Pet-friendly vacation rentals in North Side

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Popular amenities for North Side pet-friendly home rentals

Pet-friendly house rentals

Top guest favorite
The cozy living room is designed with soft seating arrangements and a wooden coffee table at the center. Natural light flows through nearby windows, enhancing the inviting atmosphere. A chandelier and wall mirror add character, while decorative accents on the table provide visual interest.
Home in Highland Park
4.97 out of 5 average rating, 121 reviews

Charming Ranch-Style Cottage

MustafaRating, 5 stars1 week 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 favorite
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
A spacious living area features sleek hardwood flooring, a large dining table with upholstered chairs, and modern lighting. A comfortable seating area is arranged around a coffee table, while decorative artwork enhances the walls. Natural light filters through the windows, creating a welcoming ambiance.
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 favorite
A cozy living area features large windows that invite natural light, complemented by red and orange accents. A television is mounted on the wall above a stylish wooden cabinet, while a colorful rug adds warmth to the space. A compact closet offers additional storage.
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.
Guest favorite
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 favorite
A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.
Home in Berwyn
4.99 out of 5 average rating, 146 reviews

Retro Modern Bungalow | fire pit | free parking

JenniferRating, 5 stars2 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
The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.
Home in Naperville
4.86 out of 5 average rating, 125 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

MicahRating, 5 stars5 days 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 favorite
An open-concept living space features a large sectional sofa in front of a vibrant area rug, with exposed wooden beams overhead. Large windows allow natural light to fill the room, revealing glimpses of the dining area and a staircase adorned with artwork.
Home in Chicago
4.95 out of 5 average rating, 152 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

AlexRating, 5 stars2 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!

Pet-friendly home rentals with a pool

Guest favorite
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 favorite
A private rooftop deck is showcased, featuring comfortable seating and a dining area with skyline views of Chicago. The space is bathed in natural light, highlighting the outdoor furniture arranged across the textured tile floor.
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!
Superhost
A modern living area showcases panoramic skyline views through large floor-to-ceiling windows. A light-colored sectional sofa is complemented by an accent pillow and a coffee table with decorative items. A sleek dining table and chairs occupy one corner, while a stylish floor lamp adds soft lighting.
Apartment in Chicago
4.94 out of 5 average rating, 31 reviews

Design + Views in Fulton Market | The Frame

ShirleneRating, 5 stars2 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
Apartment 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
A cozy living area is presented, featuring a comfortable sofa and a stylish blue chair. A wooden coffee table sits in the center, complemented by a textured rug. Large windows allow natural light, while art pieces adorn the walls, adding visual interest to the space.
Apartment 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
An outdoor pet park is visible, featuring artificial grass and agility equipment. Two ramps are positioned for pet exercise, with a fire hydrant placed on one side. A person is seen walking a dog along the park area, emphasizing the inclusive space for pets.
Apartment in Chicago
4.74 out of 5 average rating, 277 reviews

Level ◆ New Luxe Two Bedroom Corner Suite

Don Rating, 5 stars3 weeks ago
The place was spectacular. The views are breathtaking. My family and I loved the place.
Superhost
The exterior of a charming cottage is showcased, featuring a sleek dark grey facade. A series of stairs lead up to the entrance, flanked by a decorative black railing. Lush greenery surrounds the base, enhancing the inviting appeal of the home.
Apartment in Chicago
4.77 out of 5 average rating, 31 reviews

Modern unit in Bridgeport-Chicago

RijuRating, 5 stars5 days ago
Very comfortable accommodations, Newly renovated and safe on street parking. All in all a great stay for a graduation weekend.
Guest favorite
A rooftop pool area is shown with a sleek, modern design. Sun loungers are arranged around the swimming pool, surrounded by potted plants. The impressive skyline of downtown Chicago is visible in the background, reflecting off the glass facade of the high-rise building.
Apartment in Chicago
5 out of 5 average rating, 5 reviews

Luxury 3 Bed w/ Gym, Pool, Parking, Game Rm & More

CarolRating, 5 stars1 week ago
We had a great stay! The place was exactly as shown in the listing—clean, comfortable, and well-equipped. We had some minor issues with the digital locks, but the host was always very quick and helpful in resolving them. Overall, a very positive experience and we’d definitely recommend it!

