Condo holiday rentals in Oak Park

4.97 out of 5 average rating, 143 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.

Condo in Wicker Park

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.

5 out of 5 average rating, 117 reviews

A living area showcases a wooden entertainment center with a TV, flanked by a decorative console table and two lamps. The space features hardwood floors and a neutral color palette, complemented by a circular wall mirror. A staircase in the background leads to the upper level.

Condo in Clarendon Hills

Apartment in Clarendon Hills.

Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet, private bathroom/shower. Bedroom 2 - queen bed, closet. Bedroom 3 - size bed, closet. Living room has a pull-out sofa bed. Family room with gas fireplace, access to deck/outdoor area. Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

4.94 out of 5 average rating, 265 reviews

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.

Condo in Little Italy

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.

4.88 out of 5 average rating, 151 reviews

A modern living area features a blue sectional sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front of the sofa. A desk and chair are situated near a large window, allowing natural light to brighten the room.

Condo in Mayfair

Newly updated 1BD/1B in Old Irving Chicago!

Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

5 out of 5 average rating, 122 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.

An elegantly furnished dining area features a wooden table with a textured runner. Dark leather chairs surround the table, and a modern chandelier hangs above. The open kitchen, equipped with stainless steel appliances and bar seating, is visible in the background.

4.98 out of 5 average rating, 306 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Luxurious 1BR/2BA garden-level condo in vibrant Logan Square! Comfortably furnished with tons of light and amenities, conveniently located one block from the Logan Square Blue Line Station and located on a quiet street. Steps from all of the hip restaurants and nightlife in Logan Square. Huge back yard and patio with fire pit for guest use. Free on-site garage parking with remote. And, if using public transit, the Logan Square is 8 stops, ~15-20 minutes from the Loop downtown!

4.96 out of 5 average rating, 148 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.

Condo 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.

4.93 out of 5 average rating, 280 reviews

A comfortable living area features a dark sofa with colorful accent pillows and a glass coffee table. Natural light streams through large windows, which are dressed with sheer white curtains. A modern floor lamp and a single chair add functional seating options.

Condo in Humboldt Park

Modern/Spacious 2BR/2BA West Town

Light, airy and luxurious, our duplex has a self-contained, 1400 sq. ft. 2nd floor with a private street entrance. There are two bedrooms and two baths. The master bedroom has a fireplace, a private balcony and a huge bathroom ensuite. In addition there is a dining room and living room. Minimal kitchen facilities include small fridge and micro. Easy commute downtown- 20 by car, 25 by bike and 30-40 minutes via public transportation. Close to hwy and public trans.

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

This pet-friendly, Logan Square apartment is brimming with details to make your stay feel like a home away from home. All 3 bedrooms boast super-comfy queen beds with an abundance of pillows and lots of storage space for your belongings. The third bedroom is made private by a lush velvet curtain. There are two dedicated workspaces in the apartment for your work-from-anywhere lifestyle needs. A very well-appointed kitchen is begging for home-cooked meals.

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, 294 reviews

Logan Square Beauty with 2 Bedrooms W/parking

Our two-bedroom condo is beautifully appointed and has vintage charm everywhere you look. You'll have access to a shared backyard, and all of the amenities of home - while being a 10 minute walk from some of the hottest bars and restaurants in Chicago. One garage parking spot is available during your stay. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea!

4.86 out of 5 average rating, 256 reviews

A vibrant living area is highlighted by a deep blue sofa and a colorful area rug. A large wall-mounted television is positioned across from the seating, and modern artwork decorates the walls. The adjoining kitchen is visible in the background, showcasing sleek cabinetry and new appliances.

Condo in Hermosa

3D Tour! Designer Condo near Logan Square

Scan QR code in photos for a 3D Tour! What you’ll love: - Totally renovated garden unit, completed in 2021. Everything new. - Upscale furnishings & decor. - Gourmet, fully equipped kitchen w/ new appliances, coffee maker and spices. - Remote work station w/ super fast Wi-Fi (600mb). - Serta queen mattress in master. - Bunk beds w/ full and twin sized memory foam mattresses. - Heat & A/C.

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, 126 reviews

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

Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

Popular amenities for Oak Park condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.81 out of 5 average rating, 549 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.

Condo in Albany Park

Cozy Apartment with Free On-Site Parking

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.

4.99 out of 5 average rating, 197 reviews

Int. Designer’s Lakeview Duplex w/private backyard

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.

4.98 out of 5 average rating, 237 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

4.93 out of 5 average rating, 281 reviews

Condo in Tri-Taylor

The Upscale Getaway Near Downtown

4.97 out of 5 average rating, 471 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.

Condo in Ravenswood

Lincoln Square Gem!

Condo in Old Town Triangle

A modern living space features a sleek kitchen island with a sink, surrounded by light wood flooring. Large windows invite natural light, illuminating a comfortable gray sofa and a dining table with black chairs. A vibrant wall art piece adds color to the room.

4.95 out of 5 average rating, 125 reviews

NEW luxury Old Town 1-Bedroom condo

Condo in Ukrainian Village

4.89 out of 5 average rating, 196 reviews

Modern Chicago Movie Themed Apt

4.98 out of 5 average rating, 337 reviews

A spacious living area is presented, featuring a large gray sectional sofa. Natural light enters through expansive windows, illuminating the room. A fireplace and a mounted television are visible on the wall, with plants enhancing the decor around the space.

Condo in Uptown

Near Lake Michigan & Wrigley Field

Pet-friendly condo rentals

4.83 out of 5 average rating, 395 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.

Condo in Chicago

Chic and Charming Vintage Condominium in Lincoln Park

4.81 out of 5 average rating, 162 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.

Condo in East Pilsen

816 PLZN Luxury Apartment| Rooftop| Garage Parking

4.87 out of 5 average rating, 109 reviews

The living area features a comfortable sectional sofa with decorative cushions and a cozy throw. A stone fireplace adds character, while a flat-screen TV is mounted on the wall. A dining table with chairs is visible in the background, complemented by stylish wall decor.

Condo in Chicago

Cozy Lincoln Park Condo near the lake.

4.9 out of 5 average rating, 140 reviews

A modern living area features a light-colored sectional sofa adorned with blue accent pillows. A round black coffee table is positioned in the center, resting on a decorative rug. Two lamps and a piece of coastal-themed artwork complement the bright, airy atmosphere.

Condo in Bridgeport

Convenient & Spacious 3BR Condo w/Free Parking

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.

4.9 out of 5 average rating, 153 reviews

The Bagel Inn - Bright & Modern Wrigleyville 2 Bed

4.92 out of 5 average rating, 148 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.

Condo in Chicago

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

4.81 out of 5 average rating, 272 reviews

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.

Condo in Wrigleyville

Can't Beat This 2min Walk to Wrigley!

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.

4.99 out of 5 average rating, 141 reviews

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

Condo 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, 112 reviews

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

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.

Condo in Lombard

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Condo 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, 104 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, 137 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.

Condo 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.

4.96 out of 5 average rating, 114 reviews

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

A modern living area is revealed with large windows showcasing views of the lake and boats. A light-colored sofa and armchair are arranged around a glass coffee table, complemented by a floor lamp and a large TV mounted against a neutral wall.

Condo in Burbank

Iconic Style, Charming Lake View