Apartment holiday rentals in North Side

Classic Chicago Bungalow Garden Unit 1bdrm 1 bath

Classic Chicago Bungalow garden unit apartment furnished with a queen bed, living room, and everything you & your guests need to enjoy your stay in Chicago! Make yourself at home once you arrive. Traditional cable TV is not included in your stay, we do provide a smart tv, Feel free to use with YOUR own login and enjoy! Located in Chicago northwest side. Use Addison and Cicero as your cross street to determine gps and location. Your space is separate with no shared common areas. Owner lives above

Roomy Retreat | Easy Parking | Walk to Train

Light-Filled Apartment | 20 Min Downtown | O’Hare ✔ Free Street Parking ✔ Fully-Equipped Kitchen ✔ Friends/Couples/Families ✔ Walk to Cafés & Restaurants ✔ No Stairs Perfect for friends and families, our home offers easy access to sightseeing while embracing the charm of a vibrant, walkable neighborhood. 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 Cleaning

The Grotto of Logan Square

Garden unit, great for a small group looking for a base while they explore the city. 10 min walk from Logan Square Blue Line, restaurants, galleries, coffee shops and clubs. Explore the city from one of its best neighborhoods! In your downtime the space offers several chicago guide books and magazines. There is a Fire stick in the TV that has most major media apps installed. The alarm clock is also a speaker for your phone to plug into. Please make sure you read the amenities and house manual.

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Sophisticated Flat in Historic Building

Nestled in the charming Old Town Triangle of Chicago, this luxurious flat offers a seamless blend of historic charm and contemporary sophistication. With its soaring ceilings and elegant arched windows, this immaculate space boasts a truly captivating ambiance. Impeccably designed interiors ensure a truly indulgent stay, while the building's rich heritage adds an unforgettable sense of place. Treat yourself to the ultimate Chicago getaway and bask in the allure of this stunning residence.

Logan Square Garden Sanctuary

This house is located in historic Logan Square. The space is a newly renovated basement unit of an owner-occupied two-flat. It's right next to Palmer Square which is a two acre park with a jogging path, kids area, and benches. It's a perfect place to have a picnic or meet with friends. The neighborhood is very walking-friendly and there's tons of great shops and restaurants in the area. The unit has an open floor-plan with a comfy memory foam bed, futon, a full bathroom, and kitchenette.

Penthouse Near Wrigley Field

This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

Quirky Quarters at Wrigley

I think you are just going to love my apartment. The space features wonderful large street level windows in the living room and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a ten minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. There is no parking available with the apartment.

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!