Pet-friendly holiday rentals in Pilsen, Chicago

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Pilsen, Chicago pet-friendly home rentals

Pet-friendly house rentals

Top Guest favourite
Home in Whiting
4.95 out of 5 average rating, 106 reviews

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

JordanRating, 5 stars1 day ago
This was a great stay for me and my family of 5. Our kids loved the mini golf course and enjoyed chilling on the open patio. This stay was matched everything described in the listing and was quite large. The only thing I’d say negative is that due to it being an older house not all the windows lock properly which was a major security error for me especially since it was an unfamiliar area and we had our children. Other than that no complaints ! Would stay again Thanks !
Top Guest favourite
Home in North Side
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 !
Top Guest favourite
Home in Lake View
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 favourite
Home in North Park
4.96 out of 5 average rating, 173 reviews

Chicago River House -BBQ Oasis now open!

ThomasRating, 5 stars1 week ago
Even more spacious than in the photos! Well-kept place, with a fully stocked kitchen, projector, BOSE speaker, and great backyard. Double shower in the master bedroom, and strong water pressure. Entry is easy with a code. Finally, the host is VERY accommodating, flexible, and responsive. Recommended!
Guest favourite
Home in Avondale
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!
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 Logan Square
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!
Superhost
Home in Chicago
4.93 out of 5 average rating, 107 reviews

Beautiful Chicago Greystone

RoxanaRating, 5 stars2 weeks ago
Great place to accommodate a big group. Close enough to the city if you don’t want to be in the heart of the city. Responsive host

Pet-friendly home rentals with a pool

Guest favourite
Apartment in South Loop
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
Apartment in Magnificent Mile
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.
Apartment in West Loop
4.83 out of 5 average rating, 35 reviews

Level Junior Two Bedroom Suite | Fulton Market

AlannaRating, 5 stars4 weeks ago
Had such a great stay! Everything was very clean and all information given was thorough.
Apartment in Humboldt Park
4.7 out of 5 average rating, 118 reviews

Play in the Windy City and rest by the “606”

RichardRating, 5 stars5 months ago
This airbnb would be good for 2 couplesnorna family of 4. The kitchen is verynfuntional, and the living space is open and quite large. Check in/out instructions are clear. Beau was very responsive.
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
Apartment in South Loop
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
Apartment in Logan Square
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!
Guest favourite
Apartment in South Loop
5 out of 5 average rating, 5 reviews

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

ShuangRating, 5 stars6 days ago
Great value for a work trip! Easy to find, convenient amenities, and Patty was very proactive with a clear, easy check-in. Would recommend for a small group.

Private, pet-friendly home rentals

Guest favourite
Apartment in Pilsen
4.94 out of 5 average rating, 33 reviews

2 queen BR- Cozy unit near Sox stadium, Chinatown

HaleyRating, 5 stars1 day ago
Great apartment, quiet neighborhood, just what we needed for our stay!
Guest favourite
Apartment in Bronzeville
4.96 out of 5 average rating, 26 reviews

In town Close to it all

SofiyaRating, 5 stars1 week ago
Lovely home! We were here for a short time but it’s a great location and neighborhood. Ginneh was a wonderful host as well.
Superhost
Apartment in Pilsen
4.69 out of 5 average rating, 188 reviews

Heart of Pilsen

FaithRating, 5 stars1 month ago
Thank you for a wonderful stay! You were very accommodating.
Superhost
Home in Bridgeport
4.72 out of 5 average rating, 54 reviews

Animal House near Sox stadium

ChristineRating, 5 stars1 month ago
If you're traveling with a pet I would highly recommend this place! Great location and great communication throughout our stay.
Guest favourite
Apartment in Chicago
4.95 out of 5 average rating, 73 reviews

Travel To Chicago New City

JasonRating, 5 stars2 weeks ago
Khong was responsive, helpful, friendly and overall just a cool host! Khong gave us a sweet surprise when we got in and gave us local recommendations, we loved the Back of The Yards Coffeehouse and it was within walking distance. During the day it felt like a safe neighborhood, during the night it was very lively and full of people in the best way. Khong’s place was so clean and inviting. The backyard was peaceful with a beautiful view of the church. We did have a slight mishap occur when we lost the keys to Khongs place but he was very understanding and kind about the situation. Our stay was everything we hoped for and more. We would definitely return the next time we are in Chicago! 10/10 recommendation from my family and I
Superhost
Apartment in Chicago
4.83 out of 5 average rating, 53 reviews

Cozy Pilsen Apartment

ToryRating, 5 stars1 day ago
It was exactly what we needed for a weekend getaway. A great place to come back to each evening after a day of adventure. Easy walk to the Pink 'L' train that will take you right into downtown for a few bucks. Coffee shops and restaurants all within walking distance. We can't wait to come back to do the things we couldn't fit in. Thanks Rosa for sharing your home.
Guest favourite
Apartment in Heart of Italy
4.95 out of 5 average rating, 19 reviews

Loft-Inspired Retreat | Stylish Stay Near Downtown

EvanRating, 5 stars1 day ago
Loved being just a couple blocks from the Western Pink Line station and bus stops both north-south and east-west.
Guest favourite
Condo in Little Italy
4.93 out of 5 average rating, 40 reviews

Little Italy Casa

SarahRating, 5 stars1 week ago
The neighborhood was excellent, and unit was accurate to the listing photos-it actually was much roomier than I had expected. There were lots of extra towels and bedding. There are a bunch of tight steep stairs to get into the unit which was fine for us, but if mobility is an issue this might not be the place for you. We had a few issues because the cleaning crew missed a few things (no extra TP and previous tenants left bagged trash on the patio) but Leo was super responsive and took care of the problem quickly. This is a safe, beautiful place to enjoy Chicago.

Quick stats about holiday rentals that are pet-friendly in Pilsen, Chicago

  • Total rentals

    10 properties

  • Nightly prices starting at

    $50 NZD before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 properties include access to Wi-Fi

Destinations to explore

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