Pet-friendly holiday rentals in West Side

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in West Side

Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

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Superhost

An elegant 1890 Greystone building is presented, showcasing a symmetrical façade with decorative stonework. A tiered front staircase leads to a charming entryway, flanked by well-maintained landscaping. Large windows enhance natural light, while a vibrant green shrub adds a touch of color to the exterior.

Home in West Side

Beautiful Chicago Greystone

Experience the best of Chicago from this sprawling, private 4-bedroom condo. Located just 15 minutes west of the City Center, you’re perfectly positioned to explore the culinary scene of the West Loop, the lush Garfield Park Conservatory, and the energy of the United Center Transit: Steps from multiple bus lines, 2 blocks to the Blue Line, and 1 mile to the Pink Line Amenities: On-site laundry (available upon request) Local Experts: We live in the unit below and happy to give recommendations

WalkabilityPetsCheck-in

4.92 out of 5 average rating, 151 reviews

Top Guest favourite

Apartment in Oak Park

Spacious & Modern Treetop Oasis King Bed + Parking

Take a deep breath and relax in this airy and bright top floor apartment. Treetops surround the newly renovated and spacious home in a premier Oak Park location. 20 min. to downtown Chicago. Only 1/2 block to the FLW Home & Studio. Walk to dining & train. 2 bedrooms & 1 bath w/tub & shower. Open living/dining/kitchen/sunroom. Cook’s kitchen w/huge island. Primary w/king bed + deep closet. 2nd bdrm w/built-in bunk beds + desk + balcony. Private entry & deck. Shared fenced yard. Driveway parking.

WalkabilityDecorFamily

4.98 out of 5 average rating, 101 reviews

Top Guest favourite

Apartment in Logan Square

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.

Outdoor spacesPetsCleanliness

4.99 out of 5 average rating, 111 reviews

Top Guest favourite

A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.

Condo in Wicker Park

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

PetsOutdoor spacesKitchen

4.98 out of 5 average rating, 170 reviews

Superhost

A living room is featured, showcasing two blue sofas and a matching armchair arranged around a central coffee table. Soft gray curtains adorn the windows, and framed art pieces add interest to the neutral walls. A patterned area rug complements the hardwood flooring.

Apartment in West Town

*Beautiful apartment* - a few mins from the park.

Comfortable & Spacious beautifully furnished home! 2 large bedrooms, and 2 large bathrooms. Fully equipped kitchen. This is a 1500 sq ft of a home away from home with in unit laundry. Free street parking! The home is a few blocks from Humboldt Park! Blocks to the train and other nearby transportation. Easy to get a Lyft/Uber from the unit. Walking distance to restaurants, cafes and bars! Free Street parking directly in front of the building, there is no permit or parking pass needed.

Outdoor spacesWalkabilityCondition

4.89 out of 5 average rating, 110 reviews

Guest favourite

Apartment in Downtown Chicago

Luxury Loft Collection 01 - Terrace - River North

BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

PetsOutdoor spacesFamily

4.9 out of 5 average rating, 126 reviews

Top Guest favourite

The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.

Apartment in West Town

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

WalkabilityPetsAccuracy

4.97 out of 5 average rating, 636 reviews

Superhost

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Apartment in Downtown Chicago

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.

WalkabilityOutdoor spacesHospitality

4.81 out of 5 average rating, 1053 reviews

Guest favourite

A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.

Apartment in Bridgeport

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

WalkabilityOutdoor spacesGetting around

4.93 out of 5 average rating, 249 reviews

Superhost

A well-lit sleeping area features a spacious bed adorned with patterned linens and accent pillows. A wooden nightstand holds a lamp. A clothes rack stands nearby, alongside a chair with a throw pillow. Dark curtains frame a window, adding privacy to the room.

Apartment in Oak Park

Bright Boho Haven free parking

Welcome to our bright, newly constructed 1-bedroom, 1-bath Airbnb in the heart of Oak Park. Enjoy a sunny, modern space with a beautiful bathroom, free parking, and all the essentials. Just steps from grocery stores, coffee shops, and the Oak Park Blue Line stop—reach downtown Chicago in under 30 minutes. Perfect for a cozy getaway or work trip, with fast Wi-Fi, smart TV, kitchenette (no oven!) and a peaceful, walkable neighborhood. We can’t wait to host you!

WalkabilityPetsBathroom

4.84 out of 5 average rating, 126 reviews

Guest favourite

A living area features exposed brick walls and polished hardwood floors. A comfortable sofa along with two wooden side tables, each topped with a lamp, is positioned for relaxing. Large windows allow natural light to fill the space, providing views of the outdoors.

Guest suite in West Town

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

Outdoor spacesPetsCheck-in

4.87 out of 5 average rating, 233 reviews

Top Guest favourite

The modern kitchen features navy blue cabinetry and a central island with seating for three. Stainless steel appliances include a refrigerator, stove, and dishwasher. Pendant lighting hangs above the island, and a window provides natural light, complementing decorative wall art.

Apartment in Wicker Park

Stylish 2BR stunner w/ unbeatable location

Discover the perfect urban retreat in a newly renovated flat with all the modern amenities. Nestled at the border of Ukrainian Village and Wicker Park, this classic Chicago 2-flat offers modern amenities in a historic setting, tucked away in a peaceful corner just steps away from the vibrant city life of Division and Damen with its countless restaurants, watering holes, and one-of-a-kind shops.

PetsWalkabilityAccess

4.92 out of 5 average rating, 207 reviews