Holiday houses 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
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.
Apartment in Logan Square
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.

Guest favourite
A spacious bedroom features a King-sized bed adorned with two decorative pillows. Nightstands on either side hold lamps and small potted plants. Natural light enters through two windows, highlighting the light-colored walls and flooring. A closet with sliding doors provides additional storage.
Apartment in Logan Square
4.88 out of 5 average rating, 217 reviews

Cozy and Comfy 1BR Apartment in Logan Square!

Welcome to Chicago! Our 1-bedroom/1 bathroom apartment unit is perfect for getaway to Chicago. It's professionally designed with modern furniture and located in the trendy Logan Square neighborhood. Designated parking spot is NOT available, but there is plenty of street parking. NOTE: -This is a basement unit with a low ceiling ( HEIGHT: 5.9 ft.). ONLY SUITABLE FOR SOMEONE AROUND or UNDER 5.8 FT. -There are two windows in the bedroom and two windows in the living room for natural light.

Guest favourite
Apartment in Logan Square
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.

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.
Condo in Logan Square
4.98 out of 5 average rating, 309 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
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.
Apartment in Logan Square
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.

Top Guest favourite
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.
Apartment in Logan Square
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.

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, 170 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. 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. This is a quiet, owner-occupied property best suited for travelers visiting Chicago. It’s not intended for gatherings or local stays.

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.
Condo in Logan Square
4.79 out of 5 average rating, 297 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 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.
Apartment in Logan Square
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."

Guest favourite
An open living area features a comfortable sectional sofa upholstered in neutral tones, accented by colorful cushions. A large-screen TV is positioned on a simple console, while natural light from a window brightens the space. A potted plant and decorative elements add charm.
Guest suite in Logan Square
4.91 out of 5 average rating, 180 reviews

New Bright & Airy Entire Unit in Logan

This new modern unit is located in West Logan, one of the most exciting neighborhoods in Chicago. Close to public transportation, 2 blocks from the 606 Bloomingdale recreation trail, and minutes away from the best restaurants and bars in the city! Wifi, large-screen TV with streaming channels, washer/dryer, kitchenette, mini fridge, coffee/tea, board games, free street parking. You will love this custom designed & converted space!

Guest favourite
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.
Apartment in Logan Square
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.

Guest favourite
Apartment in Logan Square
4.92 out of 5 average rating, 591 reviews

2BR Bursting w/ Character in Hip Logan Square!

The unit sits on our extra wide city lot in the center of hip Logan Square! The apartment is eclectic and well decorated, with vintage touches and full of charm. For a garden unit it feels spacious, clean, bright and comes with all of the desired amenities, including access to our spacious side yard!

Popular amenities for Logan Square holiday rentals

When is the best time to visit Logan Square?

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Avg. price$181 NZD$185 NZD$205 NZD$212 NZD$247 NZD$256 NZD$263 NZD$256 NZD$232 NZD$236 NZD$212 NZD$200 NZD
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Quick stats about holiday rentals in Logan Square

  • Total holiday rentals

    Explore 460 holiday rentals in Logan Square

  • Nightly prices starting at

    Logan Square holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 39,190 verified reviews to help you choose

  • Family-friendly holiday rentals

    290 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 150 rentals that welcome pets

  • Rentals with dedicated workspaces

    330 properties have a dedicated workspace

  • Wi-Fi availability

    450 of Logan Square holiday rentals include Wi-Fi 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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