Pet-friendly holiday rentals in Lake View

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, 237 reviews

Modern vintage chic steps from Wrigley Field!

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. The vintage DNA is beautifully respected while updates provide the modern amenities you expect when traveling. 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.

4.98 out of 5 average rating, 110 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!

4.86 out of 5 average rating, 104 reviews

Lakeview / Lincoln Park Vintage

A fully-furnished and updated Vintage apartment located on the 1st floor of a 2 flat w/ rear yard, BBQ & outdoor dining table . Nestled in Chicago's iconic Lakeview/Lincoln Park, which is a perfect jumping off point to anywhere in the city. We are 2-1/2 blocks from the CTA brown line, a mile from 90/94, and a very walkable mile from Wrigley Field. The neighborhood is full of great restaurants and bars all within walking distance. Don't leave your furry friends at home, we are pet friendly!

4.98 out of 5 average rating, 180 reviews

The bedroom is designed with a spacious bed centered against an accent wall featuring geometric patterns. A plush bench is positioned at the foot of the bed. Warm lighting illuminates the room, complemented by rich curtains and wooden flooring.

Flat in Magnificent Mile

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

4.95 out of 5 average rating, 212 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!

4.99 out of 5 average rating, 137 reviews

A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.

Flat in Lincoln Park

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.

4.99 out of 5 average rating, 210 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

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

4.83 out of 5 average rating, 842 reviews

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.

Flat in Near North Side

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.

4.96 out of 5 average rating, 324 reviews

A modern gray sofa sits against a light-colored wall, complemented by a tasteful pillow. Next to it, a clear glass coffee table rests on warm wooden flooring. A dining area is visible in the background, featuring metal chairs and a round table, with natural light filtering through the windows.

Flat in Roscoe Village

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

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, 136 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.

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, 236 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.

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, 844 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Popular amenities for Lake View pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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

4.96 out of 5 average rating, 188 reviews

A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

Home in North Park

Chicago River House -BBQ Oasis now open!

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

4.98 out of 5 average rating, 172 reviews

A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.

Home in Berwyn

Retro Modern Bungalow | fire pit | free parking

4.97 out of 5 average rating, 127 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

4.94 out of 5 average rating, 116 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, 153 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

4.97 out of 5 average rating, 102 reviews

The spacious family room features a high vaulted ceiling with exposed wooden beams. A stone fireplace provides a central focal point, and a large TV is mounted above it. Comfortable seating is arranged for relaxation, complemented by a stylish area rug.

Home in Des Plaines

NEW~2 Spa Baths~Game Room~Prime Area~Big Yard~

Pet-friendly home rentals with a pool

4.89 out of 5 average rating, 66 reviews

A spacious living area features a large sectional sofa set around a modern coffee table with a textured surface. Natural light floods in through large windows, illuminating a neutral color palette. Decorative plants and stylish furniture pieces enhance the contemporary design.

Flat in Printer's Row

Downtown Penthouse Lake Views #1|Gym, Parking+Pool

4.84 out of 5 average rating, 25 reviews

A modern kitchen with dark wood cabinetry and granite countertops is complemented by stainless steel appliances. A large island with seating for six is positioned next to a dining area featuring a round table for four. Views of the lake are visible through the windows.

Flat in Magnificent Mile

Luxury Designer Penthouse NW | Pool | Gold Coast

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

4.68 out of 5 average rating, 127 reviews

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

A well-lit bedroom features two spacious beds adorned with crisp white linens and neatly arranged towels. The walls are decorated with vibrant artwork and blue LED lighting, creating a modern and cheerful ambiance. A large window provides views and natural light.

Flat in Uptown

4.63 out of 5 average rating, 19 reviews

Resort Style Flat Central to All

5 out of 5 average rating, 16 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"

4.63 out of 5 average rating, 51 reviews

An indoor pool area is framed by tall windows, allowing natural light to fill the space. Elegant seating arrangements are situated around the pool, complemented by lush vertical greenery hanging from above. Soft lighting creates a serene environment for relaxation.

Flat in Grant Park

Sentral 1 Bedroom Apt in South Loop Chicago

4.81 out of 5 average rating, 48 reviews

The exterior of a charming cottage is showcased, featuring a sleek dark grey facade. A series of stairs lead up to the entrance, flanked by a decorative black railing. Lush greenery surrounds the base, enhancing the inviting appeal of the home.

Flat in Bridgeport

Modern unit in Bridgeport-Chicago

4.88 out of 5 average rating, 8 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

Private, pet-friendly home rentals

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, 33 reviews

Full Luxury Home in Wrigleyville

4.89 out of 5 average rating, 36 reviews

A living area features large bay windows providing natural light and views of the cityscape. A modern gray sofa and two green chairs complement a geometric area rug. A glass coffee table sits in the center, while a flat-screen TV is mounted on the wall.

Flat in North Side

Centrally Located Apartment in Lincoln Park

A cozy sleeping area features a queen bed with white bedding and a decorative dark throw. Beside the bed, a small table with a lamp and a potted plant is visible. A green sofa is positioned opposite, with decorative cushions adding a pop of color.

4.7 out of 5 average rating, 23 reviews

Lush Studio Apartment

4.87 out of 5 average rating, 31 reviews

Fully Equipped 1BR Near Sights

Guest house in Lincoln Park

A cozy living area features a light grey sofa paired with a dark coffee table on a soft area rug. Light wood flooring complements the space, and a well-equipped kitchen is visible in the background, showcasing modern appliances and cabinetry. Natural light illuminates the area.

4.8 out of 5 average rating, 15 reviews

1BR/1.5BA Coach House w/Garage

4.96 out of 5 average rating, 71 reviews

The kitchen features dark walnut cabinets and granite countertops, highlighted by under-cabinet lighting. High-end stainless steel appliances, including a refrigerator and range, are prominently displayed. A dining area is visible with a wooden table and chairs, enhancing the space's functionality.

Apartment in Lake View

Lakeview Luxury Condo

4.95 out of 5 average rating, 60 reviews

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.

Flat in Wrigleyville

Wrigleyville Oasis with Huge Garage