Argyle Vacation Packages
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Top Argyle Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,088, price is now CA $735 per person
CA $735
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,054 reviews)
The staff were fantastic, and the beds were insanely comfortable/blankets were soft and plush. The location is advantageous- lots of shopping, food, and things to do nearby. Getting an Uber from this location was a breeze and took less than five minutes. The Valet service for Staypineapple was also good. Would definitely recommend!
Reviewed on May 1, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,383, price is now CA $896 per person
CA $896
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip 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
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,501, price is now CA $979 per person
CA $979
per person
Jun 21 - Jun 24
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
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 16 hours 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
Argyle Hotel Deals
Baymont by Wyndham Rockford
662 N Lyford Rd Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from May 20 to May 21
CA $109
CA $124 total
May 20 - May 21
includes taxes & fees
9/10 Wonderful! (1,626 reviews)
I have a beautiful experience every time I go there, no issues ever
Reviewed on May 7, 2026
Riverview Inn & Suites, an Ascend Collection Hotel
700 W Riverside Blvd Rockford IL
Fully refundable
The price is CA $137 per night from May 18 to May 19
CA $137
CA $156 total
May 18 - May 19
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
Room was very big. Breakfast was descent. Room was very clean
Reviewed on May 6, 2026
Holiday Inn Rockford by IHG
7550 E State Street Rockford IL
Fully refundable
The price is CA $161 per night from May 17 to May 18
CA $161
CA $183 total
May 17 - May 18
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Was overall satisfied, but had an issue with the complementary breakfast that came with the reservation. The issue was resolved, and we moved on.
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.
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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.
