Apartment holiday rentals in Logan Square

A spacious living area is positioned in front of large bay windows, allowing natural light to illuminate the space. A comfortable sofa is complemented by a recliner chair and decorative pillows. A simple television stand offers entertainment options, while a potted plant adds a touch of greenery.

4.97 out of 5 average rating, 149 reviews

Serene Logan Sq Apt | Walk to Dining & Blue Line

Step into the vibrant heart of Logan Square and experience the comfort of this classic, Chicago-style apartment, just one block from Logan Square Boulevard. Perfect for guests exploring the city or visiting family in the neighborhood, this updated space blends modern amenities with vintage character. You’re steps from top restaurants, bars, coffee shops, and the Logan Square Farmer’s Market. Downtown attractions like Navy Pier and Millennium Park are easily accessible via the Blue Line or Uber.

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An inviting studio space features warm wooden paneling and a dark couch. A coffee table with magazines and guidebooks is centrally positioned. Soft lighting is provided by wall sconces, and a bed is visible in the background, accented by a colorful wall art piece.

4.92 out of 5 average rating, 465 reviews

The Grotto of Logan Square

Garden unit, great for a small group looking for a base while they explore the city. 10 min walk from Logan Square Blue Line, restaurants, galleries, coffee shops and clubs. Explore the city from one of its best neighborhoods! In your downtime the space offers several chicago guide books and magazines. There is a Fire stick in the TV that has most major media apps installed. The alarm clock is also a speaker for your phone to plug into. Please make sure you read the amenities and house manual.

ValueLocationWi-Fi

4.93 out of 5 average rating, 107 reviews

The Colorful Little Apartment

Cozy 1-bedroom basement apartment located in vibrant Logan Square where you’ll find great restaurants, bars, and cafés. There's a bus stop half a block away and a large grocery store one block away. Free street parking. The unit boasts many amenities to make your stay comfortable, including a full kitchen, a bedroom with a queen size bed, and a living room with a futon bed. The ceiling is low in some areas, making the unit better suited for people who are 5ft., 10in. (177.80 cm) or shorter.

LocationFamilyHospitality

A light blue sofa is positioned against a textured brick wall, complemented by three framed artworks above. A small, round white coffee table sits in front of the sofa. The adjacent area reveals a glimpse of the dining space and kitchen, featuring natural light from the window.

4.89 out of 5 average rating, 184 reviews

Bright Logan Square 1BR | Walk to Blue Line

Enjoy all that Logan Square offers with this 1 BR apartment on the 2nd floor of a charming 4-flat building. Updated kitchen with basic necessities. High speed internet included with smart tv & security system in place. One block from Palmer Square Park, 5-minute walk from CTA (California) Blue Line, walk to shops and restaurants and experience Chicago at its best! Perfect for couples, solo travelers, or remote workers looking for a comfortable and convenient home base

ValueFamilyAccuracy

The entry to the studio features a full-size bed adorned with white bedding. Natural light enters through large windows, illuminating the space. A television is mounted on the wall opposite the bed, and a door leads to an outdoor area, framed by a charming entryway.

4.77 out of 5 average rating, 391 reviews

Private Logan Square Studio

A private second floor walk up vintage studio apartment right in the heart of Logan Square. Located just half a block north of the picturesque Logan Boulevard and three blocks (5-8 minute walk) from the Logan Square blue line stop which is great for getting around the city. Logan Square is a 15 minute train ride into the loop and 20 minutes out to O'Hare. This studio is convenient for the weary O'Hare traveler or perfect for a private getaway from the hustle of Chicago.

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A comfortable living area is furnished with a plush couch adorned with decorative pillows. A light-colored coffee table sits atop a patterned area rug, accompanied by a stylish console table featuring a vintage printer and decorative items. Soft natural light enters through two windows.

4.96 out of 5 average rating, 110 reviews

Bright, Spacious 2BR Apt In Heart of Logan Square!

Live like a local in this charming 2 bed, 1 bath garden apartment in a classic Chicago two-flat in Logan Square. Renovated top to bottom, the space is stylish, cozy, and full of character. Just a 5-min walk to the Blue Line, top restaurants, cafes, and shops. Grab coffee from a nearby café and explore the city, or hit the Sunday farmers market for local flavor. Logan Square is one of Chicago’s most vibrant neighborhoods—and this home puts you right in the heart of it.

LocationFamilyNearby

A comfortable living area features two dark sofas adorned with decorative pillows in blue and white. A coffee table sits in the center atop a patterned rug. A large television is mounted on a textured brick wall, complemented by plants and framed mirrors. A cityscape artwork is displayed above.

4.92 out of 5 average rating, 127 reviews

Right in the heart of Logan Square.

