Pet-friendly holiday rentals in East Rogers Park

4.97 out of 5 average rating, 116 reviews

A cozy living space features a vibrant orange sofa complemented by decorative throw pillows. A dining area with a small table stands beside a fully equipped kitchen. Artwork adorns the walls, while natural light streams through windows, enhancing the inviting atmosphere.

Apartment in Lake View

Chic & Comfy • Close to Wrigley

Welcome to your comfy, cozy, cheerful hideaway in the beautiful Buena Park!☀️ Buena Park is a little-known gem. Our home is just blocks from the lakefront (4 blocks), Wrigley (6 blocks), and the major L-line in Chicago (1 block)...yet, you'd never know it given how peaceful and serene it is! We live here part-time, so rest assured you'll have everything you need for a comfortable and enjoyable stay. We ask you please respect our place, and that you enjoy the trinkets + personal items we have!

4.99 out of 5 average rating, 153 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.

Flat in Edgewater

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

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, 341 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!

4.89 out of 5 average rating, 199 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.

Flat 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.

4.97 out of 5 average rating, 575 reviews

The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.

Flat in Noble Square

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Apartment in East Rogers Park

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

4.93 out of 5 average rating, 274 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed, TV, dining table, & partial kitchenette. NOTE: No full kitchen.

4.83 out of 5 average rating, 174 reviews

A spacious living area showcases a light-colored sectional sofa paired with two vibrant blue accent chairs. A round glass coffee table sits at the center, complemented by a light rug. The open kitchen features dark cabinetry and modern appliances, enhancing the contemporary design.

Apartment in Chicago

Rogers Park Stay Near Loyola, Transit w/ Parking

Our 3 bedroom and 2 bathroom condo has a perfect open layout for any size group that is traveling together. You'll have a ton of open space to share and feel at home, while also choosing from 3 bedrooms to get some privacy as well. Each bedroom has a queen size bed, while the master bedroom also has its own full size private bathroom. Feel free to stay in and cook with our fully equipped kitchen, enjoy the 65 inch Roku TV, and gather around the very large island.

4.95 out of 5 average rating, 111 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, 113 reviews

The exterior of a three-unit building features a blend of brick and stone elements, with large windows providing ample natural light. A well-maintained lawn includes shrubs and small trees, complemented by a walkway leading to a blue door beneath a covered entryway.

Flat in Evanston

3 BR Evanston Apt near Chicago

3 Miles to Northwestern and 2.5 to Loyola Universities. Enjoy local shopping, entertainment & restaurants in Evanston. Walk, bike or drive to Lake Michigan's beautiful beaches. CTA to Chicago nearby. Two BRs with king beds and a third BR with a full. LR has turntable, records, Netflix, Max, Disney+, Hulu... Enjoy a ping pong table and puzzles. Work space in two bedrooms. Kitchen has a stove, oven, microwave, coffee maker, and toaster. Free off-street parking.

4.98 out of 5 average rating, 116 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, 157 reviews

A spacious living area is adorned with floral wallpaper, featuring a comfortable gray sofa and a wooden coffee table. Two white chairs are positioned around a woven rug. An open kitchen area is visible, equipped with modern appliances and green bar stools at the counter.

Flat in Andersonville

Andersonville's Secret Garden: 2 beds, 1 bath

This serene retreat is tucked away amongst the tree-lined streets of the Lakewood Balmoral historic district. Guests can venture just two blocks to dive into the hustle and bustle of Andersonville, with its incredible food scene and unique local shopping spots. Those looking to explore all that Chicago has to offer will enjoy easy access to the CTA redline, major bus routes, and Divvy stations (our shared bike provider).

4.94 out of 5 average rating, 118 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

Cozy Rogers Park 2 Bedroom Flat

Welcome to our beautiful neighborhood in East Rogers Park! Enjoy serene tree-lined streets of classic brick Chicago homes, and easy access to many restaurants, coffee shops, public transit, and gorgeous Lake Michigan beaches! This is a safe and friendly neighborhood, the perfect place to get a coffee and take a walk. We are just a few blocks from the Loyola Redline “L” stop, with service to all Chicago has to offer.

Popular amenities for East Rogers Park pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.98 out of 5 average rating, 116 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

4.96 out of 5 average rating, 192 reviews

Home in North Park

The Chicago River House – City Escape Meets Nature

4.98 out of 5 average rating, 183 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

4.97 out of 5 average rating, 132 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

4.96 out of 5 average rating, 163 reviews

An open-concept living space features exposed wood beams and large windows allowing natural light to flood in. Comfortable seating is provided by a large sectional and cozy couches, while a vibrant rug adds warmth. A rustic green table sits in the center, enhancing the inviting atmosphere.

Home in Logan Square

The Grand Kimball Lodge, Logan Square, Sleeps 14

4.93 out of 5 average rating, 123 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, 158 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

4.82 out of 5 average rating, 262 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

Pet-friendly home rentals with a pool

4.77 out of 5 average rating, 240 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.

Flat in The Loop

Stylish Corner 2 Bedroom in the Heart of Chicago |

4.9 out of 5 average rating, 48 reviews

Flat in The Loop

Prime Downtown 2BR with Resort Amenities

The living area features two gray sofas arranged around a glass coffee table on a patterned rug. A flat-screen TV is placed on a stand, and a well-equipped kitchenette is visible in the background. Soft lighting is provided by floor lamps and overhead fixtures.

Flat in Humboldt Park

4.66 out of 5 average rating, 128 reviews

Play in the Windy City and rest by the “606”

5 out of 5 average rating, 17 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"

4.88 out of 5 average rating, 89 reviews

A spacious living area is highlighted by a plush blue sectional sofa adorned with yellow and patterned throw pillows. Natural light filters through a large window, revealing a view of the city. A wooden coffee table is centered on a colorful area rug, accompanied by contemporary decor.

Flat in Printer's Row

DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool

Flat in Printer's Row

South Loop | Rooftop With In & Out Parking

4.92 out of 5 average rating, 13 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.

Flat in South Loop

Modern 2BR South Loop Apt, McCormick & Wintrust

5 out of 5 average rating, 10 reviews

Home in Elmhurst

Elmhurst 4BR Home with Pool | Mid-Term Ready

Private, pet-friendly home rentals

4.81 out of 5 average rating, 114 reviews

A well-lit bedroom features a spacious bed with neatly arranged towels. A small desk and chair are positioned against the wall. Two framed artworks hang above the bed, and natural light enters through the window, which is fitted with sheer blinds.

Flat in Humboldt Park

Chic 2BR in Logan Square

Apartment in Wrigleyville

The image showcases a residential building with multiple stories and a set of wooden stairs leading to the entrance. A fenced outdoor area includes a picnic table and a grill, offering a space for gatherings. A parking structure is located in the background.

4.79 out of 5 average rating, 243 reviews

Wrigley Residence in Iconic Wrigley Rooftop

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, 456 reviews

Peaceful Portage Park Apartment

4.9 out of 5 average rating, 431 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

4.95 out of 5 average rating, 223 reviews

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.

Flat in Roscoe Village

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

4.94 out of 5 average rating, 144 reviews

A two-flat brick building is set in a green and landscaped area, featuring large windows that allow natural light inside. A set of stairs leads up to the main entrance, which is flanked by plants and outdoor greenery.

Flat in Lincoln Square

Beautiful, sunny 2nd floor 3BR/1BA w free parking

4.95 out of 5 average rating, 243 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