Ski-in/Ski-out holiday rentals in Illinois

Grand Avenue Apt 2/west Loop & Newly Renovated!

Welcome! The Grand Avenue apt #2 is a spacious and Scandinavian design inspired 2 bed/1 bath apartment located in the West Loop neighborhood, one of the premier live/work spaces and top restaurant/bar scene in the city of Chicago. The apartment has been newly renovated with a beautiful dining area and kitchen, newly appointed bedrooms with Casper mattresses and a cozy living room. The apartment includes a private outdoor balcony, a large backyard, in unit washer/dryer and electric fireplace.

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.

Lakefront Barn for Big Group

The Lake Linda Barn is a wonderful secluded country getaway for large groups. You have sleeping for up to 9 people and that's not even putting people on the couches (allowable...just let me know for extra bedding) It's a chance to reconnect with nature and leave the stress of life behind. You have access to the host's garden and the opportunity to sit on a beautiful private 44 acre lake and enjoy quiet sunsets or a the famous 30 min. "bird walk" around the lake.Clean, simple, rustic space.

Beautiful Three Bedroom Apartment Near Loyola

Welcome to our beautiful 3 bedroom apartment just blocks from Loyola University. Fully furnished apartment with one queen bed, two full beds, and one pull-out futon. Amenities include full kitchen, dining room, and 2 bathrooms. WiFi, cable, 3 televisions throughout the apartment and sunroom and back yard too! Close to public transportation, the lake, and dozens of dining options within walking distance. One (1) City Street Parking Pass will be provided for each night of your stay.

Newly Rehabbed! 2br with Vintage Charm

Our 2 bed garden apartment in Ravenswood will be the ideal home base for your stay! Located in one of Chicago's vibrant Northside neighborhoods, you’ll experience local charm outside your door. The home has space for 5 and a newly renovated kitchen, though you may not have time to cook with many family-owned restaurants within walking distance! The Montrose Brown Line is only 3 blocks away, taking you downtown in 30 minutes and Lakeview/Lincoln Park in even less.

3BR Luxury Modern Apartment

This is the place to be in downtown Chicago! This new building offers you comfort and luxury in one of the most desirable locations. Flooded with natural sunlight the spacious living room, fully equipped kitchen and bedrooms open up to a stunning mesmerizing view. The modern apartment building offers a sun-filled outdoor pool, a fitness center and beautiful appointed outdoor courtyard. Enjoy those summer days in your luxury apartment or the amenities outside.

Pro Cleaned & Isolated West Loop Coach House

Mimi & Paul's historic ivy-covered coach house has a private entrance and an airy queen bedroom. The renovated kitchen is outfitted with European-sized appliances - though you'll probably have no time to cook, since you're surrounded by the best restaurants Chicago has to offer. All of the essentials are provided to make your stay easy and comfortable... paper products, soaps, shampoo/conditioner/body wash, towels, linens and even coffee/tea!

Bright Converted Storefront In Roscoe Village

Our Roscoe Village two-bedroom condo is a spacious converted storefront that can accommodate up to six people - which is great, since this neighborhood has so much to offer! There are incredible restaurants, antiquing, we're a short walk to Wrigleyville, and about a half hour on the CTA to the Loop. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea!