Pet-friendly holiday rentals in East Rogers Park

Guest house in Lincoln Square

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

4.89 out of 5 average rating, 352 reviews

Private Coach house near Lincoln Square!

Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville, and Lincoln Square. This little piece of heaven offers the privacy of a detached home with a fenced oversized yard perfect for puppies to run around in or enjoy a beer from one of our many local breweries. The house provides a full-size kitchen and bath with a walk Less than 1 mile to the closest CTA and 1.5 from Wrigley. Pets Allowed! Bathroom/Shower updated Feb 2025!

4.98 out of 5 average rating, 227 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.

Apartment in Lake View

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

4.9 out of 5 average rating, 439 reviews

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.

Flat in Logan Square

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

4.94 out of 5 average rating, 122 reviews

A cozy living room features a large smart TV mounted on the wall, and a plush sectional sofa with a soft throw draped over it. Armchairs are positioned nearby, alongside a wooden bookshelf. A vibrant area rug adds warmth to the space, with a window letting in natural light.

Flat in Chicago

The Loyola Garden Flat: Huge 2BR Near Lake

Enjoy a massive 2BR garden suite in East Rogers Park. Our "Urban Den" offers a sprawling layout with room to relax—perfect for avoiding that "snowed-in" feeling. Winter-Ready & Convenient: Commuter's Dream: 2-block walk to the Red Line, minimizing time in the cold. Warm & Quiet: Naturally insulated and private. Prime Access: 2 blocks to Loyola; 4 blocks to the Lake. Classic Chicago charm steps from local coffee and transit. Ideal for university visits or a spacious lakeside escape!

4.95 out of 5 average rating, 115 reviews

The spacious garden studio features a cozy living area with a textured sofa adorned with decorative pillows. A stylish coffee table is positioned in front, complementing an adjacent dining area. The kitchenette showcases modern appliances, while warm lighting enhances the welcoming ambiance.

Flat in Edgewater

Edgewater Studio on Paulina

Our garden unit is nestled in the charming Edgewater neighborhood of Chicago, just a short walking distance from the vibrant Andersonville area where you will find several shopping and dining options. Situated in a convenient location, our unit offers easy access to public transit options including bus routes and Red Line as well as permitted street parking. We look forward to hosting, where comfort, convenience, and the best of Chicago's neighborhoods await you.

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

Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa

4.93 out of 5 average rating, 245 reviews

A bright living area features large bay windows with natural light filtering through. A white sofa is complemented by decorative pillows and a coffee table adorned with flowers. A mirror adorns the wall, enhancing the sense of space and light.

Flat in Lake View

Penthouse Near Wrigley Field

This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

4.83 out of 5 average rating, 180 reviews

A spacious living area is highlighted by a large sectional sofa positioned around a light area rug. Natural light filters through the floor-to-ceiling windows, while a sleek TV is mounted on the wall. Decorative plants and modern furnishings add to the inviting atmosphere.

Apartment in Chicago

Marvelous Condo w/ Pri Prkng Cls to Transit &Beach

Enjoy this light-filled, roomy 3BR/2BA condo featuring an open, airy layout ideal for families, friends, or groups. Each bedroom includes a comfortable queen bed, and the master boasts a private full bathroom. Cook meals in the fully stocked kitchen, gather around the spacious island, or unwind in the living area with a 55" Sony TV. With generous space to relax and connect, this condo offers a true home-away-from-home experience in Chicago.

4.85 out of 5 average rating, 131 reviews

A spacious sleeping area features a large bed topped with neutral-toned linens and decorative pillows. Two bedside lamps provide soft lighting beside nightstands. A plush rug adds warmth to the floor, and a comfortable chair is positioned in the corner under a world map wall decor.

Flat in East Rogers Park

Enjoy In-Unit Laundry a King Bed!

Located in wonderful West Ridge, this is a private garden/basement apartment with only 6 steps down. Separate entrance, as well as in-unit washer and dryer. 5 Minute walk to: - Famous Devon Ave for delicious cultural cuisine - Fresh Markets - Bus stops 5 - 10 Minute drive to: - The beach - Groceries (Jewel Osco, Food For Less, Mariano’s) - Indian Boundary Park - Target, Walmart - Long Horn, Olive Garden Red Lobster & more

4.98 out of 5 average rating, 128 reviews

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.

