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, 309 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.

Flat 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.

4.84 out of 5 average rating, 206 reviews

A colorful mural featuring a heart symbol is prominently displayed. The heart is surrounded by a sunburst pattern and flanked by vibrant decorative elements in various colors. The word 'PILSEN' is written across the heart in a bold font, emphasizing the community's identity.

Flat in Lower West Side

Downtown & UC Nearby · Transit at Your Door

•Steps from the Damen Pink Line •Minutes to downtown Chicago via car or train •Easy access to major expressways I‑290 and I‑55 •Near major attractions like the United Center/Chinatown/Greektown/UIC/ West Loops nightlife and the Medical District •Vibrant cultural neighborhood - experience Pilsen’s rich art scene and authentic local dining •Ceiling height approx. 6’3” - please keep in mind when reserving •Memory Foam mattress •Guests must be 25+, have a verified account, and positive reviews

4.9 out of 5 average rating, 150 reviews

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.

Flat in Lower West Side

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.

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.

4.82 out of 5 average rating, 301 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 (1 folds to couch), 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

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

4.91 out of 5 average rating, 298 reviews

A spacious living area features large windows allowing abundant natural light. Exposed Chicago brick adds character to the space, while hardwood floors extend throughout. A comfortable sectional sofa, a chic armchair, and a tasteful area rug create a welcoming atmosphere. A television and decorative furnishings are also visible.

Flat in West Town

✨Spacious Centrally Located West Loop Loft✨

✔ FREE Fitness classes at The Barre Code included ✔ FREE STREET PARKING - Msg for more info ✔ PETS ok w/ prior approval ✔ HUGE 1300 sq ft loft style, but walls go to the ceiling ✔ CLEAN & sanitized ✔ Cozy & bright ✔ FAMED, historic Chicago pink brick ✔ Soap & other toiletries included ✔ Bedrooms are in back & quiet ✔ Central Location: -Close to trains & bus -6-10 mins to popular neighborhoods & hot restaurants ⚠️Construction noted in older reviews was completed in Nov '24

4.92 out of 5 average rating, 104 reviews

A spacious living area features a mustard-colored sectional couch, accompanied by a small side table. Large windows allow natural light to fill the room, illuminating the modern decor. A flat-screen TV is mounted on the wall, and a cozy reading nook is visible through an open door.

Apartment in Grant Park

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because: -Central Location near public transit (no car needed!) -FAST WIFI -En-suite Laundry -Lake & Park are outside our front door -Comfy Queen beds -1 Closed & 1 Loft style bedroom -Shared Rooftop Deck with stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you're interested in booking, see our FAQs below.

4.88 out of 5 average rating, 338 reviews

A spacious living area features a stylish gray sofa and a large white coffee table at its center. Dark curtains frame the windows, allowing natural light to illuminate the space, which is adorned with arcade games and art on the walls.

Flat in Wicker Park

Logan Square Video Game Loft

Treat yourself to a unique stay in this hip video game themed studio. Enjoy the comfort of this large, bright space—and the games and artwork on display—during your trip. Explore the happening neighborhood scene in the Logan/Bucktown/Wicker Park area via the 606 walking trail (right outside the door) or walk two blocks to the Blue Line el stop for easy access to downtown or the airport. *Please be sure to review the Other Things to Note section as well as our house rules.

4.95 out of 5 average rating, 184 reviews

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.

Flat in Bridgeport

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)

4.91 out of 5 average rating, 209 reviews

An open studio layout features a spacious sleeping area with a bed dressed in soft linens. A plush couch and a rocking chair provide seating options. The concrete floor adds a modern touch, complemented by a decorative area rug. A kitchenette and dining area are visible in the background.

Flat in Chicago

Private, spacious studio close to Medical District

Fully equipped 900 sf garden apartment in owner occupied building. Private exterior entrance with smart lock. Open floor plan with large kitchen. Energy efficient, very clean and exceptionally comfortable with radiant floor heating. Free and plenty of street parking available. Easy access to Mt. Sinai (less than 1/2 mile) the Illinois Medical District (2 miles), and McCormick Place (5 miles). Ideal for medical students.

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.

4.96 out of 5 average rating, 144 reviews

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!

Popular amenities for Pilsen 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

4.91 out of 5 average rating, 399 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, 192 reviews

Home in North Park

The Chicago River House – City Escape Meets Nature

4.82 out of 5 average rating, 217 reviews

A cozy living area is displayed with a pair of beige sofas, accented by decorative pillows. Framed wall art complements the decor. A soft rug is positioned on the wooden floor, while a lampshade on a side table adds subtle illumination.

Home in Blue Island

Warm and comfortable inviting Suburban home !

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

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

4.91 out of 5 average rating, 175 reviews

A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.

Home in Chicago Ridge

Quiet cul-de-sac with huge fenced in backyard

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

Pet-friendly home rentals with a pool

Serviced apartment in River North

4.8 out of 5 average rating, 100 reviews

Level ◆ Brand New Luxe One Bedroom

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"

4.74 out of 5 average rating, 277 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

4.57 out of 5 average rating, 23 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

Flat in Printer's Row

South Loop | Rooftop With In & Out Parking

5 out of 5 average rating, 10 reviews

Home in Elmhurst

Elmhurst 4BR Home with Pool | Mid-Term Ready

Private, pet-friendly home rentals

4.74 out of 5 average rating, 348 reviews

An open living space is divided into areas for relaxation and sleeping. A large bed with soft linens is showcased next to a contemporary TV stand. A sectional sofa is positioned to create a cozy sitting area, complementing the natural light filtering through the curtains.

Flat in Bridgeport

Sunny 1BR Walk-Up Bridgeport | Easy Street Parking

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.

4.93 out of 5 average rating, 27 reviews

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.

Flat in Lower West Side

Duplex Luxury Apartment with King Suite

4.9 out of 5 average rating, 107 reviews

The living area features a comfortable sofa and a glass coffee table, complemented by a large TV. Natural light is allowed in through the expansive windows adorned with light curtains, while decorative items and a bookshelf add character to the room.

Guest suite in Woodlawn

PRIVATE 2-bedroom 1.5 bath w/ living room

4.99 out of 5 average rating, 376 reviews

The living area features a comfortable sofa, paired with two woven armchairs. A rustic wooden coffee table sits at the center, adorned with a vase of fresh flowers. Natural light illuminates the space through two large windows, framed by soft curtains.

Flat in Forest Park

Walk to Oak Park from Our Sunny Turn of the Century Apt

4.95 out of 5 average rating, 149 reviews

The living area features exposed brick walls and wooden beams, complemented by a gray sectional sofa and a dark blue armchair. A flat-screen television is mounted on the wall. A coffee table sits atop a patterned rug, and a workspace is located in the corner with a desk and lamp.

Flat in Bucktown

Garden Unit Getaway-Bucktown

4.97 out of 5 average rating, 149 reviews

A modern living area features a green sofa positioned in front of a glass coffee table on a patterned rug. An open kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light fills the space, enhancing its welcoming atmosphere.

Apartment in Uptown

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen