Location

Dates

Guests

Vacation rentals in Chicago

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 total for 31 nights

Dec 8, 2026 – Jan 8, 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 total for 31 nights

Jan 26 – Feb 26, 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)

$492.26 USD total for 3 nights

Nov 6 – 9, 2026

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/ night(excl. fees & taxes)

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/ night(excl. fees & taxes)

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)

$1,465.00 USD total for 3 nights

Nov 6 – 9, 2026

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

Epicurean experience home

6 bedrooms·4 baths

Chicago • Illinois

$3,600.00 USD total for 3 nights

Nov 6 – 9, 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 total for 32 nights

Nov 6 – Dec 8, 2026

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 total for 3 nights

Nov 9 – 12, 2026

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois

Chicago Lakefront · Fire Pit Patio · Beach Across image 1

Chicago Lakefront · Fire Pit Patio · Beach Across image 2

To the right: two plush couches and a large window. Opposite you: a mounted TV and a table with four chairs. To the right of the table is a corner desk with a lamp. A large rug anchors the center floor. Simple, clear, and easy to navigate.

Chicago Lakefront · Fire Pit Patio · Beach Across image 4

Chicago Lakefront · Fire Pit Patio · Beach Across image 5

Chicago Lakefront · Fire Pit Patio · Beach Across

1 bedroom·1 bath

Chicago • Illinois

5(1 review)

$467.00 USD $373.60 USD total for 3 nights

Nov 8 – 11, 2026

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

2 bedrooms·1 bath

Elmwood Park • Illinois

4.63(8 reviews)

$1,200.00 USD $1,095.00 USD total for 7 nights

Nov 6 – 13, 2026

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

2 bedrooms·1 bath

Elmwood Park • Illinois

4.5(4 reviews)

$30,120.00 USD $18,120.00 USD total for 30 nights

Nov 6 – Dec 6, 2026

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

2 bedrooms·1 bath

Elmwood Park • Illinois

5(2 reviews)

$30,150.00 USD $25,650.00 USD total for 30 nights

Nov 6 – Dec 6, 2026

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

2 bedrooms·1 bath

Elmwood Park • Illinois

5(3 reviews)

$30,150.00 USD $25,650.00 USD total for 30 nights

Nov 6 – Dec 6, 2026

Master Bedroom 2nd floor

1500Main EVANSTON

1500Main EVANSTON

2 bedrooms·1½ baths

Evanston • Illinois

5(166 reviews)

$1,140.42 USD total for 4 nights

Nov 16 – 20, 2026

Ruby’s Retreat - 4BD/3BA+Office in Western Springs

4 bedrooms·3 baths

Western Springs • Illinois

$6,506.85 USD $5,908.67 USD total for 30 nights

Aug 28 – Sep 27, 2027

Cozy Retreat Near Oakbrook Center

Cozy Retreat Near Oakbrook Center

Cozy Retreat Near Oakbrook Center

Cozy Retreat Near Oakbrook Center

Cozy Retreat Near Oakbrook Center

Cozy Retreat Near Oakbrook Center

4 bedrooms·2 baths

Oakbrook Terrace • Illinois

$787.00 USD total for 3 nights

Nov 9 – 12, 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

$1,230.00 USD total for 3 nights

Nov 9 – 12, 2026

Front of the house

Entrance to the unit

Middle Level of the House with Working Space

2 bedrooms·1 bath

Darien • Illinois

4.73(44 reviews)

$494.76 USD total for 4 nights

Nov 6 – 10, 2026

Charming ranch home with vibrant fall views and glowing sunset curb appeal

*King bed *Outdoor Living *Sought-After Area

*King bed *Outdoor Living *Sought-After Area

Charming backyard lounge with cozy deck seating and private garden vibe

Cozy boho lounge with greenery, armchairs, and warm natural accents

King bed Outdoor Living *Sought-After Area

3 bedrooms·1½ baths

Northbrook • Illinois

5(135 reviews)

$1,492.00 USD total for 3 nights

Nov 19 – 22, 2026

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

$171 – $526/ night(excl. fees & taxes)

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 1

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 2

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 3

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 4

Stylish, Sun-Filled Retreat - Minutes to O’Hare! image 5

Stylish, Sun-Filled Retreat - Minutes to O’Hare!

2 bedrooms·2 baths

Wheeling • Illinois

$625.00 USD total for 3 nights

Nov 6 – 9, 2026

Modern Oasis in Glen Ellyn

Modern Oasis in Glen Ellyn

Modern Oasis in Glen Ellyn

Modern Oasis in Glen Ellyn

Modern Oasis in Glen Ellyn

Modern Oasis in Glen Ellyn

3 bedrooms·2½ baths

Glen Ellyn • Illinois

$2,920.00 USD total for 3 nights

Nov 6 – 9, 2026