Pet-friendly holiday rentals in North Side

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Popular amenities for North 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
Guest favourite
Home in Chicago
4.94 out of 5 average rating, 148 reviews

BoHo House - A Chic, 1903 Chicago Workers Cottage

niratiRating, 5 stars2 weeks ago
Adam was a great host and very responsive. We loved our stay. The house was clean and the house is easily accessible to everything. Would definitely recommend!
Top guest favourite
Home in Berwyn
4.99 out of 5 average rating, 146 reviews

Retro Modern Bungalow | fire pit | free parking

JenniferRating, 5 stars4 days ago
This exquisite MCM GEM in Berwyn was the perfect home base for us while visiting Chicago. Every corner is curated with unique and authentic MCM touches, all with the contemporary creature comforts one could want and then some. Everything was sparkling clean and April was a superb host. We hope to come again, & highly recommend!!
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
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!
Top guest favourite
Home in Chicago
4.98 out of 5 average rating, 121 reviews

Charming 3-BED in Lincoln Park/ Old Town & Parking

LindaRating, 5 stars4 days ago
Shuang went out of her way to meet our early check in request. She’s a great communicator and made sure that we had a good experience. The location was perfect and located on a quiet street. Highly recommended!

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
Flat 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
Flat in Chicago
4.55 out of 5 average rating, 11 reviews

South Loop | Rooftop With In & Out Parking | 2

StephanieRating, 5 stars2 weeks ago
Great apartment and location! Hands down the most responsive host. TAIMS even provided parking recommendations at Wrigley Field. Thank you for a great stay in Chicago!
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
4.79 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
Apartment in Chicago
4.78 out of 5 average rating, 9 reviews

Lincoln Square Condo

BenRating, 5 stars3 weeks ago
Allen's place is great, I stayed for five days and loved it! My highest compliment is that it's super well-equipped, to the point it feels lived-in (in a good way). For example, the kitchen is stocked better than mine, you'll find it easy to make a meal here. The rest of the unit is well thought out, too. My one piece of advice is to pay reallyyy close attention to the check-in instructions. There are multiple entrances to the complex, and they look similar. You might end up trying the wrong lockbox 10 times if you're not careful :) Overall, I highly recommend this place! Friendly neighbors as well!
Guest favourite
Flat in Chicago
4.91 out of 5 average rating, 64 reviews

1 bedroom apt near Michigan Lake

XiaoweiRating, 5 stars1 day ago
This is the second time I stayed in the apartment. Everything was good as the last time. Good location and clean rooms. Would stay again in future visits if it is available.
Guest favourite
Flat in Chicago
4.99 out of 5 average rating, 137 reviews

Near 606 Trail | Free Garage Parking | W&D |LUXTEL

CathyRating, 5 stars3 weeks ago
What can I say??? Yolanda’s place was super clean, easy to get to and very comfortable and up to date on every level. We felt right at home and was within walking distance to our son’s apartment. We love Chicago and staying here made it even more enjoyable. Pictures do not do justice to. We will stay here again when we’re in Chicago again.
Superhost
Flat in Chicago
4.94 out of 5 average rating, 47 reviews

Lincoln Park Apartment, Steps from the Park

SydneyRating, 5 stars2 months ago
Great place to stay. Super quiet even though it was in a perfect location. Would definitely stay again!
Superhost
Flat in Chicago
4.79 out of 5 average rating, 48 reviews

Logan Square Oasis

MichaelRating, 5 stars6 months ago
Really liked the neighborhood. Was a short walk to the blue line. The place was perfect and will come back again.
Top guest favourite
Guest house in Chicago
4.98 out of 5 average rating, 311 reviews

Private coach house near transit shops & nightlife

JosephRating, 5 stars2 weeks ago
Justin’s spot was the perfect home away from home, Chicago style. Cute private two story mini house with an extremely nice interior and everything you need for a short or long stay. The location is also excellent, placed within walking distance of bus routes heading right into downtown Chicago and a great little food mart minutes away on foot. Highly recommend and will be using again!
Guest favourite
Flat in Chicago
4.91 out of 5 average rating, 53 reviews

Montrose Gardens

JoyceRating, 5 stars2 days ago
This was a very cute one bedroom apartment. It was perfect for my husband, myself and my daughter. Extremely clean. So sweet they left treats and snacks! Host was very nice and accommodating. Would definitely stay again!

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