Family-friendly vacation rentals in Pilsen, Chicago

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Pilsen, Chicago

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Guest favorite

Apartment in Chicago

4.97 out of 5 average rating, 236 reviews

Stylish First Flr. Studio. Best Location Division+Hermitage.

Clean! Private! Studio located in the popular Ukrainian Village. This quiet unit is located in a charming 19th century pink brick Victorian cottage. It is a great retreat from work or play when visiting Chicago. This welcoming space features modern amenities, stylish decor with unique artwork, tall ceilings and an inviting color palette. Hermitage House Studio a perfect home away from home with in unit laundry, cable with On Demand and green filled backyard patio perfect for sipping your morning coffee or tea. Need 2nd space same building? Check out airbnb.com/h/chicago-hermitage-loft2 This private –very hip studio apartment - completely renovated and newly decorated is set up like a posh hotel suite with all the amenities of home!! Used for guests only this cozy and modern first floor apartment is set in an 1892 vintage brick cottage with a beautiful outdoor rear patio on a quiet tree lined street! This richly colored designer decorated space with all original artwork has comfort in mind. It has plenty of seating including a comfortable leather sofa, a cool desk area and raised bar. Hardwood floors throughout living space, 9’ ceilings, washer/ dryer, central air and heating, hotel like bathroom with soaking tub and an in unit stacking washer/dryer. Modern white kitchen has granite countertops, quartz sink, gas stove-oven, dishwasher, garbage disposal , microwave. The kitchen has many fun gadgets like French press coffee maker, electric tea pot and more. Everything is available for you to use. The high counter with barstools separates the kitchen from the living/sleeping space. The relaxing bedroom area accommodates 2 with a queen pillow top Serta mattress, great lighting, beautiful Mediterranean blue curtains and storage end tables filled with additional blankets. A full aero bed can accommodate a third person if needed. There is a custom closet system with great storage for personals, shoes and folded clothing. Perfect for a couple or an Airbnb business user! Flat screen TV with cable and movie channels Fast Wi-Fi This unit is located in the quiet first floor rear of this building. The first floor rear patio is yours to enjoy! The upper level deck is private. This unit features a digital locks. You will be able to pick your own code before check-in. I am readily available but will respect your privacy unless you need me. I live in the building (Sometimes out of town) but always accessible by phone or internet if anything is needed but the place is yours to enjoy! Located just steps off bustling Division Street this neighborhood has it all without the fuss of downtown. Within walking distance there are restaurants with cuisines from around the world as well as comfort food. Nightlife options including live music and sports venues. There is boutique shopping, art galleries, a local gym and even a mini Target. This cozy Studio is quick walk from the Division St. Blue-Line train that will get you downtown or to O'hare Airport in minutes. Just two blocks to the Division Blue line running from O’Hare and downtown at the intersection of Division/Ashland/Milwaukee This is a great walking neighborhood but it is easily accessible to many buses, cabs, trains and even the new shared Divvy bike station just a block from the studio. If you choose to drive there is zoned parking permits available- 1 per day. I will happily provide directions to attractions, neighborhoods, great food, groceries, coffee and nightlife

Jan 26 – Feb 2

ﺩ.ﺇ598 per night

Guest favorite

Guest suite in Chicago

4.8 out of 5 average rating, 166 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!

Sep 7 – 14

ﺩ.ﺇ420 per night

Guest favorite

Apartment in Chicago

4.88 out of 5 average rating, 160 reviews

Bright, Gorgeous Apt Private Parking available

Trendy Pilsen area 7 rooms for large groups and families Sleeps 7 - registered guests only, Please have accurate guest count on reservation before check in Pricing does fluctuate with additional guests. Please note that all guests will be required to send photo ID. Fully functional kitchen & washer/dryer Steps to Pink Line CTA station 1.5 blocks, Cermak bus Close to Chinatown, West/South Loops Beds-2 queen, 1 full/twin (bunk) Walking distance to great food Reg: R20000053720

Jan 7 – 14

ﺩ.ﺇ491 per night

Guest favorite

Guest suite in Lincoln Square

4.95 out of 5 average rating, 242 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Ask about winter specials!

Nov 7 – 14

ﺩ.ﺇ359 per night

Guest favorite

Apartment in Pilsen Historic District

4.9 out of 5 average rating, 154 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?)

Oct 20 – 27

ﺩ.ﺇ718 per night

Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 300 reviews

Vintage Bridgeport Apartment

This AirBNB is located within Bridgeport, on Chicago's South Side. You're only a short walk from grocery stores, restaurants, bars, cafes, and whatever else you may need on your trip. We welcome all with open arms. All religions, nationalities, genders. No smoking inside the building, including the back porch. We are no longer accepting new guests with pets. If you stayed with us in the past with a pet they are more than welcome back!

Jul 8 – 15

ﺩ.ﺇ550 per night

Guest favorite

Townhouse in Near West Side

4.85 out of 5 average rating, 276 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.

Nov 3 – 10

ﺩ.ﺇ366 per night

Superhost

Apartment in Pilsen Historic District

4.81 out of 5 average rating, 192 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.

Feb 2 – 9

ﺩ.ﺇ571 per night

Guest favorite

Apartment in Bridgeport

4.98 out of 5 average rating, 171 reviews

Bridgeport Garden Apartment

Enjoy a peaceful stay at this colorful, creative, artsy and relaxing garden unit apartment in the heart of Bridgeport. Located a few blocks away from Bridgeport's best bars and restaurants. This unit is good for couples, solo adventurers, business travelers and families (with kids). Street parking is free, and I’m readily available via phone or in person (I live a few minutes away).

Aug 19 – 26

ﺩ.ﺇ406 per night

Guest favorite

Condo in West Town

4.97 out of 5 average rating, 705 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.

ﺩ.ﺇ367 per night

Superhost

Apartment in Chicago

4.92 out of 5 average rating, 152 reviews

Urban Pilsen Apt. near Downtown

Cozy, urban Pilsen apartment in "Heart of Italy" with authentic old-style Italian restaurants. The apartment is very warm and open, has a gourmet kitchen, lots of natural light and is conveniently located 2 miles from the UIC Medical District, 3 blocks from the Pink Line and under 4 miles from downtown Chicago.

Feb 10 – 17

ﺩ.ﺇ412 per night

Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 491 reviews

2BR Bursting w/ Character in Hip Logan Square!

The unit sits on our extra wide city lot in the center of hip Logan Square! The apartment is eclectic and well decorated, with vintage touches and full of charm. For a garden unit it feels spacious, clean, bright and comes with all of the desired amenities, including access to our spacious side yard!

Apr 8 – 15

ﺩ.ﺇ532 per night