Chicago Private Home Rentals
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Featured Private Holiday Homes in Chicago
Spacious Retreat Near Convention Centers 4 Bedroom Home by RedAwning
Spacious Retreat Near Convention Centers 4 Bedroom Home by RedAwning
10.0 out of 10, Exceptional, (1)
Charming Contemporary Family Home 3 Bedroom Home by RedAwning
Charming Contemporary Family Home 3 Bedroom Home by RedAwning
Modern Luxury Amenities Near Woodfield Mall 2 Bedroom Home by RedAwning
Modern Luxury Amenities Near Woodfield Mall 2 Bedroom Home by RedAwning
Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning
Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning
Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover
Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover
The Elmhurst Experience
The Elmhurst Experience
Lake view house
Lake view house
6 Bed Whole House In Chicagolands Trendy Berwyn 6 Bedroom Home by AllSet Turnover
6 Bed Whole House In Chicagolands Trendy Berwyn 6 Bedroom Home by AllSet Turnover
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Find out more about Chicago
Find out more about Chicago
Chicago Private Holiday Homes information
Number of reviews | 55,629 |
|---|---|
Accommodation | 8 Private Holiday Homes |
Lowest Price | S$151 |
Highest Price | S$312 |
Recent Reviews in Chicago
Recent Reviews in Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
5/5 Excellent
"Amazing experience. "
A verified traveller stayed at Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Posted 9 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
More Accommodation Types in
All Accommodation Types
Be inspired: Top Private Holiday Homes destinations in 2025
- Holiday Homes in Singapore
- Holiday Homes in Taipei
- Holiday Homes in Seoul
- Holiday Homes in Katong
- Holiday Homes in Tokyo
- Holiday Homes in Sentosa Island
- Holiday Homes in Johor Bahru
- Holiday Homes in Penang
- Holiday Homes in Phuket
- Holiday Homes in Little India
- Holiday Homes in Bangkok
- Holiday Homes in Batam
- Holiday Homes in Jurong
- Holiday Homes in Osaka
- Holiday Homes in Kuala Lumpur
- Holiday Homes in Bali
- Holiday Homes in Bugis Village
- Holiday Homes in River Valley
- Holiday Homes in Tampines
- Holiday Homes in Bukit Timah
More ways to book
Expedia's Latest Trends
Hotels
Hotels in Downtown ChicagoMcCormick Place hotelsHotels in San FranciscoMiami Hotels with Early Check InGurnee Hotels with smoking roomsLos Angeles Hotels with free airport shuttleAmarillo Budget HotelsAnchorage Hotels with free airport shuttleFort Lauderdale Hotels near Shopping AreasHotels in SeattleNew York Hotels with free airport shuttleHotels in Las VegasWaukegan Hotels with smoking roomsHotels in New YorkEvanston Budget HotelsNaperville Hotels with smoking roomsHotels in Los Angeles
Activities
Packages