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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Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 386 reviews

Beautiful & Inspiring Three Bedroom Home in Roscoe Village

Dim the lights and kick back on the couch, in the evening after a day’s adventures, leaving all cares behind. The stunning apartment located in a historic 1895 Chicago building, has a modern, ultra-cool feel, with an inspiring vibe and sensational light fixtures. Roscoe Village is a charming “village within the city” filled with taverns, independen shops and cute cafes. Being only a short walk to the train and a 15-minute cab ride to Chicago's downtown landmarks, this home has the perfect combination of convenience, comfort, and cool. Free street parking easily accessible (no onsite parking). The home is designed with every type of traveler in mind. Whether you're in Chicago on business, having fun with friends, visiting family, and vacationing with your children, you'll find this universal home to have every desired amenity. Business travelers can enjoy awesome high speed internet and a creative office space with great natural light. For groups of friends, the bedrooms feature a ton of closet space, giant dining / living room for catching up over a drink, and a full brand new kitchen to cook in. For traveling families and little ones, the office transforms into a kids room with a travel crib and changing mat. I’m always available to make sure your stay is nothing less than 5-Stars! I can be reached by text or phone, and always around to answer a question or handle a concern. Just 5 miles from downtown, Roscoe Village is a charming, laidback “village within the city” filled with casual taverns, independent shops, and cute cafes that spill out onto the sidewalks during the warm weather months. This cozy little pocket is an eclectic mix of unique boutiques, classic frame and brick homes, and locally owned eateries. *Paulina-Lincoln/Roscoe Brown Line is only a 9 minute walk! *Armitage Avenue shopping: 6 stops @ Armitage stop *River North nightlife: 9 stops @ Merchandise Mart stop *Loop stuff: 10 stops @ Washington / Wells *State & Michigan Avenue shopping: 10 stops @ State / Lake *1 mile from Wrigley Field action *1 block from Roscoe Street’s fun bars and restaurants *0.6 miles from Chicago’s newest and largest Whole Foods *1.7 miles from Regal Cinemas theater No parties and no drugs of any kind. We appreciate you respecting our neighbors. Pets are subject to breed restrictions. Pet fees: 1st pet: $125 per reservation for up to 2 nights and $45 per night after. 2nd pet: $50 per reservation for up to 2 nights and $45 per night after.

Guest favourite

Townhouse in Chicago

4.85 out of 5 average rating, 166 reviews

Downtown Elegance ✨ Private Yard Parking

This unique space features designer kitchen, art by a local artist throughout, marble master bath and most incredible location. Walk to everything Chicago has to offer- Downtown, Mag Mile; North ave beach, zoo and Lincoln park, restaurants, bars, boutiques of Gold Coast and Old Town from this spacious townhouse on a quiet neighborhood street in historic Old Town. 4 bedrooms, 4 baths, 2 outdoor spaces, kitchen plus a bar, 1 car parking, laundry. Pets are welcome! Message me if you have questions!

Superhost

Apartment in Oak Park

4.82 out of 5 average rating, 179 reviews

Reno btrm; Big family escape, W/parking, love pets

This apartment is on the top floor of an owner occupied two flat. It's located in a very quiet, family friendly neighborhood. The skylights bring in a ton of natural light. There is a full kitchen available with pots, pans, flat ware and dishes. I'll supply coffee/tea and snacks! It's a great option for short and long term stays. Dog friendly with an additional fee per animal ($25/day). Laundry available for a small fee. Brand new renovated bathroom with awesome shower. Thanks! Hannah and Emma

Top Guest favourite

Home in Forest Park

4.99 out of 5 average rating, 104 reviews

NEW Gather in spacious 3 bedroom 2 bath home

CA relief: if IL is an option for temporarary housing, please reach out! I have 4 properties I will do whatever I can. Introducing Mohr Cottage in the heart of Forest Park. Spacious & recently updated 3 bedroom 2 full bath 2 story home is perfect for families or large groups looking space & comfort. Quiet residential neighborhood, blocks from restaurants, shops, coffee. Dogs welcome. Near public transportation, easy access to expressway to downtown Chicago. STRICT Non-smoking property.

Superhost

Home in Naperville

4.85 out of 5 average rating, 118 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Superhost

Apartment in Chicago

4.83 out of 5 average rating, 113 reviews

Chic Penthouse In Perfect Wrigleyville Location

Bright and open top floor apartment within easy walking distance to many of the best sites in Chicago: Wrigley Field, Lake Michigan, Lincoln Park, top notch neighborhood restaurants, pubs, and entertainment, and many more! With so much to do in the area and easy access to public transit you're sure to have jam-packed days of exploring and enjoying the city. After a long day, come back to this peaceful apartment to relax, recharge, and prepare to do it all again tomorrow. Book today!

Guest favourite

Home in Elmhurst

4.96 out of 5 average rating, 107 reviews

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

Superhost

Apartment in Chicago

4.88 out of 5 average rating, 283 reviews

River North's Rock N Roll

Decorated with rock n' roll memorabilia located above a trendy restaurant. This cozy apartment also features high ceilings and a carved canopy bed. Minutes to Mag Mile and the Loop! Free parking available. Only blocks from Michigan Avenue shopping district and blocks from downtown loop. CTA Brown line station across the street. River North Art Galleries, Great Dining, Millennium Park and all that Chicago has to offer only minutes away. Wrigley Field in 15 minutes.

Guest favourite

Guest suite in Chicago

4.94 out of 5 average rating, 156 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

Guest favourite

Condo in Chicago

4.91 out of 5 average rating, 334 reviews

Susie's Space. 2BR easy parking & pet friendly

Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

Superhost

Apartment in Oak Park

4.76 out of 5 average rating, 149 reviews

1BR Apartment - Walk to Shops - Downtown OAK PARK

Your family will be close to everything when you stay at this centrally-located place. - 4 min drive to the train - 2 min drive to grocery stores & shopping - 20 min drive to Downtown Chicago Enjoy the historic neighborhood and see Frank Lloyd architecture nearby. ➢ Everything is sanitized/washed/cleaned after every guest ➢ Fast, Dedicated Wifi ➢ 2 Smart TVs (Living Room, Bedroom) ➢ Fully equipped + stocked kitchen / bathroom ➢ Pack 'n Play

Guest favourite

Home in Worth

4.87 out of 5 average rating, 131 reviews

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

This beautiful, newly remodeled, spacious, 3 bed 2 bath ranch style home is set back on a large lot. Located close to a major hwy, restaurants and a shopping. Just 15 minute to Midway Airport, 25 mins to O'Hare, and 25 mins to Downtown Chicago. Its a great spot to get to everything! Perfect for families, vacationers, and business travelers. You must be 21 or older to book. You must provide a valid photo of your D.L. or State ID upon request.