
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.

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!

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.

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.

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.

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!

Fully Furnished Apartment Wicker Park Free Parking
Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

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!

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit
This generously sized, quiet apartment, located in the highly sought-after Lincoln Park neighborhood, offers convenient access to acclaimed restaurants and boutiques, all within a five-minute walk. Its private entrance and proximity—less than four blocks—to both the Red and Brown Line "L" stations ensure effortless access to Chicago's attractions, most within a two- to five-stop train ride. Zoned parking permits are provided.

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!
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!

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Lux Urban 3BR/3BA Duplex + Parking!

Tea Studio in Wicker Park Spring Factory

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

Chic 1 BR w 1 G Parking| W Park Nightlife nearby

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

Sounds Of The City

Penthouse Near Wrigley Field

Wicker Park Historic, Art-Filled, Urban Oasis #2

Lincoln Square Gem!

Garden on Warren

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

Kasa | Elevate your stay, Premium 1BD | Chicago

Ukrainian Village Garden Retreat
Family-friendly home rentals with a pool

Upscale High-Rise Apt · Rooftop Pool + Views

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool

Level One Bedroom Suite | Fulton Market

Professional's Playground (Fitness Center • Sauna)

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

50th Floor Mag Mile Views, Balcony, Pool, Gym

Beautiful Corner 2 Bedroom in the Loop | Roof Deck
When is the best time to visit Old Town?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,567 GYD | G$39,687 GYD | G$52,846 GYD | G$45,327 GYD | G$59,948 GYD | G$71,645 GYD | G$66,632 GYD | G$57,024 GYD | G$59,530 GYD | G$67,468 GYD | G$57,859 GYD | G$48,042 GYD |
| 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 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 G$16,710 GYD per night before taxes and fees

Verified guest reviews
Over 5,330 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

Wi-Fi availability
50 of Old Town vacation 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
- Pet-friendly rentals Old Town
- Apartment rentals Old Town
- House rentals Old Town
- Rentals with a fireplace Old Town
- Rentals with a patio Old Town
- Rentals with a washer and dryer Old Town
- Rentals with outdoor seating 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
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Six Flags Great America
- Soldier Field
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Wilmot Mountain Ski Resort
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Washington Park Zoo




