Location

Dates

Guests

Vacation rentals in Oakbrook Terrace, Illinois, United States

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

Luxury 3BR w/ Balcony • Spa Bath • 10 Min Downtown

3 bedrooms·2 baths

Chicago • Illinois

$989.00 USD total for 3 nights

Sep 7 – 10, 2026

Workspace in the living room

Ashland

3 bedrooms·1 bath

Chicago • Illinois

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)

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 1 – 5, 2026

Free cancellation

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

$1,011.00 USD total for 3 nights

Sep 7 – 10, 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)

$447.00 USD $357.60 USD total for 3 nights

Sep 7 – 10, 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

5(92 reviews)

$169 – $1,105/ 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

Sep 7 – 10, 2026

Living Room with 65" TV

Living Room with 65" TV

Indoor Swim Spa

Charming Garden Retreat

5 bedrooms·3½ baths

Evanston • Illinois

$4,583.78 USD total for 3 nights

Sep 7 – 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(130 reviews)

$399 – $1,343/ 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)

$800 – $835/ night(excl. fees & taxes)

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

$777.00 USD total for 3 nights

Sep 7 – 10, 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)

$998.28 USD $967.10 USD total for 3 nights

Sep 7 – 10, 2026

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

$1,543.01 USD $1,459.86 USD total for 3 nights

Sep 7 – 10, 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)

$2,688.30 USD $2,531.76 USD total for 3 nights

Sep 7 – 10, 2026

Waterfront Cottage/sauna/kayaks/firepit/dock image 1

Waterfront Cottage/sauna/kayaks/firepit/dock image 2

Waterfront Cottage/sauna/kayaks/firepit/dock image 3

Waterfront Cottage/sauna/kayaks/firepit/dock image 4

Waterfront Cottage/sauna/kayaks/firepit/dock image 5

Waterfront Cottage/sauna/kayaks/firepit/dock

1 bedroom·1 bath

Fox River Grove • Illinois

4.88(40 reviews)

$765.00 USD total for 3 nights

Sep 7 – 10, 2026