
Pet-friendly holiday rentals in Cook County
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Cook County
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

1920s fully updated unique open artist loft space
True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost
Outdoor spacesWalkabilityAmenities

Paradise on the Boulevard!
Amazing 2 bedroom garden apartment, located in the heart of the highly desirable Logan Square. This luxurious space with heated polished concrete floors & spa inspired bathroom is situated on the Historic Logan Boulevard, just steps from CTA Blue Line. Fabulous restaurants and coffee shops across the street. The apartment has a private entrance & access to a fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Peace, convenience & excitement are right here.
PetsWalkabilityFamily

RetroModern Bungalow | free parking | pet friendly
Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a pup-friendly, fenced-in backyard. With central HVAC, speedy WiFi, a dedicated workspace, and a pack-n-play crib available at no cost. Central location—just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage and catch the train a few blocks away.
WalkabilityPetsLocation

SW Evanston Private, Stylish, Spacious Suite
Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.
PetsWalkabilityNearby

Kasa | Views from your Private Balcony | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.
Outdoor spacesPetsAir conditioning

Lovely top floor 2BR/2BA, steps from everything!
BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.
PetsWalkabilityEV charging

A Comfortable Stay While You are Away in Oak Park
Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.
WalkabilityPetsComfort

Cozy Home in Brookfield
Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).
WalkabilityOutdoor spacesIndoor spaces

Quiet Oasis: Cozy, Private, Fenced Yard & Office
Private, pet-friendly 2-bedroom single-level retreat near Chicago, ideal for 4 guests + infant. Features a dedicated remote workspace with 413 Mbps Wi-Fi, fully equipped kitchen, and a spacious private backyard with a gas grill. Perfect for remote workers, cycling enthusiasts, and brewery lovers, offering easy access to nature trails, 6 local breweries, and casinos. Enjoy a quiet escape just 30 minutes from the city.
PetsOutdoor spacesCheck-in

Cozy Home near O'Hare & fun Hubs
Relax with the whole family at this peaceful place to stay. Experience comfort and convenience at our newly remodeled cozy house, perfectly situated near O'Hare Airport, Allstate Arena, and Rosemont Theater. Ideal for travelers and entertainment enthusiasts, this charming Airbnb offers modern amenities and a warm ambiance, ensuring a delightful stay. Book now and enjoy the best of Rosemont!
Outdoor spacesPetsAccuracy

Picture Perfect 3Bed Steps from Train and FLW
Welcome to your beautiful 3 bedroom home-away-from-home! From the Insta-worthy forest room to the cozy fireplace reading nook to the modern ice crusher in the kitchen, we've put so much thought into this home that we're sure you won't ever want to leave. Welcoming and newly updated, this unit is close to restaurants, shopping, the best of Frank Lloyd Wright, and the train to the city.
Outdoor spacesWalkabilityAir conditioning

Worth It! 3 bedroom ranch home
Relax with the whole family at this peaceful place to stay. Just minutes from walking parks, outdoor concert venue, golfing, and down town! Comfy and inviting Ranch style home offers 3 bedrooms, a fully equipped kitchen, flat screen TVs, and large windows. The private backyard has a patio, and bbq grill. A real home away from home, we look forward to your new booking.
Outdoor spacesWalkabilityDecor
Popular amenities for Cook County pet-friendly home rentals
Pet-friendly house rentals

Cozy three bedroom home in Munster , Indiana.
Outdoor spacesWalkabilityBeach

Quiet cul-de-sac with huge fenced in backyard
PetsWalkabilityFamily

Sophisticated Twnhm in Prestigious Lincoln Park
WalkabilityPetsGetting around

Dog Friendly Cozy North Naperville 3 BED/2 BA Home
Outdoor spacesWalkabilityAccuracy

Cozy & comfy w/free parking & W/D
WalkabilityPetsParks

California King Bed | Fast Wi-Fi | 75" Smart TV
PetsWalkabilityBathroom

Cozy 2 bedroom house/w garage in Skokie
WalkabilityOutdoor spacesValue

Suburban Serenity~Grill, Fire pit, Big yard~
WalkabilityOutdoor spacesCheck-in
Pet-friendly home rentals with a pool

Beautiful Corner 2 Bedroom in the Loop | Roof Deck
PetsOutdoor spacesDecor

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more
PetsWalkabilityLong stay

Farm Themed Guesthouse!
Outdoor spacesPetsHeating

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony
Outdoor spacesPetsAccess

DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
Outdoor spacesPetsAir conditioning

Cozy Duplex Down in Wicker Park East w/ Parking
PetsWalkabilityAccuracy

Level Junior Two Bedroom Suite | Fulton Market
Outdoor spacesPetsIndoor spaces

Paradise with Pool & Games
PetsComfortDecor
Private, pet-friendly home rentals

Cozy Lakeview Studio with Private Access
PetsOutdoor spacesTV

Modern Garden apartment (WHOLE UNIT)
WalkabilityOutdoor spacesDecor

Beautiful home near the Windy City!
WalkabilityPetsLayout

Loft-Inspired Pilsen Retreat | 10 min to Downtown
WalkabilityHeatingWi-Fi

Modern Charming Home w/Pergola & games
Outdoor spacesWalkabilityValue

UChicago Condo | 2 Baths, Private Parking & Entry
PetsWalkabilityHospitality

Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard
WalkabilityOutdoor spacesLocation

3BR/2BA + Pull Out Sofa Bed + No Stairs + Backyard
PetsWalkabilityLong stay
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- Wrigley Field
- Soldier Field
- United Center
- Lincoln Park
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- Chicago River Walk
- The Field Museum
- University of Chicago
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Donald E Stephens Convention Center
- Union Park
- Beachwalk Vacation Rentals
- Frank Lloyd Wright Home and Studio
- Washington Park Zoo
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