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, 298 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.

4.97 out of 5 average rating, 160 reviews

A modern bathroom showcases a mid-century modern vanity in natural wood with two drawers. Above it, a round mirror is complemented by a pendant light. A white toilet is positioned nearby. White hexagon tiles cover the floor, while a skylight fills the room with natural light.

Apartment in Avondale

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

4.97 out of 5 average rating, 110 reviews

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

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, 293 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!

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, 101 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.

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.

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, 699 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."

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!

The exterior of a garden apartment showcases a charming brick facade, complemented by decorative stonework and a covered porch. Lush greenery frames the entrance, while a wrought-iron fence surrounds the inviting front yard, creating a welcoming atmosphere.

4.96 out of 5 average rating, 253 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.

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Popular amenities for Logan Square, Chicago vacation rentals

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BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Logan Square, Chicago

4.96 out of 5 average rating, 91 reviews

A charming raised brick ranch home with a welcoming front porch is displayed. The exterior features large windows, a wooden front door, and a neat landscaping area with greenery, enhancing the curb appeal along a tree-lined street.

Home in Logan Square

City Cottage in Logan Square-Avondale

AshleyRating, 5 stars1 month ago

We loved this cute little house! Super walkable and close to lots of stuff in Logan Square; although we thoroughly enjoyed the peacefulness of hanging out in the private backyard. Would definitely stay again!

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.

4.83 out of 5 average rating, 46 reviews

Sunny garden apartment in West Logan Square

NatRating, 5 stars6 days ago

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

A spacious dining area features a wooden table accompanied by colorful chairs. A mid-century sideboard reflects natural light from large windows adorned with blinds. Houseplants add greenery, while artistic decor and a modern lighting fixture enhance the inviting atmosphere.

4.9 out of 5 average rating, 404 reviews

Sunny Logan Square Artists' home

SarahRating, 5 stars2 weeks ago

Beautiful location, close to transit and very walkable to great lunch and coffee spots and a local grocery store. I especially appreciated all the details like gorgeous plants in every room and every utensil you might need for you r stay. Hosts were welcoming and provided excellent local recommendations.

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.

A well-organized closet features multiple shelves and hanging space, providing ample storage for clothing and belongings. A small plastic storage unit is placed at the bottom, adding to the functional design. Natural light brightens the space through a nearby window.

5 out of 5 average rating, 7 reviews

Romantic & Cozy/walk to restaurants, bars, parks

BenRating, 5 stars1 month ago

Pretty great!

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 Humboldt Park

Amazing Fun Condo, City view next to 606 Trail!

StephRating, 5 stars6 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!

The kitchen area features modern gray cabinetry paired with granite countertops. A sink is positioned on the countertop, accompanied by kitchen utensils and a small plant. The open layout allows visibility of the living space in the background, enhancing a sense of connectivity.