Holiday rentals with breakfast in Northwest Side

"Your Cozy 2nd Home-Near O'Hare\Rosemont\Downtown

“More Than Just a Stay—10+Years of Trusted Superhost Hospitality.” Welcome to your Chicago retreat, designed to make you feel at home the moment you arrive. Whether you’re here for business, family, or adventure, our cozy home gives you the perfect blend of comfort & connection. Unbeatable Location • O’Hare Airport-14mins • Downtown Chi.-18mins • Rosemont Theatre- Entertainment District & Donald E.Stephens Convention C.-10mins • Allstate Arena-13mins “Where every trip feels like home”

Fairfield Flat, Airy Vintage Rehab

This remodeled first floor apartment is close to the California Pink Line Station, Pete's Fresh Market, and Douglass Park. Pilsen and West Loop night life a short train ride away. Situated in a quiet corner of Little Village, our neighborhood of predominately Mexican and Black multi-generational families is teeming with tamale stands, paleta vendors, and children playing. Great for couples or friends, though parents have expressed frustration with the hard, or uneven surfaces, and the stairs.

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

A Quiet Stay While You Are Away Oak Park

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

On the Boulevard in Logan Square

The space is a completely renovated two bedroom garden apartment in a vintage (1918) 7 unit building on the Boulevard in Logan Square's National Register Historic and City of Chicago Landmark Districts. Logan Square is on the northwest side of Chicago, on the CTA Blue Line, which runs from O'Hare Airport to downtown Chicago's Loop, then continues on past the University of Illinois at Chicago and the West Side Medical Center to the suburban villages of Oak Park and Forest Park.

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

Cozy French Inspired Cottage in rural setting

Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

Pretty Suite in Lincoln Park w/HVAC +free parking

Location, location, location! Located in one of Chicago’s best neighborhoods, Lincoln Park near DePaul university. 3 blocks from the CTA trains. Entire Private SUITE with small KITCHENETTE in lower level of 3 story apartment building. Access to all the shopping, restaurants and bars that Lincoln Park has to offer. Leave your car in the free, far right parking space in back of the apartment building, and explore Chicago by foot, bike, Uber or train.

Cozy Garden-Subterranean Apartment

JAN-FEB Special, check out lower then average prices. Our cozy Lincoln Square one bedroom apartment sleeps 2, has a fully furnished kitchen, and is close to Lincoln square shops and great restaurants/carry-out. Ample street parking & close to public transportation. Entrance to the apartment at back of building. Sorry no pets, we both have allergies and my husband has asthma and cannot tolerate pet dander.

Wicker Park 7 Beds Crash Pad

Welcome to High Society BNB, your home away from home in the city. Go check us out! This 2 level apartment is a great location for a group to stay or an individual that wants more space than a hotel room. There are 2 floors with living/kitchen on the main floor and 2 bedrooms downstairs in our fully renovated basement. There are a total of 7 beds (6 comfy mattresses and 1 futon)!

Cheerful Remodel Prime Location

Relax in this newly remodeled and beautifully decorated apartment while recharging from a long day of sightseeing in the big city! If you have a car, great, we have parking! If not, awesome, we are a block from the Green Line train to downtown! With a 5 minute walk to Whole Foods, Trader Joes, and downtown Oak Park, you can't get a better location than this!