Title: Holiday Rentals Highwood from £117: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Hotels in Highwood](https://expedia.co.uk/Highwood-Hotels.d115190.Travel-Guide-Hotels)[Highwood Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Highwood.d115190.Car-Hire-Guide)[Highwood Holidays](https://expedia.co.uk/Highwood.d115190.Holidays-City-Breaks)

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## Check prices for these dates

In two weeks

[13 Mar - 15 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=115190&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[24 Apr - 26 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=115190&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=115190&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[19 Jun - 21 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=115190&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Highwood holiday rentals

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119610000/119600300/119600217/768bfea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/120000000/119610000/119600300/119600217/71ef1eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119610000/119600300/119600217/e8214cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119610000/119600300/119600217/1e6ca342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!

[](https://www.expedia.co.uk/Chicago-Hotels-The-Pleasant-Hill-Cottage-Storybook-Luxury-Near-Lake-Michigan-Heart-Of-It-All.h119600217.Hotel-Information)

Highwood

£912

includes taxes & fees

1 Mar - 2 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-The-Pleasant-Hill-Cottage-Storybook-Luxury-Near-Lake-Michigan-Heart-Of-It-All.h119600217.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792834/e8c7e2dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792834/5e4daba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792834/c7d9d0bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792834/bb8a78a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nice 1BR Spot, Unwind & Relax

[](https://www.expedia.co.uk/Chicago-Hotels-Furnished-1-Bedroom-Sunlit-Space.h116792834.Hotel-Information)

Lincoln Square

9.8/10

Exceptional

(26 reviews)

"Very clean & cozy! Conveniently located by great shopping & restaurants!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

SHERI C.

£132

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Furnished-1-Bedroom-Sunlit-Space.h116792834.Hotel-Information)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115200000/115194000/115193975/d00e73e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115200000/115194000/115193975/ae0bfa5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/116000000/115200000/115194000/115193975/92edc8b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/116000000/115200000/115194000/115193975/25dfdc8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy studio in Andersonville Chicago

[](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Studio-In-Andersonville-Chicago.h115193975.Hotel-Information)

Edgewater

9.6/10

Exceptional

(62 reviews)

"Great room and host"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathy T.

£122

includes taxes & fees

8 Mar - 9 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Studio-In-Andersonville-Chicago.h115193975.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/322fd87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/87e615f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, computer monitors](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/b07f764c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/06df6711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2-bedroom apartment just 2 minutes drive to Wrigley Field

[](https://www.expedia.co.uk/Chicago-Hotels-2-Bedroom-Apartment-Just-2-Minutes-Drive-To-Wrigley-Field.h105887915.Hotel-Information)

North Center

9.6/10

Exceptional

(59 reviews)

"Nice property, great location, super helpful host!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carin O.

£221

includes taxes & fees

1 Mar - 2 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-2-Bedroom-Apartment-Just-2-Minutes-Drive-To-Wrigley-Field.h105887915.Hotel-Information)

![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/691b4cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/5f8949d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/0c96778e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792819/5f81cc96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Homey 2BR Apt w/ Parking

[](https://www.expedia.co.uk/Chicago-Hotels-Homey-2BR-Apt-W-Parking.h116792819.Hotel-Information)

Portage Park

9.4/10

Exceptional

(9 reviews)

"The location was ideal for us and had a grocery store, a Starbucks and CVS close by . The neighborhood was safe for walking around . Beds comfortable and whole place was very clean . I would stay here again . "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sharlene T.

£149

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Homey-2BR-Apt-W-Parking.h116792819.Hotel-Information)

![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/bc53e5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/253117f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/f18cb47c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/a5376f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Sunlit 1BR Apartment

[](https://www.expedia.co.uk/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.Hotel-Information)

Irving Park

9.2/10

Wonderful

(12 reviews)

"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brandon M.

£132

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/2c7aa314.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/12a5de83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/f36c801f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/0a306ef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic 2BR Haven Near Irving Park

[](https://www.expedia.co.uk/Chicago-Hotels-Chic-2BR-Haven-Near-Irving-Park.h116793191.Hotel-Information)

Irving Park

9.8/10

Exceptional

(10 reviews)

"Ample accommodations for two adults. Clean and in great condition!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathy D.

£149

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Chic-2BR-Haven-Near-Irving-Park.h116793191.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/255dfec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/bea75315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/7523a52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792861/fce51bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Apartment in Chicago

[](https://www.expedia.co.uk/Chicago-Hotels-1BR-Apartment-In-Chicago.h116792861.Hotel-Information)

North Center

9.0/10

Wonderful

(17 reviews)

"Very clean and the host was easy to work with. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Scott S.

