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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,277, price is now CA $895 per person
CA $895
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
The gym is on 43 floor.. amazing

Reviewed on May 31, 2026

Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Price was CA $2,463, price is now CA $1,671 per person
CA $1,671
per person
Aug 12 - Aug 16
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
No reviews
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,769, price is now CA $1,239 per person
CA $1,239
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (395 reviews)
Great location and well maintained property!

Reviewed on May 29, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,060, price is now CA $1,471 per person
CA $1,471
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great room, professional staff, no complaints.

Reviewed on May 31, 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $1,795, price is now CA $1,285 per person
CA $1,285
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Staff was amazing and very helpful, gave us a lot of great recommendations for places to check out and also upgraded our room for free. The room was very nice, a little tight but that is expected in Chicago. Bathroom was perfect great shower, amazing view from room and bathroom window. Very conveniently located, quick walk from the train. Highly recommend and would stay again

Reviewed on Jun 1, 2026

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Highland Park Hotel Deals

Courtyard by Marriott Chicago Highland Park/Northbrook

Courtyard by Marriott Chicago Highland Park/Northbrook

3 out of 5
1505 Lake Cook Road Highland Park IL
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Jun 29 to Jun 30
CA $161
CA $178 total
Jun 29 - Jun 30
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Our first room was facing the highway. Even at 3am, it was no stop cars and road noise. It sounded like we were camping next to the road. We switched rooms to other side and it was quieter. The second room wasn’t cleaned properly, there was a lot of hair in the shower. The only food is at the Starbucks ..."

Reviewed on Jun 1, 2026

Courtyard by Marriott Chicago Highland Park/Northbrook
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is CA $220 per night from Jun 28 to Jun 29
CA $220
CA $251 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,601 reviews)
"The hotel its under renovation but still clean, rooms are clean and the staff is very friendly. 100% Recommended"

Reviewed on Jun 1, 2026

Hyatt Regency O'Hare Chicago
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 $216 per night from Jun 28 to Jun 29
CA $216
CA $257 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very Good! (1,532 reviews)
"great for price. location and rooms wonderful Food/dinning needs much help."

Reviewed on Jun 1, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 2,694 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.
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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

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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.

Naval Base Great Lakes
Navy Pier

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
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.