BEST LOCATION IN LOGAN SQUARE!! Brand new stylish 3 bed, located in the heart of the highly desirable Logan Square neighborhood. This luxurious space is situated right by the historic Logan Square Boulevard, literally 10 STEPS AWAY from the CTA 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.

ValueFamilyLaundry

A charming Victorian home with a distinctive turret is set in a neighborhood featuring well-kept gardens and tree-lined streets. The porch with white railings leads to a welcoming entrance, while neighboring houses display a mix of architectural styles amidst lush greenery.

4.99 out of 5 average rating, 134 reviews

Logan Square Garden

This 3-bedroom garden apartment anchors a Victorian home in one of Chicago's coolest neighborhoods. It's convenient, clean & cozy on a quiet, tree-lined residential block, steps from restaurants, nightlife, retail, etc. We're 5 blocks from the Logan Square CTA Blue Line stop, midway between O'Hare & downtown Chicago. Private entry, new kitchen and bath, Wi-Fi, desks & comfy beds. Nice and affordable for a couple, but the apartment can accommodate up to 5.

ValueFamilyNearby

A bright living room is illuminated by natural light from large windows. A white sofa is paired with two orange chairs, complemented by vibrant cushions. A coffee table with a striped design sits centrally, surrounded by decorative plants and artwork on the walls.

4.95 out of 5 average rating, 738 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

LocationFamilyLong stay

A spacious living area is depicted, featuring a large, sectional leather couch in a warm tan hue. Colorful framed art posters adorn the walls, adding visual interest. A wooden coffee table and a dining area with a wooden table and chairs are visible in the background.

4.95 out of 5 average rating, 280 reviews

Close to coffee, commuting, restaurants & bars

Cozy, comfortable, beautiful first floor unit in an owner-occupied graystone in trendy Logan Square. Furnished and spacious (1100 sq feet) 2 BR with an office space. Close to all public transportation, buses, trains, and Divvy - Chicago's bike-share program. Easy access to the highway if you need to commute to the city or to the suburbs while you are staying here. Lots of restaurants and bars within walking distance.

FamilyLocationIndoor spaces

A cozy living area features a sectional sofa with a vibrant throw pillow, complemented by a mid-century armchair. A colorful area rug adds warmth to the hardwood floor. Large windows with blinds provide ample natural light, while a decorative lamp and a globe accent the space.

4.97 out of 5 average rating, 274 reviews

Spacious apartment in Logan Square

Ideal location 2 blocks from beautiful Palmer Square Park and short walk to Logan Boulevard. Enjoy the many great restaurants and bars in the neighborhood. Take a stroll or a bike ride on the 606 elevated path. One bedroom with queen size bed. Large open floor plan and air mattress for extra guests. Easy access to public transportation.

ValueFamilyAccess

A warm living area features a black leather sofa adorned with colorful throw pillows. A glass coffee table rests on a patterned rug, while two accent chairs provide additional seating. Natural light streams in through a window, complemented by decorative plants and wall art.

4.95 out of 5 average rating, 329 reviews

Cozy and Spacious! Logan Square Apartment

Enjoy the local Chicago comforts of a traditional Logan Square apartment decorated with vintage charm. Home to some of the city's most celebrated food and nightlife, Logan Square is one of Chicago’s most exciting neighborhoods with an energy unlike any other in Chicago. And you're only a quick trip to downtown!

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Popular amenities for Logan Square apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.94 out of 5 average rating, 177 reviews

A welcoming entryway features a rustic bench with a decorative pillow that reads 'Home.' The walls are adorned with wainscoting, and a piece of artwork in warm tones is displayed above the bench. A white door and doorknob are visible, contributing to the bright ambiance.

Apartment in Avondale

Custom Apartment in the heart of Avondale

FamilyLocationWalkability

Apartment in Roscoe Village

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.95 out of 5 average rating, 251 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

ValueFamilyWi-Fi

4.71 out of 5 average rating, 200 reviews

Cozy 2BD/1BA in Charming Logan Square

LocationValueComfort

4.98 out of 5 average rating, 243 reviews

A spacious living room features a large gray sectional sofa with colorful accent pillows. Natural light fills the space through large windows adorned with woven shades. A wooden coffee table sits at the center, complemented by a decorative bowl. A sleek desk with a monitor is positioned in one corner.

Apartment in North Side

5* City Oasis: Logan Square/Avondale Neighborhood

LocationFamilyAir conditioning

The exterior of a historic Chicago Graystone building is presented, featuring a grand entrance with wide steps leading to a covered porch. Lush green grass fills the yard, framed by well-maintained landscaping and a wrought-iron fence, with large windows reflecting natural light.

4.99 out of 5 average rating, 164 reviews

Newly-renovated historic home in Logan Square

LocationFamilySleep quality

A modern living area features a green velvet couch paired with two sleek white chairs. A round coffee table sits in the center, accented by decorative items. Artwork with a geometric pattern adorns the wall, complemented by a contemporary floor lamp.

