Family-friendly vacation rentals in Chicago

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chicago

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favourite

Rental unit in Wicker Park

4.97 out of 5 average rating, 254 reviews

Stylish First Flr. Studio. Best Location Division+Hermitage.

Clean! Private! Studio located in the popular Ukrainian Village. This quiet unit is located in a charming 19th century pink brick Victorian cottage. It is a great retreat from work or play when visiting Chicago. This welcoming space features modern amenities, stylish decor with unique artwork, tall ceilings and an inviting color palette. Hermitage House Studio a perfect home away from home with in unit laundry, cable with On Demand and green filled backyard patio perfect for sipping your morning coffee or tea. Need 2nd space same building? Check out airbnb.com/h/chicago-hermitage-loft2 This private –very hip studio apartment - completely renovated and newly decorated is set up like a posh hotel suite with all the amenities of home!! Used for guests only this cozy and modern first floor apartment is set in an 1892 vintage brick cottage with a beautiful outdoor rear patio on a quiet tree lined street! This richly colored designer decorated space with all original artwork has comfort in mind. It has plenty of seating including a comfortable leather sofa, a cool desk area and raised bar. Hardwood floors throughout living space, 9’ ceilings, washer/ dryer, central air and heating, hotel like bathroom with soaking tub and an in unit stacking washer/dryer. Modern white kitchen has granite countertops, quartz sink, gas stove-oven, dishwasher, garbage disposal , microwave. The kitchen has many fun gadgets like French press coffee maker, electric tea pot and more. Everything is available for you to use. The high counter with barstools separates the kitchen from the living/sleeping space. The relaxing bedroom area accommodates 2 with a queen pillow top Serta mattress, great lighting, beautiful Mediterranean blue curtains and storage end tables filled with additional blankets. A full aero bed can accommodate a third person if needed. There is a custom closet system with great storage for personals, shoes and folded clothing. Perfect for a couple or an Airbnb business user! Flat screen TV with cable and movie channels Fast Wi-Fi This unit is located in the quiet first floor rear of this building. The first floor rear patio is yours to enjoy! The upper level deck is private. This unit features a digital locks. You will be able to pick your own code before check-in. I am readily available but will respect your privacy unless you need me. I live in the building (Sometimes out of town) but always accessible by phone or internet if anything is needed but the place is yours to enjoy! Located just steps off bustling Division Street this neighborhood has it all without the fuss of downtown. Within walking distance there are restaurants with cuisines from around the world as well as comfort food. Nightlife options including live music and sports venues. There is boutique shopping, art galleries, a local gym and even a mini Target. This cozy Studio is quick walk from the Division St. Blue-Line train that will get you downtown or to O'hare Airport in minutes. Just two blocks to the Division Blue line running from O’Hare and downtown at the intersection of Division/Ashland/Milwaukee This is a great walking neighborhood but it is easily accessible to many buses, cabs, trains and even the new shared Divvy bike station just a block from the studio. If you choose to drive there is zoned parking permits available- 1 per day. I will happily provide directions to attractions, neighborhoods, great food, groceries, coffee and nightlife

Guest favourite

Rental unit in Edgewater

4.93 out of 5 average rating, 406 reviews

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Guest favourite

Guest suite in West Town

4.96 out of 5 average rating, 329 reviews

Secret Garden | Noble Square | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Superhost

Condo in West Town

4.86 out of 5 average rating, 457 reviews

Humboldt Park Traveler's Lodge

Come stay at my gorgeous condo! Featuring exposed brick, a private entrance, stainless steel appliances, and a queen bed --> all on a quiet tree lined street! It's a perfect place to re-energize between big city adventures. Free street parking, and a 5 min walk to some of the best independently owned shops, restaurants, and bars in the city. Also, the massive and incredible Humboldt Park is also just a 5 min walk away! Please reach out for recommendations - I love giving them to people!

Guest favourite

Rental unit in Roscoe Village

4.96 out of 5 average rating, 267 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".,

Superhost

Rental unit in Logan Square

4.77 out of 5 average rating, 360 reviews

Private Logan Square Studio

A private second floor walk up vintage studio apartment right in the heart of Logan Square. Located just half a block north of the picturesque Logan Boulevard and three blocks (5-8 minute walk) from the Logan Square blue line stop which is great for getting around the city. Logan Square is a 15 minute train ride into the loop and 20 minutes out to O'Hare. This studio is convenient for the weary O'Hare traveler or perfect for a private getaway from the hustle of Chicago.

Guest favourite

Condo in West Town

4.97 out of 5 average rating, 752 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.

Guest favourite

Rental unit in East Rogers Park

4.84 out of 5 average rating, 368 reviews

Cozy Garden Unit In Edgewater

Cozy vintage garden apartment, walking distance to University Loyola, trains, shopping and restaurants. Perfect for family or 2 adults and kids. Full-sized bed and sofa bed in living room. Spacious, clean, airy with six windows for natural light. Laundry in next room. Enclosed one car garage space included.

Guest favourite

Guest suite in Lincoln Square

4.91 out of 5 average rating, 444 reviews

Cozy, Quiet, Garden Getaway!

Quiet 1BD garden apartment in Northcenter/Lincoln Square. 10 minutes to the el and Lincoln Square, one of the best neighborhoods in Chicago. Full kitchen, bathroom, cable and internet. Tree lined street close to two parks and a river walk. ****WE DO NOT RENT TO FILM CREWS****