Pet-friendly holiday rentals in Wrigleyville

4.95 out of 5 average rating, 237 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

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

4.98 out of 5 average rating, 228 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

4.77 out of 5 average rating, 243 reviews

Cozy Bedroom in Wrigleyville (Entire Apt)

You can’t beat this location! Right in the middle of Boystown and steps from Wrigley Field, you’ll be surrounded by some of the city’s best bars, restaurants, and nightlife. Cubs Stadium is just one block away, and the Addison Red Line station is a quick 5-minute walk, making it easy to explore all of Chicago. No shared space: Due to updated COVID-19 policies, this unit is now 100% private. Once you book, the entire place is yours and the additional listing will be blocked immediately.

A spacious dining area features a wooden table surrounded by black metal chairs. Natural light filters through large windows, illuminating a welcoming living space visible in the background with comfortable seating and light-colored decor.

4.86 out of 5 average rating, 333 reviews

Comfy/Elegant Home by Wrigley, Garage Spot & Yard

This chiq duplex home near Wrigley Field is a hidden gem. It features 6 beds, a garage parking spot; and a fenced yard; with 5 bedrooms, 3 baths, a spacious living & dining area and fast gigabit internet. In an unbeatable location close to many popular attractions, this home is the perfect base for your Chicago adventures. 6 min drive to: -Wrigleville -Andersonville & Boystown -Montrose Beach -Uptown, Green Mill, Riviera / Aragon Theaters 15-20 min drive: Cloudgate, Downtown, Loop!

An inviting living space features large windows allowing natural light, framed by exposed brick walls. A round dining table is surrounded by modern chairs, while a comfortable sectional sofa is positioned near a cozy fireplace, enhancing the warm ambience. Stylish decor elements add character to the room.

4.97 out of 5 average rating, 251 reviews

Modern vintage chic steps from Wrigley: park free

Vintage touches and modern updates in the heart of Wrigleyville! Includes off street parking. Close enough to see Wrigley Field from the building, yet the block is charming and quiet. Close to the lake and Boystown. Charming vintage DNA meets modern amenities. Large deck. You will love the exposed brick and original millwork while enjoying huge new windows, an open floor plan, chef's kitchen, stylish decor, and spa like bathroom. Chicago Shared Housing Registration: R22000093584

An elegant stone entrance is framed by lush green ivy, leading to a wooden door beneath a decorative awning. A charming fountain, featuring three tiers, adds a serene element to the outdoor area, surrounded by abundant foliage and creating a peaceful environment.

4.99 out of 5 average rating, 140 reviews

CASA NEWPORT

Second floor, one bedroom apartment, with an additional queen pullout couch located in a beautiful historic district in Lakeview. Just steps away from Halsted street/Boystown/Wrigley field. Conveniently located to shopping, restaurants, subway (EL) and grocery stores. Close to lakefront, jogging path and bike path. Complementary street parking passes available. The apartment does NOT have airconditioning. It does have a window unit in the bedroom from April to September.

4.97 out of 5 average rating, 159 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

Welcome to our charming home in the peaceful yet centrally located Buena Park neighborhood, housed in an updated antique building. This prime location offers easy access to the Red and Purple train lines, as well as multiple bus routes, making it easy to explore Chicago. You’ll be within walking distance of Wrigley Field, Clark St. bars, Montrose Beach, Lakeview, Boystown, and the iconic Green Mill. A perfect blend of quiet comfort and proximity to Chicago’s best attractions.

Apartment in Wrigleyville

The living area features a mix of modern and industrial design, with exposed brick walls and hardwood flooring. A cozy sectional sofa, accented by colorful pillows, complements a stylish area rug. A kitchen area with dark cabinetry and stainless-steel appliances is visible in the background.

4.8 out of 5 average rating, 264 reviews

Can't Beat This 2min Walk to Wrigley!

My home is a half block from Wrigley Field. You can be to the ballpark in 2 minutes (or Murphy's)! Enjoy your pregame afternoon feeling the buzz of the neighborhood from the private deck. Room for 6 to sleep comfortably in a Queen, 1 Twin plus a Twin over Full Bunk Bed and a Murphy Bed. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea! I have extensive information for you - let's chat!

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.

4.93 out of 5 average rating, 247 reviews

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.

4.93 out of 5 average rating, 260 reviews

A bright living area features large sliding glass doors that open to a balcony. Two elegant chairs and a cozy couch are arranged around a coffee table. Greenery adds a fresh touch to the space, with softly colored walls creating a calming ambiance.

Flat in Uptown

Designer 3br with Balcony & Elevator on Clark!

My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago - You'll love the neighborhood - its vibrant food and arts scene is uniquely diverse in Chicago. A mile north of Wrigley Field - Just to the east, Montrose Beach is a nice break from the city - if work is what brings to you to town, the nearby Brown line will take you right to the Loop. I provide all the essentials to make your stay easy and comfortable.

