
House vacation rentals in Northwest Side
Find and book unique houses on Airbnb
Top-rated house rentals in Northwest Side
Guests agree: these houses are highly rated for location, cleanliness, and more.

The Chicago River House – GIANT wall projector!
Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture
LocationValueAir conditioning

Modern Gazebo Sleeps 17 Birthday Anniversary
Treat yourself to this Chicago getaway with 16 of your friends & family. Be inspired to create culinary delights in our celebrated 5 stars outdoor kitchen. Reboot & relax in each of our thoughtfully designed powered by SOLAR ENERGY throughout. After a memorable night in OR an adventurous night out you will ask yourselves, 'Why don't we do this more often?' 15 mins to Downtown, O’Hare airport, West Loop. 20 mins to Lakeview, Wrigleyville, Boystown, Logan Square, Bucktown & Wicker Park.
FamilyValueQuiet

City Cottage in Logan Square-Avondale
Our two-bedroom home has been beautifully appointed for a relaxing stay. You'll have access to all the amenities of home with a private backyard space. The location is conveniently located between Avondale and Logan Square neighborhoods. It's a 14-minute walk to either the Belmont Blue Line or Logan Square Blue Line stops that take you to Downtown or O'Hare Airport. Walk to great restaurants, coffee shops, bars, music venues, vintage boutiques, Logan Square Farmers Market, and more!
LocationValueNearby

Kid friendly 2 bedroom w/ private office
Private first-floor 2-bed apartment in hip Logan Square. Full bath, kitchen, WFH space and separate entrance. Walk to restaurants, cafes, parks, Blue Line/bus, 5 mins from bike rental/606 trail. We are kid/family friendly! We live upstairs with two young kids. Our ideal guest is comfortable with some family noise and apartment living. Cozy, convenient, and perfect for travelers seeking an authentic neighborhood stay! Please read other notes for more info!
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The Evergreen House
Relax and feel at home on the first floor apartment (completely private) of my Chicago 2-Flat. This home away from home is well stocked with anything that you might need whether you are staying for 2 nights or 2 months. There are 3 televisions with Wifi and Netflix throughout the apartment. There is a nice backyard that you are welcome to use and street parking is free. Washer and Dryer available in the basement. The highways and bus are also nearby.
ValueLocationLaundry

Northside Chicago Getaway
This home is a classic Chicago bungalow that has been recently updated. There are some special features including whole home audio, a 75" TV with 9.1 Dolby atmosphere surround sound, a 3-person sauna, complete kitchen, fire pit out back and private parking for 2 cars. The Home is located in the Mayfair Park area of Chicago and offers a taste of the City life but also has a little space to breathe. Hope you enjoy it as much as I have over the years!
LocationValueAmenities

Victorian House in Heart of Rogers Park
Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa
FamilyValueGetting around

Cozy Home in Brookfield
Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).
ValueFamilyParking

Modern Aesthetic 3bd Family Haven w/ King Bd, Yard
Unwind in this spacious, family-friendly haven in Elk Grove Village. Featuring a king bed, modern amenities, and a private yard, it’s the perfect spot for a relaxing getaway or a convenient home base to explore the area. The home is centrally located near O'hare Airport and Woodfield Mall, plus it is conveniently located near the intersection of Chicago's two major highways: I-90 and I-290, ready to take you to your destination.
ValueFamilyHeating

Oak Park Victorian by FLW Studio
Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.
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Modern Boho house in Lombard 7 min to Metra
Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!
ValueFamilySleep quality

Cozy Home near O'Hare & fun Hubs
Relax with the whole family at this peaceful place to stay. Experience comfort and convenience at our newly remodeled cozy house, perfectly situated near O'Hare Airport, Allstate Arena, and Rosemont Theater. Ideal for travelers and entertainment enthusiasts, this charming Airbnb offers modern amenities and a warm ambiance, ensuring a delightful stay. Book now and enjoy the best of Rosemont!
LocationFamilyAccess
Popular amenities for Northwest Side house rentals
House rentals with a pool

Pardizes Suites
LocationFamilyComfort

Chic Fulton Market Oasis + Curated Comfort & Style
ValueFamilyLaundry

Rosemont 4BD2BA house with Pool
ValueFamilyParking

Pool, 30 mins to CHI, 3 Kings, Outdoor Space, BBQ
FamilyValueIndoor spaces

Riverwoods Nature Retreat
FamilyLocationHospitality

Luxury Loft with Private Pool and Movie Theater
ValueFamilyHospitality

Backyard Paradise/ Private Pool + Peaceful Stay
LocationFamilyTV

Luxe indoor pool tree house minutes to Chicago
CleanlinessBathroomAmenities
Weekly house rentals

Entire 3 BR+2 office areas & deck, top floor condo
FamilyValueGetting around

NEW! 3BR/2.5B Duplex in Noble Sq
FamilyLocationQuiet

Modern 2Bdrm Westchester/Chicago Home.With Hot tub
ValueFamilyKitchen

Cool Quiet Coach House, Private Access + Patio
LocationValueIndoor spaces

BoHo House | Chic, 1903 Chicago Workers Cottage
LocationValueWifi

Entire first floor in Lincoln Square!
ValueFamilyBackyard

A Comfortable Stay While You are Away in Oak Park
LocationValueNearby

The Hamlin | Logan Square Home 4BR/2BA w Parking!
ValueLocationQuiet
Private house rentals

Beautiful 4 BR Family Home near Wrigley
ValueFamilyParks

Division St Designer Home In Heart of Wicker Park
ValueLocationSolo travel

Big house in the BEST Location!
LocationFamilyKitchen

New Home | O'Hare Airport
ValueFamilyParking

Accommodation for 2 people (basement)
FamilyValueComfort

Spacious Retro Logan Square Loft
FamilyValueAccess

Charming 3-BED in Lincoln Park/ Old Town & Parking
FamilyValueHospitality

Rooftop Skyline | 5 Ensuites | Games | DT 14 mins
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Destinations to explore
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- Wrigley Field
- Soldier Field
- United Center
- Lincoln Park
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- Chicago River Walk
- The Field Museum
- University of Chicago
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Donald E Stephens Convention Center
- Union Park
- Beachwalk Vacation Rentals
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort





