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 total por 3 noches

20–23 oct 2026

"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 por 3 noches

27–30 oct 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 por 3 noches

2–5 nov 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 total por 3 noches

20–23 oct 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 total por 3 noches

20–23 oct 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 por 3 noches

20–23 oct 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 total por 3 noches

20–23 oct 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 total por 3 noches

20–23 oct 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 por 3 noches

26–29 oct 2026

Fort Washington Railway Room, King Bed, Sofa Bed
Fort Washington Railway Room, King Bed, Sofa Bed
Fort Washington Railway Room, King Bed, Sofa Bed
Fort Washington Railway Room, King Bed, Sofa Bed
Fort Washington Railway Room, King Bed, Sofa Bed

Fort Washington Railway Room, King Bed, Sofa Bed

1 bedroom·2½ baths
Chicago • Illinois

156,00 $ USD total por 3 noches

20–23 oct 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 total por 3 noches

9–12 nov 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 total por 3 noches

20–23 oct 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

718,13 $ USD total por 3 noches

20–23 oct 2026

Space for relaxing and a table for everyone
Gourmet chef's kitchen & space for all!
Beautiful space for family vacation, girls getaways
MFL 2 West
MFL 2 West

MFL 2 West

3 bedrooms·2 baths
Chicago • Illinois
4.95(206 reviews)

2307,68 $ USD 1991,16 $ USD total por 3 noches

6–9 nov 2026

Spacious open 4 bedroom vacation rental loft
MFL 2 East
MFL 2 East
Skyline views
Brick & timber loft with full hight walls for privacy

MFL 2 East

4 bedrooms·3 baths
Chicago • Illinois
4.93(120 reviews)

2378,69 $ USD 2051,49 $ USD total por 3 noches

25–28 oct 2026

Fab space for the whole group!
MFL 3 East
Fully stocked chef's kitchen
MFL 3 East
MFL 3 East

MFL 3 East

4 bedrooms·4 baths
Chicago • Illinois
4.99(93 reviews)

3104,93 $ USD 2668,80 $ USD total por 3 noches

20–23 oct 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

3072,70 $ USD total por 31 noches

27 oct – 27 nov 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

2919,23 $ USD total por 31 noches

20 oct – 20 nov 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

2913,05 $ USD total por 31 noches

3 nov – 4 dic 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

2753,40 $ USD total por 31 noches

26 ene – 26 feb 2027

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

6336,75 $ USD 5755,58 $ USD total por 30 noches

28 ago – 27 sept 2027

4 BR • Theater Room • Gym • Walk to Lincoln Park!
4 BR • Theater Room • Gym • Walk to Lincoln Park!
4 BR • Theater Room • Gym • Walk to Lincoln Park!
4 BR • Theater Room • Gym • Walk to Lincoln Park!
4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 bedrooms·2 baths
Chicago • Illinois

1868,66 $ USD total por 3 noches

20–23 oct 2026

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

Ashland

3 bedrooms·1 bath
Chicago • Illinois
Apartment with breathtaking 360 degree views
Apartment with breathtaking 360 degree views
Apartment with breathtaking 360 degree views
Apartment with breathtaking 360 degree views
Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

3 bedrooms·3 baths
Chicago • Illinois

2090,00 $ USD total por 5 noches

20–25 oct 2026