Make smores while you relax around a cozy fire!
Everything is within easy reach for the chef of the house.
Comfortable seating for eight.
For your convenience, there are hardwired ethernet connections in select spots on the main level.
Gaze at this unique Chicago skyline, handcrafted by the artist from scraps of wood.

NEW Comfy Suburban Chicago Oasis w/ River Access!

5 bedrooms·2½ baths
Bolingbrook • Illinois
5(8 reviews)

$2,072.35 USD $1,979.31 USD total for 3 nights

Sep 7 – 10, 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

Sep 7 – 11, 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

$1,289.00 USD total for 3 nights

Sep 7 – 10, 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

$2,672.00 USD total for 3 nights

Sep 7 – 10, 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

$935.04 USD total for 3 nights

Sep 7 – 10, 2026

Desirable chic home in a Prime Location!
Desirable chic home in a Prime Location!
Desirable chic home in a Prime Location!
Desirable chic home in a Prime Location!
Desirable chic home in a Prime Location!

Desirable chic home in a Prime Location!

4 bedrooms·2 baths
Oakbrook Terrace • Illinois

$987.00 USD total for 3 nights

Sep 8 – 11, 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
Modern Tranquil Boho Getaway in Glen Ellyn
Modern Tranquil Boho Getaway in Glen Ellyn
Modern Tranquil Boho Getaway in Glen Ellyn
Modern Tranquil Boho Getaway in Glen Ellyn
Modern Tranquil Boho Getaway in Glen Ellyn

Modern Tranquil Boho Getaway in Glen Ellyn

4 bedrooms·2 baths
Glen Ellyn • Illinois

$1,008.00 USD total for 3 nights

Sep 8 – 11, 2026

Wind down under the cozy lighting at the end of your day. Relax in the hot tub or gather around the fire table.
Regulation size pickleball court with Sport Court surface is only shared with guests who book the Guest Quarters.
The LED lights on the corn hole boards can make playing in the evening more adventurous.
Warning! Playing these games may cause competitive natures to rise and may lead to tears and belly aches from too much laughing.
View down from the top of the stairs.Caution! Top step is more shallow than other steps.

Deer Run Log Cabin

3 bedrooms·2 baths
Yorkville • Illinois

$1,543.01 USD $1,459.86 USD total for 3 nights

Sep 7 – 10, 2026

Private deck with fire table, seating, BBQ grill, hot tub, and glowing café lights—perfect for relaxing nights outdoors.
The onsite pickleball court has a Sport Court surface and is shared with the guests in the Cabin. Deer frequently pass by the court.
Relax by the fire table in the gazebo.
The corn hole boards have LED lighting that make playing at dusk more exciting.
Shared Space: Bond and laugh over some board games.

Deer Run Guest Quarters

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

$998.28 USD $967.10 USD total for 3 nights

Sep 7 – 10, 2026

Regulation size pickleball court with Sport Court surface on site!
Unwind on the deck under the cafe lights or around the fire pit.
There is plenty of comfortable seating so everyone in your group can have a seat without crowding each other. There are even throw blankets and pillows for additional comfort.
Relax in the 7-person hot tub under the cafe lights at night.
Everyone in your group can sit around the table together as it seats up to 12 people. There are also 2 additional seats at the kitchen island..

Deer Run Lodge

4 bedrooms·3 baths
Yorkville • Illinois
5(1 review)

$2,688.30 USD $2,531.76 USD total for 3 nights

Sep 7 – 10, 2026

Walk to Downtown! 6-Bedroom Home
Walk to Downtown! 6-Bedroom Home
Walk to Downtown! 6-Bedroom Home
Walk to Downtown! 6-Bedroom Home
Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

6 bedrooms·3 baths
St. Charles • Illinois

$1,011.00 USD total for 3 nights

Sep 7 – 10, 2026

Sleeps 18 • 7BR • Gym • Game Room • Theater
Sleeps 18 • 7BR • Gym • Game Room • Theater
Sleeps 18 • 7BR • Gym • Game Room • Theater
Sleeps 18 • 7BR • Gym • Game Room • Theater
Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater

7 bedrooms·3 baths
Chicago • Illinois

$3,005.91 USD total for 3 nights

Sep 7 – 10, 2026

Elmwood Park 2 BR Condo (Great for Kids!)
Elmwood Park 2 BR Condo (Great for Kids!)
Elmwood Park 2 BR Condo (Great for Kids!)
Elmwood Park 2 BR Condo (Great for Kids!)
Elmwood Park 2 BR Condo (Great for Kids!)

