Location

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Vacation rentals in Darien, Illinois, United States

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 totaal voor 5 nachten

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

3 bedrooms·2 baths

Chicago • Illinois

4.95(206 reviews)

$ 2.883,29 USD $ 2.450,81 USD totaal voor 3 nachten

6–9 nov 2026

Spacious open 4 bedroom vacation rental loft

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 totaal voor 3 nachten

3–6 nov 2026

Fab space for the whole group!

Fully stocked chef's kitchen

MFL 3 East

4 bedrooms·4 baths

Chicago • Illinois

4.99(93 reviews)

$ 2.841,00 USD $ 2.445,91 USD totaal voor 3 nachten

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 totaal voor 3 nachten

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 totaal voor 3 nachten

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 totaal voor 3 nachten

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 totaal voor 32 nachten

5 nov – 7 dec 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 totaal voor 3 nachten

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 totaal voor 3 nachten

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 totaal voor 3 nachten

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(excl. kosten & belastingen)

Workspace in the living room

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 totaal voor 3 nachten

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 totaal voor 3 nachten

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 totaal voor 3 nachten

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 totaal voor 3 nachten

8–11 nov 2026

Master Bedroom 2nd floor

1500Main EVANSTON

1500Main EVANSTON

2 bedrooms·1½ baths

Evanston • Illinois

5(166 reviews)

$ 1.140,42 USD totaal voor 4 nachten

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 totaal voor 6 nachten

3–9 nov 2026

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 totaal voor 3 nachten

3–6 nov 2026