Pet-friendly holiday rentals in Portage Park

4.87 out of 5 average rating, 187 reviews

A charming single-family home features a well-maintained facade with a red front door and neatly trimmed lawn. Stairs lead up to the entrance, while a simple walkway is bordered by greenery. The exterior is accented by sunny blue skies and fluffy clouds.

Bungalow in Portage Park

"Your Cozy 2nd Home-Near O'Hare\Rosemont\Downtown

“More Than Just a Stay—10+Years of Trusted Superhost Hospitality.” Welcome to your Chicago retreat, designed to make you feel at home the moment you arrive. Whether you’re here for business, family, or adventure, our cozy home gives you the perfect blend of comfort & connection. Unbeatable Location • O’Hare Airport-14mins • Downtown Chi.-18mins • Rosemont Theatre- Entertainment District & Donald E.Stephens Convention C.-10mins • Allstate Arena-13mins “Where every trip feels like home”

Guest suite in Portage Park

The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.

4.94 out of 5 average rating, 459 reviews

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

4.97 out of 5 average rating, 140 reviews

The modern kitchen showcases sleek white cabinetry and a spacious island topped with a white marble surface. Stainless steel appliances, including a gas stove and a refrigerator, are complemented by glass-front cabinets displaying elegant dishware. Soft blue lighting highlights the room's contemporary design.

Home in Portage Park

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

Treat yourself to this Chicago getaway with 14 of your friends & family. Be inspired to create culinary delights in our celebrated 5 stars outdoor kitchen. Reboot & relax in each of our thoughtfully designed powered by SOLAR ENERGY throughout. After a memorable night in OR an adventurous night out you will ask yourselves, 'Why don't we do this more often?' 15 mins to Downtown, O’Hare airport, West Loop. 20 mins to Lakeview, Wrigleyville, Boystown, Logan Square, Bucktown & Wicker Park.

The living area features a vibrant blue sofa complemented by a colorful hammock, surrounded by greenery. A wooden dining table with four chairs sits prominently, while artistic decor is displayed on the walls and a large mirror reflects natural light from multiple windows.

4.9 out of 5 average rating, 439 reviews

Sunny Logan Square Artists' home

2nd floor classic Chicago 2flat with lots of light. 3 bedrooms available, with 2 additional sofabeds. Great if you and family/group of friends are in town for an event and want to stay together. Grocery store 1.5 blocks away. Quiet street. Parking is decent. New bath has all marble walls, extra long/deep tub and rain shower. 1 mile walk to the Logan Square CTA Blue Line and Logan Square brunch/night-life. 5 min walk to Metra. Walk to 606 trail. Chicago Registration Number: R24000117459

4.98 out of 5 average rating, 191 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

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at 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.

4.96 out of 5 average rating, 142 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 Avondale

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

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Guest suite in Portage Park

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

4.95 out of 5 average rating, 183 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

4.77 out of 5 average rating, 357 reviews

A cozy living area is defined by a modern gray sofa and two red armchairs, adorned with decorative cushions. A black coffee table sits atop a patterned rug, while a television is positioned on a sleek stand. Natural light filters through small windows covered with dark curtains.

Apartment in Irving Park

ITALIAN garden apt/kids friendly/great location!!

Ciao! My name is Viviana I am Italian and I live with my family, my husband and 2 girls, I hope you will enjoy our cozy guest garden APARTMENT within our home, featuring a queen size bed, a sofa bed good for a small person or a toddler, 2 twin foldable beds, TV where you can enjoy cable channels, movies and other amenities like, laundry, little kitchenette with a MINI refrigerator, microwave, snacks and hot plates if you like to cook something. Arrivederci!

4.92 out of 5 average rating, 133 reviews

The open-concept living space features natural light streaming through skylights and a mix of wooden accents and plants. A comfortable green sofa and a chair are positioned along the walls, while a sliding barn door leads to the adjacent bedroom area.

Apartment in Avondale

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

Cozy one bedroom attic apartment in Avondale located on top of a 3 story building. Close to Milwaukee, restaurants, and bars. A perfect crash pad for touristing in Chicago. You have your own entrance but since people in this building are working from home, and need to sleep at night, no loud music or partying is allowed at any time! But then, there is no need to bring the party home - you have everything you need just outside the door!

Apartment in Magnificent Mile

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.

4.98 out of 5 average rating, 128 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.

Apartment in Lincoln Square

A bright living area is presented with a patterned armchair and a cozy sofa adorned with a colorful throw. A wooden coffee table is positioned in front, while a window with sheer curtains frames the view of the outdoor porch area.

4.95 out of 5 average rating, 413 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

4.97 out of 5 average rating, 463 reviews

A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.

Condo in Lincoln Square

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

Popular amenities for Portage 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, 121 reviews

A spacious two-story home features a covered front porch with a wooden railing and steps leading up to the entrance. Large windows allow natural light into the interior. A well-maintained yard surrounds the home, with a fenced area providing privacy.

Home in Forest Park

Step Outside to Shops and Restaurants

4.91 out of 5 average rating, 402 reviews

A spacious dining area features a large table surrounded by six chairs. Natural light is provided by two windows with sheer curtains. A unique light fixture hangs above, and a vase with flowers is centered on the table, contributing to the room's welcoming ambiance.

