Leaf River Vacation Packages
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Top Leaf River Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,343, price is now CA $960 per person
CA $960
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Lobby was under construction which wasn’t attractive but also not disruptive. Hotel was fine but not glamorous. Room was small.
Reviewed on Apr 16, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,577, price is now CA $1,005 per person
CA $1,005
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop 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
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,348, price is now CA $1,671 per person
CA $1,671
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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
Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Price was CA $1,759, price is now CA $1,310 per person
CA $1,310
per person
Jun 19 - Jun 22
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,006 reviews)
The rooms are nice. I was a little disappointed to find out there would be a hold of 80 dollars each day on a credit card
Reviewed on Apr 14, 2026
Leaf River Hotel Deals
Baymont by Wyndham Rockford
662 N Lyford Rd Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Apr 26 to Apr 27
CA $87
CA $99 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (1,583 reviews)
Parking lot was well lite
Reviewed on Apr 17, 2026
Riverview Inn & Suites, an Ascend Collection Hotel
700 W Riverside Blvd Rockford IL
Fully refundable
The price is CA $146 per night from Apr 26 to Apr 27
CA $146
CA $166 total
Apr 26 - Apr 27
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
The stay was great and the staff were absolutely amazing and helpful. I did not like how we had to switch rooms due the carpets being re done and then getting transferred into a room over looking a parking lot instead of the beautiful river, which would have been nice giving that was my first rooms ...
Reviewed on Apr 16, 2026
Holiday Inn Rockford by IHG
7550 E State Street Rockford IL
Fully refundable
The price is CA $151 per night from Apr 26 to Apr 27
CA $151
CA $172 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
When booking this room I had specifically asked if there was a hot tub and they had said yes but there is not one. Also had asked if they do rides to the casino also said yes but they don’t. Waited in line for a long time on checking into hotel, need more then one person during “peak hours” otherwise ...
Reviewed on Mar 27, 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.
