Apartment holiday rentals in Skokie

5 out of 5 average rating, 296 reviews

A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.

Flat in Lincoln Park

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

4.94 out of 5 average rating, 108 reviews

A modern living area features a grey sectional sofa and a light-colored armchair positioned around a soft area rug. Two windows allow natural light to enter, and wall art decorates the walls. Steps lead to an upper level, contributing to an open and inviting layout.

Flat in Avondale

Best Deal in Chicago | Great Food & Free Parking

Clean & modern Avondale apt close to Blue Line, perfect for urban explorers! Stylish decor, comfy bed, and a cozy ambiance await. Explore nearby cafes, bars, and boutiques, or hop on the train for downtown adventures. Easy to access & great neighborhood. Easy permit parking (free passes provided) on street allows for the ability to drive or take public transportation wherever you want to explore. Avondale has been voted one of the best neighborhoods in Chicago! Come see what the fuss is about.

4.96 out of 5 average rating, 103 reviews

The living room features a cozy seating arrangement with two dark chairs and a sofa, set around a central table. A decorative rug adds warmth to the wooden flooring. Natural light floods in through large windows, while a ceiling fan enhances airflow in the space.

Flat in Norwood Park

Spacious and Cozy 3BR Apt Near ORD / Metra

Welcome to our charming and cozy apartment. This apartment is designed to be your home away from home in Chicago. From the moment you step inside you will be captivated by the tasteful decor and attention to detail. The apartment is located in a great neighborhood close to public transit and highways. Also, you will find plenty of restaurants, cafes, shop, and entertainment options nearby. Our apartment offers a comfortable and inviting atmosphere perfect for your next vacation or business trip.

A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.

4.97 out of 5 average rating, 537 reviews

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

4.97 out of 5 average rating, 580 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

4.94 out of 5 average rating, 176 reviews

A spacious bed with patterned bedding rests against a geometric accent wall painted in dark blue and vibrant yellow. Two nightstands with lamps are positioned on either side, contributing to the cozy and modern aesthetic of the room.

Flat in Maywood

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

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.

4.98 out of 5 average rating, 114 reviews

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.

4.92 out of 5 average rating, 132 reviews

The open-concept living space features natural light streaming through skylights and a mix of wooden accents and plants. A comfortable green sofa and a chair are positioned along the walls, while a sliding barn door leads to the adjacent bedroom area.

Flat in Avondale

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

Cozy one bedroom attic apartment in Avondale located on top of a 3 story building. Close to Milwaukee, restaurants, and bars. A perfect crash pad for touristing in Chicago. You have your own entrance but since people in this building are working from home, and need to sleep at night, no loud music or partying is allowed at any time! But then, there is no need to bring the party home - you have everything you need just outside the door!

A charming two-story house features a yellow exterior with white trim and a covered porch. Hanging plants adorn the porch, while lush greenery and well-kept landscaping surround the property. A pathway leads to the front steps, framed by stone accents and garden plants.

4.98 out of 5 average rating, 134 reviews

Charming one bedroom apartment

Downtown Evanston. Cozy quiet area. Lovely studio 1-bedroom apartment. Ideal for a couple or business travelers. One queen size bed. TV & WiFi, microwave, AC & dishwasher. Free off-street parking. Close walk to Northwestern U, Lake Michigan, several supermarkets & many restaurants. Minutes to Metra, Davis & Dempster CTA stations. About 40 minutes to downtown Chicago on CTA Purple Express & less time on Metra. Non-smoking.

4.89 out of 5 average rating, 697 reviews

A spacious living area is visible, featuring a comfortable seating arrangement with two sofas and a round coffee table. A large television is positioned on a stand across from the seating. The kitchen area, accessible through an open entry, showcases modern appliances and dining seating.

