Holiday rentals in North Side

Cute Chicago Attic Loft! Walk to CTA, Easy Travel

Welcome to our newly renovated attic in-law suite in our vintage, 120 year old Chicago home! This bright, airy loft boasts a brand new full bathroom with a large, beautiful walk in shower. The unit has a newly built kitchenette with vintage hardware, a new fridge and freezer, and microwave. Conveniently located between O'Hare and Downtown Chicago, this space is situated perfectly for your Chicago visit! We’re a 2min drive from I-90 & I-94, a 5min walk to the train, and a 2min walk to the bus.

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

Jumbo 1 bedroom condo with free parking and more!

Spacious & modern 1 bdrm condo in a quiet and safe neighborhood in Chicago. The neighborhood is culturally significant and diverse! Close to O'hare airport ( 8 miles), Midway airport (13 miles), and downtown Chicago (10 miles). Close to CTA/public transportation. Well equipped with smart locks for self-check in. Keurig, air fryer and brand new King Size bed with premium linens! Smart TV with apps, and desk/printer for WFH. Coin laundry in basement! Long term rentals welcome! Hablo español.

King Sleep Number Bed – No Cleaning Fee

Unwind in luxury on a king-sized Sleep Number bed, refresh in a sleek marbled bathroom, and channel your inner chef in a farmhouse-inspired kitchen with many amenities. This bright and airy space is the perfect retreat after a day of exploring. Located near CTA bus stops, getting around the city is a breeze. Whether you're here for business or pleasure, our home offers the ideal mix of comfort, style, and convenience. Book your stay today and experience Chicago in elevated comfort!

Garden Suite — Studio Apartment

Welcome to your cozy Garden Suite, offering the perfect balance of comfort and privacy. This charming apartment features a private entrance, ensuring you have a peaceful and uninterrupted stay. Enjoy the convenience of your own fully equipped kitchen, complete with a stove, refrigerator, microwave, and all the essentials to prepare your favorite meals. Located just minutes away from local attractions, shops, and public transport, it’s the ideal home base for exploring the area.

Sunny Apt Close to O'hare + Easy Parking + Dog OK

Sunny and spacious 2nd floor, 1 bedroom apartment in Jefferson Park - 10 minute drive to O'Hare, 20 minutes to downtown. Flexible, self-check-in Easy and free street parking Bedroom with 1 king bed Radian heating in winter Recently updated with central air conditioning Well equipped kitchen (no dishwashing machine) No washer & dryer Free WiFi Smart TV for streaming House trained & friendly dogs are welcome Could sleep more than 2 people with an air mattress if needed.

1 bedroom apt near Michigan Lake

Escape to your urban oasis by the shores of Lake Michigan! This charming one-bedroom apartment is your haven in the heart of the vibrant Loyola Park neighborhood. Unwind in a cozy retreat that blends modern comforts with the energy of city living. Savor the warmth of the inviting decor and cook up a storm in the well-equipped kitchen. Step out to revel beaches of Lake Michigan and enjoy effortless access to public transport. Come to relaxation and excitement-all in one!

Logan Square Garden Suite

Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. This is a perfect space for solo travelers or couples. This is also a great space if you are traveling with a small child or infant. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine.