Pet-friendly holiday rentals in Old Town, Chicago

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Old Town, Chicago pet-friendly home rentals

Pet-friendly house rentals

Guest favourite

Home

4.94 out of 5 average rating, 122 reviews

Spacious Full Home Near the Heart of Wrigleyville

SusieRating, 5 stars4 months ago
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.
Superhost

Home

4.87 out of 5 average rating, 114 reviews

Urban Chic 3beds w/2bath + free parking & W/D

LillianRating, 5 stars1 month ago
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.
Guest favourite

Home

4.9 out of 5 average rating, 362 reviews

Private 3rd Floor Apartment

KyleRating, 5 stars1 month ago
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.
Guest favourite

Home

4.96 out of 5 average rating, 161 reviews

Chicago River House -Large private entire home

RichardRating, 5 stars2 weeks ago
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 .
Guest favourite

Home

4.94 out of 5 average rating, 127 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

TonyRating, 5 stars1 month ago
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.
Guest favourite

Home

4.93 out of 5 average rating, 114 reviews

Quiet cul-de-sac with huge fenced in backyard

JamiaRating, 5 stars1 week ago
Our stay was great! Great location! Tom was very accommodating. Would definitely stay again when I’m in town
Superhost

Home

4.76 out of 5 average rating, 75 reviews

Cheerful 2+ bedroom home w free parking

CharlotteRating, 5 stars2 months ago
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.
Guest favourite

Home

4.91 out of 5 average rating, 106 reviews

Adorable house Madison Street w/ 2 car garage!

AmyRating, 5 stars1 month ago
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 reviews

Level ◆ Brand New Luxe One Bedroom

GregRating, 5 stars1 week ago
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.
Superhost

Flat

4.83 out of 5 average rating, 78 reviews

Quiet but in the Heart of City walk Everywhere

DeshawnRating, 5 stars1 week ago
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 reviews

Gold Coast Dream: Sleek Studio/Perfect City Vibes”

StevenRating, 5 stars2 months ago
Amazing location in the heart of downtown chicago

Flat

4.83 out of 5 average rating, 224 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

JimRating, 5 stars2 weeks ago
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 reviews

Long term rental-Delightful one bdrm pool house

JenniferRating, 5 stars28 months ago
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
Superhost

Flat

4.78 out of 5 average rating, 40 reviews

Sentral 2 Bedroom Apt in South Loop Chicago

CaseyRating, 5 stars1 week ago
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!
Guest favourite

Flat

4.9 out of 5 average rating, 67 reviews

DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool

ChantaRating, 5 stars2 weeks ago
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!
Superhost

Flat

4.81 out of 5 average rating, 63 reviews

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!

BrandieRating, 5 stars2 months ago
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 favourite

Guest house

4.88 out of 5 average rating, 292 reviews

Private Coach house near Lincoln Square!

MeganRating, 5 stars2 weeks ago
We enjoyed our stay at the couch house. It was inviting and perfect for our needs. Thank you!
Guest favourite

Flat

5 out of 5 average rating, 16 reviews

Bright and full of life!

AlexRating, 5 stars2 months ago
Esmirina’s place was perfect and just what I was looking for for the weekend. Loved the friendly animals hanging around the outside :)
Guest favourite

Flat

4.96 out of 5 average rating, 28 reviews

Short Drive to Hospitals/Airports/Downtown Chicago

LonRating, 5 stars2 months ago
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.
Guest favourite

Apartment

4.92 out of 5 average rating, 222 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

AngelaRating, 5 stars1 week ago
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.
Superhost

Home

4.87 out of 5 average rating, 62 reviews

A Comfortable Stay While You are Away in Oak Park

EricRating, 5 stars3 weeks ago
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.
Superhost

Flat

4.76 out of 5 average rating, 72 reviews

Artsy Chicago Abode: Steps to Shops & Restaurants

ColinRating, 5 stars6 months ago
Had a nice stay. Did the trick as a place to sleep while exploring the city. Good location
Guest favourite

Flat

4.92 out of 5 average rating, 251 reviews

Skylights, King Bed, 2 bedrooms

CarrieRating, 5 stars4 weeks ago
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!
Guest favourite

Townhouse

4.98 out of 5 average rating, 64 reviews

𓃥Wicker Cozy Corner w/Parking on site

AnnaRating, 5 stars1 week ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Old Town
  7. Pet-friendly rentals