Pet-friendly holiday rentals in Northwest Side

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Northwest Side pet-friendly home rentals

Pet-friendly house rentals

Top guest favourite
Home in Highland Park
4.97 out of 5 average rating, 121 reviews

Charming Ranch-Style Cottage

MustafaRating, 5 stars2 weeks ago
We stayed at Alix’s for one night. Our stay at Alix’s place was quite comfortable. Everything was exactly as described. We made use of the devices provided like the iron and ironing table, and the hairdryer. To my wife’s delight, the bathroom also had individually packaged makeup remover wipes! Body lotion was also provided. The air conditioning worked perfectly and we were able to sleep comfortably. Would recommend!
Top guest favourite
Home in Chicago
4.98 out of 5 average rating, 108 reviews

Flat in Lincoln Park 2-Flat Central to Everything

OlivierRating, 5 stars1 month ago
We stayed for a week with 2 children of 8 and 10. The place is larger than we expected; which is nice. The street and neighborhood are both really nice. Train is close; which is very handy to visit the city. Close to Lincoln park and many restaurants and shops. This place was very comfortable, private and quiet. Brian was also also very flexible with check in and check out times. Definitely recommended !
Superhost
Home in Bensenville
4.83 out of 5 average rating, 100 reviews

Skyway w/ Shuffleboard

HeatherRating, 5 stars1 month ago
Wonderful house for our group of 10 ladies! Blaine was great and prompt with all communication. Would definitely stay again and recommend to others
Top guest favourite
Home in Chicago
4.9 out of 5 average rating, 367 reviews

Private 3rd Floor Apartment

RickRating, 5 stars1 month ago
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.
Superhost
Home in Naperville
4.85 out of 5 average rating, 126 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

MicahRating, 5 stars1 week ago
Nice place tucked into a quiet, safe neighborhood. Backyard was outstanding. (We wish the weather had cooperated so we could have spent more time outside) One level home with comfy beds and furniture throughout. Kitchen was spacious and clean. Plenty of extra towels and blankets.
Guest favourite
Home in Chicago Ridge
4.92 out of 5 average rating, 139 reviews

Quiet cul-de-sac with huge fenced in backyard

MeganRating, 5 stars1 day ago
Great place for the price. Tom was a great host, always willing to help when needed. Thank you for starting the fire every night for us. Great location to have some privacy and not far from downtown. Would recommend!
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 152 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

AlexRating, 5 stars3 weeks ago
Staying at the Grand Kimball Lodge was fantastic! From Bob's proactive communication to his flexibility around check in times, the stay was as seamless as it was memorable. We had a group of 9 and everyone had their own bed, which is rare being so centrally located. The sauna was an excellent bonus, and we'd be happy to come back, thanks again!
Guest favourite
Home in Forest Park
4.91 out of 5 average rating, 110 reviews

Adorable house Madison Street w/ 2 car garage!

KellyRating, 5 stars5 days ago
Jill's home in Forest Park was lovely. It was centrally located with easy access to activities downtown and in the suburbs. Also, the proximity to Madison Street is fantastic. We also appreciate Jill's friendliness and flexibility.

Pet-friendly home rentals with a pool

Guest favourite
Home in Highland Park
4.91 out of 5 average rating, 145 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

MaryRating, 5 stars2 weeks ago
We had a great stay overall. From start to finish, Kailash was extremely helpful, friendly and responsive. We needed a long-term stay with 2 big dogs, and this house worked great for us. We didn't get to use the pool much because the weather didn't cooperate, but the pool and patio area are gorgeous. The location is great, close to everything - grocery stores, restaurants, etc. There is a trail behind the house (accessible through a gate in the back yard), and it leads to a beautiful and huge forest preserve - beautiful for walks/hikes in the woods! The kitchen was a great space for us, and it had everything we might need for cooking, etc. The house was very comfortable for our family, and we would come again. Thank you, Kailash!
Guest favourite
Serviced apartment in Chicago
4.95 out of 5 average rating, 42 reviews

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool

MatildaRating, 5 stars1 month ago
Stayed here for my girls trip and it was a super convenient location! It was our first time visiting Chicago, and it was perfect. Had the most beautiful view we loved the private patio. Beds were all comfy and the hosts were extremely communicative the entire stay. Would definitely stay again!
Guest favourite
Flat in Chicago
5 out of 5 average rating, 8 reviews

Luxury Designer Penthouse NW | Pool | Gold Coast

ReginaRating, 5 stars1 week ago
Beautiful apartment in Chicago’s Gold Coast area - lots to do, easy walking distance to shops, restaurants and Oak Street Beach (and a view of the beach from the dining room). Well appointed building with a rooftop pool, gym and lounge. Quiet neighbors on the floor.
Superhost
Townhouse in Forest Park
5 out of 5 average rating, 4 reviews

Forest Park Oasis - Dog Friendly - Parks - the "L"

MeghanRating, 5 stars1 day ago
Excellent place to stay, easy access to highway, quick ride to downtown
Superhost
Flat in Chicago
4.94 out of 5 average rating, 31 reviews

