Apartment holiday rentals in Chicago

4.92 out of 5 average rating, 189 reviews

Apartment in Uptown

Vibrant, Sunny & Spacious 2 bd 1 ba Uptown Condo

Welcome to your home away from home in Uptown! My bright and inviting condo offers a perfect blend of comfort and convenience, with your own sunny living room to relax, fully-equipped kitchen and formal dining room, spacious private bedroom, serene sunroom with full bed for extra guests, and a workspace for business travelers. Short walk from the lakefront and Montrose Beach, and a 6-minute walk to the 24/7 Wilson Red Line, this location is excellent for exploring all that Chicago has to offer.

Superhost

A cozy living area features exposed brick walls, a rustic wooden coffee table, and a large leather sofa. A flat-screen television is positioned in front of the seating, while natural light enters through the windows. A vintage fan rests nearby, and additional storage is provided by a bookshelf.

Apartment in Humboldt Park

4.86 out of 5 average rating, 492 reviews

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed --> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

4.98 out of 5 average rating, 226 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

5 out of 5 average rating, 118 reviews

Inspired, luxe living in Logan Square on BLVD #1

Welcome to our Palmer Square House! In the heart of hip Logan Square. Enjoy a rare opportunity to experience Boulevard living. "Live like a local" in one of Chicago's most visited & vibrant neighborhoods. 1915 historic 2-flat has been renovated with luxurious amenities. Lots of windows provide natural light. Chef's kitchen is beautiful & functional. Option to rent PH at same time if available. Primary bathroom has serious spa vibes. NO CLEANING FEES! Very fast WiFi. 65" Smart TV QLED.

4.97 out of 5 average rating, 197 reviews

Apartment in North Side

Lincoln Park 2bed/2bath in Historic Neighborhood

Just steps from the lively center of Chicago's Lincoln Park and poised above the quiet, tree-lined streets of the coveted Arlington-Deming neighborhood, this residence on the top floor of a three-story walkup is the perfect for families that want to be close to it all! Lake Michigan, Lincoln Park Zoo, multiple parks, transportation, dining, nightlife, and more. We provide one daily parking permit per night of your stay so you can access free street parking.

Apartment in Old Town Triangle

A cozy living area is presented with a daybed adorned with blue linens and colorful throw pillows. Light filters through two windows covered with sheer curtains. A wooden coffee table is positioned in front of a neutral-toned sofa, complemented by a bookshelf displaying various decorative items.

4.88 out of 5 average rating, 181 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

4.9 out of 5 average rating, 176 reviews

A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.

Apartment in Gold Coast

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

4.95 out of 5 average rating, 135 reviews

An open kitchen and dining area features exposed wooden beams and stylish light fixtures. A modern dining table with black chairs provides seating, while a lounge chair is positioned nearby. Decorative plants and art add warmth to the contemporary space.

Apartment in Wicker Park

Modern Izakaya Studio in Wicker Park

Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

5 out of 5 average rating, 150 reviews

A spacious living area features a comfortable sectional sofa, a wooden dining table with matching chairs, and a cozy reading nook with an armchair. Large windows allow natural light to fill the room, which includes a decorative fireplace and tasteful artwork on the walls.

Apartment in Wicker Park

Stunning Wicker-Park Flat with Parking!

Enjoy a stylish experience at this centrally-located gem. Beautifully renovated 3 bedroom, 2 bath full floor flat. While quietly situated on the 3rd floor, you can walk out your front steps to all that Wicker Park and Division street has to offer. Coffee shops, bars, unlimited restaurants, green space, farmers market, gyms, grocery stores, and so much more. Easy and nearby public transit.

Apartment in Lincoln Square

A bright living area is showcased with large windows allowing natural light. Red and orange artwork adorns the walls, while a gray ottoman centers the room. Seating consists of a gray sofa and an armchair with a geometric pattern, accompanied by decorative lamps on either side.

4.97 out of 5 average rating, 462 reviews

Lincoln Square Gem!

Very nice and updated condo in the heart of Lincoln Square! Lots of fun design elements and artwork await. This sunny condo is in the 2nd floor of a 2-flat building with friendly neighbors. My partner and I live on the first floor. You can walk to all that Lincoln Square has to offer! The Brown Line (Western stop) is just 2.5 blocks away for an easy commute to downtown!

4.99 out of 5 average rating, 679 reviews

The bright living area features a blue sofa with decorative pillows, a wooden coffee table, and a desk chair facing a small workspace. Natural light enters through multiple windows, showcasing the hardwood flooring and modern decor elements, including a framed cityscape artwork.

Apartment in Lake View

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and an en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

4.95 out of 5 average rating, 104 reviews

A modern living room features a light-colored sectional sofa adorned with various cushions. A sleek black coffee table sits in front of it, and a mounted television occupies the wall above a low console. Soft lighting highlights the textured wall panels.

Apartment in Bucktown

Wicker Park/Bucktown condo with outdoor patio

This freshly remodeled condo decorated in the Japandi style is set in the trendy yet peaceful neighborhood of Bucktown - a perfect base for exploring Chicago. A short walking distance to 2 Blue line CTA stops (Western and Damen), it is surrounded by quaint neighborhood bars, restaurants, and coffee shops as well as grocery stores and trendy shopping.

Popular amenities for Chicago apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.81 out of 5 average rating, 546 reviews

A comfortable living area features a sectional sofa adorned with throw pillows, complemented by a cozy armchair. Soft lighting is provided by standing and table lamps. A decorative painting hangs on the wall, and a small television is positioned across from the seating arrangement.

