Title: Highwood Vacation Rentals from CA $210: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=115190&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=115190&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=115190&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=115190&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Highwood vacation rentals

![Exterior detail](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/7966b3f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/1fab42f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/5445a025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/3e0125af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quaint Bungalow, near Great Lakes Naval Base

[](https://www.expedia.ca/Chicago-Hotels-Quaint-Bungalow.h32067984.Hotel-Information)

Mundelein

9.8/10

Exceptional

(69 reviews)

"We had a great stay! The area was peaceful and felt safe. "

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

Yoselin V.

CA $187

CA $463 total

includes taxes & fees

Apr 11 - Apr 12

[](https://www.expedia.ca/Chicago-Hotels-Quaint-Bungalow.h32067984.Hotel-Information)

![Iron/ironing board, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/bfe9ce5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/a91f2fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/w1017h1536x0y0-87b71443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793093/bd243cfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Uptown Studio Gem Sum

[](https://www.expedia.ca/Chicago-Hotels-Uptown-Studio-Gem-Sum.h116793093.Hotel-Information)

Uptown

7.4/10

Good

(6 reviews)

"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."

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

Darryl C.

CA $90

CA $224 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Uptown-Studio-Gem-Sum.h116793093.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/81360f2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/d6084ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/9a4a0623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/2405682e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy & Furnished 2BR Unit

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Furnished-2BR-Unit.h116792828.Hotel-Information)

Lincoln Square

9.2/10

Wonderful

(17 reviews)

"Very cozy, amenities in great condition."

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

Kaitlin T.

CA $131

CA $316 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Furnished-2BR-Unit.h116792828.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)

![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792834/0c570d8c.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)

![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)

### Nice 1BR Spot, Unwind & Relax

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

Lincoln Square

9.8/10

Exceptional

(31 reviews)

"This was a great apartment in the heart of Lincoln Square. The kitchen is fully equipped, the bed was comfortable and there are a lot of amenities and public transportation close by. I will definitely be staying hear again! "

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

Lisa

CA $122

CA $278 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Chicago-Hotels-Furnished-1-Bedroom-Sunlit-Space.h116792834.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)

![Exterior](https://images.trvl-media.com/lodging/106000000/105890000/105888000/105887915/06df6711.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)

![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)

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

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

North Center

9.6/10

Exceptional

(65 reviews)

"Great host, quick communication, and wonderful place to stay in Chicago. Well thought out and made our stay enjoyable. Highly recommend, we will book it again next time we are in Chicago. "

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

Justin P.

CA $187

CA $459 total

includes taxes & fees

Apr 5 - Apr 6

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

![Smart TV](https://images.trvl-media.com/lodging/115000000/114670000/114666300/114666210/6385a4ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114670000/114666300/114666210/d60dd8ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114670000/114666300/114666210/0713424a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/115000000/114670000/114666300/114666210/22c26f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

[](https://www.expedia.ca/Barrington-Hotels-FRIENDS-Inspired-Studio-In-Beautiful-Barrington-With-WiFi.h114666210.Hotel-Information)

Barrington

9.8/10

Exceptional

(8 reviews)

"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"

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

Adam B.

CA $133

CA $239 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Barrington-Hotels-FRIENDS-Inspired-Studio-In-Beautiful-Barrington-With-WiFi.h114666210.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)

![1 bedroom, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/122000000/121900000/121897900/121897813/91e8971e.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)

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

### Evanston Garden Guest House

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

North Evanston

CA $139

CA $281 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-Evanston-Garden-Guest-House.h121897813.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.ca/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.

CA $131

CA $316 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Stylish-And-Roomy-2BR-In-Chicago.h116792691.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 crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/37dc9163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/eec54680.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)

### Great Layout – Spacious 2BR Apt

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

Rogers Park

8.8/10

Excellent

(8 reviews)

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

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

KM W.

CA $138

CA $324 total

includes taxes & fees

Apr 5 - Apr 6

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

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

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792817/fa6b84cf.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)

### 1BR/1BA City Comfort

[](https://www.expedia.ca/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.

CA $96

CA $244 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-1BR1BA-City-Comfort.h116792817.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)

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

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793191/aadb2c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chic 2BR Haven Near Irving Park

[](https://www.expedia.ca/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.

CA $143

CA $330 total

includes taxes & fees

Apr 22 - Apr 23

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

![Interior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/ca60baaa.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)

![Exterior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/76fecaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Riverwoods

9.8/10

Exceptional

(78 reviews)

"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."

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

Kyle M.