4.83 out of 5 average rating, 124 reviews

Wrigley Oasis! Steps from the Field! - 3BR/1BA!

Sports fans' dream! Family Friendly comfort! Just steps away from Wrigley Field, this 3BR/1BA fully furnished apartment is the place to stay to experience all Wrigleyville has to offer. Close to the Red Line train and multiple bus stops, you can quickly and easily visit all the Chicago attractions. This gorgeous 2 flat is located on a quiet residential street. Temporary street parking permits will be provided when requested.

A welcoming hallway features dark hardwood floors and gray walls adorned with art. A cozy seating area includes light-colored sofas facing a wooden coffee table. A colorful area rug with a sports theme adds vibrancy, while laundry machines are discreetly integrated into the cabinetry.

4.92 out of 5 average rating, 387 reviews

The Clubhouse Wrigleyville

Beautifully remodeled apartment steps from Wrigley Field and bars. Half block from the field and One block away from the Wrigleyville night life. The apartment is right next to all the action but just far enough for a quiet night sleep. You will be pleasantly surprised how quiet my block is one hour after the game ends. Walking distance to the beach and a block from the red line.

Popular amenities for Wrigleyville 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

4.94 out of 5 average rating, 131 reviews

An open-concept dining and kitchen area is featured, with a long wooden table accompanied by several chairs. A spacious kitchen island with seating sits nearby, and a warm wooden floor enhances the inviting space. Natural light fills the room, highlighting the exposed brick wall.

Home in Lake View

Spacious Full Home Near the Heart of Wrigleyville

4.9 out of 5 average rating, 211 reviews

An open and airy living space is highlighted by high ceilings and vibrant red beams. Large windows allow natural light to fill the room, complemented by palm tree decor and ceiling fans. The minimalist furniture invites relaxation in a colorful and modern setting.

Home in Wicker Park

ALOHA Tropical Penthouse in Wicker Park Sleeps 14

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

4.83 out of 5 average rating, 152 reviews

A spacious living area features a dark sectional sofa adorned with yellow accent pillows, complemented by a cozy throw blanket. A circular mirror hangs above a standing lamp, while decorative wall art adds visual interest. A dining table with chairs is situated in the background.

Home in Oak Park

Urban Chic 3beds w/2bath + free parking & W/D

4.96 out of 5 average rating, 197 reviews

Home in North Park

The Chicago River House – GIANT wall projector!

4.98 out of 5 average rating, 165 reviews

A stylish living room features a glass coffee table atop a textured rug, surrounded by two orange, velvet armchairs and a plush, patterned sofa. A decorative fireplace is framed by elegant vases, with a mirror reflecting natural light from the windows.

Home in Wicker Park

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

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

Pet-friendly home rentals with a pool

4.79 out of 5 average rating, 132 reviews

Flat in River North

Level ◆ Brand New Luxe One Bedroom

4.76 out of 5 average rating, 247 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 |

4.82 out of 5 average rating, 50 reviews

A modern living area is displayed, featuring large windows that provide city views. A gray sectional sofa complements a circular coffee table on a light area rug. A wall-mounted flat-screen television is present, alongside a cleanly designed console. A spacious bed is visible in the background.

Flat in Fulton Market

Level Junior Two Bedroom Suite | Fulton Market

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, 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"

4.67 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.

Flat in West Loop

Two 2BR Apts for Business & Leisure Groups

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

4.95 out of 5 average rating, 413 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 Ravenswood

Bright family-friendly Lincoln Square 2-bed 1-bath

The living space features exposed brick walls that blend with modern kitchen elements. A spacious light-colored couch is arranged around a round black coffee table on a patterned area rug. A wall-mounted TV is visible, alongside sleek kitchen appliances, enhancing the contemporary design.

5 out of 5 average rating, 47 reviews

Full Luxury Home in Wrigleyville

5 out of 5 average rating, 6 reviews

Deco Luxe Retreat 3BR • Steps to Wrigley + Garage

5 out of 5 average rating, 7 reviews

Shorter Walk To Wrigley Than A Home Run

A spacious living area is presented with a mix of seating options, including a green sofa and a neutral couch adorned with colorful throw pillows. A patterned rug covers the floor under a coffee table, and a staircase leads to an upper level, enhancing the open layout.

4.9 out of 5 average rating, 30 reviews

*Best of Northalsted*

A bright living area features large windows allowing natural light to fill the space. A brick fireplace serves as a focal point, complemented by framed artwork depicting cacti. Comfortable chairs and a wooden coffee table are arranged on a patterned rug, with a potted plant adding a touch of greenery.

4.96 out of 5 average rating, 67 reviews

Wrigleyville Oasis with Huge Garage

Apartment in Noble Square

A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.

4.97 out of 5 average rating, 874 reviews

Great location. Free parking.

The facade of a historic three-story building is featured, displaying light-colored stone with decorative trim and large windows. A set of wooden stairs leads to the entrance, framed by a wrought iron fence and small landscaping, showcasing a blend of classic and modern architecture.