Design + Views in Fulton Market | The Frame

ShirleneRating, 5 stars3 weeks ago
My family and I had a wonderful stay in Chicago! The space was beautifully designed, comfortable, and exactly as described. We truly appreciated the thoughtful touches, like the refrigerated breakfast items, earplugs, and eye mask. Our host was responsive and made check-in and checkout seamless. The location was perfect for exploring the city, with easy access to restaurants and shops. Thank you so much for your warm hospitality! We would absolutely stay here again. Highly recommended!
Superhost
Flat in Chicago
4.8 out of 5 average rating, 10 reviews

South Loop | Rooftop With In & Out Parking | 1

NilimaRating, 5 stars1 week ago
Elegant furnishings & easy check-in & check-out. Good neighbour hood
Superhost
Flat in Chicago
4.79 out of 5 average rating, 70 reviews

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

FedericoRating, 5 stars1 week ago
Kevin and Kayla’s unit on W Diversey Ave was a cozy and convenient spot for our Chicago trip. The space was clean, well-equipped, and had everything we needed, with quick access to buses and the Blue Line. The only minor downside was some occasional dog-walking noise from the unit above, but as it has already been mentioned before, it is to be expected. Mattresses were a bit wobbly for our tastes but it's a matter of preference. Overall a great, cozy place on a very convenient location in Chicagoland. What really stood out was Kevin’s excellent hosting—he went out of his way to make us feel at home, regularly checking if we needed anything, and was quick to help in-person when we had a small hiccup on our last day. Super responsive and friendly and a true host!
Superhost
Flat in Chicago
4.77 out of 5 average rating, 31 reviews

Modern unit in Bridgeport-Chicago

RijuRating, 5 stars1 week ago
Very comfortable accommodations, Newly renovated and safe on street parking. All in all a great stay for a graduation weekend.

Private, pet-friendly home rentals

Guest favourite
Flat in Chicago
4.88 out of 5 average rating, 50 reviews

Cute & Cozy Chicago Basement

AracelyRating, 5 stars1 week ago
it was our second time staying there and everything was as perfect as the first. will definitely be staying there again on my next trip to Chicago
Superhost
Flat in Oak Park
4.89 out of 5 average rating, 28 reviews

Modern NEW Deluxe Studio in Oak Park

AshlynRating, 5 stars2 weeks ago
This was the perfect spot for our weekend trip! Oak Park was the cutest little town and very easy to get to downtown Chicago. The listing was just like the pictures, and the check in/out process was one of the easiest we’ve ever had! Would definitely stay here again😊 Only thing to note is you are able to hear the street noises, and if the sun is something that will wake you up in the morning, be aware that it is shining through those beautiful big windows! Overall, an amazing experience!
Guest favourite
Flat in Chicago
4.92 out of 5 average rating, 38 reviews

Portage Park Pad

ConnorRating, 5 stars1 week ago
great location for walkability and transit, super convenient and pet friendly! Also surprised to get a garage parking spot, a nice amenity.
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 20 reviews

Big house in the BEST Location!

Mary Anne KarungariRating, 5 stars6 days ago
We had a wonderful stay. The house was clean, we had all we needed to make meals and the beds were comfortable. We would have appreciated blinds in the two smaller bedrooms but enjoyed the rooms nonetheless. My friends say Thank you for your hosting.
Superhost
Home in Chicago
4.86 out of 5 average rating, 56 reviews

Luxe King Beds-Private Gym-Huge Backyard-Crib

JamieRating, 5 stars3 days ago
We had a wonderful stay at this Airbnb! The house was roomy, cozy, and super comfortable. Everything was clean and beautifully decorated, with a charming backyard and deck that made it feel extra special. The bedrooms were each uniquely themed and absolutely gorgeous, and the beds were incredibly comfy—everyone slept like a dream. The water pressure in the shower was perfect, and the hosts were kind and accommodating throughout our stay. Highly recommend this place if you’re looking for a relaxing and well-kept spot to unwind!
Top guest favourite
Flat in Chicago
5 out of 5 average rating, 26 reviews

3BR Haven | Gym | Workspace | Quiet Location

AdamRating, 5 stars1 month ago
Good location, amenities, and a great experience staying here at Ella and Peter’s listing. Highly recommend!
Superhost
Apartment in Elmwood Park
4.6 out of 5 average rating, 15 reviews

Top Floor Condo near airport

ColleenRating, 5 stars3 weeks ago
There were four of staying at Issa’s home, and it was incredibly comfortable and clean. It was really nice to have access to a full kitchen, and both bathrooms were great. Would definitely recommend to anyone needing a comfortable stay with lots of room.
Guest favourite
Flat in Chicago
4.92 out of 5 average rating, 13 reviews

Cozy Casa by O’Hare Airport

KenilaRating, 5 stars5 days ago
We found this place after canceling a sketchy place we were originally planning to stay at. The place was very clean and clutter free. Everything was within 20-40 minute drive with Chicago’s traffic. He had very clear instructions and rules. Great place at a great price!

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