Luxurious Condo in Top Rated Neighborhood
Luxurious Condo in Top Rated Neighborhood
Luxurious Condo in Top Rated Neighborhood
Luxurious Condo in Top Rated Neighborhood
Luxurious Condo in Top Rated Neighborhood

Luxurious Condo in Top Rated Neighborhood

1 bedroom·1 bath
Chicago • Illinois
4.46(28 reviews)

$3,600.00 USD total for 30 nights

Oct 26 – Nov 25, 2026

Living Room
Dining Room
Kitchen
Family Room
Family Room

Ruby’s Retreat - 4BD/3BA+Office in Western Springs

4 bedrooms·3 baths
Western Springs • Illinois

$6,336.75 USD $5,755.58 USD total for 30 nights

Aug 28 – Sep 27, 2027

Cozy Retreat Near Oakbrook Center
Cozy Retreat Near Oakbrook Center
Cozy Retreat Near Oakbrook Center
Cozy Retreat Near Oakbrook Center
Cozy Retreat Near Oakbrook Center

Cozy Retreat Near Oakbrook Center

4 bedrooms·2 baths
Oakbrook Terrace • Illinois

$1,204.00 USD total for 3 nights

Oct 29 – Nov 1, 2026

Spacious Home with 4 Full Baths
Spacious Home with 4 Full Baths
Spacious Home with 4 Full Baths
Spacious Home with 4 Full Baths
Spacious Home with 4 Full Baths

Spacious Home with 4 Full Baths

4 bedrooms·4 baths
Willowbrook • Illinois

$1,464.00 USD total for 3 nights

Oct 31 – Nov 3, 2026

Cozy Home Sleeps 10 Lombard Chicago Suburb
Cozy Home Sleeps 10 Lombard Chicago Suburb
Cozy Home Sleeps 10 Lombard Chicago Suburb
Cozy Home Sleeps 10 Lombard Chicago Suburb
Cozy Home Sleeps 10 Lombard Chicago Suburb

Cozy Home Sleeps 10 Lombard Chicago Suburb

3 bedrooms·2 baths
Lombard • Illinois

$841.88 USD total for 3 nights

Oct 26 – 29, 2026

Front of the house
Entrance to the unit
Backyard
Bedroom 1
Bedroom 1

Middle Level of the House with Working Space

2 bedrooms·1 bath
Darien • Illinois
4.73(44 reviews)

$494.76 USD total for 4 nights

Oct 26 – 30, 2026

Charming ranch home with vibrant fall views and glowing sunset curb appeal
*King bed *Outdoor Living *Sought-After Area
*King bed *Outdoor Living *Sought-After Area
Charming backyard lounge with cozy deck seating and private garden vibe
Cozy boho lounge with greenery, armchairs, and warm natural accents

*King bed *Outdoor Living *Sought-After Area

3 bedrooms·1½ baths
Northbrook • Illinois
5(135 reviews)

$1,478.00 USD total for 3 nights

Nov 18 – 21, 2026

Arlington Heights Home
Arlington Heights Home
Arlington Heights Home
Arlington Heights Home
Arlington Heights Home

Arlington Heights Home

1 bedroom·1 bath
Arlington Heights • Illinois

$806.76 USD total for 3 nights

Oct 26 – 29, 2026

Charming Getaway in Homewood Near Chicago
Spacious Living Room, opened up to the Dining Room
Modern Fully Stocked Kitchen
Upstairs Living Room, off the Master Bedroom
Private workspace

Charming Getaway in Homewood Near Chicago

3 bedrooms·1½ baths
Homewood • Illinois

$833.00 USD total for 3 nights

Nov 17 – 20, 2026

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 1
Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 2
Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 3
Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 4
Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 5

Stylish, Sun-Filled Retreat - Minutes to O’Hare!

2 bedrooms·2 baths
Wheeling • Illinois

$625.00 USD total for 3 nights

Oct 26 – 29, 2026

Modern Oasis in Glen Ellyn
Modern Oasis in Glen Ellyn
Modern Oasis in Glen Ellyn
Modern Oasis in Glen Ellyn
Modern Oasis in Glen Ellyn

Modern Oasis in Glen Ellyn

3 bedrooms·2½ baths
Glen Ellyn • Illinois

$3,285.00 USD total for 3 nights

Nov 1 – 4, 2026

Modern Boho Entire Home in Glen Ellyn
Modern Boho Entire Home in Glen Ellyn
Modern Boho Entire Home in Glen Ellyn
Modern Boho Entire Home in Glen Ellyn
Modern Boho Entire Home in Glen Ellyn

Modern Boho Entire Home in Glen Ellyn

4 bedrooms·2 baths
Glen Ellyn • Illinois

$844.00 USD total for 3 nights

Oct 26 – 29, 2026