Holiday houses in Portage Park

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Quick stats about holiday rentals in Portage Park

  • Total holiday rentals

    Explore 120 holiday rentals in Portage Park

  • Nightly prices starting at

    Portage Park holiday rentals start at $102 NZD per night before taxes and fees

  • Verified guest reviews

    Over 6,100 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Portage Park holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Portage Park rentals

  • 4.8 Average rating

    Portage Park stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in Portage Park

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Apartment in Portage Park
4.97 out of 5 average rating, 30 reviews

Cozy Retreat in Pleasant Portage Park, Chicago.

Welcome to your home away from home! Our charming unit is located in the heart of Portage Park, one of Chicago’s most vibrant and family-friendly neighborhoods. Whether you’re here for business, a weekend getaway, or to explore the Windy City, this space is the perfect base for your stay. Very picturesque neighborhood located 5 minutes from the blue line train which runs from O’hare Intl Airport to Downtown Chicago. 10 min drive to Interstate 90 & Interstate 94. Quiet time strictly enforced!

Guest favourite
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.
Guest suite in Portage Park
4.94 out of 5 average rating, 470 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

Top Guest favourite
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.
Apartment in Jefferson Park
4.97 out of 5 average rating, 263 reviews

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.

Guest favourite
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.
Apartment in Portage Park
4.86 out of 5 average rating, 266 reviews

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.

Top Guest favourite
Apartment in Portage Park
5 out of 5 average rating, 13 reviews

No Place Like Home/ The Emerald Stay

Welcome to The Emerald Stay — a thoughtfully designed One bedroom apartment with modern decor and subtle nods to The Wizard of Oz. Stylish, comfortable, and full of charm, it’s the perfect place to unwind and feel at home. Our apartment is perfectly located between downtown Chicago and O’Hare airport. Walking distance to the Irving Park bus stop, which can take you to the Blue Line train to downtown. If driving, there is quick access to I-90/94 highway nearby. No Smoking. No parties.

Guest favourite
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.
Guest suite in Portage Park
4.89 out of 5 average rating, 117 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.

Superhost
The living room features large windows dressed in sheer curtains, allowing abundant natural light to fill the space. A modern sectional sofa, accented with colorful cushions, is positioned around a central coffee table. A decorative area rug complements the elegant hardwood flooring, while a sleek TV is mounted above a cozy fireplace.
Condo in North Side
4.95 out of 5 average rating, 163 reviews

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Guest favourite
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
4.97 out of 5 average rating, 234 reviews

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.

Top Guest favourite
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
4.96 out of 5 average rating, 136 reviews

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!

Guest favourite
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.
Apartment in Portage Park
4.94 out of 5 average rating, 138 reviews

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!

Guest favourite
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.
Apartment in Portage Park
4.84 out of 5 average rating, 213 reviews

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.

Guest favourite
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.
Guest suite in Portage Park
4.94 out of 5 average rating, 171 reviews

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!

Popular amenities for Portage Park holiday rentals