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 gesamt für 3 Nächte

9.–12. Nov. 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)
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 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

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

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

Ashland
Living room
Workspace in the living room
Bedroom 1
Bedroom 2

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 gesamt für 3 Nächte

3.–6. Nov. 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 gesamt für 3 Nächte

8.–11. Nov. 2026

Main Floor
Master Bedroom 2nd floor
Dining area
1500Main EVANSTON
Main Floor

1500Main EVANSTON

2 bedrooms·1½ baths
Evanston • Illinois
5(166 reviews)

1.140,42 $ USD gesamt für 4 Nächte

16.–20. Nov. 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 gesamt für 3 Nächte

3.–6. Nov. 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 gesamt für 3 Nächte

3.–6. Nov. 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 gesamt für 3 Nächte

5.–8. Nov. 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 gesamt für 3 Nächte

3.–6. Nov. 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 gesamt für 3 Nächte

19.–22. 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)
balcony
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 gesamt für 3 Nächte

3.–6. Nov. 2026