
Pet-friendly holiday rentals in Old Town, Chicago
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Old Town, Chicago
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Old Town, Chicago pet-friendly home rentals
Pet-friendly house rentals

Home
4.94 out of 5 average rating, 122 reviewsSpacious Full Home Near the Heart of Wrigleyville
Dustin was a great host! Super quick response to a few questions we had while we were there. The space was outstanding! Plenty of room for all 7 of us and everything was there that we needed-and then some!! We thoroughly enjoyed our stay.

Home
4.87 out of 5 average rating, 114 reviewsUrban Chic 3beds w/2bath + free parking & W/D
Tiffany was very informational from the very start of booking. Quick response time, easy instructions to follow. The home was exactly what me and my family needed to spend some time together during the holiday. I will definitely book again in the future.

Home
4.9 out of 5 average rating, 362 reviewsPrivate 3rd Floor Apartment
I’ve stayed at many Airbnbs, and Karen was by far the best host I’ve ever had! From the start of our trip, she was incredibly responsive, guiding us to a parking spot and ensuring a smooth check-in process. Throughout our stay, she kept in touch to make sure everything was going well, which we truly appreciated. Karen genuinely cared about our experience and went above and beyond to make sure we had an amazing trip. If you’re looking for the perfect place to stay in Chicago, look no further than Karen’s! You won’t regret it.

Home
4.96 out of 5 average rating, 161 reviewsChicago River House -Large private entire home
Kim was a excellent host. The Airbnb was very cleanWalking distance to coffee shops, stores and restaurants. Kim was very responsive to whatever we needed .I would highly recommend .

Home
4.94 out of 5 average rating, 127 reviewsBoHo House - A Chic, 1903 Chicago Workers Cottage
Boho House is an awesome representation of old Chicago. It’s outside most of the hustle and bustle of the city, while still close enough to EVERYTHING you want to do and see. I wish we could have stayed longer since there are so many iconic places to visit in Chicago. Adam and his crew have a great place here, and were very prompt in answering any questions we had. I would definitely stay here again.

Home
4.93 out of 5 average rating, 114 reviewsQuiet cul-de-sac with huge fenced in backyard
Our stay was great! Great location! Tom was very accommodating. Would definitely stay again when I’m in town

Home
4.76 out of 5 average rating, 75 reviewsCheerful 2+ bedroom home w free parking
Had such a great time in Chicago at this spot! Perfect for us and the dogs. It is a great neighborhood to take the dogs walking in and the house is so cozy. We didn't want to leave! Thanks.

Home
4.91 out of 5 average rating, 106 reviewsAdorable house Madison Street w/ 2 car garage!
My family of four (two kids) stayed here for a few nights before a flight at Chicago O’Hare. We really enjoyed the comfortable home and slept well! Jill was so kind and helpful. We really loved the area as well- walkable to a super cute street of shops and restaurants! We also appreciated the garage and felt very safe. We would stay here again!
Pet-friendly home rentals with a pool

Flat
4.77 out of 5 average rating, 73 reviewsLevel ◆ Brand New Luxe One Bedroom
What isn’t to like about this place? Amazing building, incredible views (from the unit I was in), beautiful unit, great amenities, perfect location, friendly staff. I will be staying here whenever I visit Chicago in the future.

Flat
4.83 out of 5 average rating, 78 reviewsQuiet but in the Heart of City walk Everywhere
Cloud9’s spec was better than advertised. Great location the building is peaceful and quiet. Everything was just like the description said it will be. Definitely will stay here again!!

Flat
4.64 out of 5 average rating, 67 reviewsGold Coast Dream: Sleek Studio/Perfect City Vibes”
Amazing location in the heart of downtown chicago

Flat
4.83 out of 5 average rating, 224 reviewsSpectacular Corner 2BR Penthouse in the Loop | Roo
What an awesome place! Cool funky lobby that smells amazing. I felt super safe and really appreciated how clean the apartment was. There is an English pub connected to the building that is fantastic too!

