Title: Highland Park Vacation Packages & Trips 2025/2026 from CA $424 | Expedia.ca

  

[Hotels in Highland Park](https://expedia.ca/Highland-Park-Hotels.d8345.Travel-Guide-Hotels)[Vacation Rentals in Highland Park](https://expedia.ca/Highland-Park-Vacation-Rentals.d8345.Travel-Guide-VacationRentals)[Things to do in Highland Park](https://expedia.ca/Things-To-Do-In-Highland-Park.d8345.Travel-Guide-Activities)[Highland Park Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-Park.d8345.Car-Rental-Guide)

![](https://images.trvl-media.com/place/8345/f94c1586-cba7-48ff-b89e-bbef42b23b5f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Highland Park Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Emily

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Better together

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#### Your Highland Park Vacation

Planning your next big adventure is a piece of cake with a Highland Park vacation package. The neighborhood of Riverwoods, which is great for nature, makes a superb base to uncover the marvels of this unique city. If sightseeing is part of the plan during your trip to Highland Park, check out well-known attractions like [Chicago Botanic Garden](https://www.expedia.ca/Chicago-Botanic-Garden-Chicago.d6064029.Vacation-Attraction), [Lake Forest College](https://www.expedia.ca/Lake-Forest-College-Chicago.d6156570.Vacation-Attraction) and [Northbrook Sports Complex](https://www.expedia.ca/Northbrook-Sports-Complex-Chicago.d6186877.Vacation-Attraction). Whoever you're escaping with and whatever you plan to spend, your dream Highland Park vacation is just clicks away with Expedia.

## Top Highland Park Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $424

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=MkQLtkNAfofyS6wruIyPfFV32wspsu4zIPrnE9ENk3Kae8oh5lRoFkg3je7KA19_)

![Art Villa ](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/93a33738_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Art Villa

West Town

CA $1,107

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

10/10 Exceptional! (2 reviews)

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-28/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=115163763&paandie=true&dealMarker=b5uwRSeJQQuigeUJXT0sGs1ZdI8JucJ3uREyGL_S5u00eVShsLdWsaC4KOPYotOO)

![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Orrington / Evanston

Downtown Evanston

CA $739

per person

Dec 6 - Dec 13

found 13 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

7.6/10 Good! (1,003 reviews)

The location of the Orrington is excellent but the star of the Orrington is delfinitely its staff. They were friendly, helpful and handled busy and problem situations with grace and solutions. Gotta love the midwest!

Reviewed on Oct 10, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-06/2025-12-13/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19722&paandie=true&dealMarker=3N3YfoFxJicbUeztIgTC6rWoirc6qGjCwDkxyTNqvpSI3MOzdiT2yEUJEaYeD2Tf)

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $496

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=MkQLtkNAfofyS6wruIyPfNwfNcnlqYY1zsZttuPe0ICleFAYdOD_o3qLG9iF7nN6)

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $791

per person

Dec 12 - Dec 14

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,761 reviews)

The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.

Reviewed on Oct 20, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-14/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=zsdb7AqbqTyQd7e-XzjFSynEn7c1uvrgLRnPSfW015JSMQL1-yCgWMIDxdwc75Ow)

## Ready to book your vacation to Highland Park?

Choose your dates

## Highland Park Hotel Deals

![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave, Rosemont, IL

Fully refundableReserve now, pay when you stay

CA $165

CA $189 total

Nov 23 - Nov 24

includes taxes & fees

8.6/10 Excellent! (2,087 reviews)

Nice

Reviewed on Oct 20, 2025

[](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=5403&PinnedHotelID=5403&HadPinnedHotel=true&regionId=8345)

![Claridge House](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/5ea33759_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Claridge House

1244 N Dearborn Parkway, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $125

CA $188 total

Nov 5 - Nov 6

includes taxes & fees

8.8/10 Excellent! (1,425 reviews)

EXCELLENT Staff, clean, central located

Reviewed on Oct 18, 2025

[](https://expedia.ca/Hotel-Search?startDate=05%2F11%2F2025&endDate=06%2F11%2F2025&selected=22684&PinnedHotelID=22684&HadPinnedHotel=true&regionId=8345)

![Holiday Inn Chicago O'Hare – Rosemont by IHG](https://images.trvl-media.com/lodging/88000000/87710000/87702800/87702727/7dd32bc5_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Holiday Inn Chicago O'Hare – Rosemont by IHG

6600 Mannheim Road, building 2, Rosemont, IL

Fully refundable

CA $150

CA $173 total

Nov 23 - Nov 24

includes taxes & fees

8.8/10 Excellent! (2,481 reviews)

