The Pilsen Hideaway | Cozy Private Room
The Pilsen Hideaway | Cozy Private Room
The Pilsen Hideaway | Cozy Private Room
The Pilsen Hideaway | Cozy Private Room
The Pilsen Hideaway | Cozy Private Room

The Pilsen Hideaway | Cozy Private Room

1 bedroom·1 bath
Chicago • Illinois

$257.00 USD total for 3 nights

Nov 12 – 15, 2026

Chicago Townhome with Roof Deck image 1
Chicago Townhome with Roof Deck image 2
Chicago Townhome with Roof Deck image 3
Chicago Townhome with Roof Deck image 4
Chicago Townhome with Roof Deck image 5

Chicago Townhome with Roof Deck

3 bedrooms·3 baths
Chicago • Illinois
5(43 reviews)

$840.00 USD total for 3 nights

Nov 15 – 18, 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

$1,106.00 USD total for 3 nights

Nov 12 – 15, 2026

2BD/1 BA with summer patio in quiet Roscoe Village
2BD/1 BA with summer patio in quiet Roscoe Village
2BD/1 BA with summer patio in quiet Roscoe Village
2BD/1 BA with summer patio in quiet Roscoe Village
2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2 bedrooms·1 bath
Chicago • Illinois
4.97(98 reviews)

$460.79 USD total for 3 nights

Nov 29 – Dec 2, 2026

Hyde Park 2BR UChicago Medical Museums 20% OFF
Main Bedroom
Hyde Park 2BR UChicago Medical Museums 20% OFF
Hyde Park 2BR UChicago Medical Museums 20% OFF
Quick view of upstairs "half kitchen," middle of tile restoral. NOTE there is a microwave and induction burner, NO STOVE.

Hyde Park 2BR UChicago Medical Museums 20% OFF

2 bedrooms·1 bath
Chicago • Illinois
5(4 reviews)
$233/ night(excl. fees & taxes)
Step into serenity at our welcoming retreat. Follow detailed check-in directions to unlock the smart lock for secure access. Relax in the cozy living room with a 30" Smart TV and a collection of board games. Outside, unwind in the serene backyard.
Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.
Unwind in our inviting sanctuary. Seamless check-in with detailed instructions and a smart lock. Cozy up in the relaxing living room, equipped with a 30" Smart TV and a selection of board games. Step outside to a tranquil backyard with a pergola.
Step into tranquility with seamless check-in and a smart lock. Explore local treasures with our custom guidebook. Outside, unwind in the serene backyard oasis, complete with a pergola, fire-pit, outdoor gas grill, and picnic table dining.
Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.

Artistic Stay near Hyde Park: 2 Living, Courtyard

3 bedrooms·2½ baths
Chicago • Illinois
4.9(106 reviews)

$1,284.00 USD total for 3 nights

Nov 13 – 16, 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 15 – 18, 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 15 – 18, 2026

New Modern 3BR • Gym • Workspace • Quiet Location
New Modern 3BR • Gym • Workspace • Quiet Location
New Modern 3BR • Gym • Workspace • Quiet Location
New Modern 3BR • Gym • Workspace • Quiet Location
New Modern 3BR • Gym • Workspace • Quiet Location

New Modern 3BR • Gym • Workspace • Quiet Location

3 bedrooms·2 baths
Chicago • Illinois

$1,298.30 USD total for 3 nights

Nov 12 – 15, 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 16 – 20, 2026

Luxurious Condo in Top Rated Neighborhood
Luxurious Condo in Top Rated Neighborhood
Luxurious Condo in Top Rated Neighborhood
Luxurious Condo in Top Rated Neighborhood
Luxurious Condo in Top Rated Neighborhood

Luxurious Condo in Top Rated Neighborhood

1 bedroom·1 bath
Chicago • Illinois
4.46(28 reviews)

$3,600.00 USD total for 30 nights

Nov 12 – Dec 12, 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

$6,506.85 USD $5,908.67 USD total for 30 nights

Aug 28 – Sep 27, 2027

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)

$1,500.00 USD total for 3 nights

Nov 19 – 22, 2026

Modern Boho Entire Home in Glen Ellyn
Modern Boho Entire Home in Glen Ellyn
Modern Boho Entire Home in Glen Ellyn
Modern Boho Entire Home in Glen Ellyn
Modern Boho Entire Home in Glen Ellyn

Modern Boho Entire Home in Glen Ellyn

4 bedrooms·2 baths
Glen Ellyn • Illinois

$901.00 USD total for 3 nights

Nov 12 – 15, 2026