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 Chicago
4.91 out of 5 average rating, 87 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Nov 30 – Dec 7
Home in Berwyn
5.0 out of 5 average rating, 77 reviewsRetro Modern Bungalow | free parking | fire pit
Nov 3 – 10
Home in Wilmette
4.98 out of 5 average rating, 92 reviewsUnique porcelain-enamel paneled "Lustron" home
Sep 11 – 18
Home in Maywood
4.83 out of 5 average rating, 60 reviewsMaywood Relaxation
Feb 21 – 28
Home in Chicago
4.96 out of 5 average rating, 27 reviewsLakeview Condo
Dec 6 – 13
Home in Highland Park
4.98 out of 5 average rating, 59 reviewsCharming Ranch-Style Cottage
Nov 28 – Dec 5
Home in Chicago
5.0 out of 5 average rating, 15 reviewsChicago Home by Midway near Downtown Attractions
Oct 19 – 26
Home in Chicago
4.98 out of 5 average rating, 87 reviews3BD Home Mins from Airport | Free Wi-Fi + Parking
Sep 11 – 18
House rentals with a hot tub
Home in Homewood
4.91 out of 5 average rating, 106 reviewsPeaceful & Private Hot Tub Vacation Home Getaway
Jun 7 – 14
Home in Chicago
4.85 out of 5 average rating, 292 reviewsLux Urban 3BR/3BA Duplex + Parking!
Sep 24 – Oct 1
Home in Chicago
4.93 out of 5 average rating, 71 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Aug 15 – 22
Home in Chicago
4.88 out of 5 average rating, 16 reviewsHot Tub Logan Family Designer Home
May 20 – 27
Home in Westchester
4.76 out of 5 average rating, 21 reviewsModern 2Bdrm Westchester/Chicago Home.With Hot tub
Jan 20 – 27
Home in Palatine
4.85 out of 5 average rating, 39 reviewsPrivate Room with attach bath and personal kitchen
Sep 19 – 26
Home in Elmhurst
4.93 out of 5 average rating, 46 reviewsLuxe 3BR, 2BA + Hot Tub
Aug 22 – 29
Home in Chicago
5.0 out of 5 average rating, 16 reviewsWrigley Penthouse w/Private Roof Deck and Parking
Nov 6 – 13
House rentals with a pool
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Aug 17 – 24
Home in Chicago
4.86 out of 5 average rating, 37 reviewsLuxury Cabin in Lakeview
Jul 7 – 14
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Home in Schaumburg
New place to stayParadise 4BR w/ Pool & Games
Nov 12 – 19
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Jul 18 – 25
Home in Chicago
4.8 out of 5 average rating, 15 reviews2Bed+2Bath PentHouse in South Loop
Feb 2 – 9
Home in New Lenox
4.74 out of 5 average rating, 34 reviewsCheerful home. Heated pool, Hot tub!
Jul 31 – Aug 7
Home in Olympia Fields
4.58 out of 5 average rating, 31 reviewsLuxurious South Suburban Villa
Oct 15 – 22
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
- House rentals United States
- Guesthouse rentals United States
- Townhouse rentals United States
- Earth house rentals United States
- Rentals with a patio Chicago
- Bed and breakfasts Chicago
- Lakehouse rentals Chicago
- Condo rentals Chicago
- Apartment rentals Chicago
- Monthly Rentals Chicago
- Rentals with a fireplace Chicago
- Smoking-friendly rentals Chicago
- Rentals with breakfast Chicago
- Townhouse rentals Chicago
- Mansion rentals Chicago
- Hotel rentals Chicago
- Rentals with a washer and dryer Chicago
- Pet-friendly rentals Chicago
- Rentals with beach access Chicago
- Rentals with a fire pit Chicago
- Rentals with outdoor seating Chicago
- Rentals with an EV charger Chicago
- Beachfront rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Boutique hotel rentals Chicago
- Family-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Rentals with an accessible height bed Chicago
- Rentals with a home theater Chicago
- Rentals with a sauna Chicago
- Cottage rentals Chicago
- Fitness-friendly rentals Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Rentals with pools Chicago
- Rentals with lake access Chicago
- House rentals Downtown Chicago
- House rentals Milwaukee
- Lakehouse rentals Milwaukee
- Lakehouse rentals Lake Geneva
- House rentals Lake Geneva
- Tiny house rentals Illinois
- Lakehouse rentals Illinois
- Treehouse rentals Illinois
- House rentals Illinois
- Townhouse rentals Illinois
- Guesthouse rentals Illinois
- House rentals Cook County
- Guesthouse rentals Cook County
- Townhouse rentals Cook County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes