Apartment with breathtaking 360 degree views
Apartment with breathtaking 360 degree views
Apartment with breathtaking 360 degree views
Apartment with breathtaking 360 degree views
Apartment with breathtaking 360 degree views

Apartment with breathtaking 360 degree views

3 bedrooms·3 baths
Chicago • Illinois

2.090,00 $ USD gesamt für 5 Nächte

3.–8. Nov. 2026

Space for relaxing and a table for everyone
Gourmet chef's kitchen & space for all!
Beautiful space for family vacation, girls getaways
MFL 2 West
MFL 2 West

MFL 2 West

3 bedrooms·2 baths
Chicago • Illinois
4.95(206 reviews)

2.883,29 $ USD 2.450,81 $ USD gesamt für 3 Nächte

6.–9. Nov. 2026

Spacious open 4 bedroom vacation rental loft
MFL 2 East
MFL 2 East
Skyline views
Brick & timber loft with full hight walls for privacy

MFL 2 East

4 bedrooms·3 baths
Chicago • Illinois
4.93(120 reviews)

2.186,67 $ USD 1.889,69 $ USD gesamt für 3 Nächte

3.–6. Nov. 2026

Fab space for the whole group!
MFL 3 East
Fully stocked chef's kitchen
MFL 3 East
MFL 3 East

MFL 3 East

4 bedrooms·4 baths
Chicago • Illinois
4.99(93 reviews)

2.841,00 $ USD 2.445,91 $ USD gesamt für 3 Nächte

3.–6. Nov. 2026

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

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

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

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

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

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

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

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

Ashland

3 bedrooms·1 bath
Chicago • Illinois
Wind down under the cozy lighting at the end of your day. Relax in the hot tub or gather around the fire table.
Regulation size pickleball court with Sport Court surface is only shared with guests who book the Guest Quarters.
The LED lights on the corn hole boards can make playing in the evening more adventurous.
Warning! Playing these games may cause competitive natures to rise and may lead to tears and belly aches from too much laughing.
View down from the top of the stairs.Caution! Top step is more shallow than other steps.

Deer Run Log Cabin

3 bedrooms·2 baths
Yorkville • Illinois

2.112,80 $ USD 2.007,17 $ USD gesamt für 3 Nächte

3.–6. Nov. 2026

Private deck with fire table, seating, BBQ grill, hot tub, and glowing café lights—perfect for relaxing nights outdoors.
The onsite pickleball court has a Sport Court surface and is shared with the guests in the Cabin. Deer frequently pass by the court.
Relax by the fire table in the gazebo.
The corn hole boards have LED lighting that make playing at dusk more exciting.
Shared Space: Bond and laugh over some board games.

Deer Run Guest Quarters

1 bedroom·1 bath
Yorkville • Illinois
5(1 review)

1.066,65 $ USD 1.024,00 $ USD gesamt für 3 Nächte

4.–7. Nov. 2026

Regulation size pickleball court with Sport Court surface on site!
Unwind on the deck under the cafe lights or around the fire pit.
There is plenty of comfortable seating so everyone in your group can have a seat without crowding each other. There are even throw blankets and pillows for additional comfort.
Relax in the 7-person hot tub under the cafe lights at night.
Everyone in your group can sit around the table together as it seats up to 12 people. There are also 2 additional seats at the kitchen island..

Deer Run Lodge

4 bedrooms·3 baths
Yorkville • Illinois
5(1 review)

3.339,01 $ USD 2.838,16 $ USD gesamt für 3 Nächte

4.–7. 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

Family&Pet Friendly-No Stairs-Kingbeds-Peaceful. image 1
Gather, dine and unwind. Kids are welcome at the table too!
Cook , connect and savor meals ina space where modern kitchen meets no fuss chilling.
Dream in king sized comfort, along with the convenience of an ensuite
Unpack without having to reach for the floor with the luggage racks. Connect your laptop to the provided monitor for work with a corner desk and ergonomic chair.

Single-Family Home. Fully Furnished

3 bedrooms·2 baths
Minooka • Illinois
5(16 reviews)

1.935,00 $ USD gesamt für 6 Nächte

3.–9. Nov. 2026

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