£132

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-1BR-Apartment-In-Chicago.h116792861.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792932/9b3edef7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792932/8ac7acd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792932/cffd5d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792932/7d8930ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ideal 2BR Getaway Close to Attractions

[](https://www.expedia.co.uk/Chicago-Hotels-Spacious-2BR-Near-Dining-Shops.h116792932.Hotel-Information)

Rogers Park

8.4/10

Very good

(7 reviews)

"Loved this sweet space tucked into a special neighborhood in the city. Space was clean & comfortable, wonderful shower & a nice respite from city life. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ever

£148

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Spacious-2BR-Near-Dining-Shops.h116792932.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/18141b19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/f03a031d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/fcd2f6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/c9324d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Homey 1BR Space Apartment

[](https://www.expedia.co.uk/Chicago-Hotels-Light-Filled-1-Bedroom-Apt.h116792945.Hotel-Information)

Lincoln Square

9.8/10

Exceptional

(14 reviews)

"Clean and great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Margo M.

£132

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Light-Filled-1-Bedroom-Apt.h116792945.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/591973f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/d81d6c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/ca60baaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/079e5c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Master qtr close to nature & easy urban facilities

[](https://www.expedia.co.uk/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information)

Riverwoods

9.8/10

Exceptional

(77 reviews)

"Nice , private and peaceful definitely will be back "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

BRANDEN J.

£147

includes taxes & fees

5 Mar - 6 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information)

![Iron/ironing board, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/613980fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/9655a9e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/e0a42d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/bb63d017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trendy & Comfy Studio Unit

[](https://www.expedia.co.uk/Chicago-Hotels-Trendy-Comfy-Studio-Unit.h116792702.Hotel-Information)

Portage Park

9.0/10

Wonderful

(6 reviews)

"Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Courtney V.

£125

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Trendy-Comfy-Studio-Unit.h116792702.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/1897ede8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/43d43840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/fca43c92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/68407ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish and Roomy 2BR in Chicago

[](https://www.expedia.co.uk/Chicago-Hotels-Stylish-And-Roomy-2BR-In-Chicago.h116792691.Hotel-Information)

Edgewater

9.0/10

Wonderful

(14 reviews)

"Clean room, easy, check-in, great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

brent w.

£154

includes taxes & fees

4 Mar - 5 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Stylish-And-Roomy-2BR-In-Chicago.h116792691.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/08f44095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/2a679a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/0265aebc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792678/f623e866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic & Fully Furnished 2BR Apartment

[](https://www.expedia.co.uk/Chicago-Hotels-Chic-Fully-Furnished-2BR-Apt.h116792678.Hotel-Information)

Avondale

10/10

Exceptional

(2 reviews)

"Our stay was great! The apartment is very clean and comfortable. Nicely furnished. On a residential street in a lovely neighborhood. Wifi and A/C units worked well (we were there in August). We found street parking pretty easily. And Kristine was a really responsive host. Would absolutely stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie D.

£231

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Chic-Fully-Furnished-2BR-Apt.h116792678.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/614f0803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/51e2b785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/136df166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/2629eaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful 1BR Escape in Evanston

[](https://www.expedia.co.uk/Chicago-Hotels-Peaceful-1BR-Escape-In-Evanston.h116792370.Hotel-Information)

South Evanston

8.6/10

Excellent

(7 reviews)

"Nice apartment in Evanston, perfect for my 2 night stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul W.

£155

includes taxes & fees

18 Mar - 19 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Peaceful-1BR-Escape-In-Evanston.h116792370.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792817/60def6bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792817/ba32d1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792817/d4f46544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792817/61b7f262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR/1BA City Comfort

[](https://www.expedia.co.uk/Chicago-Hotels-1BR1BA-City-Comfort.h116792817.Hotel-Information)

Lincoln Square

7.2/10

Good

(7 reviews)

"Great location, very clean. Easy check in and check out. Great communication."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Thomas L.

£132

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-1BR1BA-City-Comfort.h116792817.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792822/1d9ed1e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792822/daec8fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792822/b2ab5672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792822/332b86b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lovely 2BR with Parking Near United Center & Wrigley

[](https://www.expedia.co.uk/Chicago-Hotels-2BR-Airy-Apt-W-Free-Parking.h116792822.Hotel-Information)

Portage Park

9.2/10

Wonderful

(5 reviews)

"Cleanliness. Roomy. Comfortable mattresses. Fluffy, white bath towels. Ample towel racks in bathrooms. Attentive hostess. Off street parking greatly appreciated but garage door opener should be operative."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

MARGARET L.

£152

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-2BR-Airy-Apt-W-Free-Parking.h116792822.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121900000/121897900/121897813/7fa5d76f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121900000/121897900/121897813/1410339c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121900000/121897900/121897813/42288562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/122000000/121900000/121897900/121897813/a118b57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Evanston Garden Guest House

[](https://www.expedia.co.uk/Chicago-Hotels-Evanston-Garden-Guest-House.h121897813.Hotel-Information)

North Evanston

£149

includes taxes & fees

1 Mar - 2 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Evanston-Garden-Guest-House.h121897813.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/b78ebb24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/37dc9163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/9fcd9cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/7a4fe0f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Layout – Spacious 2BR Apt

[](https://www.expedia.co.uk/Chicago-Hotels-Great-Layout-Spacious-2BR-Apt.h116793118.Hotel-Information)

Rogers Park

10/10

Exceptional

(5 reviews)

"Clean, comfortable, and would definitely stay again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

KM W.

