The Picket Fence
The Picket Fence
The Picket Fence
The Picket Fence
The Picket Fence

The Picket Fence

2 bedrooms·2 baths
Marion • Illinois
The Euclid House — 6BR Near UChicago & Hospitals
The Euclid House — 6BR Near UChicago & Hospitals
The Euclid House — 6BR Near UChicago & Hospitals
The Euclid House — 6BR Near UChicago & Hospitals
The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

6 bedrooms·3 baths
Chicago • Illinois

$1,100.00 USD total for 3 nights

Nov 9 – 12, 2026

All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!
All Ease Private Stay |Traveler's Top Fave!!

All Ease Private Stay |Traveler's Top Fave!!

1 bedroom·2 baths
Chicago • Illinois

$8,607.15 USD total for 3 nights

Aug 28 – 31, 2027

The Beaumont Retreat
The Beaumont Retreat
The Beaumont Retreat
The Beaumont Retreat
The Beaumont Retreat

The Beaumont Retreat

2 bedrooms·1 bath
Greenville • Illinois

$707.17 USD total for 3 nights

Nov 6 – 9, 2026

The Beaumont Suite !
The Beaumont Suite !
The Beaumont Suite !
The Beaumont Suite !
The Beaumont Suite !

The Beaumont Suite !

1 bedroom·1 bath
Greenville • Illinois

$636.67 USD total for 3 nights

Nov 6 – 9, 2026

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)

$2,023.53 USD $1,932.93 USD total for 3 nights

Nov 6 – 9, 2026

6 bedroom! Pool Table, Gaming Area, Firepit & More image 1
6 bedroom! Pool Table, Gaming Area, Firepit & More image 2
6 bedroom! Pool Table, Gaming Area, Firepit & More image 3
6 bedroom! Pool Table, Gaming Area, Firepit & More image 4
6 bedroom! Pool Table, Gaming Area, Firepit & More image 5

6 bedroom! Pool Table, Gaming Area, Firepit & More

6 bedrooms·3 baths
Joliet • Illinois
4.92(24 reviews)

$2,440.00 USD total for 3 nights

Nov 8 – 11, 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)

$467.00 USD $373.60 USD total for 3 nights

Nov 8 – 11, 2026

Cozy 2 Bed/1 Bath Unit
Cozy 2 Bed/1 Bath Unit
Cozy 2 Bed/1 Bath Unit
Cozy 2 Bed/1 Bath Unit
Cozy 2 Bed/1 Bath Unit

Cozy 2 Bed/1 Bath Unit

2 bedrooms·1 bath
Peoria • Illinois

$3,600.00 USD $3,000.00 USD total for 30 nights

Nov 6 – Dec 6, 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

Nov 6 – 10, 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

Nov 6 – 9, 2026

Luxe Home with Michelin Star Kitchen & King Beds image 1
Luxe Home with Michelin Star Kitchen & King Beds image 2
Luxe Home with Michelin Star Kitchen & King Beds image 3
Luxe Home with Michelin Star Kitchen & King Beds image 4
Luxe Home with Michelin Star Kitchen & King Beds image 5

Luxe Home with Michelin Star Kitchen & King Beds

5 bedrooms·2 baths
Bolingbrook • Illinois
5(7 reviews)

$2,537.00 USD total for 3 nights

Nov 6 – 9, 2026

Enjoy beautiful sunsets.
Family living room with a pull out sofa, great for large families.
Pura Vida Lake Home Retreat
Beautiful water views throughout the whole house, large sliding door makes it perfect for indoor/outdoor living.
Pura Vida Lake Home Retreat

Pura Vida Lake Home Retreat

2 bedrooms·2 baths
Greenville • Illinois

$1,437.75 USD total for 3 nights

Nov 6 – 9, 2026

Enjoy a peaceful evening roasting smores, enjoying the lake and just relaxing by the water.
Comfortable living room with gorgeous lake views
Bed 1 | 2nd Floor | Queen bed
Elevated deck with spectacular views
Lake Shore Cottage- Decatur, IL

Lake Shore Cottage- Decatur, IL

3 bedrooms·2½ baths
Decatur • Illinois
5(16 reviews)

