendly holidays in Chicago

Price found within the past 48 hours. Click for updated prices.
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was £2,147, price is now £1,534 per person
£1,534
per person
28 May - 1 Jun
found 20 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.

Reviewed on 14 Apr 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was £2,526, price is now £1,912 per person
£1,912
per person
28 May - 1 Jun
found 20 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,727 reviews)
Always a great stay! Love this hotel. Great area with great restaurants and fun things to do close by.

Reviewed on 11 Apr 2026

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was £2,036, price is now £1,576 per person
£1,576
per person
28 May - 1 Jun
found 20 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Wonderful restaurant, amazing food.

Reviewed on 18 Apr 2026

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

How to find a pet-friendly holiday in Chicago

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

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

pet-friendly package holidays start at £1,209, 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 Chicago 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 Chicago with hot tubs?

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

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

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

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

Top Pet-friendly Chicago Hotels

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
505 N State Street Chicago IL
  • 10 min drive from Wrigley Field
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the pool and the restaurant ...
9.2/10 Wonderful! (2,541 reviews)
It was a great experience. The room was neat and room service was excellent. Would stay here again in the future. The view from the pool room is also beautiful.

Reviewed on 18 Apr 2026

The Royal Sonesta Chicago River North
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
203 N Wabash Ave Chicago IL
  • 11 min drive from Wrigley Field
Stay at this boutique hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,397 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, ...

Reviewed on 14 Apr 2026

Sports Illustrated Resorts Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
  • 13 min drive from Wrigley Field
Stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a health club. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (2,733 reviews)
The hotel is awesome. Three of us stayed in a double queen room. See surprised with two bathrooms. Everything was clean and well maintained. Staff was excellent! Very professional and personal able. Will stay here again. Thanks!

Reviewed on 18 Apr 2026

Hilton Chicago
See all 5,600 properties in Chicago
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.

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* 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.