Title: Highland Park Vacation Rentals from CA $137: Short-Term Rentals for 2026 | Expedia.ca

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![The Elizabeth Hubert Malott Japanese Garden

One of many, many scenic vistas to be found while strolling through the Chicago Botanic Gardens. 

Looking for an escape from the usual tourists activities while visiting Chicago? Located about 30 miles north of the City, the Gardens are absolutely worth the effort to get there.

The Chicago Botanic Garden opened a little more than 40 years ago. Last year, more than one million people visited the Garden's 26 gardens and four natural areas, uniquely situated on 385 acres on and around nine islands, with six miles of lake shoreline. The Garden also has a renowned Bonsai Collection.

#colorful](https://images.trvl-media.com/place/6064029/3606bcd7-2687-438e-84c0-cd4a425b27d2.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by throwingsofas

# Highland Park Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=8345&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=8345&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=8345&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=8345&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Highland Park vacation rentals

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107450000/107448900/107448844/941666cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/108000000/107450000/107448900/107448844/97d08368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107450000/107448900/107448844/ee0c40af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107450000/107448900/107448844/fecbb59d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stunning & Stylish Downtown Studio - Highland Park

[](https://www.expedia.ca/Chicago-Hotels-Stunning-Stylish-Downtown-Studio-Highland-Park.h107448844.Hotel-Information)

Highland Park

8.8/10

Excellent

(6)

"Everything was as described. Parking is secure. Location is quiet, inside a nice neighborhood "

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

Alissa S.

CA $95

CA $225 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Chicago-Hotels-Stunning-Stylish-Downtown-Studio-Highland-Park.h107448844.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113170000/113163400/113163361/f7b14a1c_edited_1872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113170000/113163400/113163361/w5900h3553x0y0-377c05fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball, table tennis](https://images.trvl-media.com/lodging/114000000/113170000/113163400/113163361/44a84cdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113170000/113163400/113163361/w5900h3544x0y0-4dc76139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

[](https://www.expedia.ca/Chicago-Hotels-Sunset-Manor-Opulent-Mansion.h113163361.Hotel-Information)

Highland Park

10/10

Exceptional

(1)

CA $886

CA $1,560 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Chicago-Hotels-Sunset-Manor-Opulent-Mansion.h113163361.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115110000/115105700/115105639/51c65ba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115110000/115105700/115105639/0174e5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/116000000/115110000/115105700/115105639/cd4b6329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, table tennis](https://images.trvl-media.com/lodging/116000000/115110000/115105700/115105639/f4cf3535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Highland Park Family Ranch - Walk to Lake & Metra to Chicago!

[](https://www.expedia.ca/Chicago-Hotels-Highland-Park-Family-Ranch-Walk-To-Lake-Metra-To-Chicago.h115105639.Hotel-Information)

Highland Park

[](https://www.expedia.ca/Chicago-Hotels-Highland-Park-Family-Ranch-Walk-To-Lake-Metra-To-Chicago.h115105639.Hotel-Information)

![Business Apartment, City View | Private kitchen](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/0374aa13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/9649f522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![75-inch Smart TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/7fc927d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, City View](https://images.trvl-media.com/lodging/119000000/118640000/118632100/118632066/6a748c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ENVITAE Hotel 4 Bedroom Luxury Apartments

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

Near North Side

10/10

Exceptional

(8)

"We loved at our stay at this property. It was one of the best stays we have had on vacation."

