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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Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 326 reviews

Bright, Modern Apartment in a Vintage Greystone

Enjoy morning coffee by the sunny bay window in this vintage apartment with classic modern style. The apartment features vintage charm with modern amenities, queen memory foam bed in bedroom and queen sofa bed in living room. Parking is available in the back lot for an additional $25 per night. For reservations over three weeks, we require a cleaning every 2 weeks at a cost of $60 per cleaning. Apartment is located on the 3rd floor of a three story building and you will need to climb stairs. This is a large 1100 square foot fully renovated 1 bedroom apartment on the third floor of a beautiful vintage Chicago Grey Stone. Located directly on Chicago Ave. The space was thoughtfully designed by the design firm of Inside Home with the modern traveler in mind. The furnishings are a mix of vintage and new pieces specially curated for the space. The bedroom features a queen memory foam mattress as well as a 42" TV. The kitchen is equipped with cutlery, cooking utensils, coffee maker, espresso machine, pots & pans, baking sheets. Walking Rating of 96! You will have access to the full 1100 square foot apartment as well as a parking spot if needed located directly out back for an additional $20 per night, please notify us at the time of booking if you will require parking and we will add this fee to your reservation. There is also a washer and dryer in the basement if need (please request access) We will be on site at the furniture store located on the ground floor of the building should you need anything during your stay. Ukrainian Village is a historic community known for the contemporary restaurants, bars, and shops along bustling Chicago and Division Streets, but explore the neighborhood further to discover homes and businesses as old as the city itself. You are steps away from the 66 bus, which will take you directly to Navy Pier, rent a bike and explore the city or catch a cab right out side the front door or jump on the blue line "EL" train. This apartment has a walk rating of 96, bike rating of 90 and a transit rating of 72! This apartment is located on the third floor of a three story walk up. There is a additional queen bed in the sofa of the main room and all the additional bed linens are located in the bedroom night stand and closet.

Feb 6 – 13

$126 per night

Guest favorite

Apartment in Chicago

4.85 out of 5 average rating, 160 reviews

Your brand new Chicago suite (unit 1F)

Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.

$59 per night

Guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 188 reviews

Attic cozy guests suite near South Loop in Chicago

We invite you to visit Chicago and stay in our attic cozy apartment near South Loop in Bridgeport. Parking is available on the street. 15 minute walking distance to CTA Train-Orange and Red lines. CTA bus stop 5 minutes away. Downtown Chicago 15 minutes away with a car. Uber/Lyft - $7.00-12.00. Apartment is located 20 minutes away by foot from U.S. Cellular field (White Sox) and 10 minutes away by car from Soldier Field (Bears). You can also reach Wrigley Field with the CTA Red Line.

$97 per night

Guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 242 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. Ask about winter specials!

Dec 1 – 8

$84 per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 237 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".,

Nov 13 – 20

$90 per night

Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 300 reviews

Vintage Bridgeport Apartment

This AirBNB is located within Bridgeport, on Chicago's South Side. You're only a short walk from grocery stores, restaurants, bars, cafes, and whatever else you may need on your trip. We welcome all with open arms. All religions, nationalities, genders. No smoking inside the building, including the back porch. We are no longer accepting new guests with pets. If you stayed with us in the past with a pet they are more than welcome back!

Jul 10 – 17

$127 per night

Guest favorite

Townhouse in Chicago

4.85 out of 5 average rating, 275 reviews

CITY CONDO with GARAGE 7 min Walk to Train

Experienced Super-host offers private spacious & sunny condo 3 miles from Chicago "Loop" Lakefront and Museums. Large one bedroom with king size premium mattress, and full sized sofa-bed sleeps 4. 1 FREE garage PARKING wi-fi , washer & dryer. BUS to city center is across the street. 10 minute ride to city center. Walk to United Center Bulls/Blackhawk games /concerts and large international grocery store. Note- WE DO NOT HOST SMOKERS.

Nov 3 – 10

$80 per night

Guest favorite

Apartment in Blue Island

4.93 out of 5 average rating, 264 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Oct 26 – Nov 2

$121 per night

Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 170 reviews

Bridgeport Garden Apartment

Enjoy a peaceful stay at this colorful, creative, artsy and relaxing garden unit apartment in the heart of Bridgeport. Located a few blocks away from Bridgeport's best bars and restaurants. This unit is good for couples, solo adventurers, business travelers and families (with kids). Street parking is free, and I’m readily available via phone or in person (I live a few minutes away).

Aug 7 – 14

$96 per night

Guest favorite

Condo in Chicago

4.97 out of 5 average rating, 703 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

$97 per night

Superhost

Apartment in Chicago

4.92 out of 5 average rating, 152 reviews

Urban Pilsen Apt. near Downtown

Cozy, urban Pilsen apartment in "Heart of Italy" with authentic old-style Italian restaurants. The apartment is very warm and open, has a gourmet kitchen, lots of natural light and is conveniently located 2 miles from the UIC Medical District, 3 blocks from the Pink Line and under 4 miles from downtown Chicago.

Sep 25 – Oct 2

$98 per night

Superhost

Apartment in Chicago

4.78 out of 5 average rating, 210 reviews

Heart of Chicago 2BD + Parking

Comfortably fits 5. Two private bedrooms and a daybed in the living room with trundle. Impecable bathroom with great lighting. State of the art stainless steel appliances for a quick meal at home before a day in town. Warm cotton towels and clean linen. Interested yet? Ask me about my space :)

Sep 9 – 16

$97 per night