Elmwood Park 2 BR Condo (Great for Kids!)

2 bedrooms·1 bath
Elmwood Park • Illinois

$5,473.31 USD total for 30 nights

Sep 7 – Oct 7, 2026

Top Rated Condo • 65” TV • Family-friendly 2BR
Top Rated Condo • 65” TV • Family-friendly 2BR
Top Rated Condo • 65” TV • Family-friendly 2BR
Top Rated Condo • 65” TV • Family-friendly 2BR
Top Rated Condo • 65” TV • Family-friendly 2BR

Top Rated Condo • 65” TV • Family-friendly 2BR

2 bedrooms·1 bath
Elmwood Park • Illinois

$5,363.31 USD total for 30 nights

Sep 7 – Oct 7, 2026

Elmwood Park 2 BR Condo
Elmwood Park 2 BR Condo
Elmwood Park 2 BR Condo
Elmwood Park 2 BR Condo
Elmwood Park 2 BR Condo

Elmwood Park 2 BR Condo

2 bedrooms·1 bath
Elmwood Park • Illinois

$5,425.04 USD total for 30 nights

Sep 7 – Oct 7, 2026

Top Rated Condo • King Bed • Safe Historic Location
Top Rated Condo • King Bed • Safe Historic Location
Top Rated Condo • King Bed • Safe Historic Location
Top Rated Condo • King Bed • Safe Historic Location
Top Rated Condo • King Bed • Safe Historic Location

Top Rated Condo • King Bed • Safe Historic Location

2 bedrooms·1 bath
Elmwood Park • Illinois

$4,789.71 USD total for 30 nights

Sep 7 – Oct 7, 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)

$1,200.00 USD $1,095.00 USD total for 7 nights

Sep 7 – 14, 2026

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)

$30,120.00 USD $18,120.00 USD total for 30 nights

Sep 7 – Oct 7, 2026

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)

$30,150.00 USD $25,650.00 USD total for 30 nights

Sep 7 – Oct 7, 2026

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)

$30,150.00 USD $25,650.00 USD total for 30 nights

Sep 7 – Oct 7, 2026

Elmwood Park Remodeled Studio Condo
Elmwood Park Remodeled Studio Condo
Elmwood Park Remodeled Studio Condo
Elmwood Park Remodeled Studio Condo
Elmwood Park Remodeled Studio Condo

Elmwood Park Remodeled Studio Condo

1 bedroom·1 bath
Elmwood Park • Illinois

$5,152.28 USD total for 30 nights

Sep 7 – Oct 7, 2026

Family&Pet Friendly-No Stairs-Kingbeds-Peaceful. image 1
Gather, dine and unwind. Kids are welcome at the table too!
Cook , connect and savor meals ina space where modern kitchen meets no fuss chilling.
Dream in king sized comfort, along with the convenience of an ensuite
Unpack without having to reach for the floor with the luggage racks. Connect your laptop to the provided monitor for work with a corner desk and ergonomic chair.

Single-Family Home. Fully Furnished

3 bedrooms·2 baths
Minooka • Illinois
5(16 reviews)

$1,935.00 USD total for 6 nights

Sep 7 – 13, 2026

Chicago Stay *Steps to Viral La Catedral Café* image 1
Chicago Stay *Steps to Viral La Catedral Café* image 2
Chicago Stay *Steps to Viral La Catedral Café* image 3
Chicago Stay *Steps to Viral La Catedral Café* image 4
Chicago Stay *Steps to Viral La Catedral Café* image 5

Chicago Stay *Steps to Viral La Catedral Café*

2 bedrooms·1 bath
Chicago • Illinois
$140/ night(excl. fees & taxes)