Search Holiday Homes in Chicago
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
In two weeks
In one month
In two months
In three months
Browse Select Chicago Holiday Homes
Our top choices for Chicago holiday homes

Charming Contemporary Family Home 3 Bedroom Home by RedAwning
Charming Contemporary Family Home 3 Bedroom Home by RedAwning

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

Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning
Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning

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)

Modern Luxury Amenities Near Woodfield Mall 2 Bedroom Home by RedAwning
Modern Luxury Amenities Near Woodfield Mall 2 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
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
Top Chicago Hotel Reviews

Freehand Chicago
10/10 Excellent
Find out more about Chicago
Find out more about Chicago
Chicago Holiday Homes information
Number of reviews | |
---|---|
Accommodation | 8 Holiday Homes |
Lowest Price | |
Highest Price |