Vacation rentals in Logan Square, Chicago

A wooden deck features two intricately designed metal chairs and a small table. Potted plants are placed nearby, and greenery from a tree is visible through the railing, providing a natural ambiance.

4.96 out of 5 average rating, 297 reviews

Logan Square 2nd Floor Chicago Victorian

Walk up the stairs to your sunny 7 rm, 2 queen bedrooms with full kitchen & 10' ceiling. 1/2 block the 2.9 mile walking/running/biking 606/Bloomingdale Trail that travels over other neighborhoods you can explore. In 2024, 'Time Out Magazine' voted Logan Square, one of the top 'Cool Neighborhoods in the World'. Walking distance to many restaurants, bars, breweries (beer & coffee) 20 min. walk to the Blue Line 'L' for O'Hare or Downtown. Rosa's - 'Chicago's Best Blues Club' - NY Times- 3 blocks

A vintage brick building features an inviting entrance with a maroon awning. The path is framed by well-maintained greenery, leading to dual wooden doors. Large windows are positioned above, allowing natural light to illuminate the space.

4.91 out of 5 average rating, 425 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.

Apartment in Humboldt Park

A spacious living area is highlighted by sloped ceilings and wooden beams. A comfortable sectional sofa and a coffee table are nestled on a well-kept area rug. A television is positioned against the wall, while natural light filters in through two skylights.

4.99 out of 5 average rating, 138 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Guest suite in Logan Square

A staircase featuring wooden steps leads upward, bordered by a textured brick wall. A single window allows natural light to brighten the space. A decorative Chicago flag is mounted on the wall, adding a touch of local character.

4.97 out of 5 average rating, 292 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!

A stone pathway meanders through a lush garden filled with ferns and various greenery. Overhead, a wooden pergola is partially covered with climbing plants, adding to the serene ambiance. Natural light filters through the foliage, creating a tranquil setting for relaxation.

4.93 out of 5 average rating, 126 reviews

Logan Square Garden Sanctuary

This house is located in historic Logan Square. The space is a newly renovated basement unit of an owner-occupied two-flat. It's right next to Palmer Square which is a two acre park with a jogging path, kids area, and benches. It's a perfect place to have a picnic or meet with friends. The neighborhood is very walking-friendly and there's tons of great shops and restaurants in the area. The unit has an open floor-plan with a comfy memory foam bed, futon, a full bathroom, and kitchenette.

Superhost

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, 368 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.

The exterior of a three-story apartment building is visible, featuring white siding and multiple windows. A shaded front yard is bordered by a black wrought iron fence. The building is flanked by two neighboring residences, showcasing a blend of architectural styles in a tree-lined street.

4.9 out of 5 average rating, 100 reviews

Bright & Cozy 1-Bedroom Apartment in Logan Square

Bright and charming top floor apartment in the trendy Logan Square neighborhood. Located on a quiet tree lined residential street with multiple restaurants, bars, and coffee shops within walking distance. The CTA blue line station is an easy 20min walk or 10min bus ride away. Or hop on a Divvy Bike; the rental station is located at the end of the block. The 606 Bloomingdale Trail is less than 2 blocks away and is your direct route to endless amenities and destinations.

Superhost

A reflective metallic sculpture, known as 'The Bean,' is situated in an urban park surrounded by tall skyscrapers. Visitors are seen nearby, engaging with the sculpture, while trees and landscaping add a touch of nature to the bustling city environment.

4.84 out of 5 average rating, 165 reviews

Funky & newly remodeled 1 bed in Hip Logan Square

Recently remodeled 1 bedroom garden apartment with a fun aesthetic in hip Logan Square. Walking distance to top bars, restaurants and coffee shops such as Sugarmoon, Park & Field, Best Intentions, Lou Malnatis, Damn Fine Coffee Bar and many more. Blocks from the 606 Trail, 90/94 & public transportation. Lovely shared front yard landscaped with florals + garden beds. We will pass along a welcome guide with a list of all our favorite places in the neighborhood!

4.94 out of 5 average rating, 125 reviews

Guest suite in Avondale

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 suite in Logan Square

A modern kitchenette is showcased, featuring a compact refrigerator and various coffee-making appliances. Colorful artwork is displayed above the counter, adding visual interest. Shelves hold decorative plants and kitchen essentials, with a sleek, wooden countertop and light-colored flooring enhancing the contemporary design.

4.91 out of 5 average rating, 147 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!

The exterior of a historic graystone building is showcased, featuring a symmetrical façade with large windows. Lush greenery climbs along the side, while steps lead up to a welcoming entrance with a covered porch. Natural light enhances the building's stone texture.

