Holiday rentals in Logan Square, Chicago

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Top-rated holiday rentals in Logan Square, Chicago

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Guest favourite

Flat in Logan Square

4.96 out of 5 average rating, 376 reviews

King Bed, Huge Spa Shower, Dining Destination

This home was designed with love! Inspired by our favorite boutique hotels - nestled on a tree-lined street in Logan Square, a locals-only destination for brunch, coffee, craft beer and cocktails. Relax in the massive custom steam shower or catch up on HBO on the 50” WiFi TV. Luxe details throughout -premium espresso, memory foam beds and upgraded linens, fully-equipped kitchen. Both bedrooms have private baths, lots of outlets and huge walk-in closets. Easy parking! Central location- Quick walk to Blue Line Train (DIRECT to ORD) - 10 / 15 min to anywhere- Loop, Wicker Park, Lincoln Park! We have tried to attend to every detail- I love boutique hotels and I wanted our Airbnb to reflect that experience. This is a two-bedroom, two-bath private apartment and the garden level of our historic greystone, a classic Chicago property type. The space was newly renovated for friends and family - a luxurious city getaway surrounded by our favorite restaurants. It is warm and cozy with in-floor heat. Truly easy street parking, a rarity in the city. Five minute walk to train at Logan Square Blue Line (20 min direct connection to O’Hare Airport/ORD) and around the corner from top-rated restaurants-blocks to Fat Rice, Longman & Eagle, and Lula, all Michelin rated. Don’t miss brunch at Jam, pozole at Quiote and tiki drinks at Lost Lake, ranked one of the fifty best bars in the world- all walkable. The master has a king-size memory foam bed, individual reading lights with dimmers, and an ensuite bath with massive walk-in steam / rain shower. Second bedroom has a cozy memory foam double bed, private ensuite bath with new oil-rubbed bronze fixtures and cast iron Kohler tub. Both beds have premium 100% cotton linens, black out shades, nightstands with convenient outlets, and walk-in closets -- plenty of room for luggage. Our brand new kitchen has lots of bells and whistles -a Bosch convection oven, garbage disposal, ice maker, filtered water built into the sink and pantry with starter items for cooking. We offer unlimited Nespresso and a french press with whole bean Intelligentsia, our favorite local coffee. Enjoy a night in with our 50" 4K WiFi TV - HBO, Netflix, Amazon Prime, and Spotify Premium are logged in and ready to go. Private entrance. Lots of extras while preserving the character of a classic Chicago home. You're welcome to enjoy the backyard (we have great neighbors). Trash / recycling through gate behind yard. Shared free laundry. I'll meet you at check-in if possible and make some recommendations. I have lived in Chicago since 2001 and love to share tips about my favorite city in the world. I'm a real estate agent and easy to reach, but otherwise, the home is yours to enjoy! Diner’s paradise! Four blocks to Blue Line- This cozy garden retreat is a half block to the neighborhood’s famous Logan Boulevard, lined with park space and historic mansions. Steps to independent coffee shops, brunch and the city’s best cocktails. Walk to tropical drinks at Lost Lake, Michelin rated gastropub Longman and Eagle, fresh pasta at Daisies and local favorite Lula. You’re also an easy eight minute walk to the Logan Square Blue Line. Easy / free street parking. Logan Square is extremely central. We are a four block walk to Blue Line Train (which connects directly to ORD/O’Hare Airport!) and joins all trains with a 15 minute ride South toward the Loop. The Blue Line runs underground and does not share tracks- it is by far the fastest city train line. This neighborhood is particularly easy for cabs as you are only 2 minutes from the 90/94 Expressway: - 10 minutes to Wicker Park - 10 minutes to Lincoln Park - 8 min to West Loop/Fulton Market -15/20 min to Magnificent Mile/Wrigley This is the garden (ground) level of a two-flat- You will hear occasional footsteps above but residents are respectful and polite- they are two professional women and not early risers! Based on my personal spent time in the unit, this will not impact your experience in a significant way. Although we have honored historic details wherever possible, this is a brand new apartment with great insulation. We offer a white noise machine just in case. Ceilings are over 7 ft and while not soaring, tall guests have been comfortable. The unit has radiant in-floor heating (no cold feet!) controlled in your unit with a traditional thermostat. Because it is an English garden and partially below grade, the temperature is very stable. We have window air conditioners for summer.

14–21 Jan

$220 SGD per night

Guest favourite

Flat in Logan Square

4.91 out of 5 average rating, 373 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.

20–25 Sep

$176 SGD per night

Guest favourite

Flat in Logan Square

4.96 out of 5 average rating, 164 reviews

2BR Centrally Located in Cozy Hip Logan Square

Explore one of Chicago's most popular neighborhoods, Logan Square, home to hipsters, artists, techies and foodies. I am inclusive and welcome all! The bnb is 1.5 blocks from the El blue line direct from O'hare airport, 25 minutes to downtown Chicago (via El blue line), and a 15 minute drive to the United Center. You can walk to plenty of great restaurants, bars, parkland space, and in the summer, Italian ice and a great farmer's market every Sunday. There is plenty of street parking.

3–10 Oct

$181 SGD per night

Guest favourite

Guest suite in Logan Square

4.97 out of 5 average rating, 226 reviews

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

1–8 Oct

$152 SGD per night

Guest favourite

Flat in Avondale

4.97 out of 5 average rating, 118 reviews

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.

8–15 Jul

$162 SGD per night

Superhost

Flat in Logan Square

4.9 out of 5 average rating, 283 reviews

Modern Logan Square Apartment, steps from train!

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.

23–30 Dec

$180 SGD per night

Guest favourite

Flat in Logan Square

4.9 out of 5 average rating, 257 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! Early Check-Ins and Late Check-Outs are difficult to accommodate.

18–25 Jan

$158 SGD per night

Guest favourite

Flat in Humboldt Park

4.98 out of 5 average rating, 107 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.

20–27 Oct

$165 SGD per night

Guest favourite

Guest suite in Logan Square

4.97 out of 5 average rating, 239 reviews

Stylish Studio in Historic Logan Square

Brand new, unique 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 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 fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Convenience & excitement are easily accessible!

10–17 Sep

$207 SGD per night

Guest favourite

Flat in Logan Square

4.89 out of 5 average rating, 339 reviews

Sunny Logan Square Artists' home

2nd floor classic Chicago 2flat with lots of light. 3 bedrooms available, with 2 additional sofabeds. Great if you and family/group of friends are in town for an event and want to stay together. Grocery store 1.5 blocks away. Quiet street. Parking is decent. New bath has all marble walls, extra long/deep tub and rain shower. 1 mile walk to the Logan Square CTA Blue Line and Logan Square brunch/night-life. 5 min walk to Metra. Walk to 606 trail.

11–18 Jan

$148 SGD per night

Guest favourite

Flat in Logan Square

4.93 out of 5 average rating, 208 reviews

Cozy Private Coach House

This is a cozy 1 bedroom unit in a private coach house. Excellent location in the middle of trendy Logan Square! Please Inquire about winter time longer stays! Stays 30+ days avoid local taxes! I have a 28 night minimum in the winter, until the end of February or possibly March. But I recommend putting in at least 30 days to avoid those taxes!

15–22 Oct

$186 SGD per night

Guest favourite

Flat in Logan Square

4.96 out of 5 average rating, 220 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.

7–14 Sep

$238 SGD per night