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.
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Price was CA $1,290, price is now CA $958 per person
CA $958
per person
Sep 14 - Sep 17
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (622 reviews)
James at the front desk was absolutely incredible. It was a quick stay due to storms in the area, but James' professionalism and care added some positivity to an otherwise stressful travel experience.
Reviewed on Jun 22, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,102, price is now CA $1,251 per person
CA $1,251
per person
Jul 28 - Jul 31
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,029, price is now CA $1,412 per person
CA $1,412
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views
Reviewed on Jun 22, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $2,041, price is now CA $1,476 per person
CA $1,476
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Overall, the hotel was okay for the price, but pretty basic. The room was very simple and lacked some expected amenities—there were no slippers provided, which was a bit disappointing. Also, the area around the bed wasn’t very clean, which affected the overall experience.
I paid $170 per night, and for that price, I expected a bit more attention to cleanliness and comfort. It’s not terrible, but definitely not great either.
Reviewed on Jun 22, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was CA $1,360, price is now CA $1,007 per person
CA $1,007
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,984 reviews)
Great location very basic accommodations
Reviewed on Jun 21, 2026
Highland Park Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jun 28 to Jun 29
CA $180
CA $205 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,720 reviews)
"Breakfast was great!"
Reviewed on Jun 22, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jul 1 to Jul 2
CA $174
CA $207 total
Jul 1 - Jul 2
includes taxes & fees
8.2/10 Very Good! (1,635 reviews)
"Good recommendation"
Reviewed on Jun 22, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $359 per night from Jul 4 to Jul 5
CA $359
CA $422 total
Jul 4 - Jul 5
includes taxes & fees
8.4/10 Very Good! (2,321 reviews)
"I love how convenient this hotel is. However they should FIRE their designer. Whoever thought shag carpets work with rolling luggage has never been a guest at the hotel. The room hallways have a lower profile carpet but still difficult. Even the maintenance people joke about it; not really funny ..."
Reviewed on Jun 22, 2026
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.
Discover the most popular places to visit in Highland Park
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highland Park
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
CA $69
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
