Orangeville Vacation Packages
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Top Orangeville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,681, price is now CA $2,431 per person
CA $2,431
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,849, price is now CA $1,308 per person
CA $1,308
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!
Reviewed on Jun 18, 2026
The Emily Hotel
Downtown Chicago
Price was CA $1,918, price is now CA $1,396 per person
CA $1,396
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Comfortable, modern rooms and great location.
Reviewed on Jun 19, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,349, price is now CA $1,714 per person
CA $1,714
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.
Reviewed on Jun 20, 2026
Orangeville Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is CA $179 per night from Jul 20 to Jul 21
CA $179
CA $199 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (904 reviews)
"Great property! Comfy beds, helpful staff. I highly recommend Country Inn and Suites in Freeport."
Reviewed on Jun 16, 2026
Hampton Inn Freeport
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Jul 2 to Jul 3
CA $161
CA $179 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (476 reviews)
"Breakfast was good and safe parking was available"
Reviewed on Jun 15, 2026
Country Inn & Suites by Radisson, Stockton, IL
200 Dillon Ave Stockton IL
The price is CA $142 per night from Jul 1 to Jul 2
CA $142
CA $157 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (676 reviews)
"The breakfast was not appealing at all and the shower in my room had so much pressure that you had to watch which way you stood to avoid injuries."
Reviewed on Jun 20, 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.
