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Family-friendly vacation rentals in South Side

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in South Side

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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A cozy living area features a plush green sofa adorned with patterned throw pillows. A textured rug covers the floor, while a wooden staircase leads to the lofted sleeping area. Natural light filters through the window, illuminating the space.

Guest suite in Chicago

4.96 out of 5 average rating, 338 reviews

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

A spacious living room features large windows draped with light curtains, allowing natural light to fill the space. A comfortable sofa and loveseat are positioned around a decorative area rug, with a television mounted on a cabinet. A rocking chair adds additional seating.

Apartment in Evanston

4.94 out of 5 average rating, 141 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 18 min walk for trains to city, 5 min drive to lake. Wifi

The entrance to the vintage home is framed by lush greenery, showcasing a well-maintained front yard. A charming porch features seating near the steps, inviting relaxation. Large windows provide plenty of natural light, enhancing the home's welcoming appearance.

Apartment in Chicago

4.84 out of 5 average rating, 211 reviews

Cozy Northside Apt near Transp&Beach&Free St Prkng

PRIVATE Entrance, One Bedroom Apt w/ LVG RM near Lake Michigan in beautiful, residential & diverse neighborhood. FREE on street PARKING, OR driveway spot for Addt fee. Sleeps up to 6. *It has a Kitchenette, Full Bath, WiFi, Cable TV, in unit W/D. Close to METRA TRAIN (1 block & 18 min to loop/city center), Bus Stop 1 block & the CTA "L" (elevated) Red Line to City 7 blocks away. Enjoy our proximity to Public Transit, Beaches, Loyola & NW Universities. Great for family, friends & kids.

The image displays a doorway leading to a clean and modern bathroom featuring a white vanity and toilet. A towel rack holds neatly rolled towels, while natural light enters through a window, illuminating the space. The hardwood floor adds warmth to the overall aesthetic.

Apartment in Chicago

4.84 out of 5 average rating, 279 reviews

4BDRM Gorgeous Apt Pilsen Private Prking Available

Stylish Retreat for Groups in Vibrant Pilsen Welcome to our 7-room home in lively Pilsen, perfect for families and groups of up to 10. Enjoy spacious comfort in a prime location. Explore vibrant murals, visit Simone's bar, and savor Sunday brunch at Dusek's. Catch a concert at Thalia Hall or sing at nearby karaoke or grab dim sum. Conveniently located just down the street from Chinatown and close to McCormick Place. Ideal for conventions and city adventures. Book now for an unforgettable stay!

Top guest favorite

A living room features a large bay window with multiple panes, offering a view of greenery outside. A comfortable sofa is adorned with colorful pillows, complemented by a contemporary armchair and side tables. Warm light is provided by a nearby lamp.

Apartment in Chicago

4.98 out of 5 average rating, 246 reviews

North Side Near Wrigley Lakeview Walk Everywhere!!

Located on a beautiful tree lined street one block from the thriving Southport Corridor, one of the hottest neighborhoods in Chicago. You'll love the convenience of being just steps from the Southport Brown Line "L" Stop, you can see the City without ever needing to drive. Steps to outstanding restaurants, bars and shopping. Going to Wrigley Field? Enjoy a 10 minute walk down some of the most beautiful streets in Chicago. Ideal for families seeking comfort, style and a convenient location.

A narrow hallway leads to a kitchen area, featuring a white gas stove and a quaint wooden bench along one side. A bulletin board filled with notes and photos decorates the wall. Natural light streams through a nearby window, illuminating the space.

Apartment in Chicago

4.95 out of 5 average rating, 693 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 cozy living area features a comfortable sofa and two armchairs, with natural light entering through multiple windows. The space is decorated with framed artwork on the walls and a small side table. A television is positioned for easy viewing.

Condo in Chicago

4.83 out of 5 average rating, 339 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

A cozy living area is furnished with two grey sofas adorned with black-and-white checkered pillows. Red chairs are positioned near a wooden side table. A sideboard with magazines adds a touch of practicality, while three windows provide natural light, framed by white blinds.