$1,001.10 USD total for 3 nights

Nov 15 – 18, 2026

Motorcycle bar in the "Secret" room
Inviting living room, gas fireplace, frame smart TV
Fun basement bar! Snow cone machine, cotton candy machine
Community pool- 8 min drive away, open year round
Primary bedroom, king bed, main floor with ensuite bedroom

Galena Haven Hideaway

4 bedrooms·4½ baths
Galena • Illinois

$2,442.00 USD total for 3 nights

Nov 6 – 9, 2026

Lounge seating | Umbrella
Daisy Lane- Normal, IL
Step into The Escape, where arcade classics, pinball, and a friendly game of darts turn an ordinary evening into a vacation highlight. Challenge your crew, cheer from the sofa, or settle in for a laid-back night together. Just one more game? Yes, please!
Daisy Lane- Normal, IL
Daisy Lane- Normal, IL

Daisy Lane- Normal, IL

2 bedrooms·1½ baths
Normal • Illinois
5(15 reviews)
$173 – $824/ night(excl. fees & taxes)
Some of our many Arcades available for free play during your stay with us!
Pac-Man wall mural designed by local artist
The Pac-Man Room
Orange couch can be used to sleep on for one person
House of Arcade!

House of Games® - Play, Relax, Unwind

3 bedrooms·2½ baths
Bloomington • Illinois

$717.62 USD $694.22 USD total for 3 nights

Nov 15 – 18, 2026

Hobbit Home at The Shire of Marseilles -Coming Soo
Hobbit Home at The Shire of Marseilles -Coming Soo
Hobbit Home at The Shire of Marseilles -Coming Soo
Hobbit Home at The Shire of Marseilles -Coming Soo
Hobbit Home at The Shire of Marseilles -Coming Soo

Hobbit Home at The Shire of Marseilles -Coming Soo

1 bedroom·1 bath
Marseilles • Illinois

$15,075.00 USD total for 3 nights

Nov 6 – 9, 2026

★ "This Airbnb is a gem! I’d highly recommend this spot—100%!"
LUXE Vintage Green Loft 10min to Downtown, Beach
[Bedroom #2] Queen bed, workspace & baby play pen
LUXE Vintage Green Loft 10min to Downtown, Beach
[Bedroom #1] King bed, stocked mini fridge & baby crib

LUXE Vintage Green Loft 10min to Downtown, Beach

3 bedrooms·3 baths
Chicago • Illinois

$2,342.00 USD total for 3 nights

Nov 6 – 9, 2026

Hidden Grove is a magical place. A calm, resorative space great for relaxing, disconnecting from every day stresses and connecting with loved ones.
Magical patio area featuring an easy light propane fire table and comfortable lounge seating plus edison lighting for evening chill time.
Hidden Grove- Heyworth, IL
Vaulted ceilings for a charming and unforgettable stay
Hot tub lighting

Hidden Grove- Heyworth, IL

2 bedrooms·1 bath
Heyworth • Illinois
5(21 reviews)

$826.95 USD total for 3 nights

Nov 16 – 19, 2026

Imagine enjoying your Chicago vacation in this comfortably furnished living room, equipped with a 80-inch smart TV, you will be able to enjoy movie nights, sports games, and more with family & friends. Comes with Netflix included.
Central | BBQ Deck | Family-Friendly Pueblo Magíco
Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!
Central | BBQ Deck | Family-Friendly Pueblo Magíco
Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!

Central | BBQ Deck | Family-Friendly Pueblo Magíco

5 bedrooms·2 baths
Chicago • Illinois

$2,411.00 USD total for 3 nights

Nov 6 – 9, 2026

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown
Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown
Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown
Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown
Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

3 bedrooms·2 baths
Chicago • Illinois

$1,937.00 USD total for 3 nights

Nov 6 – 9, 2026

Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!
Movie Room, Garden Oasis in Central Manor
Send us a message to pair this with a SUV Rental for half off! Traveling in groups > 12? Send us a message to book our other vacation homes close by at a discount! If you send us a message, we probably will work out a deal that fits your budget! TY!
check out what people are saying!
Enjoy the natural light, and artwork while enjoying your stay in Chicago!

Movie Room, Garden Oasis in Central Manor

3 bedrooms·2 baths
Chicago • Illinois

$2,096.00 USD total for 3 nights

Nov 6 – 9, 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

Nov 6 – 9, 2026