Family-friendly holiday 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.

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Guest favourite

Guest suite in Chicago

4.96 out of 5 average rating, 331 reviews

Secret Garden @ The Noble Farmhouse | 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.

Guest favourite

Flat in Evanston

4.94 out of 5 average rating, 136 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 18 min walk for trains to city, 5 min drive to lake. Wifi

Guest favourite

Flat in Chicago

4.84 out of 5 average rating, 209 reviews

Cozy Northside Apt near Trans&Beach&Free St Prking

PRIVATE Entrance, One Bedroom Apt w/ LVG RM near Lake Michigan in beautiful, residential & diverse neighborhood. FREE on street PARKING, OR driveway spot for Addt fee. Sleeps up to 6. *It has a Kitchenette, Full Bath, WiFi, Cable TV, in unit W/D. Close to METRA TRAIN (1 block & 18 min to loop/city center), Bus Stop 1 block & the CTA "L" (elevated) Red Line to City 7 blocks away. Enjoy our proximity to Public Transit, Beaches, Loyola & NW Universities. Great for family, friends & kids.

Superhost

Flat in Chicago

4.84 out of 5 average rating, 275 reviews

4BDRM Gorgeous Apt Pilsen Private Prking Available

Stylish Retreat for Groups in Vibrant Pilsen Welcome to our 7-room home in lively Pilsen, perfect for families and groups of up to 10. Enjoy spacious comfort in a prime location. Explore vibrant murals, visit Simone's bar, and savor Sunday brunch at Dusek's. Catch a concert at Thalia Hall or sing at nearby karaoke or grab dim sum. Conveniently located just down the street from Chinatown and close to McCormick Place. Ideal for conventions and city adventures. Book now for an unforgettable stay!

Guest favourite

Flat in Chicago

4.98 out of 5 average rating, 238 reviews

North Side Near Wrigley Lakeview Walk Everywhere!!

Located on a beautiful tree lined street one block from the thriving Southport Corridor, one of the hottest neighborhoods in Chicago. You'll love the convenience of being just steps from the Southport Brown Line "L" Stop, you can see the City without ever needing to drive. Steps to outstanding restaurants, bars and shopping. Going to Wrigley Field? Enjoy a 10 minute walk down some of the most beautiful streets in Chicago. Ideal for families seeking comfort, style and a convenient location.

Guest favourite

Flat in Chicago

4.92 out of 5 average rating, 198 reviews

Charming Apt. near Wrigley/Cubs, Ravenswood/Uptown

Welcome to our family-friendly & cozy 1-bedroom/1 bathroom apartment! We are walking distance from Wrigley Field, Montrose Beach, Andersonville restaurants, Green Mill Jazz Club, Riviera, Lincoln Square, Target and grocery. Close to Red, Purple & Brown CTA trains and 22, 78 bus lines to reach airports & top sights. Street parking is open & free (check signage!) We are a smoke-free home directly across from a school with playground in a very quiet & safe neighborhood: Ravenswood/Uptown.

Guest favourite

Flat in Chicago

4.92 out of 5 average rating, 245 reviews

2 Miles to MDW 11 Miles DTWN Free Parking Wi-Fi

*50" & 43" 4K HDTVs with Streaming only, 300mbps WiFI *1 King, 2 Queen, 2 Twin Size beds *High-quality printer, Paper Shredder *Office Space with Glass White Board *Pack n Play, Stroller, Baby bathtub, high chair *Central Air/Heat *In-unit Washer/Dryer *In-unit Dry Cleaning Machine *1 Parking Space + St. Parking *Jacuzzi Tub *Fully Equipped Kitchen *Toiletries 24 steps up to the 2nd floor. 2nd door.

Guest favourite

Flat in Chicago

4.95 out of 5 average rating, 686 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

Superhost

Apartment in Chicago

4.83 out of 5 average rating, 332 reviews

Lively Wicker Park 2br, Steps to Damen Blue Line

Rehabbed 2BR 1BA garden unit in the very popular neighborhood of Wicker Park/Bucktown! 2 queen beds and full of amenities. Just a block from everything this neighborhood has to offer and 2 blocks from the 'L' to take you downtown or to O'hare Airport. Premium location to effortlessly walk from our quiet side street and be in the heart of all the entertainment! I provide all the essentials to make your stay easy and comfortable!

Superhost

Flat in Chicago

4.9 out of 5 average rating, 188 reviews

Fairfield Flat, Airy Vintage Rehab

This remodeled first floor apartment is close to the California Pink Line Station, Pete's Fresh Market, Lagunitas Brewery & Tap Room and Douglass Park. Pilsen and West Loop night life just a short train ride away. Situated in a quiet corner of Little Village, our neighborhood of predominately Mexican and Black multi-generational families is teeming with tamale stands, paleta vendors, and children playing.

Guest favourite

Townhouse in Chicago

4.95 out of 5 average rating, 257 reviews

The Nancy’s gorgeous , Spacious Urban Getaway

This conveniently located and newly renovated townhouse in Edgewater features tons of sunlight and plenty of room for large families or groups. Near the lakefront, Loyola University, Andersonville, and tons of great restaurants and bars. In close proximity to the Red line "El" train, the city bus (22 Clark) and just four (4) miles from Evanston and Northwestern University.

Guest favourite

Flat in Chicago

4.9 out of 5 average rating, 173 reviews

Clean, spacious, walk to Wrigley! Self check-in!

Park your car and forget it- or just leave it at home! Charming 3 BR first floor apartment in a Victorian building in the ultimate location, perfectly situated between Wrigleyville and Lincoln Park in the beautiful, vibrant Lakeview neighborhood. Guys seriously… this is the ideal neighborhood for a Chicago getaway or visit with family.