Family-friendly holiday rentals in Old Town

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Old Town

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

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Top guest favourite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Flat in Lincoln Park
5 out of 5 average rating, 286 reviews

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.

Top guest favourite
A cozy living area showcases a navy blue sofa facing a decorative fireplace and a wall-mounted television. Two armchairs and a round dining table create a functional seating arrangement. Natural wood flooring and built-in shelves enhance the spacious feel, complemented by greenery throughout.
Flat in Old Town Triangle
4.89 out of 5 average rating, 246 reviews

Lincoln Paradise– Steps to Park & Zoo!

This semi-basement apartment is located on a tree lined street full of gorgeous, historic buildings. With easy access to shopping, dining and drinking via Wells St & North Avenue- you'll love this location! Walking distance from Lincoln Park, the Lakefront, North Ave Beach, and the Lincoln Park Zoo. Feel right at home with the bright and welcoming layout, with every convenience of home provided. This garden unit is spacious, you'll have plenty of room to relax during your stay in the Windy City!

Top guest favourite
A light and airy living room is showcased, featuring a comfortable sofa adorned with decorative pillows. Two armchairs are positioned nearby, and a coffee table sits at the center. Natural light filters through two windows, and a large television is mounted on the wall.
Flat in Lincoln Park
4.96 out of 5 average rating, 129 reviews

English garden apt. in the heart of Lincoln Park

Welcome to this new, totally furnished apartment in the heart of East Lincoln Park…only a 3 minute walk to the Lincoln Park Zoo! Apartment has been completely renovated with high finishes throughout. Living room boasts a 50” television with Dish TV, internet and a queen sleeper sofa! Gourmet kitchen with granite counter tops with an eat-in bar height counter top. Truly gourmet kitchen! Bedroom with en-suite European styled bathroom. Wall mounted television in the bedroom. In unit laundry.

Top guest favourite
The living area showcases a dark blue accent wall, complemented by a modern light fixture. A cozy sectional sofa is framed by two framed artworks, while a round coffee table holds decorative items. An adjacent dining space features a light wood table surrounded by chairs and a built-in cabinet.
Home in Lincoln Park
4.97 out of 5 average rating, 150 reviews

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.

Guest favourite
An open living and dining area features neutral-colored walls and natural light from multiple windows. A spacious white sofa is positioned across from a mounted television. A modern dining table is accompanied by four chairs, while a closet and laundry unit are neatly integrated into the space.
Flat in Lincoln Park
4.87 out of 5 average rating, 269 reviews

Beautiful 2BR Apartment in Old Town

Want to experience Chicago neighborhood charms, there is no better place to start than the Old Town Historic District. This 2 bedroom apartment is part of a Victorian-era building while interior has been updated for modern style living. You can enjoy lake front trail in the Summer, Bears football in the Fall, year end holiday shopping in the Winter, and Blackhawks playoffs in the Spring. With both Red and Brown line only a few blocks away, getting around in Chicago does not get any easier.

Top guest favourite
A cozy bedroom is featured, showcasing a tufted headboard and a spacious bed dressed in crisp white linens. Flanking the bed are two nightstands with stylish lamps. Light filters through two small windows near the ceiling, illuminating the soft gray walls.
Flat in Lincoln Park
4.96 out of 5 average rating, 452 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.

Superhost
The living area features a spacious sofa and a cozy lounger chair, arranged around a central coffee table. Natural light enters through multiple windows, highlighting the hardwood floors. A workspace with a desk and a mirror is positioned nearby, complemented by decorative plants.
Flat in Old Town
4.89 out of 5 average rating, 136 reviews

OLD TOWN GARDEN GETAWAY

Take it easy at this unique and tranquil getaway! Guests love this space because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Privacy is hard to beat in this beautiful courtyard! - Extremely Fast WiFi - Pillow-top Bamboo mattress and SMART TV in each bedroom - Exceptional workspace - 5-10 minute (0.4 mile) walk from Clark/Division red line station (CTA L) We look forward to hosting you!

Guest favourite
An open-concept living area features a spacious dining table surrounded by black chairs. A modern kitchen showcases stainless steel appliances and upper cabinets. Natural light fills the room through multiple windows, while a comfortable sofa is positioned nearby, welcoming relaxation in the thoughtfully designed space.
Apartment in Lincoln Park
4.77 out of 5 average rating, 246 reviews

Modern Luxury In Old Town - Sleeps 4

Stay in one of the best neighborhoods in Chicago - Old Town! Recently renovated spacious top floor condo with all modern amenities, in a classic 19th century Chicago home in one of the best parts of the city with access to dining, bars, entertainment and more. Ideal for traveling families and friends, and plenty of Chicago culture nearby, from nearly every era. A neighborhood bar with Frank Sinatra's favorite ribs! Michelin-starred restaurants!

Guest favourite
A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.
Flat in Lake View
4.94 out of 5 average rating, 142 reviews

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Superhost
A spacious living room features a brown leather sofa and a rustic coffee table. A wall-mounted TV is visible, alongside a decorative lamp on an end table. The open kitchen can be seen in the background, accentuated by painted white-brick walls.
Flat in Old Town
4.77 out of 5 average rating, 304 reviews

Superb 2BR Old Town APT, PRIME LOCATION!(+Parking)

Cozy apartment right in the center of Old Town and right by all the action on Wells st, you are able to walk to some of the hottest and most popular attractions. This open-floor apartment offers two bedrooms, a spacious living room, and a brand new kitchen! You will love your stay here! 5 minute walk (0.4 miles) to Clark/Division Red-line stop (CTA L) which will take you to all downtown attractions in minutes!

Top guest favourite
A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.
Apartment in Noble Square
4.97 out of 5 average rating, 842 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
A modern living area showcases a comfortable gray sofa with decorative pillows. A sleek coffee table is positioned in front of the sofa, accompanied by a small bowl holding a plant. Bright natural light filters through large windows, highlighting the contemporary design.
Flat in Old Town
4.87 out of 5 average rating, 127 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Enjoy a stylish experience at this centrally-located place. Our stylish 1-bedroom Airbnb, catering to all kinds of travelers. Whether you're looking for a restful stay, a productive workspace, a central hub to explore Chicago, a night of fun at the bars and nightlife, or a snug spot to unwind and connect, our place has everything you need.

Popular amenities for Old Town family-friendly rentals

Quick stats about holiday rentals that are family-friendly in Old Town

  • Total holiday rentals

    Explore 50 holiday rentals in Old Town

  • Nightly prices starting at

    Old Town holiday rentals start at € 52 per night before taxes and fees

  • Verified guest reviews

    Over 5,010 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Old Town holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Old Town rentals

  • 4.8 Average rating

    Old Town stays are highly rated by guests – averaging 4.8 out of 5!

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