Home in Lake View

Private 3rd Floor Apartment

4.96 out of 5 average rating, 197 reviews

Home in North Park

The Chicago River House – GIANT wall projector!

4.92 out of 5 average rating, 181 reviews

A spacious living area features a vibrant orange sofa adorned with green and beige throw blankets. A stylish coffee table holds decorative items, while a large houseplant adds a touch of greenery. Natural light fills the room, highlighting the wooden staircase in the background.

Home in Avondale

BoHo House - A Chic, 1903 Chicago Workers Cottage

4.94 out of 5 average rating, 127 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

4.82 out of 5 average rating, 268 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 Lincoln Park

Spacious Luxury Townhouse - Old Town

4.97 out of 5 average rating, 162 reviews

A two-story white house is featured, displaying large windows that allow natural light to brighten the façade. The entrance is marked by a covered porch with steps leading up, while planters are placed on either side of the door against a tree-dappled background.

Home in Lincoln Park

Charming 3-BED in Lincoln Park/ Old Town & Parking

4.95 out of 5 average rating, 115 reviews

A single-story brick house is presented with a spacious front yard, featuring trimmed greenery and a walkway of stone steps leading to the front door. A driveway, visible to the right, accommodates a garage door with a dark finish.

Home in Skokie

Cozy 2 bedroom house/w garage in Skokie

Pet-friendly home rentals with a pool

4.7 out of 5 average rating, 10 reviews

A modern gourmet kitchen features light wood cabinetry and a spacious granite island. A gas stove and stainless-steel appliances are included. Soft lighting illuminates the countertops, showcasing neatly arranged dinnerware and cooking essentials, creating a functional and inviting culinary space.

Apartment in River North

Level ◆ New Executive One Bedroom & Office

5 out of 5 average rating, 18 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"

4.75 out of 5 average rating, 283 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

Apartment in Fulton Market

A spacious bedroom with large windows provides an expansive view of the city skyline. The comfortable bed is flanked by bedside tables with lamps, and art pieces are displayed on the wall. Natural light brightens the room, enhancing its modern aesthetic.

4.63 out of 5 average rating, 30 reviews

Level One Bedroom Suite | Fulton Market

4.67 out of 5 average rating, 3 reviews

The living area showcases large floor-to-ceiling windows that invite ample natural light, revealing city views. A modern sofa is positioned on a textured area rug, accompanied by a minimalist coffee table. The kitchen features sleek cabinetry and stainless steel appliances, visible in the background.

Apartment in West Loop

Two 2BR Apts for Business & Leisure Groups

A cozy living area is presented, featuring a comfortable sofa and a stylish blue chair. A wooden coffee table sits in the center, complemented by a textured rug. Large windows allow natural light, while art pieces adorn the walls, adding visual interest to the space.

4.8 out of 5 average rating, 76 reviews

Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!

Apartment in Printer's Row

South Loop | Rooftop With In & Out Parking

4.93 out of 5 average rating, 14 reviews

A spacious living area features a sectional sofa with a modern design, paired with a coffee table. Large windows offer expansive city views, while a patterned rug adds warmth. Decorative elements include a glass bar cart and various art pieces, contributing to a contemporary ambiance.

Apartment in South Loop

Modern 2BR South Loop Apt, McCormick & Wintrust

Private, pet-friendly home rentals

Apartment in North Center

A living room features a comfortable grey sofa with accent cushions, accompanied by a small coffee table. Two lamps provide lighting beside the sofa. A green chair adds a pop of color, while abstract wall art hangs above the sofa. Two windows frame the space.

4.75 out of 5 average rating, 190 reviews

1BR Apartment in Chicago

The exterior of a historic Chicago Graystone building is presented, featuring a grand entrance with wide steps leading to a covered porch. Lush green grass fills the yard, framed by well-maintained landscaping and a wrought-iron fence, with large windows reflecting natural light.

4.99 out of 5 average rating, 158 reviews

Newly-renovated historic home in Logan Square

4.93 out of 5 average rating, 466 reviews

A cozy bedroom is depicted with a spacious bed featuring white linens. On either side, elegant lamps provide soft lighting. A colorful artwork adorns the wall above the bed, and framed art pieces are visible on the nearby walls, contributing to the room's inviting feel.

Apartment in Edgewater

Andersonville Living

4.88 out of 5 average rating, 351 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.

Guesthouse in Logan Square

The living area features a wall-mounted TV opposite a light-colored loveseat and a blue armchair. A small round coffee table is situated on a textured gray rug. Natural light enters through the two windows, with modern framed art and a floor lamp adding character.

4.98 out of 5 average rating, 362 reviews

Private coach house near transit shops & nightlife

A sunlit living area features large windows framed by wooden accents, allowing natural light to illuminate the space. A comfortable futon is positioned alongside an armchair and a glass coffee table on a textured rug, with a small television and simple wooden furniture completing the layout.

4.95 out of 5 average rating, 572 reviews

2nd floor of 1908 brick two-flat in Logan Square

4.82 out of 5 average rating, 115 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