Port Barrington Vacation Packages
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Top Port Barrington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
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 14 hours 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
Level Chicago - River North
Downtown Chicago
Price was CA $1,919, price is now CA $1,301 per person
CA $1,301
per person
Aug 11 - Aug 15
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,011 reviews)
Everything was great and staff was very helpful as well, great experience overall!
Reviewed on May 31, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,950, price is now CA $1,361 per person
CA $1,361
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Beautiful place and at a breath taking spot. Staff in the front were very helpful. Good, clean and the most important thing is that its private for the guests. There is a security at the entrance of the pier so nobody can come in. Guests can take walks at the pier, but not the whole pier but some areas. Security was very helpful and understanding. 2 things that need work are:
1. Pillows: the pillows were a pain in the neck.
2. The body wash: our room had an empty bottle of body wash and wasn't replaced for 2 days. Thank goodness, we had our own. And the bodywash holder was broken as well. maybe that is the case.
Other then that, i would stay here every chance I get and would recommend it to everyone.
Thank you to all the hotel staff for making our visit so memorable.
Thank you Sable for the beautiful views, right from our room and thank you Chicago.
Reviewed on May 31, 2026
Le Méridien Essex Chicago
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 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (1,006 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
Port Barrington Hotel Deals
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
22 West Algonquin Road Arlington Heights IL
Fully refundableReserve now, pay when you stay
The price is CA $86 per night from Jun 10 to Jun 11
CA $86
CA $96 total
Jun 10 - Jun 11
includes taxes & fees
5.4/10 (1,006 reviews)
"Meh"
Reviewed on May 31, 2026
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Jun 3 to Jun 4
CA $226
CA $258 total
Jun 3 - Jun 4
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"My kids loved the waterslides everything."
Reviewed on May 30, 2026
Hyatt Regency Deerfield
1750 Lake Cook Rd Deerfield IL
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Jun 21 to Jun 22
CA $163
CA $184 total
Jun 21 - Jun 22
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"I had a great stay at the Hyatt. The hotel was clean, beautiful, and well-maintained, and the staff was friendly and helpful throughout my visit. My only suggestion would be to add microwaves in the rooms for added convenience. Other than that, everything was excellent, and I would stay here ..."
Reviewed on May 30, 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.
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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.
