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Holiday rentals in Logan Square

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Top-rated holiday rentals in Logan Square

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

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Guest favourite
Flat in Logan Square
4.7 out of 5 average rating, 195 reviews

Cozy 2BD/1BA in Charming Logan Square

This clean & comfortable 2 BD/1 BA garden unit in Logan Square is the perfect spot to come back to after a day of exploring the Windy City! Just a quick walk to the Logan Square Blue Line L stop, you'll be able to get downtown and back with ease. Cozy up by the electric fireplace when it's chilly or take a stroll through the vibrant neighborhood in nice weather. Here, you're sure to feel at home. Please note - my 2 children (9,4) live upstairs with me half time, awake 7am weekdays, 8am weekends

Top guest favourite
A bright living area features two black leather sofas adorned with vibrant orange throw pillows, facing a flat-screen TV mounted on the wall. A plush dark rug sits beneath a central coffee table, while large windows allow natural light to fill the space.
Flat in Logan Square
4.91 out of 5 average rating, 370 reviews

Logan Square Apartment!

The apartment is close to Logan 11 Bar, The Boiler Room, The Chicago Diner: Logan Square, Revolution Brewery, Cafè Mustache. You’ll love the place because of the location, the neighborhood, transport convenience (30 second walk), Divvy bikes accross street, 606 elevated path amongst countless other things to check out. Travelers, families, & big group welcome but It's NOT a place to host parties, please not that it can be rather noisy because of the bar downstairs. By train 15mins downtown.

Top guest favourite
A cozy sitting area features a vibrant orange sofa adorned with black cushions and a matching ottoman. A wooden desk with a red chair sits nearby, while a floor lamp casts a warm glow. Bright artwork depicting flowers adds a touch of color to the wall.
Guest suite in Logan Square
4.98 out of 5 average rating, 321 reviews

Stylish Studio in Historic Logan Square

Modern garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom and kitchenette is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a magical shared backyard space. The owner's treehouse deck can be reserved. An oasis in the city with exciting city easily accessible!

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
4.98 out of 5 average rating, 304 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!

Guest favourite
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.
Flat in Logan Square
4.77 out of 5 average rating, 385 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.

Guest favourite
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.
Flat in Logan Square
4.96 out of 5 average rating, 108 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.

Top guest favourite
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.
Apartment in Logan Square
4.95 out of 5 average rating, 109 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.

Top guest favourite
A lounge area features a curvy orange sofa, complemented by a black circular coffee table resting on a textured cream rug. Natural light filters through large windows, illuminating framed wall art with subtle hues. Minimalist decor creates a cozy and inviting atmosphere.
Guest suite in Avondale
4.94 out of 5 average rating, 162 reviews

Logan Square Garden Suite

Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. This is a perfect space for solo travelers or couples. This is also a great space if you are traveling with a small child or infant. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine.

Guest favourite
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.
Apartment in Logan Square
4.79 out of 5 average rating, 289 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!

Top guest favourite
A cozy living area showcases a mix of modern and rustic design elements. Exposed brick walls enhance the character of the space, while natural light filters through the windows. A comfortable sofa and a wooden coffee table are positioned atop a geometric-patterned rug.
Flat in Bucktown
4.91 out of 5 average rating, 362 reviews

Bright & Lofty Bucktown 1br

My top-floor apartment in Bucktown is the perfect space for your trip to Chicago! It's a stylish, modern rehab in a classic Chicago building, so you really see the best of what the city has to offer! It's just off beautiful Holstein Park, and easy walking distance to 2 Blue Line stops - so you can get to the Loop in under a half hour! And plenty of Logan Square favorites along Milwaukee are a 15 minute walk away - book today!

Top guest favourite
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.
Flat in Logan Square
4.97 out of 5 average rating, 270 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.

Guest favourite
A simple sleeping area features a spacious bed with neutral-toned linens. Artwork with floral patterns is displayed above the bed, while a decorative arrangement of flowers is positioned on the wall. A door leads to another room, and natural light enhances the space.
Casa particular in Logan Square
4.86 out of 5 average rating, 188 reviews

Studio apartment for 2 people maximum, comfortable and clean, very central with multiple access roads, urban transport and proximity to the train station, a variety of restaurants and shops.

Enjoy the simplicity of this accommodation located in a very central and quiet area, with easy access and very nice people. In addition to this, it has a variety of shops and restaurants nearby. We are very interested in cleanliness for the utmost convenience. Vehicles are parked on the street at no cost.

Popular amenities for Logan Square holiday rentals

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Avg. price$132 SGD$139 SGD$151 SGD$160 SGD$187 SGD$193 SGD$198 SGD$193 SGD$175 SGD$178 SGD$160 SGD$151 SGD
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Quick stats about holiday rentals in Logan Square

  • Total holiday rentals

    Explore 500 holiday rentals in Logan Square

  • Nightly prices starting at

    Logan Square holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 40,990 verified reviews to help you choose

  • Family-friendly holiday rentals

    300 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 160 rentals that welcome pets

  • Rentals with dedicated workspaces

    330 properties have a dedicated workspace

  • Wifi availability

    500 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!

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