Pet-friendly vacation rentals in Oak Park

4.87 out of 5 average rating, 153 reviews

Bright & Gorgeous- 5* Location- Queen Beds - Pkg

Leave your worries behind at this peaceful, secure retreat with plenty of space to relax. 2nd-FLOOR DUPLEX UP to THE 3rd FLOOR. Just a 15-minute drive to/from downtown. Easily walk to everything: -Groceries, sushi, coffee shop, brewery -Nightlife, live music, and great food - Playgrounds, parks, public pool, & tennis courts Enjoy all the comforts of home in a charming, urban-suburban mix. - Only 1.5 blocks to the Oak Park Av. CTA "L" Blue Line stop & I-290 Housebroken dogs welcome.

A charming three-story building is shown with a covered front porch and steps leading to the entrance. The façade features light beige stucco and dark accents, with large windows that allow natural light to flow in. Lush greenery surrounds the entrance, contributing to a welcoming setting.

4.8 out of 5 average rating, 206 reviews

Cozy modern unit w/ easy access to downtown Chi

Enjoy a newly remodeled two bedroom basement unit in the historic Oak Park suburb of Chicago. This unit is within walking distance to local cafes, amazing restaurants, ice cream shops, and a grocery store to meet your needs. Explore the nearby Frank Lloyd Wright district and the birthplace of Ernest Hemingway. Walk 2 blocks to the train leading to all neighborhoods of Chicago, or simply enjoy a relaxing stay in the cozy apartment. Easy access to nearby airports. Pets welcome with additional fee.

A comfortable living area features a light gray sofa adorned with colorful pillows. A small wooden coffee table with intricate designs sits in front of the sofa, accompanied by a floral arrangement. Art pieces hang on the walls, and natural light enters through the large window.

4.92 out of 5 average rating, 152 reviews

Cheerful Remodel Prime Location

Relax in this newly remodeled and beautifully decorated apartment while recharging from a long day of sightseeing in the big city! We are a block from the Green Line train to downtown! With a 5 minute walk to Whole Foods, Trader Joes, and downtown Oak Park, you can't get a better location than this! Pets are welcome on a case-by-case basis, please mention your pet in your inquiry so we can learn more about them prior to approval and be sure to register them when you select number of guests.

4.97 out of 5 average rating, 239 reviews

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

Home in Berwyn

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.

4.89 out of 5 average rating, 105 reviews

A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.

Home in Oak Park

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.

4.8 out of 5 average rating, 215 reviews

A spacious living area showcases a light brown sectional sofa positioned around a coffee table. Two large televisions are visible in the background, framed by dark curtains. A decorative rug and plants add warmth to the room, which is illuminated by natural light.

Guest suite in Oak Park

Private 2 BR Oak Park Garden Apt

This spacious 2 BR garden apartment is fully furnished, private Kitchen and Bathroom ! In a safe, quiet neighborhood, stay cool and comfortable while you rest. 1 block from the Austin Blue line and the 290/ Eisenhower express way. Approx 20 minutes to Downtown Chicago or Midway Airport and 30 mins to O'hare Airport. Oak Park is a wonderfully diverse community and holds the largest collection of Frank Lloyd Wright homes. It is also the childhood home of Ernest Hemingway.

4.87 out of 5 average rating, 399 reviews

A spacious living area features a modern sectional sofa in neutral tones. A sleek television is mounted on the wall opposite a minimalist coffee table. The adjoining dining area, visible through an archway, includes a round table with four chairs.

Apartment in Forest Park

Home in Forest Park Upstairs.

In this cozy apartment you will have a functional kitchen, in unit laundry, fast WiFi connection and access to a back yard.. The property is located 30 minutes from O'Hara International Airport, 20 minutes from Downtown Chicago via I-290, and 40 minutes away from Midway Airport. Forest Park is a very safe, vibrant and diverse suburb of Chicago. You will be within walking distance of many different restaurants, boutiques, bars, parks, and public transit.

