Step into serenity at our welcoming retreat. Follow detailed check-in directions to unlock the smart lock for secure access. Relax in the cozy living room with a 30" Smart TV and a collection of board games. Outside, unwind in the serene backyard.
Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.
Unwind in our inviting sanctuary. Seamless check-in with detailed instructions and a smart lock. Cozy up in the relaxing living room, equipped with a 30" Smart TV and a selection of board games. Step outside to a tranquil backyard with a pergola.
Step into tranquility with seamless check-in and a smart lock. Explore local treasures with our custom guidebook. Outside, unwind in the serene backyard oasis, complete with a pergola, fire-pit, outdoor gas grill, and picnic table dining.
Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.

Artistic Stay near Hyde Park: 2 Living, Courtyard

3 bedrooms·2½ baths
Chicago • Illinois
5(92 reviews)

$924.00 USD total for 3 nights

Oct 4 – 7, 2026

Epicurean experience home
Epicurean experience home
Epicurean experience home
Epicurean experience home
Epicurean experience home

Epicurean experience home

6 bedrooms·4 baths
Chicago • Illinois

$3,600.00 USD total for 3 nights

Sep 22 – 25, 2026

Ashland
Living room
Workspace in the living room
Bedroom 1
Bedroom 2

Ashland

3 bedrooms·1 bath
Chicago • Illinois
Chicago Lakefront · Fire Pit Patio · Beach Across image 1
Chicago Lakefront · Fire Pit Patio · Beach Across image 2
To the right: two plush couches and a large window. Opposite you: a mounted TV and a table with four chairs. To the right of the table is a corner desk with a lamp. A large rug anchors the center floor. Simple, clear, and easy to navigate.
Chicago Lakefront · Fire Pit Patio · Beach Across image 4
Chicago Lakefront · Fire Pit Patio · Beach Across image 5

Chicago Lakefront · Fire Pit Patio · Beach Across

1 bedroom·1 bath
Chicago • Illinois
5(1 review)

$447.00 USD $357.60 USD total for 3 nights

Sep 22 – 25, 2026

Chicago 2BR Condo- King Sleep Number
Chicago 2BR Condo- King Sleep Number
Chicago 2BR Condo- King Sleep Number
Chicago 2BR Condo- King Sleep Number
Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

2 bedrooms·1 bath
Elmwood Park • Illinois
4.63(8 reviews)
$150/ night(excl. fees & taxes)
Chicago 2Br 90s Condo - Very Kid Friendly
Chicago 2Br 90s Condo - Very Kid Friendly
Chicago 2Br 90s Condo - Very Kid Friendly
Chicago 2Br 90s Condo - Very Kid Friendly
Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

2 bedrooms·1 bath
Elmwood Park • Illinois
4.5(4 reviews)
$1,000/ night(excl. fees & taxes)
Chicago 2Br Condo -Nature Themed Downtown Access
Chicago 2Br Condo -Nature Themed Downtown Access
Chicago 2Br Condo -Nature Themed Downtown Access
Chicago 2Br Condo -Nature Themed Downtown Access
Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

2 bedrooms·1 bath
Elmwood Park • Illinois
5(2 reviews)
$1,000/ night(excl. fees & taxes)
Chicago 2Br Condo - Downtown Access
Chicago 2Br Condo - Downtown Access
Chicago 2Br Condo - Downtown Access
Chicago 2Br Condo - Downtown Access
Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

2 bedrooms·1 bath
Elmwood Park • Illinois
5(3 reviews)
$1,000/ night(excl. fees & taxes)
Main Floor
Master Bedroom 2nd floor
Dining area
1500Main EVANSTON
Main Floor

1500Main EVANSTON

2 bedrooms·1½ baths
Evanston • Illinois
5(166 reviews)

$1,140.42 USD total for 4 nights

Oct 13 – 17, 2026

Living Room with 65" TV
Front of House
Living Room with 65" TV
Piano Room
Indoor Swim Spa

Charming Garden Retreat

5 bedrooms·3½ baths
Evanston • Illinois
$683 – $2,275/ night(excl. fees & taxes)
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
$185/ night(excl. fees & taxes)
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

$1,189.00 USD total for 3 nights

Oct 5 – 8, 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

$1,584.00 USD total for 3 nights

Sep 29 – Oct 2, 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)
$93/ night(excl. fees & taxes)
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(130 reviews)

$1,418.00 USD total for 3 nights

Sep 27 – 30, 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

$1,195.00 USD total for 3 nights

Oct 10 – 13, 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
$200/ night(excl. fees & taxes)
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

$3,525.00 USD total for 3 nights

Oct 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

$1,214.00 USD total for 3 nights

Sep 28 – Oct 1, 2026