Holiday rentals in Harwood Heights

2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking

This 100% private apartment in the lower level is just minutes away from O'Hare, Rosemont, Allstate Arena, I90, & the CTA. About 30 minutes from downtown or Wrigley Field. This two-bedroom private apartment in a newly built single-family home has plenty of space in an open-concept living room, kitchen, & dining room for big families. You will have a separate private entrance, fast wi-fi, full kitchen, & laundry. You will have 1 queen bed, 4 twin beds, & 1 air bed. There is free street parking.

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 perfect home base for your Chicago adventure. Extra Fees: *only available upon request and approval* Early Check In@ 2pm : $50 @10am:$100 Late Checkout@ 1pm: $50 @9pm:$100 Shipping: $25 + UPS fees Required for 7+ Days: $80 Cleanin

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

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Spacious in-law Apt: 10 min to O'Hare and Downtown

Our family would love to share our in-law apt. (private entrance) in our Norwood Park house. A beautiful neighborhood, the convenience of O'Hare and the highway, and 3 ways to get downtown less than a mile away (blue line and metra). Great food, bars, grocery store, and parks all within walking distance. A great alternative to the hustle and bustle of the city but you can be in some of the best neighborhoods in the city in 15 min (Wicker Park, Lincoln Park, Logan Sq.) and downtown in 25.

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Top Rated Stay with Free Parking+King Beds+Laundry

Newly renovated, Scandinavian inspired, apartment with all the amenities we have noted that guests desire in a home away from home. 3 bedrooms that includes 2 king sized beds/1 single bed/1.5 bath with private, in-unit laundry, fast Wifi, smart TV's, large kitchen with prep island and ample free street parking at the side of the home. This unit is SUPERHOST approved, come stay with us, you will be happy that you did!

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.