
Family-friendly vacation rentals in Downtown Chicago
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Downtown 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.
5.0 out of 5 average rating, 325 reviews
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.
4.99 out of 5 average rating, 117 reviews
Highrise Hideout (Fitness Center • Sauna)
Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.
4.92 out of 5 average rating, 121 reviews
Private Downtown Retreat with Rooftop Oasis
Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.
4.98 out of 5 average rating, 127 reviews
Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Centrally located in the heart of Lincoln Park this meticulous 2 bedroom apartment is just a short walk to downtown Chicago, the Lincoln Park Zoo, lakefront, shops, restaurants and nightlife. This luxury designer 2,000 SF 1st & 2nd floor apt is bright and spacious and features everything needed to live in Chicago like a local. The apartment features two bedrooms with king & queen beds, 3 full baths, pullout couch, gourmet kitchen, central HVAC and washer/dryer. Recently completely renovated.
4.99 out of 5 average rating, 165 reviews
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.***
4.98 out of 5 average rating, 165 reviews
Luxury Loft Collection 901 - Terrace - River North
BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!
4.91 out of 5 average rating, 109 reviews
Unwind in Style Steps from the Magnificent Mile
Ideally located just half a block from Michigan Avenue, this apartment boasts high ceilings, beautiful wood floors, with thoughtfully appointed rooms for your comfort. You will have everything you need to enjoy your stay in style! PLEASE NOTE: 4th floor walk-up (NO ELEVATOR). There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard leading up to the apartment but never in the apartment.
4.98 out of 5 average rating, 443 reviews
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.
4.81 out of 5 average rating, 1051 reviews
Spacious 1-bedroom South Loop Loft I Sleep 5
Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!
4.94 out of 5 average rating, 250 reviews
Fulton Market Loft | Rooftop Fire Pit | Parking
Featured in Condé Nast Traveler and Architectural Digest. Rated top 1% of all Airbnb listings nationwide. Two-level loft in the heart of Fulton Market. Soaring ceilings, floor-to-ceiling windows, gourmet kitchen with exposed brick, 3 bedrooms, 2.5 baths, in-unit laundry, and dedicated parking. Step outside to a private rooftop terrace with fire pit and panoramic skyline views. Steps from MICHELIN-recognized Taquería Chingón and Restaurant Row.
4.96 out of 5 average rating, 291 reviews
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.
4.95 out of 5 average rating, 133 reviewsPopular amenities for Downtown Chicago family-friendly rentals
Family-friendly home rentals with a hot tub

Private hot tub - King bed suite - Free parking
4.92 out of 5 average rating, 282 reviews
Private Coach house near Lincoln Square!
4.88 out of 5 average rating, 395 reviews
Ukrainian Village 3BR/3BA • Private Patio, Parking
4.98 out of 5 average rating, 128 reviews
H&H 1896 - Spacious, Fully Stocked, & Free Parking
4.95 out of 5 average rating, 120 reviews
Entire house in Lakeview with yard and garage
4.86 out of 5 average rating, 111 reviews
Tea Studio in Wicker Park Spring Factory
4.96 out of 5 average rating, 309 reviews
Modern Getaway w/ Hot Tub, Lrg Yard, Parking
4.96 out of 5 average rating, 187 reviews
Chicago Oasis | Spa Bath, Patio & Fireplace
4.97 out of 5 average rating, 182 reviewsFamily- and pet-friendly home rentals

Large Home | Free Parking | Near Downtown
4.89 out of 5 average rating, 128 reviews
Charming 3-BED in Lincoln Park/ Old Town & Parking
4.95 out of 5 average rating, 198 reviews
Breathtaking & Chic Oasis Loc in Desirable Old Twn
4.88 out of 5 average rating, 178 reviews
Historic Old Town, Fabulous 4 Bedroom Home
4.87 out of 5 average rating, 211 reviews
Space & Style Near Downtown Parking+Walk To It All
5.0 out of 5 average rating, 103 reviews
Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!
4.91 out of 5 average rating, 136 reviews
3-bedroom exposed brick in Chicago's Wicker Park
4.98 out of 5 average rating, 170 reviews
The Chicago River House – GIANT wall projector!
4.96 out of 5 average rating, 211 reviewsFamily-friendly home rentals with a pool

50th Floor Mag Mile Views, Balcony, Pool, Gym
4.9 out of 5 average rating, 143 reviews
Fun & cozy getaway w/POOL/game room/FREE parking
4.98 out of 5 average rating, 172 reviews
"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
4.96 out of 5 average rating, 141 reviews
Cozy Duplex Down in Wicker Park East w/ Parking
4.93 out of 5 average rating, 131 reviews
Whole Flat in Private Club. Walk to L, Dining & Shows
4.9 out of 5 average rating, 600 reviews
Loop 1BR | Steps to Millennium Park & Bean
5.0 out of 5 average rating, 16 reviews
West Loop Loft|Sleeps 4, Parking, Pool, & Rooftops
5.0 out of 5 average rating, 3 reviews
Upscale High-Rise Apt · Rooftop Pool + Views
4.92 out of 5 average rating, 49 reviewsDestinations to explore
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- Indiana Dunes State Park
- 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
- Frank Lloyd Wright Home and Studio
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- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo
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