Location

Dates

Guests

Vacation rentals in Homewood, Illinois, United States

Charming Getaway in Homewood Near Chicago

Spacious Living Room, opened up to the Dining Room

Modern Fully Stocked Kitchen

Upstairs Living Room, off the Master Bedroom

Private workspace

Charming Getaway in Homewood Near Chicago

3 bedrooms·1½ baths

Homewood • Illinois

$ 1.263,00 USD totaal voor 3 nachten

31 dec 2026 – 3 jan 2027

Cute 2 br with King and Queen

Cute 2 br with King and Queen

Cute 2 br with King and Queen

Cute 2 br with King and Queen

Cute 2 br with King and Queen

Cute 2 br with King and Queen

2 bedrooms·1 bath

Park Forest • Illinois

4.95(20 reviews)

$119 – $199/ nacht(excl. kosten & belastingen)

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

The Euclid House — 6BR Near UChicago & Hospitals

6 bedrooms·3 baths

Chicago • Illinois

$ 1.100,00 USD totaal voor 3 nachten

15–18 nov 2026

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)

$ 1.013,00 USD totaal voor 3 nachten

18–21 nov 2026

What a view from my 13th floor!

Stately building entrance

Gallery Hallway looking towards Living Room

Spacious living room

My view of Jackson Harbor and partial Chicago skyline.

Art Collector's Pied-à-terre

2 bedrooms·2 baths

Chicago • Illinois

4.84(247 reviews)

$ 2.980,00 USD totaal voor 32 nachten

15 nov – 17 dec 2026

Blue Oasis

2 bedrooms·1 bath

Chicago • Illinois

$ 633,07 USD totaal voor 3 nachten

16–19 dec 2026

Large Cozy 3BR near UChicago Medical Midway Museum

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/ nacht(excl. kosten & belastingen)

Hyde Park 2BR UChicago Medical Museums 20% OFF

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/ nacht(excl. kosten & belastingen)

★ "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

$ 1.251,00 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

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

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

$ 1.104,00 USD totaal voor 3 nachten

15–18 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

$ 3.072,70 USD totaal voor 31 nachten

15 nov – 16 dec 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 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

Chic 2-bedroom apartment in beautiful Chicago. 30+ Day Stays Only

2 bedrooms·2 baths

Chicago • Illinois

$ 4.170,00 USD totaal voor 30 nachten

15 nov – 15 dec 2026

Bright & Cozy 1 Bdrm • Free Parking image 1

Bright & Cozy 1 Bdrm • Free Parking image 2

Bright & Cozy 1 Bdrm • Free Parking image 3

Bright & Cozy 1 Bdrm • Free Parking image 4

Bright & Cozy 1 Bdrm • Free Parking image 5

Bright & Cozy 1 Bdrm • Free Parking

1 bedroom·1 bath

Chicago • Illinois

4.61(64 reviews)

$ 352,00 USD totaal voor 3 nachten

15–18 nov 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

$ 1.178,00 USD totaal voor 3 nachten

15–18 nov 2026

Spacious Home with 4 Full Baths

Spacious Home with 4 Full Baths

Spacious Home with 4 Full Baths

Spacious Home with 4 Full Baths

Spacious Home with 4 Full Baths

Spacious Home with 4 Full Baths

4 bedrooms·4 baths

Willowbrook • Illinois

$ 1.103,00 USD totaal voor 3 nachten

15–18 nov 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

$ 580,40 USD totaal voor 3 nachten

15–18 nov 2026

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

$ 247,00 USD totaal voor 3 nachten

15–18 nov 2026

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

Budget-Friendly Room| Free Coffee | Downtown

1 bedroom·2 baths

Chicago • Illinois

$ 399,82 USD totaal voor 3 nachten

15–18 nov 2026

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

Solo Explorer’s Nest | Walk to Museums & Parks

1 bedroom·2 baths

Chicago • Illinois

$ 8.607,15 USD totaal voor 3 nachten

28–31 aug 2027