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 totaal voor 31 nachten

15 nov – 16 dec 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 totaal voor 31 nachten

15 nov – 16 dec 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

$ 2.931,05 USD totaal voor 31 nachten

6 dec 2026 – 6 jan 2027

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 totaal voor 31 nachten

26 jan – 26 feb 2027

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

$ 580,40 USD totaal voor 3 nachten

15–18 nov 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

$ 912,58 USD totaal voor 3 nachten

15–18 nov 2026

Cozy up in your own private cinema, thoughtfully designed for relaxed evenings and unforgettable movie nights. With stunning 4K visuals and immersive Dolby speakers, it’s the perfect escape into your favorite films.
A vibrant, retro-style space buzzing with energy—perfect for friendly competition and late-night fun. The glowing lights and arcade charm make it a favorite hangout for guests of all ages.
Theater • Game Room • Gym • Firepit • 4BR Home
🍽️ Outdoor dining set
Stay active with a sleek indoor gym designed for convenience and style. Perfect for quick workouts or full sessions, it’s fitness reimagined at home.

Theater • Game Room • Gym • Firepit • 4BR Home

4 bedrooms·2 baths
Chicago • Illinois

$ 983,34 USD totaal voor 3 nachten

15–18 nov 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 totaal voor 30 nachten

15 nov – 15 dec 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

$ 586,82 USD totaal voor 4 nachten

15–19 nov 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

$ 604,46 USD totaal voor 3 nachten

15–18 nov 2026

Near O'hare • Personal Gym & Balcony • Safe Area
Near O'hare • Personal Gym & Balcony • Safe Area
Near O'hare • Personal Gym & Balcony • Safe Area
Near O'hare • Personal Gym & Balcony • Safe Area
Near O'hare • Personal Gym & Balcony • Safe Area

Near O'hare • Personal Gym & Balcony • Safe Area

1 bedroom·1 bath
Chicago • Illinois

$ 655,96 USD totaal voor 4 nachten

15–19 nov 2026

Bright and inviting living room with a spacious sectional sofa, perfect for relaxing after a day of exploring Chicago. Floor-to-ceiling mirrored walls create an open, airy feel, while large windows fill the space with natural light.
3BR Vintage Apt • Back Yard• Walk to McKinley Park image 2
3BR Vintage Apt • Back Yard• Walk to McKinley Park image 3
Hand-painted vine and fruit mural along the upper wall near the ceiling, adding a distinctive decorative accent to the space.
3BR Vintage Apt • Back Yard• Walk to McKinley Park

3BR Vintage Apt • Back Yard• Walk to McKinley Park

3 bedrooms·1 bath
Chicago • Illinois
4.92(25 reviews)

$ 602,78 USD totaal voor 3 nachten

16–19 nov 2026

2BR • Newly Furnished Modern Apt • Near O'Hare
2BR • Newly Furnished Modern Apt • Near O'Hare
2BR • Newly Furnished Modern Apt • Near O'Hare
2BR • Newly Furnished Modern Apt • Near O'Hare
2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare

2 bedrooms·1 bath
Chicago • Illinois

$ 700,90 USD totaal voor 3 nachten

15–18 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

$ 658,26 USD totaal voor 3 nachten

15–18 nov 2026

2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill
2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill
2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill
2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill
2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

2 bedrooms·1 bath
Chicago • Illinois

$ 658,26 USD totaal voor 3 nachten

15–18 nov 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

$ 1.049,00 USD totaal voor 3 nachten

15–18 nov 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 totaal voor 3 nachten

15–18 nov 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 totaal voor 3 nachten

15–18 nov 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 totaal voor 3 nachten

16–19 nov 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 totaal voor 3 nachten

15–18 nov 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 totaal voor 3 nachten

15–18 nov 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 totaal voor 3 nachten

15–18 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

$ 187,00 USD totaal voor 3 nachten

15–18 nov 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 totaal voor 3 nachten

15–18 nov 2026