4.99 out of 5 average rating, 107 reviews

A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.

Home in Brookfield

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).

4.89 out of 5 average rating, 141 reviews

Home in Oak Park

Steps to Shops, Restaurants, Trains; 5BR, 14 Guest

Experience a spacious, pet-friendly 5-bedroom, 3-bath home in vibrant downtown Forest Park, perfect for family gatherings or group vacations. Comfortably sleeps up to 14 guests. Enjoy stylish interiors, a fully equipped kitchen, private outdoor spaces, and easy walkability to Madison Avenue's dining and shops. Convenient access to Chicago trains and private parking for 4 vehicles make this an ideal retreat.

4.93 out of 5 average rating, 354 reviews

A bedroom features a spacious bed dressed in deep blue linens, complemented by decorative pillows. The walls are painted in a rich blue, accented by round mirrors. Two bedside lamps illuminate the space, while a patterned area rug lies on the hardwood floor.

Condo in Oak Park

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.

5.0 out of 5 average rating, 390 reviews

A spacious bedroom features a large bed with dark bedding and decorative pillows. A wooden bookshelf filled with books stands against one wall, while sunlight filters through a window adorned with light curtains. A vintage dresser and bedside table complete the welcoming space.

Apartment in Forest Park

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park, right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

4.97 out of 5 average rating, 185 reviews

A spacious living area showcases a comfortable gray sectional sofa and a reclining chair. A contemporary coffee table rests on an area rug with floral patterns. A mounted TV is visible alongside a wooden credenza featuring a coffee maker and supplies, enhancing the functionality of the space.

Home in Forest Park

Gather in Spacious 3 Bedroom 2 Bath Retreat

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.

Popular amenities for Oak Park pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 345 reviews

A comfortable sleeping area features a spacious bed adorned with a decorative pillow displaying a tree branch design in earthy tones. Soft lighting from two bedside lamps provides a warm glow, while a piece of framed art hangs above the bed against a muted green wall.

Home in Forest Park

Charming dog friendly 2-Bath Bungalow Near Chicago

4.93 out of 5 average rating, 112 reviews

Home in Brookfield

Remodeled | Game room | Fire Pit | 5 Min to Zoo

4.96 out of 5 average rating, 124 reviews

A modern living area features a contemporary design with a stylish gray sofa and brown leather chairs. A sleek, geometric area rug sits beneath a coffee table, while framed black-and-white photographs line the walls. Large windows allow natural light to illuminate the space.

Home in Humboldt Park

Rooftop Skyline | 5 Ensuites | Games | DT 14 mins

4.78 out of 5 average rating, 157 reviews

A spacious living area features an array of seating options, including a light gray sofa and colorful accent chairs. Natural light floods in through multiple windows, highlighting the wood flooring and inviting decor. A dining table is situated nearby, along with a small coffee station.

Home in Elmhurst

Cozy Ranch w/ King Bed & 3 Baths – Great Location!

4.96 out of 5 average rating, 132 reviews

The collage showcases various areas of the property, including a modern living space with a wall-mounted TV, a two-story exterior featuring stone details, an outdoor patio area with seating under a pergola, a game room equipped with a ping pong table, and a bathroom with a jacuzzi tub and neatly arranged towels.

Home in Westchester

Jacuzzi, King Beds, Easy Access to DT Chicago!

4.92 out of 5 average rating, 149 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 West Side

Beautiful Chicago Greystone

4.96 out of 5 average rating, 209 reviews

A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

Home in Chicago

The Chicago River House – GIANT wall projector!

4.87 out of 5 average rating, 109 reviews

A spacious living area showcases a mix of comfortable seating, including a sectional sofa and an armchair. Natural light filters through sheer curtains, illuminating the hardwood floor. A neutral area rug lies beneath a coffee table, complementing the decorative wall features.

