Pet-friendly holiday rentals in Portage Park

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

4.96 out of 5 average rating, 194 reviews

Home in North Park

The Chicago River House – GIANT wall projector!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

4.96 out of 5 average rating, 140 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 with garage parking! 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.

4.91 out of 5 average rating, 202 reviews

A cozy seating area is highlighted by a modern electric fireplace beneath a mounted television displaying streaming options. Soft cushions and a pastel throw blanket add comfort to the light-colored chair. A touch of decor is presented with wall art and a small side table.

Apartment in Oak Park

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

4.92 out of 5 average rating, 176 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

Welcome to BoHo House – a charming, airy bohemian gem built in 1903. This beautifully designed 3BR home is just a short walk from Chicago's popular bars, restaurants, and coffee shops. Enjoy the peaceful private fenced backyard, perfect for your pup to roam, complete with an adorable outdoor space. Host a cozy patio dinner by the fire or unwind indoors with a movie. Just 20 minutes from ORD, 10 minutes to downtown, with 800+ Mbps WiFi, free coffee and snacks, and secure 2-car garage parking!

4.96 out of 5 average rating, 101 reviews

Apartment in Albany Park

Irving Park/Avondale updated vintage top unit

Experience a true Chicago neighborhood in a classic vintage (but updated) two-flat apartment just 10 minutes from Wrigley Field, 4 minutes from I-90/94 and a 15-minute walk or short bus ride to the blue line. Central air/heat and free street parking. I'm a former Super Host and capital P Perfectionist, but decided to list the space before it's perfect to help cover the cost of future renovations. As long as you don't mind not having a brand-new bath/kitchen and fresh paint, you'll love it!

Apartment in Logan Square

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, 438 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

4.9 out of 5 average rating, 201 reviews

A spacious living area features a light-colored sofa and a dark wood coffee table, surrounded by large windows that allow ample natural light. Decorative plants are placed around the room, and a brick fireplace adds a focal point, complemented by framed artwork on the walls.

Apartment in Albany Park

Huge Pet Friendly East Albany Park Apartment

Enjoy staying in a classic Chicago 2-flat w/vintage charm and modern amenities. This sunny top floor unit has an updated kitchen & bath w/everything you need including in-unit laundry & Central Air. Experience life on the border of 2 great neighborhoods, Albany Park & Ravenswood Manor. Walk to Kedzie & Lawrence for diverse cuisine or walk to Lincoln Square. Take the Kedzie Brown Line to Lakeview & Lincoln Park. $75/pet/per stay. $25/person/night after 2 guests. Check-in/out @11am/@4pm.

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, 181 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, 355 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, 132 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!

4.97 out of 5 average rating, 457 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

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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

4.83 out of 5 average rating, 120 reviews

An open living and dining area is shown, featuring a flat-screen TV mounted on a light wood unit. Comfortable seating includes a gray sofa, teal chairs, and a pink armchair. A wooden dining table is set for six. Decorative elements include wall art and a wall clock.

Home in Logan Square

California Cottage/4br prime location Logan Square

4.98 out of 5 average rating, 118 reviews

A stately Victorian house is surrounded by a landscaped garden featuring lush greenery and colorful plants. The front porch is framed by pillars and features multiple seating areas. A red front door adds a bold contrast to the dark exterior of the home.

Home in Chicago

Victorian House in Heart of Rogers Park

4.96 out of 5 average rating, 165 reviews

Home in Logan Square

The Grand Kimball Lodge, Logan Square, Sleeps 14

4.94 out of 5 average rating, 124 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

4.97 out of 5 average rating, 159 reviews

The living area showcases a dark blue accent wall, complemented by a modern light fixture. A cozy sectional sofa is framed by two framed artworks, while a round coffee table holds decorative items. An adjacent dining space features a light wood table surrounded by chairs and a built-in cabinet.

Home in Lincoln Park

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

4.87 out of 5 average rating, 104 reviews

An inviting dining area is complemented by a wooden table surrounded by six dark chairs. A large mirror reflects natural light from the windows, while contemporary artwork adorns the walls. A cozy seating area with a green sofa is visible in the background.

Home in Ranch Triangle

Sophisticated Twnhm in Prestigious S. Lincoln Park

4.9 out of 5 average rating, 129 reviews

A comfortable living area features a blue couch adorned with decorative pillows, complemented by a lighted lamp on a small side table. Two chairs are positioned nearby, and a patterned area rug covers the hardwood floor, while natural light filters through the windows.

Home in Forest Park

Adorable house Madison Street w/ 2 car garage!

Pet-friendly home rentals with a pool

4.76 out of 5 average rating, 242 reviews

A bright living area features large windows offering city views. Modern furnishings include a comfortable sofa and stylish accent chairs. A round coffee table is placed on a textured rug, complemented by indoor plants and warm lighting to enhance the ambiance.

Apartment in The Loop

Stylish Corner 2 Bedroom in the Heart of Chicago |

Apartment in Magnificent Mile

4.89 out of 5 average rating, 35 reviews

Luxury Designer Penthouse 3803 | Pool | Gold Coast

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"

Apartment in Printer's Row

A spacious bedroom is highlighted by a large king bed with a textured green headboard. Natural light floods the room through expansive windows offering views of the city and lake. A colorful area rug enhances the space, while modern artwork is displayed on the walls.

4.94 out of 5 average rating, 98 reviews

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool

4.81 out of 5 average rating, 53 reviews

An indoor swimming pool stretches along a glass wall, offering views of the outdoors. The space is highlighted by modern lounge chairs and sleek tile flooring. Natural light floods the area, enhancing the serene ambiance created by the tranquil water features.

Apartment in Grant Park

Sentral 2 Bedroom Apt in South Loop Chicago

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.

4.58 out of 5 average rating, 24 reviews

Level One Bedroom Suite | Fulton Market

Apartment in Logan Square

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

Private, pet-friendly home rentals

4.98 out of 5 average rating, 222 reviews

A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.

Condo in Lake View

RockStar Pad W3A BoysTown/Wrigley Field/Parking

4.93 out of 5 average rating, 303 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

4.84 out of 5 average rating, 107 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

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, 351 reviews

Private coach house near transit shops & nightlife

4.98 out of 5 average rating, 312 reviews

A cozy seating area features a round table surrounded by two chairs. A potted plant is positioned nearby, contributing to the fresh atmosphere. A glass coffee table rests on a patterned rug, while a comfortable gray sofa with assorted cushions is present against the wall.

Apartment in Wicker Park

Ukrainian Village Garden Retreat

4.98 out of 5 average rating, 155 reviews

A modern kitchen showcases sleek white cabinetry and a large island with seating for three on black stools. Open shelving displays various glassware. A stainless steel range hood is positioned above the gas cooktop, while natural light fills the space through windows.

Apartment in Edgewater

Newly Renovated, Spacious 2BR in Andersonville

4.98 out of 5 average rating, 126 reviews

A cozy living room features a gray sectional sofa and a teal accent chair, complemented by patterned curtains. A TV is positioned on a low stand, with framed artwork on the walls. Natural light filters through multiple windows, enhancing the vibrant decor.

Apartment in Wicker Park

Colorful Bucktown Garden Apartment