Apartment in Albany Park

Cozy Apartment with Free On-Site Parking

A comfortable living area features an orange sofa and a variety of artwork on the walls. A round coffee table sits in the center of a patterned area rug. Natural light filters through the window shades, enhancing the welcoming vibe of the space.

4.95 out of 5 average rating, 109 reviews

Spacious 3BR • Great for Groups • Fast WiFi • Pets

Apartment in Lincoln Square

A charming front porch features a small round table surrounded by two wrought iron chairs. A cozy seating area is adorned with a vibrant red blanket. Flower planters filled with lush greenery and colorful blooms enhance the inviting ambiance, with sunlight filtering through the trees.

4.96 out of 5 average rating, 139 reviews

Best Lincoln Square location. Spacious 2 bedroom

A living area features a leather sofa and two upholstered chairs, arranged around a glass coffee table. A brick accent wall provides character, while a large television sits atop a wooden console. Artworks adorn the walls, accompanied by natural light from the windows.

4.79 out of 5 average rating, 289 reviews

Logan Square Beauty with 2 Bedrooms W/parking

Superhost

A modern living area features a large black leather couch accompanied by a sleek armchair. Artistic Chicago-themed decor adorns the walls, including a vibrant sign. Natural light fills the space through window coverings, with a stylish area rug enhancing the warm ambiance.

Apartment in Ukrainian Village

4.89 out of 5 average rating, 187 reviews

Modern Chicago Movie Themed Apt

Apartment in McKinley Park

4.83 out of 5 average rating, 54 reviews

Cozy Kitties in the City 1BR by Park/Sox/Transit

An open living space features a dark blue sofa with decorative pillows, a wooden coffee table, and a patterned rug. A dining table with four chairs is positioned nearby. The kitchen is visible in the background, showcasing modern appliances and white cabinetry.

4.92 out of 5 average rating, 53 reviews

Spacious Logan Square Sanctuary

A modern multi-story building is nestled among leafy trees, featuring large windows and a sleek, minimalistic design. A wooden staircase leads to the entrance, while blooming flowers add a touch of color to the landscaped garden in front.

4.78 out of 5 average rating, 688 reviews

Spacious Evanston Unit - Walk to Northwestern U

Pet-friendly apartment rentals

4.71 out of 5 average rating, 249 reviews

Apartment

Studio flat in the heart of Chicago's Gold Coast

4.93 out of 5 average rating, 308 reviews

A bedroom features a spacious bed dressed in deep blue linens, complemented by decorative pillows. The walls are painted in a rich blue, accented by round mirrors. Two bedside lamps illuminate the space, while a patterned area rug lies on the hardwood floor.

Apartment in Oak Park

Picture Perfect 3Bed Steps from Train and FLW

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, 261 reviews

Can't Beat This 2min Walk to Wrigley!

4.99 out of 5 average rating, 136 reviews

A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.

Apartment in Lake View

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

4.92 out of 5 average rating, 378 reviews

A spacious living room features a comfortable couch with assorted pillows, a wooden coffee table, and an area rug. Large windows allow natural light to fill the room, accompanied by a ceiling fan and an entertainment unit. A decorative floor lamp and wall decor enhance the inviting space.

Apartment in North Side

Susie's Space. 2BR easy parking & pet friendly

Apartment in Edgewater Glen

A vibrant seating area is showcased with a blue couch adorned with colorful throw pillows and a brown leather sofa. A small black coffee table rests on a patterned area rug, which features geometric designs. Large windows allow natural light to fill the space.

4.98 out of 5 average rating, 133 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

4.93 out of 5 average rating, 110 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

4.83 out of 5 average rating, 178 reviews

A spacious living area showcases a light-colored sectional sofa paired with two vibrant blue accent chairs. A round glass coffee table sits at the center, complemented by a light rug. The open kitchen features dark cabinetry and modern appliances, enhancing the contemporary design.

Apartment in Chicago

Alluring Condo w/ Pri. Prkng Cls to Transit &Beach

Apartment rentals with a pool

The living area features a comfortable sofa adorned with patterned cushions, accompanied by a stylish coffee table. A modern dining setup is visible in the background, along with sleek kitchen cabinetry. Light from overhead fixtures illuminates the open layout with dark hardwood flooring.

4.96 out of 5 average rating, 109 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

A bright living area features large windows that offer city views. Comfortable seating arrangements include a pair of teal sofas and a wooden armchair. A coffee table sits at the center on a soft area rug, accompanied by a flat-screen TV mounted on a nearby wall.

4.95 out of 5 average rating, 124 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

Apartment in Elk Grove Village

4.92 out of 5 average rating, 101 reviews

Just remodeled apartment close to airport and mall

4.82 out of 5 average rating, 67 reviews

A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.

Apartment in Lombard

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

A dining area is presented with a sleek table surrounded by four black chairs. A grey sectional sofa is positioned nearby, complemented by a modern floor lamp. Large windows provide natural light, and a vibrant cityscape photo adorns the wall.

4.92 out of 5 average rating, 137 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Superhost

A cozy living area features a sectional sofa adorned with pillows and a throw pillow inscribed with 'Enjoy.' A round coffee table holds decorative items, while framed art showcases serene designs on the wall. A small dining area is visible in the background.

Apartment in Lombard

4.9 out of 5 average rating, 50 reviews

Pond View, Washer Dryer, Non Smoking Community

An open-concept living space is showcased, featuring modern kitchen appliances, a dining table with seating for six, and a comfortable sofa. Large windows allow natural light to fill the area, providing views of the outdoor landscape.