Pet-friendly vacation rentals in West Side

4.95 out of 5 average rating, 154 reviews

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Chicago

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

4.99 out of 5 average rating, 308 reviews

The living area features exposed brick walls and hardwood floors, with an arrangement of seating including a red armchair and a cozy sofa. A glass coffee table sits on a plush area rug. A wall-mounted flat-screen TV is present, alongside indoor plants and decorative elements.

Condo in Chicago

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport fireplace is not operational.

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.95 out of 5 average rating, 221 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.

4.99 out of 5 average rating, 141 reviews

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

4.98 out of 5 average rating, 181 reviews

A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.

Home in Berwyn

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is 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 or catch the train a few blocks away.

4.95 out of 5 average rating, 146 reviews

A spacious modern family room features a large sectional sofa adorned with decorative pillows. A 76” smart TV is mounted on the wall, displaying a beach scene. Natural light enters through multiple windows, illuminating the open layout that flows into a dining area with sleek furniture.

Condo in Chicago

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Luxury 4BR/2.5BA residence featuring 3 private bedrooms and an open-concept bonus room with a queen bed and full-size bunk beds—perfect for upscale families or executive groups. The spa-inspired primary suite offers a soaking tub and rain shower with multiple settings. Enjoy a modern kitchen, stylish living room with a 76” smart TV, and a large covered patio. Located near UIC, West Loop, Chinatown, McCormick Place, the lakefront, and some of Chicago’s best dining and cultural attractions.

An open living space is highlighted by polished concrete floors and an exposed timber ceiling. Large windows allow ample natural light to fill the room. A comfortable blue sofa is positioned alongside mid-century modern chairs and a dining table, creating an inviting area for relaxation and socializing.

4.75 out of 5 average rating, 209 reviews

Spectacular Corner 3BR Loft In Fulton Market | Fea

Stunning 2,500 square foot brick-and-timber luxury loft with 15 foot ceilings located in the heart of the vibrant West Loop neighborhood. This designer 3 bedroom / 2 bath corner unit was just fully renovated and is ideal for groups looking for a luxurious city escape in the middle of Chicago's best dining and nightlife. Abundant natural light and views of the streetscape below make this a truly special space. The central location is ideal for everything you want to see in the city!

4.88 out of 5 average rating, 165 reviews

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 Chicago

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

4.94 out of 5 average rating, 120 reviews

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 Chicago

Beautiful Chicago Greystone

Spacious, private, 4 bedroom condo 15 minutes directly west of the city center. Minutes away from the West Loop, Garfield Conservatory, Downtown, and United Center. Ideal public transportation access with multiple bus stops within 1 block radius, 2 blocks away from Blue Line CTA, 1 mile away from Pink Line CTA. Exquisite back porch and patio with access to grill and patio furniture. Onsite laundry per request Local hosts!

4.82 out of 5 average rating, 259 reviews

An open living area features a light-colored sofa facing a modern fireplace and a flat-screen television. A dining table with chairs is positioned nearby, while a staircase leads to the upper levels. Balanced lighting highlights the neutral tones and spacious layout.

Home in Chicago

Spacious Luxury Townhouse - Old Town

Historic 3 bedroom home in Old Town! Comfortably sleeps 6, and access to 3 levels of living space. The massive rain shower in the master bath is my favorite part, but there's plenty of luxury here to enjoy. Plus, we're right in the heart of Old Town, just steps from all of the shops and restaurants on Wells Street, and a 5 minute walk to the Sedgwick Brown/Purple line stop - you can be in the Loop in 20 minutes! Book today!

A modern living room features a warm fireplace with elegant stone detailing. Comfortable seating is provided by a plush sofa alongside a stylish armchair. Natural light enters through multiple windows adorned with blinds. Decorative elements include a wooden coffee table and contemporary wall art.

4.99 out of 5 average rating, 117 reviews

Chic 2BR Gem with Fireplace

Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. Perfect for both business and leisure travelers, our space combines modern comfort with the vibrant energy of one of the city's most coveted neighborhoods.

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.