
Highland Park Vacation Packages
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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, Lake Forest College and Northbrook Sports Complex. 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.





Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was CA $3,612, price is now CA $2,535 per person
CA $2,535
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott.
For example, there was a hair in the bed. When we reported it, the hotel changed the sheets and asked if we wanted to switch rooms, but no apology or other compensation was offered.
The service was fine but incredibly slow, which we experienced with three different requests. Two were for the same bath salts, which are already provided in the room, so it wasn’t a special request. We had to call twice, and they arrived after 45 to 55 minutes. For the third, I went down to the front desk to ask for a printer, and they offered to print the documents and send them to my room. After 45 minutes, I went back down, and it turned out they had completely forgotten about the request, so I had them printed right there.
The pool was dirty. On three different occasions over two days, there were toys left in the pool even after the people using them were already gone. The fruit in the gym was also old and had gone bad.
Reviewed on Nov 4, 2026
Highland Park Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 9 to Nov 10
CA $162
CA $193 total
Nov 9 - Nov 10
includes taxes & fees

Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
The price is CA $284 per night from Nov 27 to Nov 28
CA $284
CA $333 total
Nov 27 - Nov 28
includes taxes & fees

Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
The price is CA $200 per night from Nov 25 to Nov 26
CA $200
CA $235 total
Nov 25 - Nov 26
includes taxes & fees
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.
Stay near popular Highland Park attractions
What to do in Highland Park

Skydeck Chicago at Willis Tower
CA $60
per adult
84% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour
CA $57
per adult
94% of travellers recommend
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.








