Cozy private deck with cushioned seating and a stylish fire table
Prime Chicago base—minutes to Mag Mile, Navy Pier, parks & airports.
Bright living room with recliners, fireplace, TV, and abundant natural light
Spa-style jetted soaking tub for a relaxing, luxurious stay
Cozy fire table patio with wine—perfect for relaxing evening nights

Chicago Oasis | Spa Bath, Patio & Fireplace

1 bedroom·1 bath
Chicago • Illinois
$149 – $642/ night(excl. fees & taxes)
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
$90 – $150/ night(excl. fees & taxes)
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
$90 – $170/ night(excl. fees & taxes)
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
$85 – $266/ night(excl. fees & taxes)
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
$71 – $189/ night(excl. fees & taxes)
The Kozy Keep! 1500 Sq.ft. - Sleeps 8! image 1
The Kozy Keep! 1500 Sq.ft. - Sleeps 8! image 2
The Kozy Keep! 1500 Sq.ft. - Sleeps 8! image 3
The Kozy Keep! 1500 Sq.ft. - Sleeps 8! image 4
The Kozy Keep! 1500 Sq.ft. - Sleeps 8! image 5

The Kozy Keep! 1500 Sq.ft. - Sleeps 8!

2 bedrooms·2 baths
Olney • Illinois
4.86(56 reviews)

$465.00 USD total for 3 nights

Sep 22 – 25, 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
$73 – $180/ night(excl. fees & taxes)
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
$94 – $150/ night(excl. fees & taxes)
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)

$1,001.70 USD $970.39 USD total for 3 nights

Sep 24 – 27, 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

$1,645.57 USD $1,554.23 USD total for 3 nights

Sep 24 – 27, 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)

$2,695.14 USD $2,538.05 USD total for 3 nights

Sep 24 – 27, 2026

Beautiful living room
Beautiful new table
Primary bedroom with memory foam king bed
Screened in porch with propane fire pit
Beautiful living room

Galena Haven Gorgeous cabin 3bdrm/3bth, hot tub, k

3 bedrooms·3 baths
Galena • Illinois
5(34 reviews)

$2,226.00 USD total for 3 nights

Oct 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)

$1,783.74 USD $1,705.13 USD total for 3 nights

Sep 22 – 25, 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

Sep 22 – 25, 2026

Secluded | Quiet | Wooded
Hot tub lighting
So much character
Bed 1 | 2nd Floor | Queen Size
Tucked away yet convenient to restaurants, hiking and shops

Hidden Grove- Heyworth, IL

2 bedrooms·1 bath
Heyworth • Illinois
5(3 reviews)
$229 – $614/ night(excl. fees & taxes)
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
$700/ night(excl. fees & taxes)
Lounge seating | Umbrella
Daisy Lane- Normal, IL
Daisy Lane- Normal, IL
Daisy Lane- Normal, IL
Daisy Lane- Normal, IL

Daisy Lane- Normal, IL

2 bedrooms·1½ baths
Normal • Illinois
5(14 reviews)

$984.46 USD total for 3 nights

Sep 22 – 25, 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(20 reviews)

$812.53 USD total for 3 nights

Sep 27 – 30, 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
$231 – $1,595/ night(excl. fees & taxes)
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
$196 – $1,426/ night(excl. fees & taxes)
Screened | 50" TV | Lake Views
The Ridge- Decatur, IL
Warm vaulted ceilings, huge comfortable sofa and giant TV all add to the character and calm of The Ridge living room.
Game table | Up to 6 players
The Ridge- Decatur, IL

The Ridge- Decatur, IL

2 bedrooms·2 baths
Decatur • Illinois
5(5 reviews)

$1,143.08 USD total for 3 nights

Oct 4 – 7, 2026

Mid Century Modern Vibes! Propane fireplace! Listen to records! Enjoy nature around you!
Living room space with smart TVs, radio, record player
Private Hot tub- Use year round! No views of other homes. 6 person, wonderful jets!
Queen Bedroom with attached bathroom
Memory Foam, King Bed with views of nature!

Galena Haven Tree House

2 bedrooms·2 baths
Galena • Illinois
$250 – $410/ night(excl. fees & taxes)
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

$1,982.02 USD total for 3 nights

Oct 19 – 22, 2026

Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown
Chic & Cozy Chicago Stay • Close to Downtown

Chic & Cozy Chicago Stay • Close to Downtown

3 bedrooms·1 bath
Chicago • Illinois
$93 – $98/ night(excl. fees & taxes)