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Family-friendly vacation rentals in Pilsen, Chicago

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Pilsen, Chicago

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

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Guest suite in Douglas Park

4.78 out of 5 average rating, 180 reviews

Alewyfe Farm Urban Garden Oasis- free parking!

Stay with us at the Alewyfe Inn- a cozy bohemian garden apt on the 1st floor of an 1880's brick cottage. Charming details, stocked pantry & coffee/tea bar in the kitchenette, your own private bathroom & entrances, & HEPA/UV filter. Enjoy the front yard permaculture garden with chickens, a firepit, & BBQ! 2 blks. from Pink Line/CTA, Lagunitas, Cinespace, St. Anthony & Mt Sinai hospitals, & a view of Douglas Park. 3.5 mi to Loop... Free street parking right out front is almost always available!

Rental unit in Chicago

4.9 out of 5 average rating, 171 reviews

Royal Coach House Cottage

Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

Rental unit in Logan Square

4.96 out of 5 average rating, 414 reviews

King Bed, Huge Spa Shower, Dining Destination

This home was designed with love! Inspired by our favorite boutique hotels - nestled on a tree-lined street in Logan Square, a locals-only destination for brunch, coffee, craft beer and cocktails. Relax in the massive custom steam shower or catch up on HBO on the 50” WiFi TV. Luxe details throughout -premium espresso, memory foam beds and upgraded Italian linens, lots of outlets, and a fully-equipped kitchen. Easy parking, a rarity in the city. Central location- Quick walk to Blue Line Train

Condo in Bridgeport

4.89 out of 5 average rating, 102 reviews

Convenient & Spacious 3BR Condo w/Free Parking

Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

Rental unit in Chicago

4.81 out of 5 average rating, 191 reviews

Your brand new Chicago suite (unit 1F)

Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.

Rental unit in Pilsen Historic District

4.89 out of 5 average rating, 169 reviews

Spacious unique artist's home in Pilsen

Spacious 2 BR, 2nd floor in the wonderful Pilsen neighborhood *Pandemic Note: I am very concerned about keeping a safe environment for my guests and myself. My cleaning protocols exceed even Airbnb’s enhanced guidelines. 2.5 m. To downtown 1.6 m. To McCormack place Just 4 blocks to CTA station This is not a luxury loft, it is a hand crafted, rustic artist’s space with an open floor plan Bear in mind this building Dates to 1879. (charm?)

Townhouse in Near West Side

4.87 out of 5 average rating, 315 reviews

CITY CONDO with GARAGE 7 min Walk to Train

Experienced Super-host offers private spacious & sunny condo 3 miles from Chicago "Loop" Lakefront and Museums. Large one bedroom with king size premium mattress, and full sized sofa-bed sleeps 4. 1 FREE garage PARKING wi-fi , washer & dryer. BUS to city center is across the street. 10 minute ride to city center. Walk to United Center Bulls/Blackhawk games /concerts and large international grocery store. Note- WE DO NOT HOST SMOKERS.

Rental unit in Pilsen Historic District

4.8 out of 5 average rating, 208 reviews

In artistic Pilsen~Continental Breakfast~Near DWTN

Located in the artistic town of Pilsen; minutes away from downtown Chicago, Lake Shore drive, Shedd aquarium, United Center, UIC Pavilion and McCormick Place. Great and convenient location. Walking distance from CTA #60 bus-stop and pink line to downtown. Enjoy charming first floor, full kitchen, & bathroom. Also includes continental breakfast for first day of your stay and street parking with permit.

Rental unit in South Lawndale

4.92 out of 5 average rating, 183 reviews

Fairfield Flat, Airy Vintage Rehab

This remodeled first floor apartment is close to the California Pink Line Station, Pete's Fresh Market, Lagunitas Brewery & Tap Room and Douglass Park. Pilsen and West Loop night life just a short train ride away. Situated in a quiet corner of Little Village, our neighborhood of predominately Mexican and Black multi-generational families is teeming with tamale stands, paleta vendors, and children playing.

Condo in West Town

4.97 out of 5 average rating, 759 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.

Rental unit in Chicago

4.79 out of 5 average rating, 235 reviews

Heart of Chicago 2BD + Parking

Comfortably fits 5. Two private bedrooms and a daybed in the living room with trundle. Impecable bathroom with great lighting. State of the art stainless steel appliances for a quick meal at home before a day in town. Warm cotton towels and clean linen. Interested yet? Ask me about my space :)

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Popular amenities for Pilsen, Chicago family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in West Town

4.85 out of 5 average rating, 306 reviews

Lux Urban 3BR/3BA Duplex + Parking!

Loft in West Town

4.81 out of 5 average rating, 283 reviews

Artist Loft Duplex in a 1904 Former Factory

Rental unit in The Loop

4.74 out of 5 average rating, 43 reviews

The Professional's Playground

Home in Logan Square

4.9 out of 5 average rating, 86 reviews

LOFT606: Gigantic Sunlit Former Factory Home

Condo in Logan Square

4.98 out of 5 average rating, 257 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

Rental unit in Bronzeville

4.58 out of 5 average rating, 12 reviews

Spacious 2bdm unit 15min to Dwtn

Family- and pet-friendly home rentals

Rental unit in Roscoe Village

4.96 out of 5 average rating, 275 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

Condo in West Town

4.89 out of 5 average rating, 257 reviews

2 King Bed Condo Easy Downtown Free Street Parking

Rental unit in Logan Square

4.9 out of 5 average rating, 377 reviews

Sunny Logan Square Artists' home

Home in Uptown

4.9 out of 5 average rating, 356 reviews

Private 3rd Floor Apartment

Guest suite in Logan Square

4.97 out of 5 average rating, 271 reviews

Stylish Studio in Historic Logan Square

Guest suite in Wood Dale

4.9 out of 5 average rating, 459 reviews

The Deer Suite

Rental unit in Palos Hills

4.94 out of 5 average rating, 164 reviews

Aunt Linda's Apartment with a View in Palos

Rental unit in Logan Square

4.96 out of 5 average rating, 101 reviews

Garden Unit Getaway-Bucktown

Family-friendly home rentals with a pool

Rental unit in The Loop

4.77 out of 5 average rating, 204 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

Guest suite in Bridgeport

4.96 out of 5 average rating, 82 reviews

Sweet Home Chicago-9min downtown/pool/free parking

Guest suite in Berwyn

4.67 out of 5 average rating, 42 reviews

Music Hot Spot’s Main Level

Rental unit in The Loop

4.77 out of 5 average rating, 226 reviews

Luxury Corner 2 Bedroom in the Loop | Roof Deck

Quick stats about vacation rentals that are family-friendly in Pilsen, Chicago

Total rentals
40 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
2.4K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Destinations to explore