£149

includes taxes & fees

24 Mar - 25 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Great-Layout-Spacious-2BR-Apt.h116793118.Hotel-Information)

![Iron/ironing board, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124249/2dd26c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124249/6935f5b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124249/3e989e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124249/9b6b225b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunlit Studio with City Charm

[](https://www.expedia.co.uk/Chicago-Hotels-Sunlit-Studio-With-City-Charm.h117124249.Hotel-Information)

Rogers Park

8.0/10

Very good

(9 reviews)

"very nice room and clean. great one night stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christian B.

£125

includes taxes & fees

2 Mar - 3 Mar

[](https://www.expedia.co.uk/Chicago-Hotels-Sunlit-Studio-With-City-Charm.h117124249.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-03-12&endDate=2026-03-13&regionId=115190&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.

[Book now](https://expedia.co.uk/cheap-deals?rfrr=VR_SPRING_PROMO_115190)

## Find holiday rentals that suit your style

Aparthotels

[](https://www.expedia.co.uk/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=APARTMENT)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=VACATION_HOME)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=VILLA)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=COTTAGE)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=CONDO)

Cabins

[](https://www.expedia.co.uk/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=CABIN)

Residences

[](https://www.expedia.co.uk/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-05-26&d1=2026-05-26&endDate=2026-05-29&d2=2026-05-29&lodging=RESIDENCE)

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## Top Highwood Hotel Reviews

![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a_y.jpg)

### Hyatt Regency O'Hare Chicago

10/10 Excellent

"Room was very clean. Front Desk staff was extremely helpful with my check in and check out."

[](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information)

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg)

### Hilton Chicago O'Hare Airport

10/10 Excellent

"Great staff"

[](https://expedia.co.uk/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information)

![Hyatt Centric Chicago O'Hare](https://images.trvl-media.com/lodging/1000000/330000/328200/328182/dfbbb688_y.jpg)

### Hyatt Centric Chicago O'Hare

10/10 Excellent

"Great bartenders, 24/7 shuttle to the airport. "

[](https://expedia.co.uk/Chicago-Hotels-Hyatt-Rosemont-Near-OHare.h328182.Hotel-Information)

![Comfort Suites Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f3b451c4_y.jpg)

### Comfort Suites Chicago O'Hare Airport

10/10 Excellent

"Friendly staff and the room was nice and clean. The rooms are nicer than would appear from the outside. "

[](https://expedia.co.uk/Chicago-Hotels-Comfort-Suites-Schiller-Park-Chicago-OHare-Airport.h664918.Hotel-Information)

![Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG](https://images.trvl-media.com/lodging/1000000/30000/20400/20348/9004f7ac_y.jpg)

### Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

10/10 Excellent

"Great location."

[](https://expedia.co.uk/Chicago-Hotels-Crowne-Plaza-Hotel-Chicago-OHare.h20348.Hotel-Information)

![Hyatt Place Chicago/O'Hare Airport](https://images.trvl-media.com/lodging/1000000/30000/23000/22991/9622d90a_y.jpg)

### Hyatt Place Chicago/O'Hare Airport

10/10 Excellent

"Nice"

[](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-ChicagoOHare-Airport.h22991.Hotel-Information)

![Marriott Chicago O'Hare](https://images.trvl-media.com/lodging/1000000/10000/300/281/13bbda80_y.jpg)

### Marriott Chicago O'Hare

10/10 Excellent

"Everything is perfect"

[](https://expedia.co.uk/Chicago-Hotels-Marriott-Chicago-OHare.h281.Hotel-Information)

![Holiday Inn Chicago North-Evanston by IHG](https://images.trvl-media.com/lodging/1000000/10000/5400/5356/a2066909_y.jpg)

### Holiday Inn Chicago North-Evanston by IHG

10/10 Excellent

"Friendly staff, clean rooms, quiet. "

[](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-North-Evanston.h5356.Hotel-Information)

![Loews Chicago O'Hare Hotel](https://images.trvl-media.com/lodging/2000000/1820000/1818400/1818376/53df98b5_y.jpg)

### Loews Chicago O'Hare Hotel

10/10 Excellent

"Great as always"

[](https://expedia.co.uk/Chicago-Hotels-Loews-Chicago-OHare-Hotel.h1818376.Hotel-Information)

## Find out more about Highwood

**Everything you need to know about** **Highwood** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highwood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Highwood holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Highwood. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Highwood holiday rentals we have selected for you start as low as £117 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Highwood rentals**

At Expedia, we put the best Highwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Highwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

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- [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals)
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- [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals)
- [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals)
- [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals)
- [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations)
- [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals)
- [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals)
- [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals)
- [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals)
- [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations)
- [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations)
- [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations)
- [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations)
- [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations)

## Frequently asked questions

### Are there holiday rentals in Highwood?

### What are some of the best holiday rentals that Highwood has to offer?

### What can I see and do in Highwood?

### What are holiday rentals like in Highwood?

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