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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,225, price is now CA $837 per person
CA $837
per person
Mar 31 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!

Reviewed on Feb 27, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,763, price is now CA $1,620 per person
CA $1,620
per person
May 1 - May 7
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,406, price is now CA $853 per person
CA $853
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $2,526, price is now CA $1,815 per person
CA $1,815
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The staff were lovely. As it was our anniversary, we were given a beautiful room overlooking the water tower and the lake. The room was exceptional - the bath tub, huge! The hotel itself was within walking distance to almost everywhere - the lake, the river, the magnificent mile. There were cafes and restaurants very close by. We had a fantastic time in Chicago because of this!

Reviewed on Feb 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,188, price is now CA $865 per person
CA $865
per person
Mar 31 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

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Highland Park Hotel Deals

Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
1501 Sherman Ave Evanston IL
Fully refundable
The price is CA $119 per night from Mar 19 to Mar 20
CA $119
CA $137 total
Mar 19 - Mar 20
includes taxes & fees
8.6/10 Excellent! (1,796 reviews)
Yes, clean room. Very very comfortable bed.

Reviewed on Feb 27, 2026

Holiday Inn Chicago North-Evanston by IHG
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $267 per night from Mar 27 to Mar 28
CA $267
CA $314 total
Mar 27 - Mar 28
includes taxes & fees
8.4/10 Very Good! (2,217 reviews)
It was a very clean place in great location.

Reviewed on Feb 26, 2026

Hilton Chicago O'Hare Airport
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Mar 4 to Mar 5
CA $146
CA $171 total
Mar 4 - Mar 5
includes taxes & fees
8.2/10 Very Good! (1,290 reviews)
The room was clean and building clean. The

Reviewed on Feb 27, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 2,746 properties in Highland Park
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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Discover the most popular places to visit in Highland Park

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

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.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Highland Park

Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Highland Park

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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.