House vacation rentals in Chicago
Find and book unique houses on Airbnb
Top-rated house rentals in Chicago
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago house rentals
House rentals with free parking
Home in Des Plaines
4.78 out of 5 average rating, 309 reviewsUrban Farmhouse near O'Hare
Home in Bolingbrook
4.92 out of 5 average rating, 100 reviewsThe Sunshine Spot
Home in Winfield
4.98 out of 5 average rating, 133 reviewsCozy, Clean & Well-Stocked Home!
Home in Chicago
4.91 out of 5 average rating, 89 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Berwyn
4.99 out of 5 average rating, 83 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
4.89 out of 5 average rating, 28 reviewsPrivate Condo in Chicago w/ Parking, Near Evanston
Home in Wilmette
4.98 out of 5 average rating, 94 reviewsUnique porcelain-enamel paneled "Lustron" home
Home in Chicago
5.0 out of 5 average rating, 51 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
House rentals with a hot tub
Home in Homewood
4.91 out of 5 average rating, 106 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Home in Chicago
4.93 out of 5 average rating, 72 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Gary
4.94 out of 5 average rating, 86 reviewsSunset beach house
Home in Westchester
4.79 out of 5 average rating, 24 reviewsModern 2Bdrm Westchester/Chicago Home.With Hot tub
Home in Chicago
5.0 out of 5 average rating, 16 reviewsWrigley Penthouse w/Private Roof Deck and Parking
Home in Palatine
4.85 out of 5 average rating, 41 reviewsPrivate Room with attach bath and personal kitchen
Home in Elmhurst
4.94 out of 5 average rating, 49 reviewsLuxe 3BR, 2BA + Hot Tub
House rentals with a pool
Home in Plainfield
4.95 out of 5 average rating, 63 reviewsLarge Spanish style Home (w/heated pool)
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Home in Gary
4.82 out of 5 average rating, 213 reviewsOasis , Near Beach, Hard Rock and Dunes
Quick stats about house rentals in Chicago
Total rentals
1.8K properties
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
470 properties allow pets
Family-friendly rentals
950 properties are a good fit for families
Total number of reviews
69K reviews
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Lighthouse rentals United States
- Earth house rentals United States
- Townhouse rentals United States
- Guesthouse rentals United States
- House rentals United States
- Loft rentals Chicago
- Smoking-friendly rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a washer and dryer Chicago
- Lakehouse rentals Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Fitness-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Kid-friendly rentals Chicago
- Bed and breakfasts Chicago
- Rentals with an accessible height bed Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Rentals with pools Chicago
- Rentals with lake access Chicago
- Monthly Rentals Chicago
- Rentals with a sauna Chicago
- Rentals with a fireplace Chicago
- Waterfront rentals Chicago
- Rentals with beach access Chicago
- Mansion rentals Chicago
- Rentals with a balcony Chicago
- Apartment rentals Chicago
- Beachfront rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Boutique hotel rentals Chicago
- Townhouse rentals Chicago
- Rentals with a patio Chicago
- Rentals with an EV charger Chicago
- Townhouse rentals Downtown Chicago
- House rentals Downtown Chicago
- Lakehouse rentals Milwaukee
- House rentals Milwaukee
- House rentals Lake Geneva
- Lakehouse rentals Lake Geneva
- Treehouse rentals Illinois
- Townhouse rentals Illinois
- Tiny house rentals Illinois
- Lakehouse rentals Illinois
- House rentals Illinois
- Guesthouse rentals Illinois
- House rentals Cook County
- Townhouse rentals Cook County
- Guesthouse rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom