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

706,00 $ USD gesamt für 3 Nächte

3.–6. Nov. 2026

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(zzgl. Gebühren & Steuern)
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 gesamt für 3 Nächte

3.–6. 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)

817,00 $ USD gesamt für 3 Nächte

3.–6. 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 gesamt für 32 Nächte

5. Nov. – 7. Dez. 2026

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/ Nacht(zzgl. Gebühren & Steuern)
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/ Nacht(zzgl. Gebühren & Steuern)
★ "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

1.095,00 $ USD gesamt für 3 Nächte

3.–6. 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

1.051,00 $ USD gesamt für 3 Nächte

3.–6. 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

812,00 $ USD gesamt für 3 Nächte

3.–6. 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 gesamt für 31 Nächte

3. Nov. – 4. Dez. 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 gesamt für 31 Nächte

3. Nov. – 4. Dez. 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 gesamt für 31 Nächte

8. Dez. 2026 – 8. 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 gesamt für 31 Nächte

26. Jan. – 26. Feb. 2027

Exterior
Living area
Living area
Interior
Room

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

2 bedrooms·2 baths
Chicago • Illinois

4.170,00 $ USD gesamt für 30 Nächte

3. Nov. – 3. Dez. 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)

462,00 $ USD gesamt für 3 Nächte

4.–7. 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

804,00 $ USD gesamt für 3 Nächte

3.–6. 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

1.123,00 $ USD gesamt für 3 Nächte

3.–6. 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

822,95 $ USD gesamt für 3 Nächte

3.–6. 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

415,86 $ USD gesamt für 3 Nächte

3.–6. Nov. 2026

Best Private Room in Downtown | Free Coffee
Best Private Room in Downtown | Free Coffee
Best Private Room in Downtown | Free Coffee
Best Private Room in Downtown | Free Coffee
Best Private Room in Downtown | Free Coffee

Best Private Room in Downtown | Free Coffee

1 bedroom·2 baths
Chicago • Illinois

8.607,15 $ USD gesamt für 3 Nächte

28.–31. Aug. 2027

Private Stay w/Free Coffee | Best Stay in Chicago
Private Stay w/Free Coffee | Best Stay in Chicago
Private Stay w/Free Coffee | Best Stay in Chicago
Private Stay w/Free Coffee | Best Stay in Chicago
Private Stay w/Free Coffee | Best Stay in Chicago

Private Stay w/Free Coffee | Best Stay in Chicago

1 bedroom·2 baths
Chicago • Illinois

556,60 $ USD gesamt für 3 Nächte

3.–6. 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 gesamt für 3 Nächte

28.–31. Aug. 2027

Morning Brew & Museum Views • Downtown Solo Stay
Morning Brew & Museum Views • Downtown Solo Stay
Morning Brew & Museum Views • Downtown Solo Stay
Morning Brew & Museum Views • Downtown Solo Stay
Morning Brew & Museum Views • Downtown Solo Stay

Morning Brew & Museum Views • Downtown Solo Stay

1 bedroom·2 baths
Chicago • Illinois

8.607,15 $ USD gesamt für 3 Nächte

28.–31. Aug. 2027