Apartment in Chicago

4.86 out of 5 average rating, 125 reviews

Bingham 2/2

Short walk to Blue Line nestled on a block with easy access to Bucktown & Logan Square. Second floor duplex with a den/third bedroom on main floor. All sleeping spaces have doors. Great location for business downtown, Cubs game, parents weekend at most of our universities. Easy walk to some of Chicago's hottest restaurants, bars, breweries and coffee shops. Plus, easy access to beautiful parks. Quiet family neighborhood.

A comfortable living room features a vibrant orange sofa, complemented by a glass coffee table and a patterned area rug. Potted plants provide greenery, while light fixtures add warmth to the space. Two additional seating options are included, creating an inviting atmosphere.

Apartment in Chicago

4.9 out of 5 average rating, 198 reviews

Fairfield Flat, Airy Vintage Rehab

This remodeled first floor apartment is close to the California Pink Line Station, Pete's Fresh Market, Lagunitas Brewery & Tap Room and Douglass Park. Pilsen and West Loop night life just a short train ride away. Situated in a quiet corner of Little Village, our neighborhood of predominately Mexican and Black multi-generational families is teeming with tamale stands, paleta vendors, and children playing.

A bright, open living area features a gray sectional sofa, a coffee table, and a light-colored rug. Large windows provide ample natural light, while a ceiling fan adds comfort. A dining area and kitchen are visible in the background, enhancing the spacious feel.

Townhouse in Chicago

4.95 out of 5 average rating, 260 reviews

The Nancy’s gorgeous , Spacious Urban Getaway

This conveniently located and newly renovated townhouse in Edgewater features tons of sunlight and plenty of room for large families or groups. Near the lakefront, Loyola University, Andersonville, and tons of great restaurants and bars. In close proximity to the Red line "El" train, the city bus (22 Clark) and just four (4) miles from Evanston and Northwestern University.

The exterior of a charming Victorian house is showcased, featuring a white facade, large windows, and a decorative entryway. An American flag hangs from the porch, surrounded by greenery and a well-maintained pathway leading to the entrance.

Apartment in Chicago

4.9 out of 5 average rating, 184 reviews

Clean, spacious, walk to Wrigley! Self check-in!

Park your car and forget it- or just leave it at home! Charming 3 BR first floor apartment in a Victorian building in the ultimate location, perfectly situated between Wrigleyville and Lincoln Park in the beautiful, vibrant Lakeview neighborhood. Guys seriously… this is the ideal neighborhood for a Chicago getaway or visit with family.

Top guest favorite

A cozy living area is shown, featuring two dark leather chairs and a matching ottoman. A built-in wooden shelving unit holds books and decorative items, while a flat-screen TV is mounted above a stone fireplace. Natural light filters through the window treatments.

Home in Chicago

4.93 out of 5 average rating, 153 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

Sophisticated Roscoe & Halsted duplex w garden. Sleeps 6 - 3 beds in 3 bedrooms + 2.5 baths. Steps from bars & restaurants, 2 blocks from Wrigley Field & Lake Michigan. Perfect for sports enthusiasts, enjoy Boystown, get-aways. In addition to central heat and air conditioning, ceiling fans with remote control in each bedroom.

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Popular amenities for South Side family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern living area features a gray sectional sofa and a patterned armchair, inviting relaxation. A small round table sits beside the sofa, topped with decorative plants. Natural light floods in through large windows, illuminating the neutral-toned walls.

Apartment in Chicago

4.97 out of 5 average rating, 36 reviews

The Playwright's Palace

The spacious living area features an open layout with hardwood floors, a stylish orange accent wall, and a cozy fireplace. A large sofa and a wooden coffee table are positioned for relaxation, while a dining area and kitchen are visible in the background.

Home in Chicago

4.85 out of 5 average rating, 314 reviews

Lux Urban 3BR/3BA Duplex + Parking!

An indoor pool area features a tranquil setting with sleek lounge chairs arranged beside the water. Large glass windows allow natural light to fill the space, providing views of the outside. The tiled floor complements the modern design, creating a serene atmosphere.

Apartment in Chicago

4.73 out of 5 average rating, 59 reviews

The Professional's Playground

A modern lounge area features a spacious blue sectional sofa with decorative pillows, framed artwork on the wall, and a coffee table. An expansive view of the city skyline and lake is visible through large windows. A sleek kitchen showcases stainless steel appliances and contemporary cabinetry, while a stylish bedroom includes a four-poster bed and elegant accents.