4.77 out of 5 average rating, 590 reviews

Clean & Bright Chicago Condo - FREE Parking Spot

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A spacious basement entertainment area features a comfortable sectional sofa and a large coffee table. A pool table is positioned in the center, while a wall-mounted TV and an electric fireplace create a relaxed atmosphere. Light-colored walls and flooring enhance the space's openness.

4.84 out of 5 average rating, 135 reviews

Logan’s Cozy Inn.

FamilyValueWalkability

5 out of 5 average rating, 196 reviews

A living room is showcased with a dark sofa and an orange accent chair. A glass coffee table rests on a patterned rug. Walls are adorned with framed art, and a window unit air conditioner is present. Daylight illuminates the space through bright windows.

Apartment in Avondale

Cool City Comfort - Logan Sq. - O’Hare CTA

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Private apartment rentals

Apartment in Humboldt Park

A modern living space is depicted, featuring a dark seating arrangement with patterned cushions and a wooden coffee table. A striped rug covers the floor, and a kitchenette is visible in the background, complemented by light cabinetry. Yellow accents add a lively touch.

4.85 out of 5 average rating, 149 reviews

Logan Square 2BR Garden Unit

LocationValueAccess

4.85 out of 5 average rating, 238 reviews

A stylish shelving unit curves elegantly in the corner, holding a selection of books, decorative items, and a small plant. A flat-screen TV is displayed below, with a couple of stacked books visible on the shelves. Soft lighting enhances the modern aesthetic of the space.

Apartment in Avondale

Attic apartment in a hip neighborhood!

FamilyValueHospitality

4.79 out of 5 average rating, 123 reviews

Logan square Chicago beauty

FamilyValueAccess

4.98 out of 5 average rating, 54 reviews

The Logan Greystone

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A welcoming living area is presented with a comfortable sofa, a coffee table, and an accent rug. A wall-mounted television and stylish wooden storage unit are visible. Natural light enters through the windows, casting a warm glow on the space, which includes a dining table with chairs.

4.88 out of 5 average rating, 141 reviews

Stylish Avondale 3bed 2 bath with Parking

LocationValueAccuracy

4.93 out of 5 average rating, 138 reviews

Apartment in Bucktown

Cozy Bucktown/Logan Square Close to everything

LocationFamilyIndoor spaces

A cozy living area features a mix of comfortable seating options, including a dark gray sofa and a brown leather chair. A stone fireplace is centered beneath a large flat-screen TV. Large windows are dressed with red curtains, allowing natural light to fill the space.

4.99 out of 5 average rating, 92 reviews

Paradise on the Boulevard!

FamilyLocationGetting around

Apartment in Kilbourn Park

A studio space is presented with a spacious bed in the background, complemented by a wicker swing chair nearby. A vintage SMEG refrigerator and a dining table with stools enhance the ambiance, while a textured area rug lies on the hardwood floor beneath.

4.92 out of 5 average rating, 764 reviews

Explore Chicago from an Urban Sanctuary with Free Parking

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Apartment rentals with a hot tub

4.86 out of 5 average rating, 121 reviews

A modern living area features a light-colored sofa adorned with decorative pillows, set against large floor-to-ceiling windows that offer views of the city skyline. A textured area rug defines the space, while a coffee table displays artfully arranged decorative items. A dining table with black chairs completes the setting.

Apartment in West Loop

Top Floor Views + Central Comfort

ValueFamilyPool

4.77 out of 5 average rating, 107 reviews

Apartment in Vittum Park

Super Paradise+65 Amenities*Downtown 15 Min

FamilyValueLaundry

4.88 out of 5 average rating, 83 reviews

An indoor pool area is featured, highlighting a clean, rectangular swimming pool surrounded by large windows. Lounge chairs are positioned along one side, offering a place to relax. The space is bright with neutral-colored walls and a minimalist design.

Apartment in South Loop

The Aerial Oasis (Indoor Pool • Fitness Center)

LocationValueView

4.89 out of 5 average rating, 27 reviews

Apartment in River West

Luxury 3BD Penthouse – Private Patio+Skyline Views

LocationFamilyBathroom

4.97 out of 5 average rating, 35 reviews

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

Apartment in West Loop

Skyline Oasis: City & Lake Views

FamilyLocationWalkability

4.65 out of 5 average rating, 31 reviews

A spacious bedroom with large windows provides an expansive view of the city skyline. The comfortable bed is flanked by bedside tables with lamps, and art pieces are displayed on the wall. Natural light brightens the room, enhancing its modern aesthetic.

Apartment in West Loop

Level One Bedroom Suite | Fulton Market

LocationValueGetting around

4.9 out of 5 average rating, 60 reviews

Apartment in Chicago

Spacious 1BR | 1 Garage Parking | Nightlife nearby

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