Holiday rentals in Portage Park

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Top-rated holiday rentals in Portage Park

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Guest favourite
A studio space is presented with a spacious bed in the background, complemented by a wicker swing chair nearby. A vintage SMEG refrigerator and a dining table with stools enhance the ambiance, while a textured area rug lies on the hardwood floor beneath.
Flat in Kilbourn Park
4.92 out of 5 average rating, 763 reviews

Explore Chicago from an Urban Sanctuary with Free Parking

A vintage lovers dream! This loft was designed with a love for the past. Starting in the kitchen, you’ll see the beautiful zinc alloy countertops are complemented by gorgeous antique mirror backsplashes. You’ll have access to a stovetop, microwave, coffeemaker, as well as basic tools and kitchen supplies. There is a lovely throwback SMEG 50’s refrigerator and the shelves are all reclaimed wood. This antique lumber detail can be found throughout the loft, from the floors all the way to the night stands. The bathroom door may be recycled wood and the mirrors antique, but the shower fixtures are all Grohe. There is also a hair-dryer as well as complimentary toiletries and clean towels for your use. At the end of the day, you can sit on our funky wicker swing chair and think of all the chic guests who may have used the closet doors that were brought in from NY’s Plaza hotel! You’ll surely have the sweetest of dreams when you go to sleep on the memory foam mattress following a quick binge using the complimentary netflix. Additional amenities include self-controlled A/C and closet space with hangers, an iron and ironing board. This loft is very well kept, professionally cleaned and sanitized after each and every use. When booking this studio you will have full and private access to the entire apartment. There is a shared deck and lounge area you are welcome to use. For your convenience, we have arranged luggage drop-off/storage before and after your stay at the restaurant right down stairs - do note this is a courtesy. Our check-in and check-out process is automatic and seamless, once you book you will receive a private entry code ahead of your stay. Check-in any time after three pm as late as you'd like, check-out on or before 11 am. Due to our cleaning schedule we cannot accommodate early check-ins or late check-outs. The provided free parking spot is located a block away from the Airbnb unit Someone who’s offsite will be available as needed Set between South Old Irving and Kilbourn parks, the studio is located in one of Chicago's most historical neighborhoods. Sample the craft beer taverns and cocktail bars lining North Milwaukee Avenue. Wrigley Field is about 10 minutes away by car. The quickest and most inexpensive way to get around is via Uber or Lyft. If reaching the apartment by vehicle, there is free street parking in the surrounding neighborhood (please follow the local laws and signs). Public Transportation guide to the apartment: From Chicago O'Hare Int'l Airport: Take the Blue Train line to Irving Park Station and then transfer to the CTA #53 Milwaukee bus line to reach the apartment. You can also take the Blue Train line to Jefferson Park Station and then transfer to the CTA #56 Milwaukee bus line to reach the apartment. To/From Downtown Chicago: The CTA #56 Milwaukee bus is a very convenient and direct way to reach the Downtown Chicago Loop with a station just below the apartment. To/From Wrigley Field: Easily catch a game via the 77 or 152 buses, with a station just close by the apartment. Train and bus maps can be found and downloaded here: https://www.transitchicago.com/maps/ Please note that the provided free parking spot is located a block away from the Airbnb unit.

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.
Flat in Jefferson Park
4.97 out of 5 average rating, 249 reviews

Elegant & Clean Cottage Apt 20 minutes from O’Hare

You’ll love staying in our recently 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 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.

Top guest favourite
A charming single-family home features a well-maintained facade with a red front door and neatly trimmed lawn. Stairs lead up to the entrance, while a simple walkway is bordered by greenery. The exterior is accented by sunny blue skies and fluffy clouds.
Bungalow in Portage Park
4.87 out of 5 average rating, 187 reviews

Top-Rated 3BR Near O’Hare & Rosemont | Sleeps 6

Clean, spacious 3BR home designed for a reliable, stress-free stay. Professionally maintained and consistently rated for quality and comfort. Ideal for families, business travelers, and extended stays. Bright living area, full kitchen, and comfortable space for up to 6 guests. Hosted by an experienced Superhost focused on consistency and care. Prime Location • O’Hare Airport–14 mins • Rosemont (Dining, Entertainment, Convention Center)-10 mins • Allstate Arena–13 mins • Downtown Chicago-18 mins

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.
Flat in Jefferson Park
4.86 out of 5 average rating, 256 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.

Guest favourite
A modern living area features a blue sectional sofa facing a mounted flat-screen TV. A wooden coffee table is positioned in front of the sofa. A desk and chair are situated near a large window, allowing natural light to brighten the room.
Apartment in Mayfair
4.88 out of 5 average rating, 152 reviews

Newly updated 1BD/1B in Old Irving Chicago!

Welcome to your home away from home in the heart of one of Chicago's safest and quietest neighborhoods! This beautifully updated 1 bedroom apartment offers everything you need for a comfortable and convenient stay. It is perfect for couples, solo travelers, and business visitors. Book now for a truly unforgettable experience in the Windy City! - 1 free parking spot - 400 MB Wifi - 2 smart T.V. with access to Netflix, Hulu, Amazon and more! - Desk - Easy app paid laundry in the building.

Guest favourite
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.
Guest suite in Jefferson Park
4.93 out of 5 average rating, 146 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.

Top 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, 111 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.

Guest favourite
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.
Apartment in Avondale
4.96 out of 5 average rating, 150 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.

Top guest favourite
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.
Guest suite in Portage Park
4.95 out of 5 average rating, 190 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

Guest favourite
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
4.76 out of 5 average rating, 361 reviews

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!

Top 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, 226 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.

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.
Flat in Jefferson Park
4.94 out of 5 average rating, 124 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!

Popular amenities for Portage Park holiday rentals

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Avg. price$119 SGD$125 SGD$128 SGD$116 SGD$128 SGD$137 SGD$140 SGD$144 SGD$135 SGD$131 SGD$121 SGD$117 SGD
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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 $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,680 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    120 of Portage Park holiday rentals include wifi 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!

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