Apartment holiday rentals in Chicago

A spacious living area features a large sectional sofa arranged around a modern coffee table. Artwork adorns the wall above, with soft lighting enhancing the ambiance. A patterned area rug adds texture to the hardwood floor, while natural light enters through the adjacent windows.

4.94 out of 5 average rating, 113 reviews

Two Floor Luxury 3 Bedroom Condo in Old Town

Enjoy comfort, privacy, and elevated city living in this spacious three-bedroom, top-floor duplex apartment, located next door to The Sono Chicago in the heart of Old Town Chicago. Ideal for families, groups, or extended stays, this home offers generous space, abundant natural light, and a quiet retreat above the neighborhood. Spanning two levels on the top floor, the apartment features inviting living areas, a fully equipped kitchen, and three private outdoor decks, creating multiple spaces to

Apartment in Logan Square

A modern living area features a dark sofa facing a wall-mounted flat-screen TV. A wooden shelf with decorative items and a lamp is positioned beside a designated work space with a chair. Exposed brick walls complement the sleek kitchen area visible in the background.

Sunny Getaway Steps from Bucktown + Wicker Park

Enjoy a relaxing and chic experience steps aways from the lively, sought-after Wicker Park and Bucktown! Our home is on a quiet, tree-lined street with its own private walk-up entrance and FREE parking space. Public transportation is also very accessible. There are endless options of restaurants, bars, and shopping. The 606 trail is also steps away! We are centrally located which makes it easy and convenient to explore Chicago! Come make some memories for the weekend or as long as you'd like!

4.77 out of 5 average rating, 162 reviews

A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.

4.98 out of 5 average rating, 171 reviews

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Apartment in Little Italy

A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.

Private hot tub - King bed suite - Free parking

Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

4.92 out of 5 average rating, 283 reviews

4.95 out of 5 average rating, 175 reviews

The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.

Apartment in North Side

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Apartment in Lincoln Park

A spacious living area displays hardwood floors and elevated ceilings. A large flat-screen TV is mounted above a decorative brick fireplace. Natural light filters through multiple windows, illuminating the contemporary furniture arrangement that includes a soft sectional sofa and accent chair.

1,800ft² Parking Workspace W/D Full Kitch

• 1,800ft² | 167m² . My home is on the top floor of a four flat Brick Building . You have 3 flight of stairs to climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: The fireplace is non working

4.99 out of 5 average rating, 223 reviews

4.92 out of 5 average rating, 396 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

Sunny and spacious, 2 bedroom apartment in Avondale near the Green Exchange/ Greenhouse Loft Flexible, self check-in Easy street parking (with provided permits) Pet fee $80 per pet Bedroom 1 with a king sized bed Bedroom 2 with a full bed Air conditioning and ceiling fans Soft linens and towels Separate dining room Fully equipped kitchen Free WIFI Smart TV for streaming Garden in back with a fire pit and charcoal grill Laundry room in basement

Apartment in Ukrainian Village

Modern Chicago Movie Themed Apt

Welcome to Chicago at the Movies! An amazing fully updated apartment in the Ukrainian Village neighborhood. This midcentury modern 3 bedroom home is perfect for groups, couples, and families looking for a perfect Chicago vacation. The property is conveniently located on Grand Avenue just minutes by car, bus or train from Downtown and the Lakefront. We are also just a short 5 Minute ride to the United Center for concerts sports and more!

4.88 out of 5 average rating, 229 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.

4.89 out of 5 average rating, 195 reviews

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.

4.96 out of 5 average rating, 123 reviews

Two Bedroom w Porch in Wicker Park

Spacious two bedroom apartment with custom wood shelving and hard wood floors. Bay windows and great natural light. Gorgeous furnished porch for when the weather is nice. Quiet, tree lined street that's close to all the best bars and music venues. Short walk to Milwaukee avenue, two blocks from the Division Street blue line station which runs direct from O'hare, only two stations to downtown.

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.

4.96 out of 5 average rating, 159 reviews

Modern Izakaya Studio in Wicker Park

The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.

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.

5.0 out of 5 average rating, 186 reviews

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.

Popular amenities for Chicago apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.86 out of 5 average rating, 330 reviews

The living and dining area features a sectional sofa and a futon, complemented by a decorative area rug. A television is positioned on a media console, and a dining table with upholstered chairs is visible. Natural light enters through high windows, enhancing the spacious feel.

