Apartment holiday rentals in Chicago

The exterior of a historic building showcases large glass windows framed by green trim. Natural light streams into the space, illuminating various items displayed inside. The backdrop features a view of a nearby architectural structure, adding visual interest to the streetscape.

4.97 out of 5 average rating, 131 reviews

Private Lincoln Park Condo with 2 Parking Spots

Built in 1895 and updated in 2025, the condo provides historic charm with modern convenience. The unit is light filled with ample space to spread out and relax. The bathroom has been fully remodeled and the kitchen is updated. The unit has a private balcony deck and a landscaped common patio. The unit includes 2 free off-street parking spots. Amenities include 60" 4K Smart TV, fiber internet, Nest Thermostat & Tuft & Needle/ Casper mattresses. Enjoy living in the heart of Lincoln Park.

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.

4.97 out of 5 average rating, 146 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 North Center

A modern kitchen features green cabinetry and a marble-topped dining table surrounded by two chairs with woven seats. A geometric backsplash adds visual interest, while cookware and decorative elements are thoughtfully arranged on the shelves above. Natural light illuminates the space.

4.98 out of 5 average rating, 112 reviews

Grace House | Cozy, contemporary + convenient 2-BR

Make yourself at home in our newly renovated, spacious and immaculately clean 2-bedroom, 1-bath condo — perfect for your next family, work or friends' trip. Located on a tree-lined street in a family-friendly neighborhood and walkable to shops, restaurants, cafes, bars and more. A stone's throw to Southport Corridor/Wrigleyville/Lakeview, Lincoln Square, Roscoe Village and everything the Northside has to offer. Gigabit internet w/ WiFi and everything you need to live and thrive in Chicago.

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.

4.94 out of 5 average rating, 269 reviews

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.

4.98 out of 5 average rating, 242 reviews

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

4.96 out of 5 average rating, 151 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 Avondale

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.

4.95 out of 5 average rating, 143 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

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 cozy fireplace set into a white marble surround. Light wooden floors and neutral walls create a calming backdrop. A large sectional sofa faces a coffee table, while stylish bar stools complement the nearby kitchen island.

5 out of 5 average rating, 160 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.

4.96 out of 5 average rating, 274 reviews

An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.

Apartment in West Loop

Designer Loft in Fulton Market with Parking

Discover our spacious, two-level modern loft, perfect for business travelers. Featuring sky-high ceilings, floor-to-ceiling windows, and a newly renovated private terrace with a fire pit. Located in the heart of Restaurant Row, just two minutes from downtown. Enjoy a luxury stay with one dedicated parking spot included. Ideal for solo travelers or couples seeking a stylish urban retreat.

4.89 out of 5 average rating, 159 reviews

A brick building front displays the entrance of Steingold’s Deli, featuring large windows and a welcoming facade. Outdoor seating is arranged with wooden tables and chairs, adorned with seasonal decorations. Nearby signs and storefronts add to the bustling neighborhood atmosphere.

Apartment in Lake View

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

Location, Location... Food/Entertainment to the max! Just renovated apt. situated above and hosted by Steingold’s of Chicago (yes, bagels are included), the Midwest’s most lauded deli. Next-door to iconic Music Box Cinema. An 8 minute walk to Wrigley Field and all of its amazing neighbors. Right in the middle of Southport Corridor, Chicago’s hottest neighborhood shopping district.

4.91 out of 5 average rating, 334 reviews

A spacious living area features high ceilings and large windows, allowing natural light to brighten the space. A neutral sofa with decorative pillows faces a glass coffee table, while two brown leather chairs are positioned beside a console unit and a television.

Apartment in Old Town

Old Town Condo with Parking and Terrace

Experience Chicago from my light-filled 2-bed, 2-bath Old Town condo for 4. This urban retreat boasts 13-ft ceilings, a private terrace, dedicated workspace, and gourmet kitchen. Steps from Wells Street's best dining, Second City, Lincoln Park and North Avenue Beach. Perfect for families or professionals seeking a stylish city base with included parking in elevator building.

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, 481 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!

Popular amenities for Chicago apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.99 out of 5 average rating, 199 reviews

An inviting outdoor area features a long wooden table surrounded by six woven chairs, set upon a patterned rug. Lush greenery envelops the space, with plants bordering the brick pathway, enhancing the natural ambiance. Soft lighting from overhead strands adds warmth to the setting.

Apartment in Lake View

Int. Designer’s Lakeview Duplex w/private backyard

Apartment in Logan Square

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, 111 reviews

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

Apartment in Ukrainian Village

The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.

4.98 out of 5 average rating, 111 reviews

Ukrainian Village 3BR/3BA • Jet Tub, Private Patio

4.93 out of 5 average rating, 284 reviews

Apartment in Tri-Taylor

The Upscale Getaway Near Downtown

4.93 out of 5 average rating, 326 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

4.93 out of 5 average rating, 531 reviews

A modern living room is furnished with sleek white leather sofas arranged around a wooden coffee table. A refined fireplace serves as a focal point, framed by an art piece depicting a serene landscape. Large windows allow ample natural light to fill the space.

Apartment in River West

The Penthouse Gallery at OHC

4.92 out of 5 average rating, 152 reviews

The modern kitchen features sleek white cabinetry and stainless steel appliances, including a refrigerator and oven. A central island provides extra counter space with two black stools positioned nearby. The open layout allows a view of the adjoining living area through a doorway.

Apartment in North Side

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

4.92 out of 5 average rating, 383 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

Pet-friendly apartment rentals

4.83 out of 5 average rating, 398 reviews

A living area features two tufted gray sofas and a glass coffee table atop a patterned rug. The space is illuminated by natural light from large windows, with decorative accents including throw pillows and a cozy ottoman.

Apartment in North Side

Chic and Charming Vintage Condominium in Lincoln Park

4.81 out of 5 average rating, 165 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 East Pilsen

816 PLZN Luxury Apartment| Rooftop| Garage Parking

4.94 out of 5 average rating, 162 reviews

A spacious modern family room features a large sectional sofa adorned with decorative pillows. A 76” smart TV is mounted on the wall, displaying a beach scene. Natural light enters through multiple windows, illuminating the open layout that flows into a dining area with sleek furniture.

Apartment in East Pilsen

The Urban Oasis | Outdoor Lounge • Sleeps 10+

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.

4.91 out of 5 average rating, 110 reviews

Spacious 5-BR Apt next to transit Free Parking

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, 135 reviews

Steps from the Lake, Lovely 3-Bedroom Condo

Apartment in Lincoln Park

An open-concept living area features a spacious dining table surrounded by black chairs. A modern kitchen showcases stainless steel appliances and upper cabinets. Natural light fills the room through multiple windows, while a comfortable sofa is positioned nearby, welcoming relaxation in the thoughtfully designed space.

4.77 out of 5 average rating, 261 reviews

Modern Luxury In Old Town - Sleeps 4

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.

4.87 out of 5 average rating, 189 reviews

Lincoln Park Hideaway - 5 Min Walk to the Park!

4.81 out of 5 average rating, 245 reviews

Apartment in Grant Park

MICH AVE #5| Downtown Grant Park, Museums 2bd/2ba

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, 114 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, 130 reviews

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

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

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.

4.92 out of 5 average rating, 105 reviews

Just remodeled apartment close to airport and mall

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, 138 reviews

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

4.9 out of 5 average rating, 50 reviews

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

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.