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

$ 4.406,94 USD totaal voor 30 nachten

24 okt – 23 nov 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

$ 4.463,06 USD totaal voor 30 nachten

24 okt – 23 nov 2026

2BR w/ Workspace + Coffee Bar • Near Transit
2BR w/ Workspace + Coffee Bar • Near Transit
2BR w/ Workspace + Coffee Bar • Near Transit
2BR w/ Workspace + Coffee Bar • Near Transit
2BR w/ Workspace + Coffee Bar • Near Transit

2BR w/ Workspace + Coffee Bar • Near Transit

2 bedrooms·1 bath
Chicago • Illinois

$ 934,90 USD totaal voor 3 nachten

24–27 okt 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

$ 678,55 USD totaal voor 3 nachten

24–27 okt 2026

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

$ 3.567,74 USD totaal voor 3 nachten

24–27 okt 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

$ 691,49 USD totaal voor 4 nachten

24–28 okt 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

$ 1.384,65 USD totaal voor 3 nachten

24–27 okt 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

$ 4.118,45 USD totaal voor 30 nachten

24 okt – 23 nov 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

$ 4.683,07 USD totaal voor 30 nachten

24 okt – 23 nov 2026

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

Ashland

3 bedrooms·1 bath
Chicago • Illinois
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)

$ 2.909,38 USD $ 2.676,62 USD totaal voor 3 nachten

24–27 okt 2026

Little Village Chicago Hub - Clean & Pet Friendly
Little Village Chicago Hub - Clean & Pet Friendly
Little Village Chicago Hub - Clean & Pet Friendly
Bright living space with hardwood floors and wall-mounted streaming TV
Little Village Chicago Hub - Clean & Pet Friendly

Little Village Chicago Hub - Clean & Pet Friendly

2 bedrooms·1 bath
Chicago • Illinois

$ 549,95 USD totaal voor 3 nachten

25–28 okt 2026

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

$ 489,90 USD totaal voor 3 nachten

24–27 okt 2026

Private Stay w/Free Coffee | Best Stay in Chicago
Private Stay w/Free Coffee | Best Stay in Chicago
Private Stay w/Free Coffee | Best Stay in Chicago
Private Stay w/Free Coffee | Best Stay in Chicago
Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

1 bedroom·2 baths
Chicago • Illinois

$ 596,33 USD totaal voor 3 nachten

24–27 okt 2026

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

$ 695,47 USD totaal voor 3 nachten

24–27 okt 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

$ 774,98 USD totaal voor 3 nachten

24–27 okt 2026

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 totaal voor 3 nachten

24–27 okt 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)

$ 960,67 USD $ 922,25 USD totaal voor 3 nachten

24–27 okt 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

$ 1.887,16 USD $ 1.736,19 USD totaal voor 3 nachten

24–27 okt 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

$ 6.336,75 USD $ 5.755,58 USD totaal voor 30 nachten

28 aug – 27 sep 2027

Solo Explorer’s Nest | Walk to Museums & Parks
Solo Explorer’s Nest | Walk to Museums & Parks
Solo Explorer’s Nest | Walk to Museums & Parks
Solo Explorer’s Nest | Walk to Museums & Parks
Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

1 bedroom·2 baths
Chicago • Illinois

$ 8.607,15 USD totaal voor 3 nachten

28–31 aug 2027

Work, Explore, Rest | Ideal for Solo Guests
Work, Explore, Rest | Ideal for Solo Guests
Work, Explore, Rest | Ideal for Solo Guests
Work, Explore, Rest | Ideal for Solo Guests
Work, Explore, Rest | Ideal for Solo Guests

Work, Explore, Rest | Ideal for Solo Guests

1 bedroom·2 baths
Chicago • Illinois

$ 7.496,55 USD totaal voor 3 nachten

28–31 aug 2027

Free Coffee & Private Room - Traveler's Favorite!
Free Coffee & Private Room - Traveler's Favorite!
Free Coffee & Private Room - Traveler's Favorite!
Free Coffee & Private Room - Traveler's Favorite!
Free Coffee & Private Room - Traveler's Favorite!

Free Coffee & Private Room - Traveler's Favorite!

1 bedroom·2 baths
Chicago • Illinois

$ 8.607,15 USD totaal voor 3 nachten

28–31 aug 2027

Morning Brew & Museum Views • Downtown Solo Stay
Morning Brew & Museum Views • Downtown Solo Stay
Morning Brew & Museum Views • Downtown Solo Stay
Morning Brew & Museum Views • Downtown Solo Stay
Morning Brew & Museum Views • Downtown Solo Stay

Morning Brew & Museum Views • Downtown Solo Stay

1 bedroom·2 baths
Chicago • Illinois

$ 8.607,15 USD totaal voor 3 nachten

28–31 aug 2027