
Port Barrington Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Port Barrington Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Price was CA $1,376, price is now CA $968 per person
CA $968
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room
Reviewed on Apr 7, 2026

Le Méridien Essex Chicago
Downtown Chicago
Price was CA $2,134, price is now CA $1,509 per person
CA $1,509
per person
Jun 19 - Jun 23
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!
Reviewed on Apr 3, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $2,415, price is now CA $1,715 per person
CA $1,715
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (371 reviews)
Breakfast was good. Room was clean with great air-conditioned. Staff very nice and happy. Customer service great. Had a great experience. Will be back and would recommend to everyone.
Reviewed on Apr 11, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,900, price is now CA $1,360 per person
CA $1,360
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
I booked this stay specifically because I saw they had a steam room and Sauna. They were both very pleasant and available 24/7. The room was very high quality with great views but if the city. The game rooms looked really nice and spacious but I sadly didn’t have time to enjoy that aspect of the hotel. There is also a great cafe and bakery connected to the lobby. I’m excited to book here again with a little more time to make the most of my stay
Reviewed on Apr 11, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was CA $4,374, price is now CA $3,134 per person
CA $3,134
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
Port Barrington Hotel Deals

Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
The price is CA $137 per night from Apr 26 to Apr 27
CA $137
CA $153 total
Apr 26 - Apr 27
includes taxes & fees
8.2/10 Very Good! (1,108 reviews)
Decent facility for price.
Reviewed on Apr 12, 2026

Quality Inn Schaumburg - Chicago near the Mall
600 North Martingale Rd Schaumburg IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Apr 26 to Apr 27
CA $122
CA $141 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (1,015 reviews)
Breakfast ended at 9:30 am. We were not ready that early to make it to down to breakfast.
Reviewed on Apr 10, 2026

Hyatt Place Chicago/Hoffman Estates
2750 Greenspoint Pkwy Hoffman Estates IL
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Apr 19 to Apr 20
CA $151
CA $170 total
Apr 19 - Apr 20
includes taxes & fees
8.4/10 Very Good! (1,086 reviews)
The elevator is a little sketchy but the room was comfortable and the staff was helpful and nice
Reviewed on Apr 8, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







