Family-friendly holiday rentals in North Side

Modern Avondale Apt | Great Food & Free Parking

Clean & modern Avondale apt close to Blue Line, perfect for urban explorers! Stylish decor, comfy bed, and a cozy ambiance await. Explore nearby cafes, bars, and boutiques, or hop on the train for downtown adventures. Easy to access & great neighborhood. Easy permit parking (free passes provided) on street allows for the ability to drive or take public transportation wherever you want to explore. Avondale has been voted one of the best neighborhoods in Chicago! Come see what the fuss is about.

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

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

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.

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!

Bright Apartment

Relax in this sunny one-bedroom garden apartment in Albany Park (Not recommended for taller than 6'3"). Our apartment is perfectly located between downtown Chicago & O'Hare airport. You can go just about anywhere in the city in about 20-30 min as we are 5 minutes away from the Montrose blue line train stop, Kimball brown line train stop, and the I90/94 interstate. Please note, some areas have lower soffit ceilings.

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

Eddy Street Upstairs Apartment

Make yourself at home in our comfy, cozy upstairs apartment! Located in the Portage Park neighborhood of Chicago, we are close to great food, parks, and fun outings! You can get to O'Hare Airport in less than 20 minutes, depending on traffic. And we're about a 25 minute drive to downtown, or about 45 minutes via public transit. We have free street parking on our block!

Chicago getaway for two!

This cozy 1 bedroom 1 bath apartment on the second floor of a lovely home in Jefferson Park is the perfect place to stay in Chicago. Conveniently located near the blue line (Jefferson Park stop) and has a bus stop for 88W right in-front! This cozy 1 bedroom 1 bath apartment on the second floor of a lovely home in Jefferson Park is the perfect place to stay in Chicago.