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

Javeria

CA $1,201

CA $1,699 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Chicago-Hotels-4BR-Corporate-Suite-Central-And-Modern.h118632066.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123280000/123273200/123273189/df426e5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123280000/123273200/123273189/aca7a905.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/124000000/123280000/123273200/123273189/f4362d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/124000000/123280000/123273200/123273189/f9345773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pristine Apartment with Free Street Parking

[](https://www.expedia.ca/Chicago-Hotels-Pristine-Apartment-With-Free-Street-Parking.h123273189.Hotel-Information)

Humboldt Park

CA $301

CA $344 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Chicago-Hotels-Pristine-Apartment-With-Free-Street-Parking.h123273189.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/9bdb478c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Single Bed, City View | Living area](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Level Chicago – Old Town

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

Downtown Chicago

9.0/10

Wonderful

(398)

"Clean room cool staff enjoyed my stay will come stay again. "

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

Donald

CA $189

CA $253 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/fb27e879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/34bf7592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/65e9350a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793107/4c1d4299.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sleek 1BR Apt w/ Laundry

[](https://www.expedia.ca/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(1)

"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."

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

Anonymous traveller

CA $87

CA $232 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Chicago-Hotels-Sleek-1BR-Apt-W-Laundry.h116793107.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/1309495b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/c64cc369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/eab5965a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120510000/120508900/120508888/0412ba3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gold Coast Living: Modern Studio Unit

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

Downtown Chicago

10/10

Exceptional

(4)

"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"

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

Seynabou

CA $95

CA $228 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-Cozy-Gold-Coast-Studio-Stay.h120508888.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/50bbce16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/fd6dad17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/3815ff36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793110/31d1cbc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The One: A 1BR Stay That Feels Like Home

[](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information)

Downtown Chicago

8.4/10

Very good

(5)

"Very nice condo in a quiet neighborhood"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Patrick

CA $87

CA $232 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-All-Set-Up-Furnished-1BR-Unit.h116793110.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/e4126779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793104/61009377.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/117000000/116800000/116793200/116793104/53fb8853.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/117000000/116800000/116793200/116793104/1ab3553c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Twice as Nice: Chic 2BR Stay with Style & Space

[](https://www.expedia.ca/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.Hotel-Information)

Downtown Chicago

9.6/10

Exceptional

(14)

"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "

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

Shederia P.

CA $109

CA $284 total

includes taxes & fees

Dec 16 - Dec 17

[](https://www.expedia.ca/Chicago-Hotels-Twice-As-Nice-Chic-2BR-Stay-With-Style-Space.h116793104.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/1310976f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/2bfb9517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/716fc9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792754/a190b9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Complete 1BR Home Sum

[](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.Hotel-Information)

Downtown Chicago

CA $87

CA $232 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Equipped-Apt.h116792754.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/3ab1d1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/91c8477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/f4be1275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/102000000/101620000/101619100/101619097/bfb6cea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

[](https://www.expedia.ca/Chicago-Hotels-Artistic-Loft-Rooftop-Uptown-Montrose-Beach-GymWFH.h101619097.Hotel-Information)

Uptown

10/10

Exceptional

(48)

"Clean and quiet, perfect for nights to rest after exploring the city"

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

Joe T.

CA $66

CA $320 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Chicago-Hotels-Artistic-Loft-Rooftop-Uptown-Montrose-Beach-GymWFH.h101619097.Hotel-Information)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793196/30516fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793196/3ad3fc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793196/c1314ab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793196/0a1c99b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunny Studio in Heart of Ravenswood

[](https://www.expedia.ca/Chicago-Hotels-Sunny-Studio-In-Heart-Of-Ravenswood.h116793196.Hotel-Information)

Uptown

9.4/10

Exceptional

(6)

"It was a great stay if you want to experience a diverse, fun, authentic Chicago neigborhood. We really enjoyed it. "

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

Amer

CA $74

CA $204 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Chicago-Hotels-Sunny-Studio-In-Heart-Of-Ravenswood.h116793196.Hotel-Information)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792852/0d2a45ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792852/ad06b7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792852/35964ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792852/167366b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR Apt Beautifully Furnished

[](https://www.expedia.ca/Chicago-Hotels-2BR-Apt-Beautifully-Furnished.h116792852.Hotel-Information)

Lakeview

10/10

Exceptional

(9)

"We loved the place. The feeling of home away from home."

