Holiday rentals in Northwest Side

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Top-rated holiday rentals in Northwest Side

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Guest favourite

Flat in Chicago

4.86 out of 5 average rating, 132 reviews

Classic Chicago Bungalow Garden Unit 1bdrm 1 bath

Classic Chicago Bungalow garden unit apartment furnished with a queen bed, living room, and everything you & your guests need to enjoy your stay in Chicago! Make yourself at home once you arrive. Traditional cable TV is not included in your stay, we do provide a smart tv, Feel free to use with YOUR own login and enjoy! Located in Chicago northwest side. Use Addison and Cicero as your cross street to determine gps and location. Your space is separate with no shared common areas. Owner lives above

Superhost

Private room in Oak Park

4.73 out of 5 average rating, 298 reviews

Little Gem Double Rm Home Base for Chicago Trips!

Great home base for Chicago adventures & PREMIUM location in the epicenter of Oak Park - America's home of prairie architecture! Beautiful park/Frank Lloyd Wright homes are directly outside your door and you are only a 25-minute train ride to Millennium Park & all of Chicago! Eclectic garden level (shared) apartment decorated with fun and funky furnishings. Private Bedroom with new double size bed, deluxe bedding, towels. Shared bathroom, living room, and kitchenette. View my other 2 listings!

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 163 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Guest favourite

Flat in Chicago

4.85 out of 5 average rating, 226 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

Flat in Chicago

5 out of 5 average rating, 5 reviews

LairBnB - Garden Apartment

Welcome to LairBnB! This is a private garden apartment with separate egress in our home near 6 corners in Portage Park. The ceiling height is 76”. Guests under 6' tall will be most comfortable here. We are old school Airbnb SuperHosts who love to host adult travelers in town for work or events in Chicago. We are steps away from Milwaukee, Cicero, and Irving Park bus stops, an 8 minute walk to the Grayland Metra stop, and a 20 minute walk to the Irving Park Blue line CTA.

Top guest favourite

Guest suite in Chicago

4.95 out of 5 average rating, 20 reviews

Charming Garden Unit Portage Park

Cozy garden level guest suite with separate entrance in Portage Park! Enjoy a comfortable and private retreat (ceiling height varies 5'9"-6'9"), complete with a separate entrance for your convenience. You'll have exclusive access to a fully equipped basement, which includes a private bedroom, gym, laundry room, bathroom, Wi-Fi, living area and small kitchenette. In addition to your private space, you'll have access to shared outdoor areas, including a BBQ and fire pit.

Flat in Chicago

5 out of 5 average rating, 3 reviews

Modern Design 3 Bedroom Dandelion Apartment

Discover your stylish retreat in Avondale! This beautifully appointed 3-bedroom apartment seamlessly blends modern luxury with sustainable living. Sun-drenched, open-concept living space, leading to a chef's dream kitchen. Featuring sleek stainless steel appliances, custom cabinetry, and ample counter space, it's perfect for culinary adventures. This eco-conscious building boasts insulated walls, green construction, and solar panels providing complimentary electricity.

Top guest favourite

Flat in Chicago

4.99 out of 5 average rating, 98 reviews

Plants and Art | Near Trendy Restaurants & Bars

Light-Filled Apartment Near Chicago’s Best Restaurants & Bars • Friends & Couples • A/C • Coffee Station w/Local Beans • Fully-Equipped Kitchen Whether you’re in town to explore or unwind, you’ll love the proximity to restaurants, cafes, and live music venues.The apartment is the perfect home base for your Chicago adventure. Fees: Early Check In@ 2pm : $50 Late Checkout@ 1pm: $50 Shipping: $25 + UPS fees Required for stays of 7+ Days: $100 Mid-Stay Cleaning

Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 27 reviews

Lovely Garden Studio Apartment.

Cozy garden suite apartment in a quiet part of town. This space is located in the lower level of a Bungalow house. There are 2 other units in the building, inhabited by a nice little family and a nice person. Close to Avondale and Logan Square nightlife, and a direct bus to Blue Line Trains is within walking distance. Great backyard, full of native plants and butterflies if you're craving some outdoors. Free parking on a side street a little down the block.

Top guest favourite

Home in Chicago

4.98 out of 5 average rating, 203 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

Guest suite in Chicago

4.95 out of 5 average rating, 126 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!