Flat in Magnificent Mile

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 Edgewater Glen

A vibrant seating area is showcased with a blue couch adorned with colorful throw pillows and a brown leather sofa. A small black coffee table rests on a patterned area rug, which features geometric designs. Large windows allow natural light to fill the space.

4.98 out of 5 average rating, 133 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

Enjoy all that Chicago has to offer in this beautiful Edgewater home. Lakefront beaches are steps away, as is the red-line Granville stop. This condo is walking distance to the Loyola campus, many restaurants, grocery stores, gyms, antique stores, and more! There is ample street parking on Lakewood, often there is a space right outside the house. We provide daily parking passes for you to use during your stay.

4.95 out of 5 average rating, 412 reviews

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.

Flat in Lincoln Square

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.

Popular amenities for East Rogers Park pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

5 out of 5 average rating, 102 reviews

A bright living space features a comfortable sectional sofa, complemented by decorative pillows. Natural light filters through multiple windows adorned with wooden frames. A round wooden coffee table sits in the center atop a textured area rug, enhancing the room's cozy atmosphere.

Home in West Rogers Park

Luxury Family Home 6bed/3bath/4parking in Chicago

4.98 out of 5 average rating, 119 reviews

A spacious kitchen features sleek black countertops and a large central island. Stainless steel appliances include a refrigerator and a gas range. Natural light enters through the windows, illuminating decorative plants and kitchen essentials arranged on shelves.

Home in North Side

Flat in Lincoln Park 2-Flat Central to Everything

Home in Old Town Triangle

A cozy living area features comfortable seating with a dark blue sofa, two armchairs, and a wooden coffee table. Natural light streams through large windows adorned with decorative frames. A small decorative tree and artwork add warmth to the space, complemented by a soft area rug.

4.86 out of 5 average rating, 184 reviews

Historic Old Town, Fabulous 4 Bedroom Home

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

4.82 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

4.95 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

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

Pet-friendly home rentals with a pool

4.78 out of 5 average rating, 128 reviews

Flat in River North

Level ◆ Brand New Luxe One Bedroom

4.67 out of 5 average rating, 341 reviews

A spacious indoor garden lounge features abundant natural light streaming through large windows. Modern white furniture is arranged around a central coffee table, surrounded by lush greenery and decorative plants. The airy atmosphere is enhanced by hanging light fixtures, creating a serene and inviting space.

Flat in Grant Park

Sentral Premium 2BR Apt South Loop Chicago

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"

4.92 out of 5 average rating, 102 reviews

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.

Flat in Printer's Row

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

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.

Flat in The Loop

Stunning 3BR Penthouse in the Loop | Roof Deck

4.63 out of 5 average rating, 30 reviews

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.

Flat in Fulton Market

Level One Bedroom Suite | Fulton Market

4.8 out of 5 average rating, 76 reviews

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.

Flat in Logan Square

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

Flat in Printer's Row

South Loop | Rooftop With In & Out Parking

Private, pet-friendly home rentals

Apartment in Lincoln Park

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.

4.99 out of 5 average rating, 321 reviews

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

4.95 out of 5 average rating, 198 reviews

A modern living room features a gray sofa adorned with patterned pillows, complemented by two armchairs with light upholstery. Large windows framed by blue and white striped curtains allow natural light to illuminate the space. A round wooden coffee table sits atop a textured area rug.

Flat in Uptown

Spacious 2BR Condo + Free On-site Parking

4.84 out of 5 average rating, 333 reviews

A spacious living area features a gray sofa adorned with yellow cushions, accompanied by two beige armchairs. An archway leads to a contemporary kitchen, while soft lighting and a neutral color palette create a calm atmosphere.

Flat in Lincoln Park

Archways at the Lincoln Park Zoo 2bed/2ba

4.95 out of 5 average rating, 318 reviews

A warm living area features a black leather sofa adorned with colorful throw pillows. A glass coffee table rests on a patterned rug, while two accent chairs provide additional seating. Natural light streams in through a window, complemented by decorative plants and wall art.

Flat in Logan Square

Cozy and Spacious! Logan Square Apartment

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

4.99 out of 5 average rating, 138 reviews

A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.

Apartment in Lake View

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

4.95 out of 5 average rating, 244 reviews

A light-filled dining area features a wooden table surrounded by four chairs. A plush sofa is positioned nearby, offering a cozy option for relaxation. Large windows dressed in navy curtains provide a view of the outside, contributing to an open and inviting feel.

Flat in Jefferson Park

Entire 1st Floor Apt near O'Hare/ORD & Blue Line