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 Forest Park

4.99 out of 5 average rating, 337 reviews

Walk to Oak Park from Our Sunny Turn of the Century Apt

Soak up the vintage charm of this apartment dating back to 1908. This newly remodeled space is an elegant retreat, featuring 10-foot ceilings, local art treasures, and plush linens. A relaxing outdoor lounge area awaits after a busy day exploring. Pets are welcome on a case by case basis (contact host). The space is a charming two bedroom, one bathroom first-floor unit in a two unit historic home built in 1908. The apartment combines historic details with modern conveniences such as central heat and air, a dishwasher and washing machine and dryer access. The Monroe House is a stone’s throw from historic Oak Park and just three blocks from the CTA Blue Line making downtown Chicago a 25 minute train ride away. The condo includes additional amenities such as: •Smart TV for watching any account may you have (Netflix, Hulu etc...) •Central Air conditioning •Front and back porches for your enjoyment •Washer and dryer on site Just to the east lies historic Oak Park, and an array of attractions such as: •Brookfield Zoo •Chicago Architecture Foundation •Ernest Hemmingway Museum and Birthplace •Frank Lloyd Wright Home and Studio •Frank Llyod Wright’s Unity Temple •Oak Park Conservatory After taking in the local attractions, Chicago is only a train ride away, and it offers such noteworthy experiences as: •Shedd Aquarium •Architecture River Cruise •Skydeck Chicago •Navy Pier •The Field Museum •John Hancock Observatory •Adler Planetarium •Art Institute of Chicago •The Museum of Science and Industry You will have access to the entire unit and the basement so you can use the washing machine and dryer. We also have a back patio with a chiminea, patio table that seats 6, and a grill/smoker. You are welcome to use the backyard at anytime during your stay. We live in the top unit and are as available as you need. That being said, we very much respect your privacy and will not be checking in with you in person unless you request it. It is located in the Madison district, with acclaimed restaurants, pubs, and unique boutiques. Downtown Chicago is a 25-minute train ride away. The local brewery across the street offers delicious beers and creative meals for the whole family. We have a parking pad located behind our building. You can fit two cars on your side of the parking pad if they are parked in tandem. Some street parking is also available. We are located .4 miles from the CTA Blue Line train - Forest Park Stop. It is about a 6 - 10 minute walk from the flat. You can also take an Uber/Lyft into the city. It is about a 15 - 25 minute ride and it costs between $15 and $25. We are located about one mile from the Metra Station (Union Pacific West) and CTA Green Line - Oak Park Stop. Third bed is a queen sleeper sofa. We provide sheets and blankets for the sleeper sofa. You can smoke in the backyard. An ashtray is provided.

Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 383 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, 165 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

Guest favourite

Apartment in Forest Park

4.83 out of 5 average rating, 248 reviews

Home in Forest Park downstairs.

Enjoy a private ground floor apartment which is centrally-located with easy access , to the city. You will have a functional kitchen, laundry facility outside your back door and fast internet. Forest Park is located about 20 minutes from downtown Chicago and about 30 minutes from O’Hara international airport. You are within walking distance of many boutiques, restaurants, parks and also public transportation. Please make a note that there will be a $30 per guest fee if more than four.

Superhost

Apartment in Chicago

4.83 out of 5 average rating, 109 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, 106 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

4.89 out of 5 average rating, 281 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, 154 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, 330 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, 147 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, 129 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.