CA $137

CA $273 total

includes taxes & fees

Apr 9 - Apr 10

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

![Interior](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/39aa9dc6.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/109000000/108440000/108439800/108439787/16704f14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/86ad33f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108440000/108439800/108439787/66b0c2d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pine Beam Sloth Apartment next to Blue Line

[](https://www.expedia.ca/Chicago-Hotels-Boho-1-Bedroom-Pine-Beam-Condo-Next-To-Blue-Line.h108439787.Hotel-Information)

Irving Park

10/10

Exceptional

(6 reviews)

"Beautifully decorated, spotless unit. Conveniently located."

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

Holly G.

CA $157

CA $348 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Boho-1-Bedroom-Pine-Beam-Condo-Next-To-Blue-Line.h108439787.Hotel-Information)

![1 bedroom, iron/ironing board, travel crib, 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/a5376f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/f308661a.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)

### Charming Sunlit 1BR Apartment

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

Irving Park

9.2/10

Wonderful

(13 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.

CA $125

CA $280 total

includes taxes & fees

Apr 8 - Apr 9

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

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120320000/120317000/120316961/a9440edb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120320000/120317000/120316961/19e8f827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/121000000/120320000/120317000/120316961/0aebd803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/121000000/120320000/120317000/120316961/67445c38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Well-Equipped 2BR Unit with Parking

[](https://www.expedia.ca/Chicago-Hotels-Well-Equipped-2BR-Unit-W-Parking.h120316961.Hotel-Information)

North Evanston

10/10

Exceptional

(3 reviews)

"Great place. Super clean and easy off street parking. Thanks !"

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

Ann N.

CA $138

CA $324 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Well-Equipped-2BR-Unit-W-Parking.h120316961.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/b289aa5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/0e77b64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/bb6345e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/f7cf3b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Navy Family home -Near Lake 4BR Hot Tub

[](https://www.expedia.ca/Chicago-Hotels-Newly-Remodeled-Near-Lake-4BR-W-Hot-Tub-Games.h122068878.Hotel-Information)

Gages Lake

10/10

Exceptional

(7 reviews)

"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "

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

Danielle S.

CA $214

CA $652 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Newly-Remodeled-Near-Lake-4BR-W-Hot-Tub-Games.h122068878.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101810000/101800900/101800825/0d84e6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101810000/101800900/101800825/c95d76d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/102000000/101810000/101800900/101800825/07e06908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/102000000/101810000/101800900/101800825/88d17225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

[](https://www.expedia.ca/Chicago-Hotels-Regal-Stylish-Loft-Rooftop13-Mins-DT-4-Mins-Lake.h101800825.Hotel-Information)

Uptown

9.0/10

Wonderful

(20 reviews)

"Convenient check in and good amenities made this a pleasant place to stay near our relative in Chicago. "

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

Laura O.

CA $110

CA $389 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Chicago-Hotels-Regal-Stylish-Loft-Rooftop13-Mins-DT-4-Mins-Lake.h101800825.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)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/116000000/115200000/115194000/115193975/7bd4d71f.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)

### Cozy studio in Andersonville Chicago

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

Edgewater

9.4/10

Exceptional

(66 reviews)

"Great stay i loved it"

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

Cedes W.

CA $100

CA $210 total

includes taxes & fees

Apr 27 - Apr 28

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

![Lobby](https://images.trvl-media.com/lodging/96000000/95560000/95558000/95557991/4083d560.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/96000000/95560000/95558000/95557991/91bc164f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/96000000/95560000/95558000/95557991/f70fc045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95560000/95558000/95557991/b6f05537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bright Garden Studio

[](https://www.expedia.ca/Chicago-Hotels-Bright-Garden-Studio.h95557991.Hotel-Information)

South Evanston

8.4/10

Very good

(32 reviews)

"Great spot. Very convenient and everything we needed for a long weekend visit to Evanston."

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

William B.

CA $105

CA $344 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Chicago-Hotels-Bright-Garden-Studio.h95557991.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)

![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)

![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/b50ec1c3.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)

### Homey 1BR Space Apartment

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

Lincoln Square

9.6/10

Exceptional

(16 reviews)

"Love the location right in Lincoln Square. "

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

Ticia B.

