Holiday rentals in Logan Square, Chicago

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

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

Flat 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.

Top guest favourite

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.

Top guest favourite

Guest suite in Logan Square

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!

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

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.

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

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

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!

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.

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Popular amenities for Logan Square, Chicago holiday rentals

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Other great holiday rentals in Logan Square, Chicago

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.

4.82 out of 5 average rating, 45 reviews

Sunny garden apartment in West Logan Square

NatRating, 5 stars2 days ago

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

4.89 out of 5 average rating, 62 reviews

Sunny and Funky 2-bedroom in Logan Square

JohnRating, 5 stars1 week ago

Anton's place is a nice, cozy getaway close to lots of things in Chicago but far enough away for it to be quiet.

5 out of 5 average rating, 7 reviews

Romantic & Cozy/walk to restaurants, bars, parks

BenRating, 5 stars1 month ago

Pretty great!

4.95 out of 5 average rating, 61 reviews

Home in Humboldt Park

Private Logan Square Garden Apt

AthenaRating, 5 stars1 week ago

Had a lovely stay at Janice's place! It is located a short drive from Logan Square, which has restaurants, bars, and a blue line metro stop. There was also a bus stop just outside the neighborhood. Speaking of the neighborhood, it was very serene and private, with plenty of parking regardless of the time of day. The airbnb is a basement unit, so maybe something to keep in mind if you're on the taller side, but it was spacious, and there was minimal noise from the floor above. Shower had great water pressure! Bedroom was clean and comfortable. Janice was very communicative and clear instructions were given for checkin and checkout processes.

Top guest favourite

Flat in Avondale

5 out of 5 average rating, 36 reviews

Renovated Loft on Milwaukee Ave

ArianeRating, 5 stars2 weeks ago

We had an amazing experience at this Airbnb! The space is beautiful, with tall ceilings, sky lights, and a layout that feels open and inviting. This place is incredibly spacious, with a kitchen that was perfect for cooking and gathering. It was very clean, with clear instructions for checking in and out. The beds were super comfortable, and despite being in such a lively area, the space was surprisingly quiet. The Airbnb is located right above a bar that serves an incredible grilled cheese. One of our favorite touches was the pinball machines! A unique touch that added charm and entertainment. It's about a 15-minute drive to downtown without traffic. We appreciated the provided parking passes. However, parking could be challenging at times. The location couldn’t be better—surrounded by restaurants, cafes, bars, and shopping, all within easy walking distance. Plus, the place was loaded with amenities that made it feel like a home away from home. Would absolutely stay here again!

Apartment in Humboldt Park

4.93 out of 5 average rating, 61 reviews

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!