
Family-friendly vacation 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.

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.

Family-Friendly 2BD/2BA Prime Location (+parking)
Getaway to this authentic Old Town apartment! 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 - Privacy is hard to beat in this beautiful courtyard! - Luxurious interior design - Master en-suite w/ all the bells/whistles! - Extremely Fast WiFi - Pillow-top Bamboo mattresses - Charming neighborhood - 5-10 minute walk from red line (CTA L) We look forward to hosting you!

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.

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.

Kasa | Views from your Private Balcony | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Cozy Lincoln Park Studio - Steps to Zoo!
This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

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!

Lincoln Park Hideaway - 5 Min Walk to the Park!
800 sq ft 1 Bed 1 Bath Charming garden-level apartment right in the heart of Lincoln Park. Please note that you will need to walk down a short flight of stairs to access the unit. Close to all the best that Chicago has to offer! Walking distance to restaurants, convenience stores, and public transportation. Anything you could want for a nice trip to Chicago to visit friends and family, work relocation, or just explore our gorgeous city!

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!

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!
Popular amenities for Old Town family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Wrigley Oasis with Parking!

Top Floor Views + Central Comfort

Private Coach house near Lincoln Square!

Lux Urban 3BR/3BA Duplex + Parking!

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Pet Fndly

Tea Studio in Wicker Park Spring Factory

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

Belmont Pleasures - hot tub / arcade gaming room
Family- and pet-friendly home rentals

Wicker Park Walk-Up Condo

Flat in Lincoln Park 2-Flat Central to Everything

Cozy and Spacious! Logan Square Apartment

Archways at the Lincoln Park Zoo 2bed/2ba

Eddy Street Upstairs Apartment

Entire 1st Floor Apt near O'Hare/ORD & Blue Line

Garden on Warren

★Bright & Bold 1BR in Roscoe Village + Fireplace★
Family-friendly home rentals with a pool

Spectacular 2BR Penthouse in the Loop | Roof Deck

Skyline Oasis: City & Lake Views

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

The Executive's Escape (2BD / 2BA)

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

50th Floor Mag Mile Studio

Level Studio | Fulton Market

Sentral Studio Apt in South Loop Chicago
Quick stats about vacation rentals that are family-friendly in Old Town

Total vacation rentals
Explore 50 vacation rentals in Old Town

Nightly prices starting at
Old Town vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 5,010 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Old Town vacation 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!
Destinations to explore
- Pet-friendly rentals Old Town
- House rentals Old Town
- Rentals with a fireplace Old Town
- Rentals with a patio Old Town
- Rentals with outdoor seating Old Town
- Rentals with a washer and dryer Old Town
- Apartment rentals Old Town
- Family-friendly rentals Chicago
- Family-friendly rentals Cook County
- Family-friendly rentals Illinois
- Family-friendly rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo
- The Beverly Country Club
- Raging Waves Waterpark
- The 606