Apartment in Chicago

5 out of 5 average rating, 31 reviews

Lux Loop Retreat: Amazing Views, Free Parking

Top guest favorite

A peaceful outdoor space is presented, featuring a stone patio with wicker furniture, surrounded by lush green grass and well-maintained flower beds. A large tree provides shade, enhancing the natural ambiance of the garden area.

Condo in Chicago

4.98 out of 5 average rating, 270 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

A spacious bedroom features a large bed with neutral-toned bedding. Two matching lamps on bedside tables illuminate the area. Large windows with light fabric treatments allow natural light to enter, while a potted plant adds a touch of greenery to the room.

Apartment in Chicago

4.33 out of 5 average rating, 24 reviews

Spacious 2bdm unit 15min to Dwtn

A modern living area features a cozy seating arrangement with large windows showcasing panoramic views of the Chicago skyline. The stylish bedroom is adorned with elegant decor, while a luxurious bathroom displays sleek fixtures and essential amenities for comfort.

Apartment in Chicago

4.88 out of 5 average rating, 200 reviews

Stunning Panoramic Chicago Views & Free Parking

The exterior of a multi-story apartment building is depicted, featuring a brick facade and multiple balconies with railings. The structure is set against a clear sky, with trees visible in the foreground, contributing to the neighborhood's character.

Condo in Chicago

4.89 out of 5 average rating, 9 reviews

Bright and Beautiful Penthouse - Close to the lake

Family- and pet-friendly home rentals

A bright workspace featuring two desks is positioned against a green wall. Each desk is equipped with a desk lamp and various office supplies. Natural light enters through two windows, framed by wooden trim, highlighting the polished wooden floor.

Apartment in Chicago

4.89 out of 5 average rating, 398 reviews

Sunny Logan Square Artists' home

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

Guest suite in Chicago

4.94 out of 5 average rating, 157 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Townhouse in Chicago

4.85 out of 5 average rating, 169 reviews

Downtown Elegance ✨ Private Yard Parking

Top guest favorite

The bathroom features a tub and shower combination alongside a white vanity with dual sinks. Shelving holds neatly folded towels and essentials. Natural light is provided by a window above the sink, enhancing the spacious feel of the room.

Apartment in Chicago

4.93 out of 5 average rating, 430 reviews

Andersonville Living

A well-organized bathroom features wooden cabinetry and a spacious vanity area with dual sinks. Vanity lights create a bright environment, while two framed mirrors enhance the space. Towels and personal items are neatly arranged, providing functionality and ease of access.

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 338 reviews

a SIMPLE place

A dining area features a round wooden table surrounded by six black chairs. A faux greenery accent wall adds texture, complemented by a non-operational neon sign above. Natural light enters through two windows, illuminating the space with a neutral rug beneath the table.

Apartment in Chicago

4.94 out of 5 average rating, 237 reviews

Cool and Modern Chicago Apartment near Transit

Top guest favorite

A sunlit living area features large windows framed by wooden accents, allowing natural light to illuminate the space. A comfortable futon is positioned alongside an armchair and a glass coffee table on a textured rug, with a small television and simple wooden furniture completing the layout.

Apartment in Chicago

4.95 out of 5 average rating, 509 reviews

2nd floor of 1908 brick two-flat in Logan Square

A spacious bathroom is equipped with a double vanity featuring wooden cabinets and a white countertop. Two mirrors are mounted above the sinks, with stylish lighting fixtures above. A large walk-in shower is visible on one side, and natural light filters through a nearby window.

Apartment in Chicago

4.85 out of 5 average rating, 161 reviews

*Comfortable & Spacious Home Close to Downtown*

Family-friendly home rentals with a pool

Apartment in Chicago

4.63 out of 5 average rating, 60 reviews

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

Apartment in Chicago

4.76 out of 5 average rating, 216 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

A spacious living area features a grey sectional sofa positioned adjacent to a wooden coffee table. An art piece depicting a forest scene adorns the wall, while a dining table with chairs is visible in the background, illuminated by natural light through the window.

Guest suite in Berwyn

4.67 out of 5 average rating, 43 reviews

Music Hot Spot’s Main Level

Apartment in Chicago

4.78 out of 5 average rating, 237 reviews

Luxury Corner 2 Bedroom in the Loop | Roof Deck

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