Family-friendly holiday rentals in Portage Park

The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.

4.94 out of 5 average rating, 474 reviews

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

KitchenFamilyParking

4.97 out of 5 average rating, 267 reviews

A spacious living area displays a modern grey sofa adorned with blue accent pillows. A coffee table is positioned centrally, accompanied by a small vase of flowers. Natural light enters through large windows, illuminating wooden flooring. A dining area with a chandelier and artwork is visible in the background.

Flat in Jefferson Park

Elegant & Clean Cottage Apt 20 minutes from O’Hare

You’ll love staying in our remodeled, 1st floor apartment in the heart of the Jefferson Park neighborhood of Chicago. It comes with a spacious living area with 3 private bedrooms, 2 full bathrooms, a full kitchen,& large side yard. Only a 5 minute walk to the CTA BlueLine & Metra trains that can quickly get you downtown & to or from O'Hare airport. Our home offers you a comfortable and relaxing stay in one of Chicago’s safest areas with excellent restaurants & parks within walking distance.

FamilyKitchenWifi

4.87 out of 5 average rating, 271 reviews

A living area features a dark leather sofa with red accent pillows, paired with two leather chairs. A wooden coffee table sits centrally, surrounded by warm-toned lighting. The space opens to a kitchenette with a retro red refrigerator and tall bar seating, creating an inviting atmosphere.

Flat in Portage Park

Cozy & Comfy 1bd In Historic Portage Park Bungalow

Make yourself at home in my comfortable Portage Park one bedroom garden apartment. This spacious condo is bright and airy with warm furnishings, a kitchenette with an island, private bedroom with a full bed and a modern bathroom with a glass walk-in shower. Portage Park is Chicago’s largest Polish neighborhood and is home to vintage charm, heaps of history and classic Chicago-style bungalows. The National Veterans Art Museum is a poignant must-see while you’re here with its combat-era art.

KitchenFamilyCheckout

Guest suite in Jefferson Park

A bright bedroom features light yellow walls and a spacious bed adorned with a floral quilt. Two decorative pillows rest against the headboard. Natural light fills the room through sheer white curtains, highlighting a small bedside lamp and framed artwork on the walls.

4.93 out of 5 average rating, 164 reviews

The Vanderpool House

The Vanderpool House has a Private Suite in a historic 100 year old Chicago Bungalow just 2 blocks away from the 2nd largest transit center in Chicago. The Blue Line L stop will take you downtown, the airport, or the Rosemont Convention Center. The Metra train will take you downtown or the northwest suburbs and you have 13 bus lines will take you anywhere else. Onsite parking is available at no extra charge. Theaters, Neighborhood Restaurants, Art Museums within walking distance.

KitchenIndoor spacesGetting around

The sitting room features various seating options, including a floral-patterned sofa and orange lounge chairs. Soft lighting illuminates the space, which is accented by thatch palm leaf wall coverings and tropical decor. An exercise area is visible in the background, enhancing the room's versatility.

4.89 out of 5 average rating, 122 reviews

Tropical Bungalow Getaway in Quiet Neighborhood

Located on a quiet tree lined street, the bungalow's garden level design was influenced by the rumpus rooms of the 1950's. A private side entry, a few steps down from the rear courtyard, leads into your tropical get away. Heywood Wakefield furniture and thatch palm leaf wall covering enhance the Tiki vibe of the sitting room. An exercise area, private bedroom and bath are all accessed from this main space. While the suite is at garden level, it is always bright and airy.

Indoor spacesKitchenDecor

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

4.94 out of 5 average rating, 199 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

KitchenFamilyCondition

4.77 out of 5 average rating, 380 reviews

A cozy living area is defined by a modern gray sofa and two red armchairs, adorned with decorative cushions. A black coffee table sits atop a patterned rug, while a television is positioned on a sleek stand. Natural light filters through small windows covered with dark curtains.

Flat in Irving Park

ITALIAN garden apt/kids friendly/great location!!

Ciao! My name is Viviana I am Italian and I live with my family, my husband and 2 girls, I hope you will enjoy our cozy guest garden APARTMENT within our home, featuring a queen size bed, a sofa bed good for a small person or a toddler, 2 twin foldable beds, TV where you can enjoy cable channels, movies and other amenities like, laundry, little kitchenette with a MINI refrigerator, microwave, snacks and hot plates if you like to cook something. Arrivederci!

FamilyKitchenBack garden

4.97 out of 5 average rating, 238 reviews

A spacious living area features a dark leather sofa and a modern accent chair beside a circular glass coffee table. A patterned area rug in neutral tones lies on the hardwood floor, while a dining area with a round table and chairs is visible in the background.

Home in Portage Park

The Evergreen House

Relax and feel at home on the first floor apartment (completely private) of my Chicago 2-Flat. This home away from home is well stocked with anything that you might need whether you are staying for 2 nights or 2 months. There are 3 televisions with Wifi and Netflix throughout the apartment. There is a nice backyard that you are welcome to use and street parking is free. Washer and Dryer available in the basement. The highways and bus are also nearby.

Indoor spacesKitchenAccuracy

4.96 out of 5 average rating, 140 reviews

A modern kitchen and dining area features sleek cabinetry and a large window allowing natural light. A glass dining table with blue chairs is positioned centrally, adjacent to stainless steel appliances and counter space. Light hardwood flooring enhances the spacious look of the room.

Home in Irving Park

Northside Chicago Getaway

This home is a classic Chicago bungalow that has been recently updated. There are some special features including whole home audio, a 75" TV with 9.1 Dolby atmosphere surround sound, a 3-person sauna, complete kitchen, fire pit out back and private parking for 2 cars. The Home is located in the Mayfair Park area of Chicago and offers a taste of the City life but also has a little space to breathe. Hope you enjoy it as much as I have over the years!

Indoor spacesFamilyHospitality

4.94 out of 5 average rating, 143 reviews

A comfortable living area is furnished with a tan sectional couch and a small coffee table. A vibrant area rug adds warmth to the hardwood floors. Natural light filters through windows, illuminating wall art and a nearby plant, creating an inviting space.

Flat in Portage Park

Cozy Jefferson Park 2BR Apt

A lovely 2nd floor apartment flooded with natural light in a 2-unit building located in Jefferson Park. Conveniently located near O’hare airport, filled with small businesses, dive bars, and family-owned restaurants. Downtown Chicago will take 20-40 minutes, depending on traffic. My partner and I live in the unit below and can answer any questions you may have throughout your stay. We have created a warm and safe place for all to feel welcome!

Indoor spacesKitchenCleanliness

4.84 out of 5 average rating, 219 reviews

A brick home is presented with a small set of stairs leading to the entrance. An American flag is displayed on the front porch. Well-maintained landscaping with green grass and a shrub border surrounds the entrance, creating a neat and tidy appearance.

Flat in Portage Park

My Home Away

This lower level space of my Home is perfect for anyone looking for a nice quiet place to stay while in Chicago, it is equipped with a kitchenette a fridge coffe maker and microwave. It is close to anything and everything including plenty of FREE parking right in front, it’s close to Ohare airport , forest preserves, Lake Michigan and downtown (30m) as well. Shopping, parks and public transportation within walking distance.

FamilyKitchenCondition

A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.