"Wine" Room - 1 block from train, Victorian Charm
"Wine" Room - 1 block from train, Victorian Charm
"Wine" Room - 1 block from train, Victorian Charm
"Wine" Room - 1 block from train, Victorian Charm
"Wine" Room - 1 block from train, Victorian Charm

"Wine" Room - 1 block from train, Victorian Charm

1 bedroom·2½ baths
Chicago • Illinois

$187.00 USD total for 3 nights

Oct 27 – 30, 2026

Florence Room - 3min to CTA, Free Parking, Roomy
Florence Room - 3min to CTA, Free Parking, Roomy
Florence Room - 3min to CTA, Free Parking, Roomy
Florence Room - 3min to CTA, Free Parking, Roomy
Florence Room - 3min to CTA, Free Parking, Roomy

Florence Room - 3min to CTA, Free Parking, Roomy

1 bedroom·2½ baths
Chicago • Illinois

$157.00 USD total for 3 nights

Nov 2 – 5, 2026

Green Room, Free Parking, King Bed, 1 Block to CTA
Green Room, Free Parking, King Bed, 1 Block to CTA
Green Room, Free Parking, King Bed, 1 Block to CTA
Green Room, Free Parking, King Bed, 1 Block to CTA
Green Room, Free Parking, King Bed, 1 Block to CTA

Green Room, Free Parking, King Bed, 1 Block to CTA

1 bedroom·2½ baths
Chicago • Illinois

$187.00 USD total for 3 nights

Oct 26 – 29, 2026

Vintage Airline - Close to Train, Full Size Bed
Vintage Airline - Close to Train, Full Size Bed
Vintage Airline - Close to Train, Full Size Bed
Vintage Airline - Close to Train, Full Size Bed
Vintage Airline - Close to Train, Full Size Bed

Vintage Airline - Close to Train, Full Size Bed

1 bedroom·2½ baths
Chicago • Illinois

$157.00 USD total for 3 nights

Nov 1 – 4, 2026

Teal Room - King Bed, near CTA, 20min to Downtown
Teal Room - King Bed, near CTA, 20min to Downtown
Teal Room - King Bed, near CTA, 20min to Downtown
Teal Room - King Bed, near CTA, 20min to Downtown
Teal Room - King Bed, near CTA, 20min to Downtown

Teal Room - King Bed, near CTA, 20min to Downtown

1 bedroom·2½ baths
Chicago • Illinois

$157.00 USD total for 3 nights

Oct 26 – 29, 2026

Egyptian Room - Free Parking, 1 block to CTA
Egyptian Room - Free Parking, 1 block to CTA
Egyptian Room - Free Parking, 1 block to CTA
Egyptian Room - Free Parking, 1 block to CTA
Egyptian Room - Free Parking, 1 block to CTA

Egyptian Room - Free Parking, 1 block to CTA

1 bedroom·2½ baths
Chicago • Illinois

$187.00 USD total for 3 nights

Oct 26 – 29, 2026

Garden Room - King Bed, Sofa Bed, 1 Block to Train
Garden Room - King Bed, Sofa Bed, 1 Block to Train
Garden Room - King Bed, Sofa Bed, 1 Block to Train
Garden Room - King Bed, Sofa Bed, 1 Block to Train
Garden Room - King Bed, Sofa Bed, 1 Block to Train

Garden Room - King Bed, Sofa Bed, 1 Block to Train

1 bedroom·2½ baths
Chicago • Illinois

$157.00 USD total for 3 nights

Oct 26 – 29, 2026

Celestial Room - 20 Min to Downtown, Free parking
Celestial Room - 20 Min to Downtown, Free parking
Celestial Room - 20 Min to Downtown, Free parking
Celestial Room - 20 Min to Downtown, Free parking
Celestial Room - 20 Min to Downtown, Free parking

