Location

Dates

Guests

Vacation rentals in Illinois

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

8 bedrooms·3 baths

Chicago • Illinois

$4,957.63 USD total for 3 nights

Nov 6 – 9, 2026

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

1 bedroom·1 bath

Chicago • Illinois

$772.80 USD total for 4 nights

Nov 6 – 10, 2026

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

Chicago Condo · Luxurious Condo in Top Rated Neighborhood

1 bedroom·1 bath

Chicago • Illinois

$787.92 USD total for 4 nights

Nov 6 – 10, 2026

Safe, Walkable Streets! 1/2 mile to downtown

Color Me Home

2 bedrooms·1 bath

Marion • Illinois

$2,903.04 USD total for 28 nights

Nov 6 – Dec 4, 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

$4,507.96 USD total for 30 nights

Nov 6 – Dec 6, 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

$4,001.71 USD total for 30 nights

Nov 6 – Dec 6, 2026

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

Sleeps 4 • New Modern 1BR • Workspace

1 bedroom·1 bath

Chicago • Illinois

$779.69 USD total for 3 nights

Nov 6 – 9, 2026

King Bed • Private Backyard • Grill and Fireplace

King Bed • Private Backyard • Grill and Fireplace

King Bed • Private Backyard • Grill and Fireplace

King Bed • Private Backyard • Grill and Fireplace

King Bed • Private Backyard • Grill and Fireplace

King Bed • Private Backyard • Grill and Fireplace

5 bedrooms·2 baths

North Chicago • Illinois

$1,609.10 USD total for 3 nights

Nov 6 – 9, 2026

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

All 3 Cabins at Sunrise Hill

5 bedrooms·3 baths

Makanda • Illinois

$2,267.62 USD total for 3 nights

Nov 29 – Dec 2, 2026

3 Lake homes on private drive

Chairs and umbrella by serene lake.

A cozy backyard with a fire pit surrounded by chairs, perfect for gathering and enjoying outdoor warmth and relaxation.

Dock with slide

Playground for kids on site

The Sunset Drive Houses

11 bedrooms·7½ baths

Marion • Illinois

$3,644.03 USD total for 3 nights

Nov 8 – 11, 2026

Living room with fireplace

Front view of the cabin

Elm Cabin 2

1 bedroom·1 bath

Carbondale • Illinois

5(6 reviews)

$1,091.78 USD total for 3 nights

Nov 10 – 13, 2026

Directly above Seasonings Bistro

Large open windows with eastern light

4 seats at the dining room table and 4 breakfast bar seats

4 seats at the breakfast bar

All new appliances in the kitchen

Rado's Hideaway

2 bedrooms·2 baths

Marion • Illinois

$776.35 USD total for 3 nights

Nov 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

$2,112.80 USD $2,007.17 USD total for 3 nights

Nov 6 – 9, 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)

$3,389.15 USD $2,880.78 USD total for 3 nights

Nov 6 – 9, 2026

Chicago Getaway | Cozy 2BR Near Downtown

Thoughtful extras: coffee bar, games, full cookware & pet-friendly perks

Chicago Getaway | Cozy 2BR Near Downtown

Chicago Getaway | Cozy 2BR Near Downtown

Bright living space with hardwood floors and wall-mounted streaming TV

Chicago Getaway | Cozy 2BR Near Downtown

2 bedrooms·1 bath

Chicago • Illinois

$79 – $796/ night(excl. fees & taxes)

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

1 bedroom·2 baths

Chicago • Illinois

$465.22 USD total for 3 nights

Nov 6 – 9, 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

$4,574.19 USD total for 30 nights

Nov 6 – Dec 6, 2026

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

Luxurious Remodeled 1BR Condo

1 bedroom·1 bath

Chicago • Illinois

$938.45 USD total for 3 nights

Nov 6 – 9, 2026

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois

Peach Tree Inn Unit 5

Wecome to Peach Tree Inn

Re-imaged bank building in Cobden, IL

2 hot tubs on the patio for the 5 suites. Each hot tub seats 4-6 people comfortably.

Peach Tree Inn Unit 5

Peach Tree Inn Unit 5

1 bedroom·1 bath

Cobden • Illinois

$615.26 USD total for 3 nights

Nov 6 – 9, 2026

Songbird Lane Cabin

Songbird Lane Cabin

Songbird Lane Cabin

Songbird Lane Cabin

Songbird Lane Cabin

Songbird Lane Cabin

1 bedroom·2½ baths

Goreville • Illinois

$1,111.81 USD total for 3 nights

Nov 24 – 27, 2026

Bring the pickle ball set! Nice flat space

View from the water

"The Classic" on Country Club

The Classic

3 bedrooms·3 baths

Marion • Illinois

5(5 reviews)

$1,036.42 USD total for 3 nights

Nov 6 – 9, 2026

Tulipwood Cabin

Living room with fireplace and TV

Dining area table and chairs

Tulipwood Cabin 3

1 bedroom·1 bath

Carbondale • Illinois

5(6 reviews)

$912.19 USD total for 3 nights

Nov 8 – 11, 2026

Additional view of outdoor area

Covered hot tub

Seating around the fire pit

Ample seating for all

Front view of home

Sunset Ridge

3 bedrooms·2 baths

Carbondale • Illinois

5(1 review)

$911.93 USD total for 3 nights

Nov 8 – 11, 2026