
Family-friendly holiday rentals in Chicago
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Chicago

Total holiday rentals
Explore 5,020 holiday rentals in Chicago

Verified guest reviews
Over 338,690 verified reviews to help you choose

Pet-friendly holiday rentals
Find 1,960 rentals that welcome pets

Holiday rentals with a pool
380 properties feature pools

Rentals with dedicated workspaces
3,410 properties have a dedicated workspace

Wifi availability
4,990 of Chicago holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chicago rentals

4.8 Average rating
Chicago stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Chicago’s top spots include Millennium Park, Wrigley Field and Lincoln Park
Top-rated family-friendly rentals in Chicago
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Explore Lincoln Park from a Polished Apartment
This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.
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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.
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Luxury SOHO Styled Two-Level Townhouse - Old Town
NEWLY CONSTRUCTED TOWNHOUSE IN THE HEART OF OLD TOWN! This private luxury townhouse (duplex) is perfectly located in vibrant Old Town-surrounded by nightlife, restaurants, cultural attractions, and is only a 5 min walk to the beach, steps from Lincoln Park, and next to Second City. This 2,800 square foot townhouse features 13 foot ceilings, open floorplan, private patio, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between.
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Charming 3-BED in Lincoln Park/ Old Town & Parking
Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.
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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
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3-bedroom exposed brick in Chicago's Wicker Park
Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.
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Chic 2BR Gem with Fireplace
Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***
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Kasa | Views from your Private Balcony | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.
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Lakeview Loft-Vintage Chicago, Modern Amenities
The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.
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Modern Corner 2BR in Streeterville | Roof Deck | L
Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple directions. This bright and modern two bedroom, one bathroom corner unit is perfect for travelers looking for a stylish escape in the sky in downtown Chicago just off the Magnificent Mile and the lakefront. The building has great amenities including an amazing rooftop terrace with 360 degree views of the skyline and the lake. This is the best location in the city!
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Entire first floor in Lincoln Square!
First floor of a restored 1903 Victorian in Lincoln Square. The home is spacious with high ceilings throughout and a very open feel. You'll have the whole 1st-floor with access to the backyard with chairs & fire pit. Two bedrooms and an office with additional sleeping options (ask me!). Large dining room & eat-in kitchen. Brand new kitchen & huge new bath! Many short-term rentals in this area are third-floor walk-ups. Make your life easier and stay on the first floor!
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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.
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Popular amenities for Chicago family-friendly rentals
Family-friendly home rentals with a hot tub

Private Coach house near Lincoln Square!
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Private hot tub - King bed suite - Free parking
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Ukrainian Village 3BR/3BA • Private Patio, Parking
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Enchanted Garden Treehouse (Amenity*)
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Modern Getaway w/ Hot Tub, Lrg Yard, Parking
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H&H 1896 - Spacious, Fully Stocked, & Free Parking
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Entire house in Lakeview with yard and garage
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Tea Studio in Wicker Park Spring Factory
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Family- and pet-friendly home rentals

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
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Historic Old Town, Fabulous 4 Bedroom Home
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Beautiful, sunny 2nd floor 3BR/1BA w free parking
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Paradise on the Boulevard!
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Newly-renovated historic home in Logan Square
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Modern 1BR in Little Italy, Near West Loop
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Lincoln Square Gem!
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Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
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Family-friendly home rentals with a pool

5-Star Gold Coast Experience in a Luxe 2BR Retreat
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Fun & cozy getaway w/POOL/game room/FREE parking
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The Metropolitan Retreat (Fitness Center • Sauna)
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Whole Flat in Private Club. Walk to L, Dining & Shows
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Just remodeled apartment close to airport and mall
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Cozy Duplex Down in Wicker Park East w/ Parking
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"Serenity of Evanston" 2 BDR/2Bath Modern Suite
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Level ◆ Two Bedroom Deluxe Corner Suite + Balcony
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When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $184 SGD | $185 SGD | $217 SGD | $222 SGD | $277 SGD | $309 SGD | $275 SGD | $271 SGD | $242 SGD | $246 SGD | $220 SGD | $208 SGD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Destinations to explore
- Indianapolis Holiday rentals
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- St. Louis Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
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- Milwaukee Holiday rentals
- Traverse City Holiday rentals
- Downtown Chicago Holiday rentals
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- Rentals with an accessible-height bed Chicago
- Rentals with lake access Chicago
- Loft rentals Chicago
- Rentals with a sauna Chicago
- Private suite rentals Chicago
- Rentals with breakfast Chicago
- Lakehouse rentals Chicago
- Flat rentals Chicago
- Luxury rentals Chicago
- Hotel rooms Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Beachfront rentals Chicago
- Mansion rentals Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Boutique hotels Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Serviced apartment rentals Chicago
- Townhouse rentals Chicago
- Guest house rentals Chicago
- Family-friendly rentals Cook County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Beachwalk Vacation Rentals
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo
- Things to do Chicago
- Landmarks Chicago
- Art workshops Chicago
- Museums Chicago
- Food tours Chicago
- Architecture Chicago
- Cultural tours Chicago
- Outdoors Chicago
- Things to do Cook County
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- Things to do Illinois
- Museums Illinois
- Food tours Illinois
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- Landmarks Illinois
- Cultural tours Illinois
- Outdoors Illinois
- Architecture Illinois
- Things to do United States
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- Museums United States
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