4.96 out of 5 average rating, 256 reviews

Pelotoning while Airbnb'ing in Chicago!

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.

A red brick four-flat building is captured from street level, showcasing an ornate entrance framed by a decorative arch. Metal fire escapes are visible on either side, complementing the exterior while large windows allow light to enter. A black wrought iron fence lines the front property.

4.91 out of 5 average rating, 159 reviews

Cozy 1BR in the heart of Logan Square

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!

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Popular amenities for Logan Square, Chicago vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Logan Square, Chicago

A modern kitchen features dark cabinetry paired with light granite countertops. Stainless steel appliances are included, with a large island at its center. Natural light enters through multiple windows, illuminating the space. Decor accents and kitchen tools are neatly arranged on the countertops.

4.96 out of 5 average rating, 27 reviews

Midcentury, comfy 2bed/2bath

MarkRating, 5 stars1 month ago

Diana was great. She was immediately responsive to any question or if I needed anything. She was also very friendly and just made staying at her place very comfortable. The place has a lot of space, which is really nice. The 608 walkway is 2 blocks away and is a great walk, and allows you to exit at various points and visit the Logan Park area, and get food, etc... Getting to Wrigley or thr Frank Lloyd Wright house is a quick drive (arnd 5/6 miles). I didnt want to leave and really enjoyed my stay at Diana's place.

A lush garden area features a grassy ground and is home to chickens foraging. A wooden structure and trellis can be seen in the background, providing a shaded outdoor space. Various plants and green foliage contribute to the inviting environment.

4.82 out of 5 average rating, 45 reviews

Sunny garden apartment in West Logan Square

NatRating, 5 stars3 days ago

Cozy and great place! The neighborhood is quite safe and very close to 606. The rooms are spacious and clean.

5 out of 5 average rating, 59 reviews

A well-lit bathroom features a niche with three neutral-toned bottles labeled as shampoo, conditioner, and body wash. A small potted plant adds a hint of green against the backdrop of white hexagonal tiles and glass block windows, enhancing the space's clean design.

Guest suite in Avondale

Blue Abode off the Blue Line | Sunny & Quiet

CodyRating, 5 stars3 weeks ago

The proximity to Belmont station of the Blue Line CTA train was incredible. Plenty of places to eat and drink within walking distance. I appreciated the stylish interiors, and the Palo Santo and Sage in the bathroom. The hosts were friendly! I would stay here again when I am in Chicago.

4.93 out of 5 average rating, 61 reviews

The exterior of a modern three-story condo is depicted, showcasing a facade of light-colored brick and large windows. Lush green leaves partially frame the top of the image, while a bright sky with scattered clouds forms the backdrop.

Condo in Logan Square

Amazing Fun Condo, City view next to 606 Trail!

StephRating, 5 stars3 days ago

Ken’s place was a great stay! Such a unique home with so much to see inside—decor, art, photos, and trinkets. We enjoyed relaxing in the space between exploring the city. Would recommend to anyone who is considering staying in Chicago!

Superhost

A spacious restaurant interior features dark wooden floors and a black bar stocked with an assortment of beverages. Wooden tables and black chairs are arranged throughout the dining space, while large windows allow natural light to fill the area.

4.87 out of 5 average rating, 103 reviews

Beautiful 3 bed 2 bath in Avondale, Logan Square

Tatiana MargueriteRating, 5 stars5 days ago

Beautiful, functional, and well equipped space for a family of 6. Check in was smooth, instructions were clear, and the space was pristine. The neighborhood is very safe, walkable to great cafes + restaurants, and local transit. The fridge has filtered water and ice. There is a gym within walking distance that offers a $20 day pass. I would stay here again in a heartbeat

Casa particular in Logan Square

A cozy lounge area is furnished with a dark sofa adorned with bright yellow cushions. A wooden table sits in front, complemented by decorative plants. The wall is accented with a large mirror, and a staircase leads to the upper level, illuminated by soft overhead lighting.

4.86 out of 5 average rating, 152 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.

JuanRating, 5 stars1 day ago

Private, quiet and clean. This place will make you feel right at home! 15min walk to nearest train station and buses that will take you downtown a block away! The neighborhood has lots of restaurants and is very safe. Hosts were friendly and responsive. Highly recommended!!

4.99 out of 5 average rating, 95 reviews

Apartment in Avondale

Plants and Art | Near Trendy Restaurants & Bars

JosephRating, 5 stars1 week ago

My family and I had a great 3-night stay at Lynette and Efrain’s place. As others have said, the photos don’t quite do it justice. Pristinely clean, great layout, comfy beds, cool plants and art, and a kind & responsive host. Highly recommended and will stay again when in Chicago.