Home in Irving Park

3BD/2BA Chicago Avondale/Logan Square House

Pet-friendly home rentals with a pool

4.93 out of 5 average rating, 128 reviews

The modern kitchen features white cabinetry and a spacious island with four bar stools. A stainless steel refrigerator stands next to a gas stove and microwave. Natural light filters through large windows, illuminating the elegant countertops and sleek finishes.

Apartment in West Town

Cozy Duplex Down in Wicker Park East w/ Parking

Apartment in Downtown Chicago

A modern kitchen area features a large island with seating for four, complemented by sleek cabinetry. Floor-to-ceiling windows provide expansive views of the city skyline, allowing natural light to fill the space.

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

4.87 out of 5 average rating, 168 reviews

4.75 out of 5 average rating, 303 reviews

A bright living area features a comfortable gray sofa and two modern chairs set around a round coffee table. Large windows provide expansive views of the city, while greenery adds a touch of nature to the space. The warm lighting creates a welcoming ambiance.

Apartment in The Loop

Stunning 3BR Penthouse in the Loop | Roof Deck

4.97 out of 5 average rating, 33 reviews

A comfortable living area is presented with two soft armchairs and a light-colored couch. A media console houses a Roku TV, while a decorative electric fireplace offers warmth. Artwork adorns the walls, and natural light enters through a window with blue curtains.

Townhouse in Forest Park

Forest Park Oasis - Dog Friendly - Parks - the "L"

4.86 out of 5 average rating, 43 reviews

A modern kitchen with an expansive island features sleek countertops and stainless steel appliances. Large windows fill the open living area with natural light, showcasing city views. A comfortable seating area and dining table create an inviting space for relaxation and meals.

Apartment in West Loop

Level Two Bedroom Suite | Fulton Market

Apartment in Downtown Chicago

Luxury Designer Penthouse 3801 | Pool | Gold Coast

4.81 out of 5 average rating, 80 reviews

4.9 out of 5 average rating, 29 reviews

A spacious living area features a light-coloured sofa set positioned around a wooden coffee table, with a television mounted on the wall. A large area rug enhances the space, while plants and natural light provide a fresh atmosphere. Dining space is visible in the background.

Home in Schaumburg

Paradise with Pool & Games

Apartment in Downtown Chicago

Level ◆ Brand New Luxe One Bedroom

4.79 out of 5 average rating, 163 reviews

Private, pet-friendly home rentals

4.95 out of 5 average rating, 171 reviews

The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.

Condo in North Side

Lovely top floor 2BR/2BA, steps from everything!

4.77 out of 5 average rating, 168 reviews

A living space features a comfortable gray sofa positioned across from a flat-screen television on a low black table. A ceiling fan enhances airflow, while a large wall art piece depicts a scenic coastal view. A doorway leads to another area of the apartment.

Apartment in Berwyn

Private Garden APT/ Cozy/Warm

4.88 out of 5 average rating, 190 reviews

A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.

Loft in Brookfield

1920s fully updated unique open artist loft space

4.92 out of 5 average rating, 206 reviews

A modern kitchen and dining area are presented, featuring a sleek island with bar stools and a dining table with six chairs. Natural light is provided by large windows, and contemporary fixtures enhance the space's functionality and design.

Apartment in Evanston

New 3bd/1.5 bth Apt w/private prkg

4.87 out of 5 average rating, 191 reviews

A living area is presented with two light-colored armchairs and a glass coffee table at its center. A flat-screen television is mounted on the wall, while a decorative plant sits atop a small navy console table. A soft area rug adds warmth to the space.

Apartment in Forest Park

Spacious, Charming 3bd Unit @ Forest Park/Oak Park

5.0 out of 5 average rating, 97 reviews

Oak Park Chic Duplex King Bed•Parking•Deck•Yard

4.85 out of 5 average rating, 33 reviews

Home in Oak Park

OakPark Gem. Family-Friendly Getaway near Downtown