Place to stay
5 out of 5 average rating, 12 reviewsLong term rental-Delightful one bdrm pool house
Definitely a great stay! October 1st and we were swimming! Decor is amazing! Tv was easy to figure out and had lots of options. We had a busy day before and after our stay so we used Michael’s pool house as a relaxing stay in between and it was perfect

Flat
4.78 out of 5 average rating, 40 reviewsSentral 2 Bedroom Apt in South Loop Chicago
We loved staying here with our family of 5, and are return customers. Very conveniently located, appreciate that you can park right out front to unload, and we parked in a garage around the corner. The highlight is the beautiful pool area, even though the pool is on the smaller side, it was perfect for our kids to play in and was the highlight of their weekend too. Staff is exceptionally friendly. We’ll be back!

Flat
4.9 out of 5 average rating, 67 reviewsDTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
This two story space was absolutely beautiful, very spacious with a stunning view of the Empire State Building. The decor and vibe felt upscale, making for a really comfortable stay. Just a heads up: there are extra charges for any wear and tear, like minor spots on linens, even if you’re not sure how they got there. I’d recommend checking everything when you arrive and taking photos, just to avoid any unexpected fees. Other than that, it was a fantastic experience in a great location!

Flat
4.81 out of 5 average rating, 63 reviewsCozy Family 3BR Oasis: Park, Private Yard, & BBQ!
Was as described, nice & cozy! Bathroom is nicely updated with space for shower items. Ample kitchen storage. Welcomed our furry family member. With a responsive host! Thanks!
Private, pet-friendly home rentals

Guest house
4.88 out of 5 average rating, 292 reviewsPrivate Coach house near Lincoln Square!
We enjoyed our stay at the couch house. It was inviting and perfect for our needs. Thank you!

Flat
5 out of 5 average rating, 16 reviewsBright and full of life!
Esmirina’s place was perfect and just what I was looking for for the weekend. Loved the friendly animals hanging around the outside :)

Flat
4.96 out of 5 average rating, 28 reviewsShort Drive to Hospitals/Airports/Downtown Chicago
The place was newly remodeled, very clean and organized. Everything in the apartment was well stocked and very livable, including Roku access to open your own subscriptions Hulu, Netflix, etc. Please be aware that the location is a basement with a relatively steep flight of stairs, with safety lips on the edges.

Apartment
4.92 out of 5 average rating, 222 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Kaye's place might just be the coziest and cutest place to stay in Chicago. Close to what you need, walkable, cozy for dogs, great taste in design, and affordable. Made my trip to the dentist a little easier to take! Thank you, Kaye- don't change a thing about your space.

Home
4.87 out of 5 average rating, 62 reviewsA Comfortable Stay While You are Away in Oak Park
Jay's place more than met the needs of me and my family. While the space isn't in the heart of OP/Lake Street, everything we needed for a pleasant stay was easily accessible. The beds were comfortable, and the kitchen was well-equipped. Overall, I would recommend Jay's place to anyone visiting the OPRF area.

Flat
4.76 out of 5 average rating, 72 reviewsArtsy Chicago Abode: Steps to Shops & Restaurants
Had a nice stay. Did the trick as a place to sleep while exploring the city. Good location
Flat
4.92 out of 5 average rating, 251 reviewsSkylights, King Bed, 2 bedrooms
it was a very good stay the place was exactly as described and the beds were very comfortable! The only comment I would have was regarding the staircase getting into the apartment which was very narrow and difficult to drag suitcases up! While this was not really an issue for us I would suggest mentioning it in your listing so that in case elderly people come they know what to expect. Overall great stay!

Townhouse
4.98 out of 5 average rating, 64 reviews𓃥Wicker Cozy Corner w/Parking on site
This was the perfect Wicker Park stay! The building was easy to locate, perfectly clean, and full of amenities. I was particularly pleased with the kitchen and how spacious the home was.
Quick stats about holiday rentals that are pet-friendly in Old Town, Chicago
Total rentals
30 properties
Nightly prices starting at
£63 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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