
Orangeville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Orangeville Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Chicago Marriott Suites Deerfield
Price was CA $745, price is now CA $514 per person
CA $514
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,001 reviews)
I booked this property after a day at O'Hare airport and multiple flight cancellations. I was greeted and checked in efficiently, had a drink and dinner and retired to a very comfortable and clean room. Breakfast the next day consusted of an excellent omelet. Overall a very comfortable and well appointed hotel. Thank you!
Reviewed on Mar 16, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $2,370, price is now CA $1,523 per person
CA $1,523
per person
Jul 3 - Jul 6
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (946 reviews)
Rooms were cleaned I liked how secure the hotel was.
Reviewed on Apr 29, 2026


Wind Creek Southland Casino and Hotel
East Hazel Crest
Price was CA $1,024, price is now CA $694 per person
CA $694
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (336 reviews)
If you extend your stay you have to go down to the front desk in the morning to sign a new form and, depending on what time it is, they may not be capable of renewing your keys at that time which means you have to return again later in the day. When they asked if I wanted housekeeping I said yes and, even though I was gone from my room for 12 hours I didn't get it. Then there was a knock on my door at 10 pm when I was falling asleep and I found towels outside the door the next morning. That's not what I call housekeeping.
Reviewed on May 1, 2026

Pendry Chicago
Downtown Chicago
Price was CA $1,962, price is now CA $1,345 per person
CA $1,345
per person
Jun 25 - Jun 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Orangeville Hotel Deals

Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is CA $160 per night from May 10 to May 11
CA $160
CA $177 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (890 reviews)
Worked perfect for me
Reviewed on Apr 28, 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 May 10 to May 11
CA $107
CA $118 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (853 reviews)
From my arrival to my leaving Everyone was Very Professional and Caring. Very Helpful and my room was so comfortable. Its an older hotel but I felt very welcome, safe and the hot breakfast was a very well maintained. I really enjoyed my stay.
Reviewed on Apr 23, 2026

Hampton Inn Freeport
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from May 10 to May 11
CA $138
CA $153 total
May 10 - May 11
includes taxes & fees
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.







