
Family-friendly holiday rentals in West Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in West Side
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Beautiful Chicago Greystone
Experience the best of Chicago from this sprawling, private 4-bedroom condo. Located just 15 minutes west of the City Center, you’re perfectly positioned to explore the culinary scene of the West Loop, the lush Garfield Park Conservatory, and the energy of the United Center Transit: Steps from multiple bus lines, 2 blocks to the Blue Line, and 1 mile to the Pink Line Amenities: On-site laundry (available upon request) Local Experts: We live in the unit below and happy to give recommendations

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Rockin' 2Bed steps to shops/food/train
This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving
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.

Bright Cozy Modern-Chic Condo in Trendy West Town
Kick back & relax in your home away from home in our luxurious, spacious and peaceful abode in the heart of the West Town & Noble Square neighborhoods, close to downtown. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located near the popular Grand Avenue, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

【Central】- Eclectic Fun 1BR APT in Wicker Park
Located in the heart of Wicker Park! Just a 5-min walk from the CTA blue line Damen station. This bright second floor 1-bedroom, 1-bath apartment allows you to access EVERYTHING Chicago has to offer all within short walking distance, with great nightlife. Just walk downstairs, you will find trendy restaurants, cocktail bars, cozy coffee shops and a variety of shops in this popular neighborhood. Want to explore downtown? Uber/Lyft or Hop on the CTA "L" train to go anywhere in the city.

3 bed/2 bath by United Center w/ private parking
Welcome to the Windy City White House – a spacious, historic 150-year old home 3 blocks from the United Center & mins from downtown. 3 bedrooms feature luxury bedding. 2 bathrooms – 1 newly redone w/ a large rainfall shower head. Private deck w/ seating. Spacious living room w/ work space. Fully equipped kitchen. Private parking. It's the perfect place for friends, families, & business travelers to relax in ultimate comfort after a day exploring the city.

Quaint Comfort Studio Near Downtown/Queen Bed
Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Comfortable and Cozy Apartment
Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Enjoy the simplicity of this quiet, central home. Ubicada a of the minutes of thite as target, Walgreens, Aldi, Laundry and restaurants . We are 10 minutes away from the midway airport and 15 minutes from downtown Chicago.

Pilsen Modern Chic Retreat
Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Two Bedroom w Porch in Wicker Park
Spacious two bedroom apartment with custom wood shelving and hard wood floors. Bay windows and great natural light. Gorgeous furnished porch for when the weather is nice. Quiet, tree lined street that's close to all the best bars and music venues. Short walk to Milwaukee avenue, two blocks from the Division Street blue line station which runs direct from O'hare, only two stations to downtown.

Cozy/Spacious WFH Family Friendly w Permit Parking
Bright first-floor private apartment with free parking passes for permit-only street parking. Enjoy the wide-open windows, a private outdoor space, and two bathtubs for ultimate relaxation. Cook for yourself in the fully-equipped kitchen or explore some of the amazing restaurants nearby. Family/baby friendly with included highchair, pack n' play, crib, baby monitor, and more!
Popular amenities for West Side family-friendly rentals
Family-friendly home rentals with a hot tub

Private hot tub - King bed suite - Free parking

Checkerboard Studio, Private Outdoor Hot Tub, Yard

Chicago Oasis | Spa Bath, Patio & Fireplace

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

Private Coach house near Lincoln Square!

Enchanted Garden Treehouse (Amenity*)

Lake Home Retreat-HotTub• FirePit• Kayak• Fishing!

Modern 2Bdrm Westchester/Chicago Home.With Hot tub
Family- and pet-friendly home rentals

Newly-renovated historic home in Logan Square

Stylish 2BR Chicago/suburbs home, fully equipped.

Private coach house near transit shops & nightlife

Cozy and Spacious! Logan Square Apartment

Picturesque Apartment in Berwyn

Blue Brick Apartment in Bridgeport - Park for Free

Spacious Row Home next to Transit w Garage

Charming 3-BED in Lincoln Park/ Old Town & Parking
Family-friendly home rentals with a pool

Fun & cozy getaway w/POOL/game room/FREE parking

Top of River West: Luxe Penthouse for Groups

The Executive's Escape (Fitness Center • Sauna)

Just remodeled apartment close to airport and mall

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Spectacular 2BR Penthouse in the Loop | Roof Deck

Whole Flat in Private Club. Walk to L, Dining & Shows

Cozy Duplex Down in Wicker Park East w/ Parking
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Columbus Holiday rentals
- St. Louis Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Detroit Holiday rentals
- Milwaukee Holiday rentals
- Traverse City Holiday rentals
- Downtown Chicago Holiday rentals
- Ann Arbor Holiday rentals
- Windsor Holiday rentals
- Pet-friendly rentals West Side
- Rentals with breakfast West Side
- Waterfront rentals West Side
- Serviced apartment rentals West Side
- Rentals with an accessible height bed West Side
- Private suite rentals West Side
- Rentals with beach access West Side
- Rentals with a sauna West Side
- Rentals with a hot tub West Side
- Rentals with lake access West Side
- Townhouse rentals West Side
- Loft rentals West Side
- Apartment rentals West Side
- Condo rentals West Side
- Guesthouse rentals West Side
- Bed and breakfasts West Side
- Rentals with pools West Side
- House rentals West Side
- Hotel rooms West Side
- Family-friendly rentals Chicago
- Family-friendly rentals Cook County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- Wrigley Field
- Soldier Field
- United Center
- Lincoln Park
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- University of Chicago
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Donald E Stephens Convention Center
- Beachwalk Vacation Rentals
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort
- Washington Park Zoo
- Things to do West Side
- Food tours West Side
- Things to do Chicago
- Landmarks Chicago
- Art workshops Chicago
- Museums Chicago
- Food tours Chicago
- Architecture Chicago
- Cultural tours Chicago
- Things to do Cook County
- Landmarks Cook County
- Museums Cook County
- Cultural tours Cook County
- Architecture Cook County
- Food tours Cook County
- Art workshops Cook County
- Things to do Illinois
- Museums Illinois
- Food tours Illinois
- Art workshops Illinois
- Landmarks Illinois
- Cultural tours Illinois
- Architecture Illinois
- Things to do United States
- Shopping and fashion United States
- Cultural tours United States
- Museums United States
- Dining United States
- Architecture United States
- Workouts United States
- Art workshops United States
- Flying United States
- Wellness United States
- Food tours United States
- Wildlife United States
- Landmarks United States
- Water sports United States
- Performances United States
- Tastings United States
- Galleries United States
- Cooking United States
- Beauty United States
- Outdoors United States





