Location

Dates

Guests

Vacation rentals in Western Springs, Illinois, United States

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)

$535.93 USD total for 3 nights

Nov 9 – 12, 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/ night(excl. fees & taxes)

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)

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

$1,647.58 USD total for 3 nights

Nov 3 – 6, 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 total for 3 nights

Nov 3 – 6, 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 3 – 6, 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 5 – Dec 7, 2026

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

Arlington Heights Home

1 bedroom·1 bath

Arlington Heights • Illinois

$806.76 USD total for 3 nights

Nov 3 – 6, 2026

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

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

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 total for 3 nights

Nov 3 – 6, 2026

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 3 – 6, 2026

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

Walk to Downtown! 6-Bedroom Home

6 bedrooms·3 baths

St. Charles • Illinois

$1,228.00 USD total for 3 nights

Nov 5 – 8, 2026

6 bedroom! Pool Table, Gaming Area, Firepit & More image 1

6 bedroom! Pool Table, Gaming Area, Firepit & More image 2

6 bedroom! Pool Table, Gaming Area, Firepit & More image 3

6 bedroom! Pool Table, Gaming Area, Firepit & More image 4

6 bedroom! Pool Table, Gaming Area, Firepit & More image 5

6 bedroom! Pool Table, Gaming Area, Firepit & More

6 bedrooms·3 baths

Joliet • Illinois

4.92(24 reviews)

$2,390.00 USD total for 3 nights

Nov 3 – 6, 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)

$1,491.00 USD total for 3 nights

Nov 19 – 22, 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/ night(excl. fees & taxes)

Master Bedroom Second Floor

Family Room First Floor open to Loft Second Floor two story family room with skylights

Master Bedroom Second Floor

Kitchen First Floor

Beautiful spacious gem Oasis Manor 6 BR 4 1/2 BA

6 bedrooms·4 baths

East Dundee • Illinois

5(9 reviews)

$2,766.75 USD total for 3 nights

Nov 3 – 6, 2026