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

Sataish

CA $87

CA $253 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Chicago-Hotels-2BR-Apt-Beautifully-Furnished.h116792852.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792844/2552f52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792844/6c87ca84.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/117000000/116800000/116792900/116792844/c3adb7e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792844/f4b23065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautifully Set Up 2BR Space

[](https://www.expedia.ca/Chicago-Hotels-Comfy-2BR-In-Heart-Of-Lakeview.h116792844.Hotel-Information)

Lakeview

9.8/10

Exceptional

(21)

"The apartment worked out perfectly for our stay. Very good location for our activities and comfortable for just hanging out."

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

Linda S.

CA $87

CA $253 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Chicago-Hotels-Comfy-2BR-In-Heart-Of-Lakeview.h116792844.Hotel-Information)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792813/2de3a410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792813/8b47b4c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792813/71d6f8a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792813/927f71e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Boystown Chic 2BR Escape

[](https://www.expedia.ca/Chicago-Hotels-Boystown-Chic-2BR-Escape.h116792813.Hotel-Information)

Lakeview

10/10

Exceptional

(12)

"Very clean and amazing comfortable stay!!"

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

Justin M.

CA $83

CA $248 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Chicago-Hotels-Boystown-Chic-2BR-Escape.h116792813.Hotel-Information)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792920/85ac9610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792920/196f7de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792920/ffaa889d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792920/692acf21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 2BR with Reliable Wi-Fi

[](https://www.expedia.ca/Chicago-Hotels-Modern-2BR-With-Reliable-Wi-Fi.h116792920.Hotel-Information)

Lakeview

9.0/10

Wonderful

(6)

"Great location for seeing a Cubs game. Easy to follow "

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

David A.

CA $87

CA $253 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Chicago-Hotels-Modern-2BR-With-Reliable-Wi-Fi.h116792920.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792651/302b39e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792651/a407a048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792651/4a70cf9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792651/b86a9cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Homey Apt in Irving Park

[](https://www.expedia.ca/Chicago-Hotels-1BR-Homey-Apt-In-Irving-Park.h116792651.Hotel-Information)

Irving Park

8.8/10

Excellent

(3)

"It was wonderful and wil stay agian"

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

Crystal P.

CA $88

CA $234 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Chicago-Hotels-1BR-Homey-Apt-In-Irving-Park.h116792651.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/6818f7ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/ccec1f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/c31d7881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, offices](https://images.trvl-media.com/lodging/119000000/118410000/118409500/118409489/92a0def3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Premium Urban 4BR - Perfect Mix of Comfort & Location

[](https://www.expedia.ca/Chicago-Hotels-High-Rise-4BR-W-Views.h118409489.Hotel-Information)

Near North Side

10/10

Exceptional

(1)

"Nice place, clean property, great views "

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

Zach L.

CA $866

CA $1,548 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Chicago-Hotels-High-Rise-4BR-W-Views.h118409489.Hotel-Information)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/e7bcab40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/83c9368f.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)

![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792691/2c34ce2e.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

(10)

"It was a awesome location and clean and spacious for what we needed."

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

porschea t.

CA $80

CA $245 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Chicago-Hotels-Stylish-And-Roomy-2BR-In-Chicago.h116792691.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.

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## Top Highland Park Hotel Reviews

![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

"Clean, good breakfast, nice bartender"

[](https://expedia.ca/Chicago-Hotels-Hyatt-Place-ChicagoOHare-Airport.h22991.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

"Yes"

[](https://expedia.ca/Chicago-Hotels-Loews-Chicago-OHare-Hotel.h1818376.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

"right next to the airport. if you stay here here, exit from the front door, take a left and walk to the end of the hotel, and cross the street with a crossing guard, and you are at the airport sliding doors. quick to catch a flight staying here. also, the hotel has a great Jazz bar with live performances. the Blue Line to go to Chicago has a stop in a lower level."

