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 Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,359, price is now CA $957 per person
CA $957
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
Place is in a great location but once you go past the lobby its very dated. Small rooms and had lots of trouble getting in touch with the front desk when we needed something.
Reviewed on May 7, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,447, price is now CA $962 per person
CA $962
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,683, price is now CA $1,142 per person
CA $1,142
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again
Reviewed on May 6, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,626, price is now CA $1,148 per person
CA $1,148
per person
Jun 30 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 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 $197 per night from May 10 to May 11
CA $197
CA $234 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (1,425 reviews)
A short walk to Lake Michigan, Magnificant Mile in a peaceful neighbourhood. The gallery in the basement is also worth checking out with rich cultural history. Architecture is great too！
Reviewed on May 8, 2026
Holiday Inn Chicago North-Evanston by IHG
1501 Sherman Ave Evanston IL
Fully refundable
The price is CA $156 per night from May 26 to May 27
CA $156
CA $178 total
May 26 - May 27
includes taxes & fees
8.6/10 Excellent! (1,904 reviews)
This would be the PERFECT hotel if there was a pool! I love the staff, the location is fantastic, the parking is reasonable and connected to the hotel. I have stayed here twice in the last six weeks and both times were wonderful. The breakfast buffet is FANTASTIC and it's $10 a person. I absolutely ...
Reviewed on May 8, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from May 10 to May 11
CA $231
CA $263 total
May 10 - May 11
includes taxes & fees
8.8/10 Excellent! (2,540 reviews)
Well rested after my stay!
Reviewed on May 7, 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
Skydeck - Willis Tower Admission
CA $61
per adult
96% 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.