CA $123

CA $279 total

includes taxes & fees

Apr 27 - Apr 28

[](https://www.expedia.ca/Chicago-Hotels-Light-Filled-1-Bedroom-Apt.h116792945.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.ca/Hotel-Search?startDate=2026-04-17&endDate=2026-04-18&regionId=115190&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VACATION_HOME)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APARTMENT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CONDO)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Highwood%2C+Illinois%2C+United+States+of+America&regionId=115190&latLong=42.206909%2C-87.813685&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CABIN)

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## Top Highwood Hotel Reviews

![DoubleTree by Hilton Chicago - North Shore Conference Center](https://images.trvl-media.com/lodging/1000000/20000/15600/15560/8a058213_y.jpg)

### DoubleTree by Hilton Chicago - North Shore Conference Center

8/10 Good

"For the money totally worth it "

[](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-North-Shore-Conference-Center.h15560.Hotel-Information)

![Marriott Chicago O'Hare](https://images.trvl-media.com/lodging/1000000/10000/300/281/c9c2af9c_y.jpg)

### Marriott Chicago O'Hare

2/10 Terrible

"Needs renovation "

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

![Comfort Suites Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/27ecd933_y.jpg)

### Comfort Suites Chicago O'Hare Airport

10/10 Excellent

"Great value, staff was helpful and kind. The room was clean and decently comfortable. "

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

![Great Wolf Lodge Illinois](https://images.trvl-media.com/lodging/2000000/1880000/1871300/1871214/66f614b9_y.jpg)

### Great Wolf Lodge Illinois

8/10 Good

"Great for kids they’ll love it "

[](https://expedia.ca/Chicago-Hotels-Great-Wolf-Lodge-Illinois.h1871214.Hotel-Information)

![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/2c5e0afa_y.jpg)

### Hyatt Regency O'Hare Chicago

8/10 Good

"Our room was clean and the bed was very comfortable. I will note that we were supposed to be in a 425 square foot room with a decent sized bathroom but the room we were given was no larger that 200 square feet. "

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

![Hilton Garden Inn Chicago North Shore/Evanston](https://images.trvl-media.com/lodging/1000000/800000/791900/791825/7164f74f_y.jpg)

### Hilton Garden Inn Chicago North Shore/Evanston

8/10 Good

"Will stay at this property again "

[](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-North-ShoreEvanston.h791825.Hotel-Information)

![Holiday Inn Chicago O'Hare – Rosemont by IHG](https://images.trvl-media.com/lodging/88000000/87710000/87702800/87702727/2d32e2b3_y.jpg)

### Holiday Inn Chicago O'Hare – Rosemont by IHG

10/10 Excellent

"Very nice view clean cloom"

[](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Ohare-Airport.h87702727.Hotel-Information)

![SpringHill Suites Chicago O'Hare by Marriott](https://images.trvl-media.com/lodging/1000000/570000/561500/561495/571ff6d9_y.jpg)

### SpringHill Suites Chicago O'Hare by Marriott

10/10 Excellent

"Clean"

[](https://expedia.ca/Chicago-Hotels-SpringHill-Suites-Chicago-OHare-By-Marriott.h561495.Hotel-Information)

![Sonesta Simply Suites Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/330000/328600/328524/536eba50_y.jpg)

### Sonesta Simply Suites Chicago O'Hare Airport

10/10 Excellent

"Very friendly staff and clean hotel, quick shuttle to the airport was a bonus."

[](https://expedia.ca/Chicago-Hotels-Sonesta-Simply-Suites-Chicago-OHare.h328524.Hotel-Information)

## Find out more about Highwood

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Highwood. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Apartments in Highwood ](https://expedia.ca/Highwood-Apartments.d115190-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Highwood ](https://expedia.ca/Highwood-Private-Vacation-Homes.d115190-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Highwood ](https://expedia.ca/Highwood-Condos.d115190-aaCondos.Travel-Guide-Accommodation)
- [Motels in Highwood ](https://expedia.ca/Highwood-Motels.d115190-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Highwood ](https://expedia.ca/Highwood-Cottages.d115190-aaCottages.Travel-Guide-Accommodation)
- [Villas in Highwood ](https://expedia.ca/Highwood-Villas.d115190-aaVillas.Travel-Guide-Accommodation)
- [Aparthotels in Highwood ](https://expedia.ca/Highwood-Apart-Hotels.d115190-aaApartHotels.Travel-Guide-Accommodation)
- [Resorts in Highwood ](https://expedia.ca/Highwood-Resort-Hotels.d115190-aaResortHotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Highwood ](https://expedia.ca/Highwood-Cabins.d115190-aaCabins.Travel-Guide-Accommodation)
- [Residences in Highwood ](https://expedia.ca/Highwood-Residences.d115190-aaResidences.Travel-Guide-Accommodation)
- [Inns in Highwood ](https://expedia.ca/Highwood-Inns.d115190-aaInns.Travel-Guide-Accommodation)
- [B&B in Highwood ](https://expedia.ca/Highwood-Bed-And-Breakfast.d115190-aaBedAndBreakfast.Travel-Guide-Accommodation)

## Frequently asked questions

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