Airport shuttle was great just hard to maneuver thru ohare. Staff fantastic

Reviewed on Oct 20, 2025

[](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=87702727&PinnedHotelID=87702727&HadPinnedHotel=true&regionId=8345)

[See all 2,535 properties in Highland Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=24%2F10%2F2025&endDate=25%2F10%2F2025&regionId=8345)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### Discover the most popular places to visit in Highland Park

![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

[](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction)

![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

[](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction)

![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

[](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction)

### What to do in Highland Park

![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Architecture River Tour

CA $68

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details)

![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Architecture Center River Cruise aboard First Lady

CA $78

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details)

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details)

[See all activities in Highland Park](https://expedia.ca/things-to-do/search?rid=8345)

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![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFOElEQVR4Xu3bPXIbORBAYagcMPQR5ihztJmj8Sg8gkMFLmLVPwB6IKzk3ipvIL2XiGwC+CaDqPWW+j9U5sHfCCQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpAvK7TG1t9FLrvdzeFr+NtF8y3etredv+kNeHjWLHOBmkgMzLQKxjnAxSQOZlINYxTv6qyDHe6YnD3W34sO0R8Y2/5FF617NAQEBAJBANRAPp+Vrt1pHDPrzL1Beexa99HT3khyM6um6UQEBA5AcISAEB8T5GNN0eV/V0lQYCUkDGIpAWiAQCUv4DctpAv09LP2T0Uz6520BH/ig+AgHRQCoICAiIDT5DRr42VutDfvijuOsnKtIDKSAgIPMHIBZIAZmRa3H7vdy6+y+jqWOcDLIYTR3jZJDFaOoYJ4MsRlPHOBlkMZo6xskgi9HUMU4GWYymjnFyQBap+7M++85NpvIV+znf8R8FArIIZAoEZBHI1NdF/Kq+1XZ7S+sLfdf9xf/orfVRubgg8UQQkDYqICAgIFq/vbVHWHuX1zL60dbaSHLkRYav4e/gPZA2kkC0uFZPBAFpIwlEi2v1RJAvifiFrvmF/i5F5FGm4tO5GwKZAgEBGYH0QKTvivj218uF/uxu7yVc+9rYKIGAVBAQEJAKYhuljxD/27WfuNlc/zHX1V2M9FF2e9VHHsi7Echm88WJixHIZvPFiYsRyGbzxYmLEchm88WJixHIZvPFiYtRDhnbdSS9yIV+k0E8UR9ldqs9nZ7VAwEBAQHRQEDaZLz0D9p2X7v88qwnqiurNP/loMjT9UfxQEBA7GMQEJAKol0RP1G3+9rTdu662E6U0Yu8UNcfxVfFR+mBgICAgICcbbssBhkvf8sdr7e3fWLb+2icGFeF9JeDInf8HAgISAsEZAoERLfr2t0GD9uk1/6MFL/QfdXV9VEPBAQExAYgIBVEmxHfLp9Yh314l9eyXb8864k+6j3l/c02fvYVu4CAFBAQPRGkB9L6Zoj3dMRPPO2O1xNL2ewTfRRNVhV7uubKKn3gHkgLBAQEBKRt10A0OVGR18vap7y7yQJ1pTGKGzV5DwJSQUA0EBCQT5Bx4j6Gb9v1H3Pd24m6yi/0gcyBgFQQEJB1ICD1PaLb6/s73q/9Ine8u9eN4+l8VQgEBAQEZJe3ICDeErne3vrnbEV8ldQepW+Mj9KfzgMBAQEBAQH5CPG18klbq64mI+8ph91k9K5aH/LjaEtBQEDeB+IrQEBAFv22bYq82vbrl2fNn66GXw7GSAKJgXggICASSOx7In7iaJPpaa93XWwdNd7xm52ovwncfcX0KCAgICDWJtPTXu+62DoqCMh3Ro7xTrdXQfT/btI73kfXHs2tARkjCWQEooGAaCAVJPatEf2vyfH29nZBfOFZxrfu6yrdeHUlEBAQEBAQD0T7c0QWl/7lWb9iF3EfMvLfBO5h49HOBQEBASkgIK1dFxeQ3p8gmy3VVXrtS4pcr/1rIDoCASkgICAg1oyMfK1sjyeO9rD4bCOQuD22h8VnG4HE7bE9LD7bCCRuj+1h8dlGIHF7bA+LzzYCidtje1h8thFI3B7bw+Kzjf4AubbJVL48P/3EMKr+fbrWhyyVXw70jtcecu2HQCrIZICAgHgg9dsjfy+QVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpPo6yD+qh/Uj/nB7GAAAAABJRU5ErkJggg==)