
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.

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.

Victorian Guest Suite in Old Town
This private guest suite is the restored 1st floor of my Victorian era family home. The space has a private ground floor entrance with small front yard patio, located in the “Old Town Historic District”. Decor is Mid Century Modern. Located 1 block north of Sedgwick train station, bus stop across the street, 5 minute walk to the lake, 1/2 hour lakeside walk to downtown. Great restaurants nearby. Only registered guests are allowed on the premises. Please see booking requirements in house rules

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.

Lincoln Pk-parking-wifi-King bd-crib-kid friendly
This wonderful 2 bedroom garden apartment in superhot Lincoln Park on a block where homes sell for 4 million to 12.5 million dollars. Walk score 97 The apartment was totally renovated adding new furniture, Flatscreen TVs in both bedrooms and Livingroom, a fully stocked kitchen, superfast wifi (150 Mbps) dedicated parking space, rooftop deck, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop is 2.5 blocks from the apartment. Go to the Cubs game/downtown.

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.

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.

Travelers Retreat in Old Town Chicago
Our garden unit is decorated with treasured souvenirs, maps, art, and decor that we’ve collected from all over the world to create a travel inspired retreat for Airbnb guests. Located in Old Town, a walkable neighborhood with famed architecture, stellar dining, stand-up/sketch comedy, and local shopping. Walking distance to Brown (Sedgwick) and Red (North/Clybourn) line trains. Centrally located between Downtown/River North and Lakeview/Wrigleyville. Adjacent to Gold Coast & Lincoln Park.

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.

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!

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!

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!

Old Town Condo with Parking and Terrace
Experience Chicago from my light-filled 2-bed, 2-bath Old Town condo for 4. This urban retreat boasts 13-ft ceilings, a private terrace, dedicated workspace, and gourmet kitchen. Steps from Wells Street's best dining, Second City, Lincoln Park and North Avenue Beach. Perfect for families or professionals seeking a stylish city base with included parking in elevator building.
Popular amenities for Old Town family-friendly rentals
Family-friendly home rentals with a hot tub

Top Floor Views + Central Comfort

Private Coach house near Lincoln Square!

Chicago 3BR/3BA | Jet Tub, Private Patio & Parking

Lux Urban 3BR/3BA Duplex + Parking!

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

Tea Studio in Wicker Park Spring Factory

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Entire house in Lakeview with yard and garage
Family- and pet-friendly home rentals

Wicker Park Walk-Up Condo

Sounds Of The City

Flat in Lincoln Park 2-Flat Central to Everything

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Lincoln Square Gem!

Heart of the City Group Hub • Patio • Fireplace

Renovated 2 Bed Condo Lincoln Park w/ Free Parking

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Family-friendly home rentals with a pool

Upscale High-Rise Apt · Rooftop Pool + Views

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

The Metropolitan Retreat (Fitness Center • Sauna)

Spectacular 2BR Penthouse in the Loop | Roof Deck

Level One Bedroom Suite | Fulton Market

Whole Flat in Private Club. Walk to L, Dining & Shows

Level ◆ New Luxe Two Bedroom Corner Suite

50th Floor Mag Mile Views, Balcony, Pool, Gym
When is the best time to visit Old Town?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $278 AUD | $265 AUD | $353 AUD | $303 AUD | $401 AUD | $479 AUD | $446 AUD | $381 AUD | $398 AUD | $451 AUD | $387 AUD | $321 AUD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
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 $140 AUD per night before taxes and fees

Verified guest reviews
Over 5,700 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 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!
Destinations to explore
- Rentals with a washing machine and dryer Old Town
- House rentals Old Town
- Rentals with a fireplace Old Town
- Rentals with a patio Old Town
- Rentals with outdoor seating Old Town
- Apartment rentals Old Town
- Pet-friendly rentals Old Town
- Family-friendly rentals Chicago
- Family-friendly rentals Cook County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- University of Chicago
- Brookfield Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park




