Family-friendly holiday rentals in Oak Lawn

New by Midway Airport

Located 4 miles away from Midway Airport in Chicago, Seat Geek Stadium 4 miles away, 20min to Down Town, 15min to Amphitheatre in Tinley Park 2-Bathrooms 3-Bedrooms one with queen size bed and 2 bedrooms with 4 single beds can accommodate up to 6 people. Two TV's 4K Incl. NETFLIX & PEACOCK. Whether you're in town on business or for personal reasons our space has been meticulously designed to provide you with the best stay in the area!Digital check-in.This Airbnb operates with Village Ord. 8-875

Spacious Bolingbrook Retreat w/ Garage & Yard

Relax with the whole family at this peaceful and spacious 3-bedroom ranch home conveniently located near I-55 & I-355. Walking distance to Promenade Mall, restaurants, bars, shopping, Bass Pro Shop. Enjoy self check-in with smart lock, private attached 2-car garage, large backyard, patio, and grill. Perfect for families, work trips, or weekend getaways. Clean, safe, and only 30 minutes from downtown Chicago and major attractions. Self check-in Free parking Fast Wi-Fi Washer/dryer Backyard/patio

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

RetroModern Bungalow | pet friendly | free parking

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fenced-in, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location—just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage and/or catch the train a few blocks away.

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

Chicago Home (1st floor) by Midway near Downtown

Hello, Welcome in 1st floor apt, where 3 rooms are available with newly remodelled kitchen, bathroom and livingroom. LOCATION, convenient location, walking distance to grocery store and few restaurants near by, also walking distance to public transportation bus 62 and 62 H. 5 min driving to Midway airport and 15 min driving to downtown Chicago. Easy access to public transportation to get to Chicago downtown. In addition to convenient location, apt offers access to yard and free parking

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Private Guest Suite 2 Cozy Rooms

Private guest suite with separate entrance. Sitting room, kitchenette, bedroom w/queen bed, private bath, plus twin sofa bed in sitting room. Great alternative to hotel for business trip or visiting the area. Conveniently located in southwest suburbs of Chicago, 40 minutes from downtown by car (non rush hour) or Metra lines a few miles from the house. Set near a golf course and forest preserve, nearby to multiple restaurant and shopping districts less than 10 minutes away.

Beverly Cottage Loft

Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

Designer's Dream in the North Shore!

Welcome to the newly designed cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and parks. A cozy retreat in the wintertime to snuggle up with a great book and hot cocoa. It's also a perfect summer cottage for adventurers looking to take advantage of the beautiful landscape ! Check us out on: Instagram! longmeadowcottage

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.