Top flight + Pet-friendly hotel deals in Chicago

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

Virgin Hotels Chicago

Downtown Chicago

per person

3 Sept - 6 Sept

found 19 hours ago

Return direct flight included

Manchester (MAN) to Chicago (ORD)

9.2/10 Wonderful! (1,333 reviews)

We really enjoyed our stay but felt the price was too high for the size of the room, and the lack of places to sit in the room. Only one chair.

Reviewed on 1 Jul 2025

Park Hyatt Chicago

Downtown Chicago

per person

3 Sept - 6 Sept

found 19 hours ago

Return direct flight included

Manchester (MAN) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

Superb customer service, clean hotel!

Reviewed on 13 Jun 2025

21c Museum Hotel Chicago

Downtown Chicago

per person

11 Sept - 16 Sept

found 21 hours ago

Return direct flight included

Manchester (MAN) to Chicago (ORD)

8.6/10 Excellent! (1,719 reviews)

Located near shopping and restaurants. Easy access to Red Line trains. Rooms were smaller than expected. Not as nice as other 21c hotels. Hallways were dark and beaten up. Service was friendly. Restaurant had great happy hour.

Reviewed on 2 Jul 2025

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

per person

4 Aug - 8 Aug

found 1 day ago

Return direct flight included

Edinburgh (EDI) to Chicago (ORD)

8.8/10 Excellent! (1,796 reviews)

The staff hospitality was incredible 💖

Reviewed on 2 Jul 2025

Hotel Arista

per person

11 Sept - 16 Sept

found 18 hours ago

Return direct flight included

Manchester (MAN) to Chicago (ORD)

9.4/10 Exceptional! (1,002 reviews)

I stayed here with 2 college friends for a girl's weekend. The room was beautiful and inviting, and the beds were very comfortable. We all commented that the oversized bath towels were great! Our only complaint is related to the courtesy car- Hotel Arista offers a free car service within 5 miles of the hotel. We had the car take us to Centennial Beach. However, when we called for a pickup, we were told that the evening driver didn't show up for work, so they didn't have anyone to come get us. We got an Uber back, but it was definitely a frustrating experience.

Reviewed on 30 Jun 2025

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5* Pet-friendly holidays in Chicago

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

Park Hyatt Chicago

Downtown Chicago

per person

3 Sept - 6 Sept

found 19 hours ago

Return direct flight included

Manchester (MAN) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

Superb customer service, clean hotel!

Reviewed on 13 Jun 2025

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3 Night Pet-friendly holidays in Chicago

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

The Royal Sonesta Chicago River North

Downtown Chicago

per person

13 Aug - 16 Aug

found 18 hours ago

Return direct flight included

London (LON) to Chicago (ORD)

9.2/10 Wonderful! (1,822 reviews)

Clean and convenient hotel in a great location. The staff was very helpful and made our stay easy and enjoyable. We also had a spectacular view of the city from our room, which was a real highlight. We would absolutely stay again.

Reviewed on 4 Jul 2025

Park Hyatt Chicago

Downtown Chicago

per person

3 Sept - 6 Sept

found 19 hours ago

Return direct flight included

Manchester (MAN) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

Superb customer service, clean hotel!

Reviewed on 13 Jun 2025

Virgin Hotels Chicago

Downtown Chicago

per person

13 Aug - 16 Aug

found 18 hours ago

Return direct flight included

London (LON) to Chicago (ORD)

9.2/10 Wonderful! (1,333 reviews)

We really enjoyed our stay but felt the price was too high for the size of the room, and the lack of places to sit in the room. Only one chair.

Reviewed on 1 Jul 2025

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4 Night Pet-friendly holidays in Chicago

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

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

per person

8 Sept - 12 Sept

found 1 day ago

Return direct flight included

London (LHR) to Chicago (ORD)

9.4/10 Exceptional! (1,012 reviews)

Historical building with a few quirks (could use some updating), but service was top notch. And omg the bedding! I slept SO well! Location was perfect, close to lots of things!

Reviewed on 3 Jul 2025

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

27 Aug - 31 Aug

found 20 hours ago

Return direct flight included

London (LON) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

Superb customer service, clean hotel!

Reviewed on 13 Jun 2025

Virgin Hotels Chicago

Downtown Chicago

per person

27 Sept - 1 Oct

found 1 day ago

Return flight included

London (LHR) to Chicago (ORD)

9.2/10 Wonderful! (1,333 reviews)

We really enjoyed our stay but felt the price was too high for the size of the room, and the lack of places to sit in the room. Only one chair.

Reviewed on 1 Jul 2025

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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 £648, 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

505 N State Street, Chicago, IL

10 min drive from Wrigley Field

Stay at this 4.5-star 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 ...

9/10 Wonderful! (1,844 reviews)

"The room was spacious and clean. The staff were friendly and helpful."

Reviewed on 30 Jun 2025

Virgin Hotels Chicago

203 N Wabash Ave, Chicago, IL

11 min drive from Wrigley Field

Stay at this 4.5-star luxury hotel in Chicago. Enjoy free Wi-Fi, a nightclub and a rooftop terrace. Our guests praise the bar and the helpful staff in their ...

9/10 Wonderful! (1,342 reviews)

"We really enjoyed our stay but felt the price was too high for the size of the room, and the lack of places to sit in the room. Only one chair."

Reviewed on 1 Jul 2025

Hilton Chicago

720 S Michigan Ave, Chicago, IL

13 min drive from Wrigley Field

Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge) and a health club. Our guests praise the helpful staff and the clean ...

8.4/10 Very Good! (1,975 reviews)

"The property was very nice until we got to the room. The room seemed more dark and dingy. Very expensive for the quality of the room. Staff were extremely nice and the hotel was more central to different parks and modes of transportation."

Reviewed on 2 Jul 2025

See all 5,264 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.