Vacation Home Rentals By Owner In Chicago, IL
Rent a place that suits your needs
Most popular vacation rentals in Chicago
$1627.46
/ NightlyLuxury Penthouse: Iconic Views + Exclusive Comfort
Chicago, Illinois, United States
4
Bed
3
Bath
9
Sleeps
$3748.59
/ NightlyPrivate Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
Chicago, Illinois, United States
5
Bed
5
Bath
14
Sleeps
$3564.62
/ NightlyIconic Downtown Penthouses Getaway + City Views
Chicago, Illinois, United States
7
Bed
7
Bath
15
Sleeps
$2625.78
/ NightlyLuxury Lincoln Park Gem with Gourmet Kitchen & City Views
Chicago, Illinois, United States
4
Bed
4
Bath
10
Sleeps
$2191.40
/ NightlyLuxurious Four-Level Home with Personal Touches Everywhere
Chicago, Illinois, United States
6
Bed
5
Bath
17
Sleeps
$2141.45
/ NightlyDowntown Mich Ave - 6 Penthouses, Sleep 25
Chicago, Illinois, United States
10
Bed
9
Bath
16
Sleeps
$2087.15
/ Nightly3 Penthouses, 1 Floor, Group Stay, Sleeps 21
Chicago, Illinois, United States
9
Bed
8
Bath
21
Sleeps
$2010.43
/ NightlyLuxury House in the heart of Old Town with Parking
Chicago, Illinois, United States
5
Bed
7
Bath
12
Sleeps
$1812.40
/ NightlyPRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
Chicago, Illinois, United States
4
Bed
2
Bath
10
Sleeps
$1808.60
/ NightlyLucky Green | 9BR, Parking, Sleeps 19 | By Wrigley
Chicago, Illinois, United States
9
Bed
5
Bath
16
Sleeps
Most Popular Cities in Illinois
- Chicago
- Galena
- Ottawa
- Champaign
- Libertyville
- Peoria
- Springfield
- Waukegan
- Oak Park
- Evanston
- Rockford
- East Peoria
- Bloomington
- Marion
- Naperville
- Fox Lake
- Des Plaines
- Urbana
- Quincy
- Carbondale
- Moline
- Peoria Heights
- Creal Springs
- Skokie
- Schaumburg
- Goreville
- Belleville
- Nauvoo
- Berwyn
- Decatur
- Aurora
- Grafton
- Rosemont
- Golconda
- Makanda
- Murphysboro
- Antioch
- Normal
- Warrenville
- Saint Charles
- Elmhurst
- Geneva
- Elizabeth
- Apple River
- Zion
