Spacious Waukegan 3BR • Hot Tub & Deck
Spacious Waukegan 3BR • Hot Tub & Deck
Spacious Waukegan 3BR • Hot Tub & Deck
Spacious Waukegan 3BR • Hot Tub & Deck
Spacious Waukegan 3BR • Hot Tub & Deck

Spacious Waukegan 3BR • Hot Tub & Deck

3 bedrooms·2½ baths
Waukegan • Illinois

$1,739.67 USD total for 3 nights

Oct 19 – 22, 2026

Bright 4BR Escape • Near Six Flags & Beach
Bright 4BR Escape • Near Six Flags & Beach
Bright 4BR Escape • Near Six Flags & Beach
Bright 4BR Escape • Near Six Flags & Beach
Bright 4BR Escape • Near Six Flags & Beach

Bright 4BR Escape • Near Six Flags & Beach

4 bedrooms·2 baths
Waukegan • Illinois

$2,030.13 USD total for 3 nights

Oct 19 – 22, 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

$1,323.65 USD total for 3 nights

Oct 19 – 22, 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 10 – 13, 2026

Stunning Lake house on peaceful Sta
Stunning Lake house on peaceful Sta
Stunning Lake house on peaceful Sta
Stunning Lake house on peaceful Sta
Stunning Lake house on peaceful Sta

Stunning Lake house on peaceful Sta

5 bedrooms·2½ baths
Ingleside • Illinois
4.86(22 reviews)

$2,343.41 USD total for 5 nights

Oct 19 – 24, 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 19 – 22, 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 19 – 22, 2026

Waterfront Cottage/sauna/kayaks/firepit/dock image 1
Waterfront Cottage/sauna/kayaks/firepit/dock image 2
Waterfront Cottage/sauna/kayaks/firepit/dock image 3
Waterfront Cottage/sauna/kayaks/firepit/dock image 4
Waterfront Cottage/sauna/kayaks/firepit/dock image 5

Waterfront Cottage/sauna/kayaks/firepit/dock

1 bedroom·1 bath
Fox River Grove • Illinois
4.88(40 reviews)

$765.00 USD total for 3 nights

Oct 19 – 22, 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

$3,390.90 USD total for 3 nights

Oct 19 – 22, 2026

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

Nov 1 – 5, 2026

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

Oct 19 – 22, 2026

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

Ashland

3 bedrooms·1 bath
Chicago • Illinois
balcony
Master Bedroom Second Floor
Family Room First Floor open to Loft Second Floor two story family room with skylights
Master Bedroom Second Floor
Kitchen First Floor

Beautiful spacious gem Oasis Manor 6 BR 4 1/2 BA

6 bedrooms·4 baths
East Dundee • Illinois
5(9 reviews)

$2,730.00 USD total for 3 nights

Oct 19 – 22, 2026