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Apartment holiday rentals in Logan Square

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Quick stats about apartment rentals in Logan Square

  • Total holiday rentals

    Explore 40 holiday rentals in Logan Square

  • Nightly prices starting at

    Logan Square holiday rentals start at £44 per night before taxes and fees

  • Verified guest reviews

    Over 2,860 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Logan Square holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Logan Square rentals

  • 4.8 Average rating

    Logan Square stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated apartment rentals in Logan Square

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Top guest favourite
A bright living area features a light-colored sectional sofa, a coffee table, and a television stand. Natural light enters through three large windows adorned with wooden blinds. A floor lamp provides soft illumination, complemented by a rug with intricate patterns on the hardwood floor.
Apartment in Logan Square

Logan Square living at its best w/ bright 2 bdrm

Enjoy Logan Square in this bright, 2nd-floor apartment in a vintage Chicago three-flat from the 1880's. Consistent with the buildings of this time, the bedrooms are smaller and set up with 2 queen beds, along with a dedicated front office space. Walk to all the best restaurants, coffee shops, Palmer Square Park, and the CTA Blue Line for easy access to O'Hare airport and downtown Chicago. Free street parking on the block. Security camera located on the front porch. No children or pets, please.

4.95 out of 5 average rating, 188 reviews
Top guest favourite
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.
Apartment 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.

4.98 out of 5 average rating, 167 reviews
Top guest favourite
A spacious rooftop deck features comfortable wooden seating arranged around a circular table. The area is adorned with vibrant flowers and a decorative rug, all set against a sweeping view of the Chicago skyline under a soft blue sky.
Apartment in Wicker Park

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Escape into this spacious, Chicago Penthouse! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Private, spacious roof deck viewing the entire Chicago skyline! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out - Designated parking spot! - Steps away from blue line Damen station (800 feet)

4.93 out of 5 average rating, 225 reviews
Top guest favourite
Apartment in Logan Square

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.

5.0 out of 5 average rating, 142 reviews
Top guest favourite
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.
Apartment in Logan Square

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!

4.98 out of 5 average rating, 324 reviews
Guest favourite
A bright living area features large windows allowing natural light to flow in. A comfortable gray sofa and matching armchairs are arranged around a coffee table on an area rug. A flat-screen TV is mounted on a white media console, enhancing the inviting space.
Apartment in Logan Square

Renovated 3br Duplex In Logan Square W/parking

Our three bedroom duplex in Logan Square is tastefully decorated and ideally located for traveling families or groups who want to experience everything Chicago has to offer! We're a quick walk to the Logan Square blue line station and close to some of the best restaurants and bars in the city. One garage 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!

4.81 out of 5 average rating, 324 reviews
Guest favourite
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.

4.95 out of 5 average rating, 171 reviews
Top guest favourite
A cozy living area is highlighted by a mounted flat-screen television above a modern fireplace. A comfortable blue chair and a round coffee table are positioned on a light area rug, with warm wood flooring and a glimpse of an adjacent bedroom featuring exposed brick.
Apartment in Logan Square

Queen Beds, EV Charging, Near Train: Luxury Stay

Discover the best of city living at our Logan Square retreat, a mere stone's throw from downtown Chicago and a short walk to the train station. Perfect for urban explorers and business travelers alike, this home offers four plush queen bedrooms and sophisticated comforts like a standalone bathtub for relaxing soaks. Don’t worry about parking; our private spot includes an EV charger. Dive into the city’s vibrant life or unwind in style, your urban sanctuary awaits.

4.99 out of 5 average rating, 119 reviews
Top guest favourite
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.
Apartment in West Town

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.

4.93 out of 5 average rating, 295 reviews
Top guest favourite
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

4.92 out of 5 average rating, 393 reviews
Guest favourite
Apartment in Wicker Park

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.

4.96 out of 5 average rating, 119 reviews
Superhost
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.
Apartment in Humboldt Park

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.

4.85 out of 5 average rating, 282 reviews

Popular amenities for Logan Square apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Top guest favourite
A bright, open living space showcases a cozy sectional sofa facing a large window surrounded by potted plants. A wooden dining table with white chairs is positioned in the foreground, complemented by a stylish area rug that defines the dining area.
Apartment in Logan Square

NEW Rehabbed Sunny top floor Logan Square

4.91 out of 5 average rating, 159 reviews
Superhost
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.
Apartment in Logan Square

Sunny Getaway Steps from Bucktown + Wicker Park

4.76 out of 5 average rating, 159 reviews
Top guest favourite
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.
Apartment in North Side

Grace House | Cozy, contemporary + convenient 2-BR

4.98 out of 5 average rating, 129 reviews
Superhost
A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.
Apartment in West Town

Spacious 4 Bedroom Condo

4.95 out of 5 average rating, 217 reviews
Top guest favourite
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.
Apartment in Lincoln Park

Private Lincoln Park Condo with 2 Parking Spots

4.97 out of 5 average rating, 151 reviews
Guest favourite
A cozy living area features a modern sectional sofa adorned with colorful cushions and a vibrant area rug. A wooden coffee table provides a natural accent, while bright artwork is displayed on the walls. Natural light filters through the window, and the main entrance is visible.
Apartment in Ukrainian Village

Welcoming 2BR in Chicago's Best Neighborhood!

4.85 out of 5 average rating, 362 reviews
Top guest favourite
A living area features a brown leather sofa paired with a white lounge chair. A colorful area rug adds a vibrant touch to the space. Large windows provide natural light and a view of the trees outside, while a wooden coffee table complements the setting.
Apartment in Lake View

Lovely 2-bedroom close to Wrigley Field

4.96 out of 5 average rating, 114 reviews
Guest favourite
Apartment in West Town

Luxuriously bright 6-bedroom duplex: The Treehouse

4.93 out of 5 average rating, 164 reviews

Pet-friendly apartment rentals

Top guest favourite
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.
Apartment in Downtown Chicago

Large Remodeled Home in Lincoln Park, Sleeps 12!

4.97 out of 5 average rating, 148 reviews
Guest favourite
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, 354 reviews
Guest favourite
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

4.82 out of 5 average rating, 258 reviews
Guest favourite
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

4.89 out of 5 average rating, 180 reviews
Guest favourite
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.
Apartment in Wrigleyville

Can't Beat This 2min Walk to Wrigley!

4.81 out of 5 average rating, 287 reviews
Top guest favourite
Apartment in Lincoln Park

of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

4.99 out of 5 average rating, 352 reviews
Top guest favourite
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!

4.99 out of 5 average rating, 147 reviews
Guest favourite
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 Lincoln Park

Chic and Charming Vintage Condominium in Lincoln Park

4.83 out of 5 average rating, 419 reviews

Apartment rentals with a pool

Guest favourite
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.
Apartment in Evanston

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

4.96 out of 5 average rating, 146 reviews
Guest favourite
Apartment in Downtown Chicago

2 bed/2 bath with skyline views

5.0 out of 5 average rating, 9 reviews
Guest favourite
Apartment in Berwyn

Red Door

5.0 out of 5 average rating, 9 reviewsA 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.
Apartment in Burbank

Iconic Style, Charming Lake View

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!

Guest favourite
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.
Apartment in Evanston

"Heart of Evanston" 2br +1Bath-0.6miles to NU

4.93 out of 5 average rating, 147 reviews
Guest favourite
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.
Apartment in Evanston

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

4.96 out of 5 average rating, 122 reviews
Guest favourite
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.
Apartment in Evanston

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

4.96 out of 5 average rating, 139 reviews

Destinations to explore