Holiday houses in Northwest Side

Gorgeous 7BD Home w/ Garage

This spacious and one-of-a-kind home located in Chicago between Lakeview and Avondale will give your group all it needs! This beautiflully renovated, elegant, and newly furnished home offers multiple areas to gather. The home also comes equipped with 2 fully stocked kitchens, a full bathroom on each level, along with two bedrooms on the second floor, two bedrooms on the first floor, and 3 bedrooms in the basement with 9 total beds (7 queens/2 twins). Downtown and Ohare are both 25 minutes away!

Location · Family · Indoor spaces

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

Value · Family · Pets

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.

Family · Value · Cleanliness

Beautiful/Spacious 7BD - 4BTH Home with Garage!

Discover the charm of our newly renovated, stylishly furnished single-family home, featuring 7 bedrooms across 3 floors, including a kids' room. Nestled near Portage Park, the house boasts fully equipped kitchens and ample space for games, meetings, or relaxation. Strategically located, enjoy a quick 20-minute Uber ride to downtown Chicago's vibrant heart and a 15-minute drive to O'Hare International Airport. We're committed to ensuring a memorable and comfortable stay for all our guests.

Location · Family · Decor

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.

Location · Value · Wi-Fi

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.

Location · Value · Checkout

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.

Value · Family · Condition

New Home | O'Hare Airport

• Single Family Home | 2 Floor • Basement | Master Suite! • 4 Beds | Sleeps 8! • Commute to O'hare: 16 min (drive) • Metra Train to Downtown Chicago • Easy Street Parking • Family Friendly | Peace at Night • Building outdoor video surveillance • Noise monitoring equipment. • Kitchen is stocked | cookware | utensils • Washer | Dryer | Dishwasher in unit (free) • Rosemont Entertainment District!! • Rideshare(Uber/Lyft) • Safe, working class neighborhood

Family · Value · Backyard

Modern NEW Deluxe Studio in Oak Park

Enjoy a stylish experience at this centrally-located studio In charming Oak Park. Tourist-friendly and trendy downtown Oak Park has a buzzing restaurant district, great cafes, and an assortment of excellent storefronts, including vintage shops, boutique toy stores, mom-and-pop bookstores, and a variety of spas and salons to choose from. Parks in this world-class suburb are everywhere. Views from the unit are fabulous. This deluxe studio has it all.

Value · Location · Condition

Studio 15 Minutes From Ohare!

Please read through entire listing before booking. Enjoy a cozy, private, and spacious studio on a quiet, tree-lined street in Chicago’s Dunning neighborhood. You’ll have a full kitchen, bathroom, comfy living space, plus a large backyard and free parking. Perfect for couples or business travelers. Close to great restaurants and parks, Rosemont (10 min), O’Hare (15 min), and downtown (35–45 min; varies with traffic).

Family · Location · Indoor spaces

Accommodation for 2 people (basement)

Nota: NO HAY ÁREAS COMPARTIDAS Habitación privada con baño, sala, espacio con utensilios y algunos electrodomésticos básicos de cocina, juego de comedor para 4 personas. Estacionamiento en la calle. Barrio Belmont Cragin, ciudad de Chicago. Esta locación es perfecta, céntrica, con acceso a líneas de autobuses, tiendas, restaurantes, supermercados, a pocos pasos del Riis Park, centros clínicos y farmacias.

Location · Family · Hospitality

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!

Family · Value · Air conditioning