Family-friendly vacation rentals in Old Town, Chicago

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Old Town, Chicago

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

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Guest favorite

Apartment in Wicker Park

4.97 out of 5 average rating, 236 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 favorite

Apartment in Lincoln Park

4.99 out of 5 average rating, 158 reviews

Settle Inn Lincoln Park

Boutique destination on the quietest street in Lincoln Park. Sun-filled, third-floor walk-up in its original 1886 layout, hardwood floors and trim. Recently renovated and highly curated space is designed to foster a complete Chicago expereince. ADVENTURE - Picnic backpack with map of our favorite picnic spots BEVERAGES - Bottled still and sparkling beverages, coffee, tea and espresso; To-go coffee cups to keep you caffeinated on the move! COOKING - Brand new appliances, cookware, flatware, bakingware, utensils, milk frother, Vita-mix and Nespresso Vertuo; Recipe and ingredients for (the world's best?) chocolate chip cookies CONNECTING - Over one dozen curated games to bring together groups of children, families and adults; 4K LED TV with Hulu live, Netflix, and Amazon Prime; Pre-stamped postcards to help you share your Chicago experience with those absent CONVENIENCE - Nest thermostat; Keyless entry; Self check-in/out READING - Curated assortment of hardbound classics all within the public domain; Any book started at the Settle Inn can be downloaded and finished for free on your journey home SAFETY - Window openings limited to 5 in.; Metal bed frames with protective covers on mattresses, box springs and pillows; Quarterly pest monitoring for entire building; First aid kit SHOWERING - Individual Beekman 1802 shampoo, conditioner, body wash, lotion and face soap for each room; makeup remover pads; individual toothbrushes and Crest toothpaste SLEEPING - New hybrid (foam and innerspring) mattresses with high thread count and matching linens across all beds; Custom blackout shades TECHNOLOGY - USB outlets in every bedroom, common area and kitchen; WiFi with fastest internet available Guests have full access to our front garden. As our house is adjacent to the rear alley, there is no private parking. This quirky house placement is what affords us one of the few front yards in Lincoln Park. Street parking is (surprisingly) abundant on our well-hidden street. Complimentary 24-hour passes are available. As we live on the first floor, we are available for any questions, recommendations or issues. Please feel free to knock or message. We encourage visitors to walk to get around or during down time. The encompassing Landmark District is an outdoor museum of the unique architecture and craftsmanship of the late 1800s. One of the only homes to survive the Chicago Fire is on our block Multiple convenient and scenic options. Lake Shore Trail and Lincoln Park provide open and scenic walking routes when traveling north or south. Chicago's bike share (Divvy) operates a station <0.1 miles away. The Armitage L stop and Sedgwick L stop are both ~0.7 miles away. Proximity to Lake Shore Drive provides critical flexibility when trying to make flights during busy traffic times (i.e., all the time). Hopefully, you will meet Elly, our 15 lb. Westie. When excited she will bark (such a terrier). She only knows love and affection and is 100% great with all kids and adults.

Guest favorite

Guest suite in Chicago

4.96 out of 5 average rating, 306 reviews

Augusta's 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.

Guest favorite

Home in Lincoln Park

4.81 out of 5 average rating, 196 reviews

Spacious Luxury Townhouse - Old Town

Historic 3 bedroom home in Old Town! Comfortably sleeps 6, and access to 3 levels of living space. The massive rain shower in the master bath is my favorite part, but there's plenty of luxury here to enjoy. Plus, we're right in the heart of Old Town, just steps from all of the shops and restaurants on Wells Street, and a 5 minute walk to the Sedgwick Brown/Purple line stop - you can be in the Loop in 20 minutes! Book today! Early Check-Ins and Late Check-Outs are difficult to accommodate.

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 378 reviews

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

Guest favorite

Guest suite in Logan Square

4.97 out of 5 average rating, 238 reviews

Stylish Studio in Historic Logan Square

Brand new, unique garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Convenience & excitement are easily accessible!

Guest favorite

Guest suite in Lincoln Square

4.95 out of 5 average rating, 242 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Ask about winter specials!

Guest favorite

Apartment in Roscoe Village

4.96 out of 5 average rating, 238 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".,

Guest favorite

Apartment in Chicago

4.8 out of 5 average rating, 385 reviews

'Secret Garden' Apartment in Wrigleyville

Small garden unit in the heart of Wrigleyville. Steps from both Wrigley and Boystown. The apartment has a queen bed in the bedroom and a sitting area with a TV and mini-dining area. In addition, the apartment has mini fridge, microwave, coffee machine w/ pods, and small dining table. There is no kitchen; fortunately Chicago has a multitude of amazing restaurants to choose from! Includes full bathroom with shower and linens.

Guest favorite

Condo in West Town

4.97 out of 5 average rating, 705 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 favorite

Apartment in Chicago

4.92 out of 5 average rating, 491 reviews

2BR Bursting w/ Character in Hip Logan Square!

The unit sits on our extra wide city lot in the center of hip Logan Square! The apartment is eclectic and well decorated, with vintage touches and full of charm. For a garden unit it feels spacious, clean, bright and comes with all of the desired amenities, including access to our spacious side yard!

Guest favorite

Guest suite in Chicago

4.91 out of 5 average rating, 420 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****