"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 σύνολο για 3 νύχτες

27–30 Οκτ 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 σύνολο για 3 νύχτες

2–5 Νοε 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

181,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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

168,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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

190,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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 σύνολο για 3 νύχτες

20–23 Οκτ 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

188,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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 σύνολο για 3 νύχτες

26–29 Οκτ 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

211,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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

1.862,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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

2.338,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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

530,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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)

544,77 $ USD σύνολο για 3 νύχτες

9–12 Νοε 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 σύνολο για 31 νύχτες

27 Οκτ – 27 Νοε 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

2.919,23 $ USD σύνολο για 31 νύχτες

20 Οκτ – 20 Νοε 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

2.913,05 $ USD σύνολο για 31 νύχτες

3 Νοε – 4 Δεκ 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

2.753,40 $ USD σύνολο για 31 νύχτες

26 Ιαν – 26 Φεβ 2027

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)

767,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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

552,72 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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

538,61 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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

599,76 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 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/ νύχτα(χωρίς χρεώσεις & φόρους)
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/ νύχτα(χωρίς χρεώσεις & φόρους)
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)

972,00 $ USD σύνολο για 3 νύχτες

20–23 Οκτ 2026