
Family-friendly holiday rentals in Old Town
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Old Town

Total holiday rentals
Explore 40 holiday rentals in Old Town

Nightly prices starting at
Old Town holiday rentals start at $209 AUD per night before taxes and fees

Verified guest reviews
Over 5,600 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Old Town holiday rentals include Wi-Fi 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!
Top-rated family-friendly rentals in Old Town
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, 321 reviews
Two Floor Luxury 3 Bedroom Condo in Old Town
Enjoy comfort, privacy, and elevated city living in this spacious three-bedroom, top-floor duplex apartment, located next door to The Sono Chicago in the heart of Old Town Chicago. Ideal for families, groups, or extended stays, this home offers generous space, abundant natural light, and a quiet retreat above the neighborhood. Spanning two levels on the top floor, the apartment features inviting living areas, a fully equipped kitchen, and three private outdoor decks, creating multiple spaces to
4.94 out of 5 average rating, 110 reviews
OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)
Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Room for reg-size SUV in private driveway! - Luxurious interior design - Tranquil rooftop w/ grill - Fast WiFi - Pillow-top Bamboo mattress in each master en-suite - State of the art kitchen - Exceptional workspace - 5 minute walk from red line (CTA L) We look forward to hosting you!
4.94 out of 5 average rating, 255 reviews
Rare 1BR Lincoln Park Apt, close to everything!
Historical charm with modern updates in this 1 Bedroom Lincoln Park Condo. This is the perfect place to stay while you're in Chicago with it being steps away from Chicago's largest park, one of the country's oldest free zoos, nationally acclaimed dining, lakefront trails, museums, DePaul University and more. While you're at home, relax in the cozy living room, cook dinner in the full and updated kitchen, rinse off with the rainfall shower head, or get some rest on the queen bed in the bedroom.
4.78 out of 5 average rating, 288 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.
4.95 out of 5 average rating, 195 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.
4.96 out of 5 average rating, 165 reviews
Lincoln Pk-Kingbed-fast WIFI-Parking-crib-roofdeck
A Wonderful 2 bedroom Airbnb in the Superhot Lincoln Park neighborhood on a block where homes sell from 5 million to 12.5 million dollars. The apartment was totally renovated adding new furniture, 50-inch High-Definition Flatscreen in the Livingroom, a fully stocked kitchen, superfast wifi, parking space, rooftop deck, Patio, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop. Pack-in-play, highchair, kids. Millennium Pk, Navy Pier, Mag Mile, Museum.
4.98 out of 5 average rating, 312 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.
4.89 out of 5 average rating, 304 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!
4.88 out of 5 average rating, 164 reviews
Old Town/Lincoln Park Luxury Home Garage & Rooftop
Old town luxurious townhouse with rooftop, patio and attached garage (with Level 2 electric car charger for any type of electric car). The extra wide floor plan allows for 4 large bedrooms and 2.5 bathrooms spread over 4 levels of living. One block away from Brown Line station and 4 blocks away from Red Line station and best of Lincoln Park shopping. 10 minutes walk to North Avenue Beach or Lincoln Park Zoo. 5 minute walk to Second City, Zanies and Old Town dining & nightlife.
4.91 out of 5 average rating, 184 reviews
Historic Old Town Flat - Minutes from Downtown!
Built in 1886, our "Boland House" offers guests a rare chance to stay in an architecturally significant residence on a beautiful tree-lined street in Historic Old Town district! The original owner was chief of plasterwork projects for the "White City's" 1893 World's Columbian Exposition - combined with modern day conveniences. If you've always wanted to stay in an authentic Chicago Victorian brownstone, you've found it!
4.86 out of 5 average rating, 354 reviews
Old Town Condo: Private Terrace & Garage Parking
Experience vibrant Chicago from this modern 2-bed, 2-bath Old Town condo. Perfect for families or professionals, it features a private terrace, gourmet kitchen, dedicated workspace, and a rare dedicated parking spot. Soaring 13-ft ceilings and stylish design create a light-filled urban retreat just steps from Lincoln Park, Second City, and North Avenue Beach. Comfortably sleeps 4.
4.91 out of 5 average rating, 346 reviewsPopular amenities for Old Town family-friendly rentals
Family-friendly home rentals with a hot tub

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony
4.87 out of 5 average rating, 168 reviews
Chicago Oasis | Spa Bath, Patio & Fireplace
4.97 out of 5 average rating, 181 reviews
Ukrainian Village 3BR/3BA • Private Patio, Parking
4.98 out of 5 average rating, 125 reviews
Tea Studio in Wicker Park Spring Factory
4.96 out of 5 average rating, 307 reviews
Private hot tub - King bed suite - Free parking
4.93 out of 5 average rating, 281 reviews
33rd-Floor Penthouse with Breathtaking Views
4.83 out of 5 average rating, 145 reviews
Entire house in Lakeview with yard and garage
4.86 out of 5 average rating, 111 reviews
Private Coach house near Lincoln Square!
4.88 out of 5 average rating, 394 reviewsFamily- and pet-friendly home rentals

Sophisticated, 2-BR Condo in Old Town
4.87 out of 5 average rating, 119 reviews
Chic Home! Walk to Nightlife-Comedy-Restaurants!
4.77 out of 5 average rating, 346 reviews
Large Remodeled Home in Lincoln Park, Sleeps 12!
4.97 out of 5 average rating, 148 reviews
Kasa | Views from your Private Balcony | Chicago
4.81 out of 5 average rating, 1040 reviews
Lincoln Park Hideaway - 5 Min Walk to the Park!
4.87 out of 5 average rating, 202 reviews
Archways at the Lincoln Park Zoo 2bed/2ba
4.84 out of 5 average rating, 357 reviews
Huge Downtown Gem *Yard *Parking *Fireplace
4.88 out of 5 average rating, 165 reviews
Chic 2BR Gem with Fireplace
4.98 out of 5 average rating, 164 reviewsFamily-friendly home rentals with a pool

Fun & cozy getaway w/POOL/game room/FREE parking
4.98 out of 5 average rating, 170 reviews
Cozy Duplex Down in Wicker Park East w/ Parking
4.93 out of 5 average rating, 128 reviews
Spectacular 2BR Penthouse in the Loop | Roof Deck
4.81 out of 5 average rating, 355 reviews
Professional's Playground (Fitness Center • Sauna)
4.92 out of 5 average rating, 129 reviews
Whole Flat in Private Club. Walk to L, Dining & Shows
4.9 out of 5 average rating, 600 reviews
Harmony of Evanston 1 BDR Exec Suite w/pool & Gym
4.96 out of 5 average rating, 146 reviews
50th Floor Mag Mile Views, Balcony, Pool, Gym
4.9 out of 5 average rating, 140 reviews
Luxury Designer Penthouse 3803 | Pool | Gold Coast
4.89 out of 5 average rating, 57 reviewsDestinations to explore
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 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
- Beachwalk Vacation Rentals
- Donald E Stephens Convention Center
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort
- Washington Park Zoo