Apartment in West Town

Bold Ukrainian Village 2 Bedroom w/Garage Parking

Apartment in Lincoln Park

A stylish living area features a white sofa with bright yellow cushions, set against exposed brick walls. A flat-screen TV is positioned above a modern fireplace. A wooden staircase leads to the upper level, while a kitchen bar with dark countertops is visible on the left.

Unique Lincoln Park Duplex Apt

4.96 out of 5 average rating, 553 reviews

4.99 out of 5 average rating, 719 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

4.81 out of 5 average rating, 176 reviews

A modern living area is presented with large windows allowing ample natural light. A navy sofa sits beside a decorative coffee table on a patterned rug, with a stylish mirror and television mounted on the wall. The space features sleek wooden accents for a contemporary feel.

Apartment in West Side

816 PLZN LUX Apartment | Rooftop | Garage Parking

4.91 out of 5 average rating, 348 reviews

Old Town Condo: Private Terrace & Garage Parking

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.

Can't Beat This 2min Walk to Wrigley!

4.81 out of 5 average rating, 290 reviews

4.93 out of 5 average rating, 178 reviews

Apartment in West Side

The Urban Oasis | Outdoor Lounge • Sleeps 10+

4.97 out of 5 average rating, 509 reviews

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.

Apartment in Ravenswood

Lincoln Square Gem!

Pet-friendly apartment rentals

A comfortable living room is showcased with a grey sofa adorned with decorative pillows. A round coffee table sits on a patterned rug, and a green vintage cabinet adds a pop of color. Bright light enters through open doorways, leading to a dining area beyond.

4.97 out of 5 average rating, 150 reviews

Large Remodeled Home in Lincoln Park, Sleeps 12!

4.87 out of 5 average rating, 198 reviews

A bright living room is featured, displaying a blue sofa and yellow chairs arranged around a coffee table. A large clock adorns the blue accent wall, while natural light enters through the window. A plant adds a touch of greenery, completing the inviting space.

Apartment in Berwyn

Picturesque Apartment in Berwyn

4.81 out of 5 average rating, 264 reviews

The living room features a wall-mounted television above a wooden console, surrounded by decor and framed photos. Comfortable seating includes gray armchairs and a sectional sofa, offering a relaxed setting. Natural light brightens the space through nearby windows, enhancing the airy atmosphere.

Apartment in West Town

Chicago River West 4 Bedroom / 3 Bathroom

4.93 out of 5 average rating, 166 reviews

Apartment in West Town

Luxuriously bright 6-bedroom duplex: The Treehouse

4.98 out of 5 average rating, 149 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!

4.84 out of 5 average rating, 177 reviews

A well-lit living room features panoramic windows that provide expansive city views. Comfortable seating options include a blue chair and gray sofa, arranged around a coffee table atop a patterned rug. A television is mounted on the wall, enhancing the entertainment area.

Apartment in The Loop

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

4.86 out of 5 average rating, 121 reviews

A spacious living area is shown, featuring a large sectional sofa with decorative pillows. A glass coffee table occupies the center of the room, while a television sits on a wooden stand. The kitchen is visible in the background, with modern appliances and a dining area.

Apartment in West Side

Spacious 5-BR Apt next to transit Free Parking

4.98 out of 5 average rating, 277 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 Chicago-Wrigley/BoysTown/Parking!

Apartment rentals with a pool

An open-concept living area features large windows that invite natural light and provide a view of the cityscape. A comfortable blue sofa is adorned with patterned pillows, while a light wood coffee table sits in front of it. A dining space with black chairs complements the modern kitchen.

4.96 out of 5 average rating, 142 reviews

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

Apartment in Elk Grove Village

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.

Just remodeled apartment close to airport and mall

4.91 out of 5 average rating, 128 reviews

4.88 out of 5 average rating, 58 reviews

A comfortable living area features a dark sofa, coffee table, and a modern TV stand with a large television. A dedicated dining space with a round table for two is visible. Sliding glass doors lead to a private balcony, providing natural light and outdoor views.

Apartment in Lombard

Pond View, Washer Dryer, Non Smoking, Pet Free

5.0 out of 5 average rating, 13 reviews

Apartment in Berwyn

Red Door

A clear swimming pool is surrounded by a spacious deck featuring white lounge chairs. A fence provides privacy, and lush greenery is visible in the background, complementing the bright blue sky above.

Private room in Westchester

Lovely 2 Bed 2 Bathroom!

4.96 out of 5 average rating, 123 reviews

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

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.

4.96 out of 5 average rating, 123 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

The living area features a sectional sofa adorned with vibrant cushions beside a coffee table. Natural light filters through large windows dressed with horizontal blinds, illuminating a console with a flat-screen TV and decorative accents.