Orangeville Vacation Packages
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Top Orangeville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,567, price is now CA $920 per person
CA $920
per person
Apr 22 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (413 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,942, price is now CA $1,274 per person
CA $1,274
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,422 reviews)
Great breakfast buffet! Great location to Michigan Ave. I would stay here again.
Reviewed on Mar 3, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was CA $1,894, price is now CA $1,319 per person
CA $1,319
per person
Apr 22 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,266 reviews)
We loved are stay at the Thompson hotel. It's very clean, and is close to our favorite shops and restaurants.
Reviewed on Mar 2, 2026
4BR Corporate Suite Central and Modern
Near North Side
Price was CA $2,179, price is now CA $1,608 per person
CA $1,608
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
10/10 Exceptional! (8 reviews)
Our stay at Envitae was amazinggg!! I’m so glad I booked with them for my Chicago trip with my family. The place was so nice and clean and decorated nicely and looks exactly like the pictures! This place literally had everything we needed and was so accommodating from having soap and shampoo to pots and pans pretty anything you could think of that you may need they had stocked. Also they were checking in with us to make sure our stay was going well they even were so kind to send us gourmet doughnuts!! The views were amazing and the location was literally near everything you could think of in walking distance. I would definitely book here again! Thank you so much for having us!
Reviewed on Jan 30, 2026
Orangeville Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is CA $142 per night from Mar 22 to Mar 23
CA $142
CA $157 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (868 reviews)
Clean rooms, comfortable bed, good breakfast on the morning. Great location with plenty of dining options close by.
Reviewed on Mar 2, 2026
Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is CA $107 per night from Mar 22 to Mar 23
CA $107
CA $117 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (834 reviews)
Clean room, nice staff
Reviewed on Feb 28, 2026
Hampton Inn Freeport
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Mar 11 to Mar 12
CA $139
CA $154 total
Mar 11 - Mar 12
includes taxes & fees
8.8/10 Excellent! (458 reviews)
Clean, close to everything, parking, friendly staff
Reviewed on Feb 22, 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.
