Family-friendly holiday rentals in Logan Square, Chicago

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Logan Square, Chicago

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Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 377 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.

Guest favourite

Apartment in Chicago

4.9 out of 5 average rating, 273 reviews

Tree top 2nd floor 3 bedrm Apt

Guests can stay up on the 2nd FL of a classic Chicago two flat. 3 bedrooms. NO CLEANING FEE. We hate hidden fees and that's the only one we have control over so we're getting rid of it for you! We've hosted for 8 years now and care deeply about our space and the folks we host. We do all of our own cleaning, and live below on the 1st floor. We're available to help with anything guests may need. In the spirit of why homesharing originally became popular a decade ago, let us welcome you to CHICAGO!

Superhost

Apartment in Chicago

4.9 out of 5 average rating, 285 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.

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!

Guest favourite

Guest suite in Lincoln Square

4.95 out of 5 average rating, 243 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Level 2 EV charger available.

Superhost

Apartment in Logan Square

4.85 out of 5 average rating, 752 reviews

Hip Chicago Apartment - FREE Parking Spot Included

You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run

Guest favourite

Apartment in Roscoe Village

4.95 out of 5 average rating, 242 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Guest favourite

Condo in Chicago

4.98 out of 5 average rating, 235 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

Apartment in Logan Square

4.89 out of 5 average rating, 341 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.

Superhost

Apartment in Logan Square

4.78 out of 5 average rating, 197 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!

Guest favourite

Apartment in Chicago

4.95 out of 5 average rating, 654 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

Apartment 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.