Flat in Skokie

Cozy Garden Unit in Quiet Neighborhood

A cozy garden unit in the heart of skokie, off of a quiet residential street with plenty of street parking. Just a mile away from the Skokie-Dempster Yellow line train that leads to downtown Chicago, and within a mile from Old Orchard Mall and plenty of great eateries such as: Chick-fil-A, Portillo's, Culver's, Oberwies, Kaufman's Bagel, and more. 15 minutes away from Evanston and the Beautiful Lake Michigan shoreline!

4.95 out of 5 average rating, 114 reviews

A modern living area features a comfortable sofa adorned with patterned cushions and a golden throw. A wooden coffee table sits in front, complemented by a minimalistic television stand. Light from a floor lamp brightens the space, while potted plants add a touch of greenery.

Flat in Albany Park

Bright Apartment

Relax in this sunny one-bedroom garden apartment in Albany Park (Not recommended for taller than 6'3"). Our apartment is perfectly located between downtown Chicago & O'Hare airport. You can go just about anywhere in the city in about 20-30 min as we are 5 minutes away from the Montrose blue line train stop, Kimball brown line train stop, and the I90/94 interstate. Please note, some areas have lower soffit ceilings.

A charming two-story house is set amidst lush greenery, featuring a welcoming porch and large windows. A newly planted tree and well-maintained lawn enhance the inviting outdoor space, while the textured siding adds character to the home.

4.96 out of 5 average rating, 102 reviews

Cozy Apartment Near Shops + Train

Cozy & warm space to rest & retreat. High-end bedding and pillows, supema cotton sheets on the adjustable SleepNumber Bed. Cozy robes and blankets provided. Totally private space from the rest of the house. Keyless entry for your convenience. Free street parking available with passes provided. Nice hosts that know the area. :)

Popular amenities for Skokie apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

5 out of 5 average rating, 80 reviews

A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.

Flat in Chicago

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

4.89 out of 5 average rating, 81 reviews

A well-lit bedroom is furnished with a spacious bed draped in crisp white linens. Two windows provide natural light, and a small desk with a black chair is positioned against one wall. Art pieces add a touch of character to the neutral-toned space.

Flat in Skokie

Charming 2 bed/1 bath apt- walk 2 train/store/rest

4.9 out of 5 average rating, 438 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

4.92 out of 5 average rating, 48 reviews

A green door with two circular brass handles and a sign reading 'THE SHOP' is set against a vibrant blue brick wall. The wall showcases its texture with a smooth finish. An electrical outlet is visible to the left of the door.

Flat in Wilmette

The Shop - Trendy Studio in the heart of Wilmette

4.84 out of 5 average rating, 61 reviews

A cozy living room features a light-colored sofa and an accent chair with a geometric pattern. A round wooden coffee table is placed in the center, surrounded by a textured area rug. Natural light flows through the large windows, softly illuminating the space.

Flat in Chicago

cozy grand studio 2nd floor/near lake/public tran.

4.87 out of 5 average rating, 563 reviews

A cozy studio apartment features a comfortable bed with a bright yellow coverlet, positioned next to two windows with sheer coverings. A wooden dresser and a minimalist side table with a lamp are present. A patterned area rug adds texture to the warm-toned wood floor.

Flat in Logan Square

Logan Square Studio

4.94 out of 5 average rating, 209 reviews

A dining area features a round white table surrounded by four yellow chairs, complemented by a blue artwork on the wall. The open living space in the background contains comfortable seating and a large blue canvas art piece, with natural light filtering through the windows.

Flat in Lake View

Quirky Quarters at Wrigley

4.95 out of 5 average rating, 244 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

Private apartment rentals

5 out of 5 average rating, 4 reviews

A comfortable living area features a light gray sectional sofa arranged around a low wooden coffee table. A rug adds texture to the hardwood floor. Nearby, a workspace with a desk is present, along with a TV mounted on the wall, offering a functional and inviting space.

