Pet-friendly holiday rentals in Pilsen

4.95 out of 5 average rating, 157 reviews

An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.

Home in Bridgeport

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

4.98 out of 5 average rating, 316 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

A newly updated 1 bedroom, 1 bathroom apartment in Chicago's historic Ukrainian Village. Located a few blocks from Wicker Park, Ukrainian Village is a small historic district of Chicago filled with historic architecture. Access the apartment via a smart lock, the apartment includes everything you need for a comfortable stay, including a queen-sized bed, full kitchen, fiber high-speed internet (100+ Gbps up and down), smart TV, modern bathroom, in-unit washer & dryer, and free garage parking.

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, 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.

Apartment in Lower West Side

An open-concept living area features modern wood cabinetry and stainless steel appliances in the kitchen, with a spacious sectional couch facing a large flat-screen TV. Soft beige curtains allow natural light to fill the room, highlighting the warm wood flooring.

4.91 out of 5 average rating, 159 reviews

Unmatched Urban Retreat Close to 18th Strip & Loop

This stylish Airbnb in the very popular Pilsen neighborhood is perfect for small and large travel groups. There are 2 bedrooms with queen size beds, and the couch folds out for an additional sleeping area. The 2 full bathrooms will have everything you need to get ready to hit the town. The tall ceilings make this space for larger than life, and the unique décor gives this Airbnb a great urban feel. The fully equipped kitchen and updated appliances are perfect for those quiet nights in.

Apartment in Noble Square

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.

4.97 out of 5 average rating, 582 reviews

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 Near North Side

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

4.81 out of 5 average rating, 947 reviews

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest suite in McKinley Park

A cozy kitchen area features light blue cabinetry and essential appliances, including a microwave. A dining table is set for four, with white bowls arranged neatly. The space is illuminated by natural light, revealing a warm atmosphere complemented by a patterned rug.

4.81 out of 5 average rating, 306 reviews

Vintage Suite Home Chicago by Sox/Park/Transit

Walkout basement studio in a ca.1890 home built for laborers in the Chicago Stockyards - Please read entire listing before booking. This quiet, tree-lined neighborhood is a respite from city buzz. Get downtown in 4 stops by train or any of 5 nearby buses. Your space has great natural light, 2 comfy beds, private bath, flexible work/dining area, super-fast WiFi, and kitchen with all the essentials. Private entry via back door Free street parking Se habla español

A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.

4.93 out of 5 average rating, 198 reviews

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

4.93 out of 5 average rating, 244 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.

Apartment 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.

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, 127 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.

4.96 out of 5 average rating, 262 reviews

An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.

Condo in Fulton Market

Designer Loft in Fulton Market with Parking

Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.

Popular amenities for Pilsen pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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, 183 reviews

Historic Old Town, Fabulous 4 Bedroom Home

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

Spacious 5-Bedroom Retreat in Forest Park

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

An inviting outdoor patio area features sleek white furniture, including a curved sofa and a coffee table atop a striped rug. A hammock is suspended nearby, surrounded by lush greenery and a wooden fence, with the warm glow of lights illuminating the space.

Home in North Park

The Chicago River House – GIANT wall projector!

4.75 out of 5 average rating, 141 reviews

A four-story brick house with a peaked roof is highlighted. The entrance features a set of stairs leading up to a glass door, framed by large windows on the lower floors. A manicured hedge runs along the front of the property, with a gentle pathway visible beside the structure.

Home in Bridgeport

Chicago's Bridgeport Huge 4 Story w/Garage Parking

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

4.82 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

4.99 out of 5 average rating, 148 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

Pet-friendly home rentals with a pool

4.77 out of 5 average rating, 123 reviews

Apartment in River North

Level ◆ Brand New Luxe One Bedroom

Apartment in Magnificent Mile

4.82 out of 5 average rating, 65 reviews

Luxury Designer Penthouse 3801 | 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.

4.92 out of 5 average rating, 101 reviews

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

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.

4.62 out of 5 average rating, 29 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

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!

5 out of 5 average rating, 12 reviews

Home in Elmhurst

Elmhurst 4BR Home with Pool | Mid-Term Ready

Private, pet-friendly home rentals

Apartment in Noble Square

A modern living area is shown featuring a light-colored sectional sofa and a wall-mounted television. Natural light enters through large windows, and a small indoor plant adds a touch of greenery. A low coffee table sits in front of the seating area, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 112 reviews

Wicker Park Walk-Up Condo

An inviting living area features a spacious couch and a clear view of natural light pouring in from large windows. A dining area with a table complements the minimalist decor. The bedroom displays a cozy queen bed, with neutral tones adding to the calming environment.

4.94 out of 5 average rating, 52 reviews

2 queen BR- Cozy unit near Sox stadium, Chinatown

The living area features an original tile floor complemented by green tin walls and ceiling. A brown leather sofa is positioned alongside wooden armchairs, and a circular coffee table occupies the center. A large mirror reflects light from the windows, enhancing the space's openness.

5 out of 5 average rating, 45 reviews

Al Capone Era Speakeasy 3 BRs

4.74 out of 5 average rating, 353 reviews

Sunny 1BR Walk-Up Bridgeport | Easy Street Parking

Guest suite in Portage Park

A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.

4.95 out of 5 average rating, 152 reviews

Eddy Street Upstairs Apartment

Apartment in Lower West Side

The spacious living area features a light-colored sofa with decorative cushions, accompanied by two wooden side tables. Natural light enters through large windows, highlighting the connected dining area with a wooden table suitable for four guests. A contemporary artwork piece adorns the wall.

4.9 out of 5 average rating, 31 reviews

Duplex Luxury Apartment with King Suite

Apartment in Little Village

4.95 out of 5 average rating, 56 reviews

Easy Downtown Access from Cozy Pilsen Nest