Private, pet-friendly home rentals

Guest favorite
A spacious living area is presented with a dark sectional sofa and a single armchair. A light-colored rug anchors the seating arrangement, while a flat-screen TV is mounted on the wall. Natural light filters in through sheer curtains, complementing the neutral-toned decor.
Apartment 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
A welcoming living area is presented, featuring two comfortable sofas adorned with decorative pillows. A glass coffee table is positioned on a textured area rug, while two side lamps provide soft lighting. Natural light filters through the sheer curtains, highlighting the polished wooden floor.
Condo in Chicago
4.78 out of 5 average rating, 9 reviews

Lincoln Square Condo

BenRating, 5 stars2 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 favorite
A spacious bedroom features a queen bed with a light-colored bedspread, flanked by two bedside lamps. Natural light enters through a nearby window, illuminating the wood floors and decorative area rug. A door leads to another room with floor mattresses and a desk.
Apartment in Chicago
4.88 out of 5 average rating, 42 reviews

Bungalow suite

AmaturRating, 5 stars1 month ago
Monica’s place was an amazing stay. Everything was clean inside and was very easy to locate. The only thing I would say is that there were little bugs and centipedes all over the other room. But other than that it was a great stay.
Superhost
The spacious bedroom features a large bed dressed in crisp white linens, framed by soft side tables with gold accents. A piece of abstract artwork adorns the wall above the bed, and natural light enters through a large window with unobstructed views.
Apartment in Chicago
4.71 out of 5 average rating, 1,074 reviews

Kasa | Spectacular City Views | Chicago

GustavRating, 5 stars6 days ago
Great place. Super clean. Prime location- easy to walk to restaurants and shops. Loved my stay would do it again!
Superhost
A bright living area is depicted, featuring a dark gray sofa with green accent pillows. A wooden coffee table is positioned in front, with a small decorative item. Light-colored curtains frame the windows, and a mirror hangs on the wall, while a door leads to the bedroom.
Apartment 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.
Guest favorite
A two-story brick home features a welcoming front porch with a stoop and entrance framed by tall windows. Lush greenery and vibrant flower beds add color to the exterior, enhancing the inviting presence of the residence.
Home in Chicago
4.95 out of 5 average rating, 20 reviews

Big house in the BEST Location!

Mary Anne KarungariRating, 5 stars4 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
A welcoming living area features a light beige wall adorned with abstract framed artwork. A soft gray sofa and an accent green armchair are positioned around a round black coffee table, which holds a small floral arrangement. A mirror reflects the cozy space.
Apartment in Chicago
4.53 out of 5 average rating, 53 reviews

Exquisite Stay in N. Chi Steps From The Beach

SuzannRating, 5 stars1 week ago
This apartment was very clean. I was traveling with my adult son. We knew there was only 1 bedroom and a sleeper sofa. The sleeper sofa was not a regular pull out sofa; therefore it wasn’t very big or comfortable. This would be my only complaint about this stay. Other than this the host was extremely communicative and gave thorough instructions from check in to check out.
Guest favorite
A charming garden unit is situated within a light-colored, two-story building, framed by a white picket fence. The entrance is marked by a set of steps leading to a spacious porch, where seating may be present. Nearby trees and greenery accentuate the inviting exterior.
Apartment in Chicago
4.9 out of 5 average rating, 52 reviews

Montrose Gardens

AndrewRating, 5 stars2 weeks ago
Great location, walkable from Metra & CTA stations. Cozy space. Exactly what I needed

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