Apartment holiday rentals in Skokie

Cute & comfortable apartment on quiet street

Rest and relax at this peaceful, cozy & comfortable upstairs apartment located in a quiet, family-friendly neighborhood surrounded by local parks & tree lined streets. It's a short distance to restaurants, the lakefront, and Northwestern University. There is easy parking and it's a short walk to public transit, to other local universities, Ryan Field, Welsh Ryan Arena, Downtown Chicago, Wrigley Field, and many museums, and concert venues. Note: laundry is only available to long term guests.

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.

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. **Please note the apartment is located on the garden level and does NOT include the entire home.**

Cozy Neighborhood Escape | Near NU-Chicago-Beaches

This is a beautiful, newly renovated apartment that is cozy and contemporary! This unit is located in Evanston’s arts district, surrounded by local shops, tree lined streets, and is a short distance to restaurants, the lakefront, and Northwestern University. Evanston is a suburb just north of Chicago with easy access to the city either by car or public transit. This apartment sleeps up to 4 people and is a 1 bedroom, 1 bath with a sofa sleeper. Don’t miss out. Book Now!

Stunning, Sunny Flat with Beautiful Backyard

Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. Recent updates: New king size bed, 65-inch HD TV, washer & dryer, and more. We follow EPA/CDC protocol and prepare for your stay with intensive cleaning and disinfecting.

Cozy Garden Unit in Quiet Neighborhood

A cozy garden unit in the heart of skokie, off of a quiet residential street with plenty of street parking. Just a mile away from the Skokie-Dempster Yellow line train that leads to downtown Chicago, and within a mile from Old Orchard Mall and plenty of great eateries such as: Chick-fil-A, Portillo's, Culver's, Oberwies, Kaufman's Bagel, and more. 15 minutes away from Evanston and the Beautiful Lake Michigan shoreline!

Charming/Cozy Chicago Bungalow Garden unit 1BR/1BA

Private Cozy Chicago classic bungalow garden unit Pr1BR/1BA. Fully furnished with a queen bed, comfy living room, kitchen, and smart TV (use your own streaming logins, no cable). Private entrance, no shared spaces. Located on Chicago’s NW side near Addison & Cicero—easy access to downtown, O’Hare, and local spots. Quiet block with owner living upstairs if you need anything. Relax and enjoy your stay!

Charming Chicago Apartment | Near O’Hare+Blue Line

Bright, private upstairs apartment in a quiet NW Chicago neighborhood—just 10 minutes from O’Hare and close to the Blue Line. Enjoy a comfy king bed, full kitchen, fast WiFi, and smart TV. Walking distance to shops, restaurants, and Harlem-Irving Plaza. Free street parking, private entrance, and self check-in make your stay easy and relaxed. Ideal for solo travelers, couples, or remote work.