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

![Sonesta Simply Suites Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/330000/328600/328524/c5f12fbd_y.jpg)

### Sonesta Simply Suites Chicago O'Hare Airport

10/10 Excellent

"The hotel had all the amenities I needed for a overnight business trip"

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

![Super 8 by Wyndham Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/450000/440500/440405/938c3a03_y.jpg)

### Super 8 by Wyndham Chicago O'Hare Airport

10/10 Excellent

"Spotless room, very courteous staff, and super convenient location. "

[](https://expedia.ca/Chicago-Hotels-Super-8-By-Wyndham-Chicago-OHare-Airport.h440405.Hotel-Information)

![Hampton Inn Chicago-O'Hare International Airport](https://images.trvl-media.com/lodging/1000000/20000/14600/14509/75d50163_y.jpg)

### Hampton Inn Chicago-O'Hare International Airport

10/10 Excellent

"Great clean room"

[](https://expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-OHare.h14509.Hotel-Information)

![Holiday Inn Chicago O'Hare – Rosemont by IHG](https://images.trvl-media.com/lodging/88000000/87710000/87702800/87702727/7dd32bc5_y.jpg)

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

10/10 Excellent

"Yes"

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

"I needed a hotel room when my flight was canceled late in the day and Comfort Suites was available. It turned out to be lucky for me. The staff was very friendly and helpful. The room was great for the price. I have no complaints at all. "

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

![Motel 6 Elk Grove Village, IL - O'Hare](https://images.trvl-media.com/lodging/1000000/20000/15200/15126/d0d803a3_y.jpg)

### Motel 6 Elk Grove Village, IL - O'Hare

10/10 Excellent

"Parking was easy"

[](https://expedia.ca/Chicago-Hotels-Motel-6-Elk-Grove-Village.h15126.Hotel-Information)

## Find out more about Highland Park

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 Highland Park. 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 Highland Park ](https://expedia.ca/Highland-Park-Apartments.d8345-aaApartments.Travel-Guide-Accommodation)
- [Vacation Homes in Highland Park ](https://expedia.ca/Highland-Park-Private-Vacation-Homes.d8345-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Highland Park ](https://expedia.ca/Highland-Park-Condos.d8345-aaCondos.Travel-Guide-Accommodation)
- [Aparthotels in Highland Park ](https://expedia.ca/Highland-Park-Apart-Hotels.d8345-aaApartHotels.Travel-Guide-Accommodation)
- [Motels in Highland Park ](https://expedia.ca/Highland-Park-Motels.d8345-aaMotels.Travel-Guide-Accommodation)
- [Cottages in Highland Park ](https://expedia.ca/Highland-Park-Cottages.d8345-aaCottages.Travel-Guide-Accommodation)
- [B&B in Highland Park ](https://expedia.ca/Highland-Park-Bed-And-Breakfast.d8345-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Highland Park ](https://expedia.ca/Highland-Park-Guest-Houses.d8345-aaGuestHouses.Travel-Guide-Accommodation)
- [Villas in Highland Park ](https://expedia.ca/Highland-Park-Villas.d8345-aaVillas.Travel-Guide-Accommodation)
- [Hostels in Highland Park ](https://expedia.ca/Highland-Park-Hostels.d8345-aaHostels.Travel-Guide-Accommodation)
- [Resorts in Highland Park ](https://expedia.ca/Highland-Park-Resort-Hotels.d8345-aaResortHotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Highland Park ](https://expedia.ca/Highland-Park-Cabins.d8345-aaCabins.Travel-Guide-Accommodation)
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- [Inns in Highland Park ](https://expedia.ca/Highland-Park-Inns.d8345-aaInns.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Highland Park?

### What's the top vacation rental that Highland Park has to offer?

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### What can I see and do in Highland Park?

### What are vacation rentals like in Highland Park?

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General

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