Celestial Room - 20 Min to Downtown, Free parking

1 bedroom·2½ baths
Chicago • Illinois

$187.00 USD total for 3 nights

Oct 26 – 29, 2026

Cottage Crafts Room - Free Parking, 1 block to CTA
Cottage Crafts Room - Free Parking, 1 block to CTA
Cottage Crafts Room - Free Parking, 1 block to CTA
Cottage Crafts Room - Free Parking, 1 block to CTA
Cottage Crafts Room - Free Parking, 1 block to CTA

Cottage Crafts Room - Free Parking, 1 block to CTA

1 bedroom·2½ baths
Chicago • Illinois

$187.00 USD total for 3 nights

Oct 26 – 29, 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

$945.00 USD total for 3 nights

Oct 26 – 29, 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

$1,063.00 USD total for 3 nights

Oct 26 – 29, 2026

Chicago Getaway | Cozy 2BR Near Downtown
Thoughtful extras: coffee bar, games, full cookware & pet-friendly perks
Chicago Getaway | Cozy 2BR Near Downtown
Chicago Getaway | Cozy 2BR Near Downtown
Bright living space with hardwood floors and wall-mounted streaming TV

Chicago Getaway | Cozy 2BR Near Downtown

2 bedrooms·1 bath
Chicago • Illinois

$528.95 USD total for 3 nights

Oct 26 – 29, 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

$1,166.00 USD total for 3 nights

Oct 26 – 29, 2026

Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

2 bedrooms·1 bath
Chicago • Illinois

$2,913.05 USD total for 31 nights

Oct 26 – Nov 26, 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

$3,072.70 USD total for 31 nights

Oct 27 – Nov 27, 2026

Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown
Stylish & Comfy Stay • Close to Downtown

Stylish & Comfy Stay • Close to Downtown

2 bedrooms·1 bath
Chicago • Illinois

$2,771.40 USD total for 31 nights

Jan 26 – Feb 26, 2027

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

$2,931.05 USD total for 31 nights

Dec 8, 2026 – Jan 8, 2027

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)

$541.45 USD total for 3 nights

Nov 9 – 12, 2026

Modern Western Logan Square Flat Healy Metra Stop
Modern Western Logan Square Flat Healy Metra Stop
Modern Western Logan Square Flat Healy Metra Stop
Modern Western Logan Square Flat Healy Metra Stop
Modern Western Logan Square Flat Healy Metra Stop

Modern Western Logan Square Flat Healy Metra Stop

2 bedrooms·1 bath
Chicago • Illinois
4.75(24 reviews)

$738.50 USD total for 3 nights

Oct 26 – 29, 2026

Sleeps 4 • Stylish Stay with Workspace
Sleeps 4 • Stylish Stay with Workspace
Sleeps 4 • Stylish Stay with Workspace
Sleeps 4 • Stylish Stay with Workspace
Sleeps 4 • Stylish Stay with Workspace

Sleeps 4 • Stylish Stay with Workspace

1 bedroom·1 bath
Chicago • Illinois

$479.81 USD total for 3 nights

Oct 26 – 29, 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

$458.64 USD total for 3 nights

Oct 26 – 29, 2026

Sleeps 7 • Huge Projector • Designated Workspace
Sleeps 7 • Huge Projector • Designated Workspace
Sleeps 7 • Huge Projector • Designated Workspace
Sleeps 7 • Huge Projector • Designated Workspace
Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace

2 bedrooms·1 bath
Chicago • Illinois

$523.32 USD total for 3 nights

Oct 26 – 29, 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)
Large Cozy 3BR near UChicago Medical Midway Museum
Living Room
Main bedroom from desk area
Second bedroom -- a headboard has been added (didn't get a picture of that yet).
Third bedroom, desk and closet

Large Cozy 3BR near UChicago Medical Midway Museum

3 bedrooms·1 bath
Chicago • Illinois
5(8 reviews)
$349/ night(excl. fees & taxes)