Flat in Skokie

30-Night Minimum Stay 3BR 1.5 Bath 2 Car Parking

4.85 out of 5 average rating, 438 reviews

A small entryway is illuminated by soft natural light filtering through a lace curtain. A vase of white roses sits atop a white table, with a radiator located below it. Beige walls with a minimalist aesthetic offer a warm welcome.

Flat in Edgewater

Cozy Garden Unit In Edgewater

4.77 out of 5 average rating, 30 reviews

A cozy living area features a black futon and a wooden chest of drawers. A large flat-screen TV is mounted on the wall, providing entertainment options. Natural light enters through a small window, complemented by a decorative indoor plant placed nearby.

Flat in Jefferson Park

Updated in May 2025 • Private Floor • Free Parking

4.93 out of 5 average rating, 465 reviews

A cozy bedroom is depicted with a spacious bed featuring white linens. On either side, elegant lamps provide soft lighting. A colorful artwork adorns the wall above the bed, and framed art pieces are visible on the nearby walls, contributing to the room's inviting feel.

Flat in Edgewater

Andersonville Living

4.94 out of 5 average rating, 105 reviews

A spacious living area is highlighted by a light-colored sofa adorned with various cushions. A round coffee table sits in front, complemented by a cozy armchair. The open kitchen is visible in the background, featuring modern appliances and a warm wood finish.

Flat in Edgewater Glen

1-Bedroom Apt by Andersonville & Lakefront

4.93 out of 5 average rating, 83 reviews

A charming garden unit is situated within a light-colored, two-story building, framed by a white picket fence. The entrance is marked by a set of steps leading to a spacious porch, where seating may be present. Nearby trees and greenery accentuate the inviting exterior.

Flat in Albany Park

Montrose Gardens

4.92 out of 5 average rating, 116 reviews

A comfortable living area features a light gray sofa adorned with colorful pillows. A small wooden coffee table with intricate designs sits in front of the sofa, accompanied by a floral arrangement. Art pieces hang on the walls, and natural light enters through the large window.

Flat in Forest Park

Cheerful Remodel Prime Location

4.85 out of 5 average rating, 130 reviews

A spacious sleeping area features a large bed topped with neutral-toned linens and decorative pillows. Two bedside lamps provide soft lighting beside nightstands. A plush rug adds warmth to the floor, and a comfortable chair is positioned in the corner under a world map wall decor.

Flat in East Rogers Park

Parking & In-Unit Laundry & Now a King Bed!

Apartment rentals with a hot tub

4.92 out of 5 average rating, 74 reviews

An indoor pool area is featured, highlighting a clean, rectangular swimming pool surrounded by large windows. Lounge chairs are positioned along one side, offering a place to relax. The space is bright with neutral-colored walls and a minimalist design.

Flat in South Loop

The Aerial Oasis (Indoor Pool • Fitness Center)

5 out of 5 average rating, 10 reviews

Flat in Grant Park

60th Flr Lake Views, A Stay Above It All, Sleeps 5

4.97 out of 5 average rating, 34 reviews

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

Flat in Fulton Market

Skyline Oasis: City & Lake Views

4.6 out of 5 average rating, 25 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

5 out of 5 average rating, 6 reviews

A spacious living area is characterized by large, comfortable leather sofas arranged around a glass coffee table. A modern entertainment center with a television is visible, showcasing a serene beach scene. The room features hardwood floors and abundant natural light from windows.

Flat in West Town

Modern 4BR West Town Duplex | Best for LongStays

4.96 out of 5 average rating, 46 reviews

A decorative lantern with a warm, flickering candle sits on a wooden table in the foreground. In the background, a black sofa is paired with light-colored throw pillows, while framed black-and-white photographs adorn the walls. Soft lighting from hanging fixtures creates a cozy ambiance.

Flat in Wicker Park

Chic 1 BR in Wicker Parl|1 FREE Garage Parking

4.95 out of 5 average rating, 155 reviews

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Flat in Dunning

Belmont Pleasures - hot tub / arcade gaming room