Sterling Vacation Packages
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Your Sterling Vacation
The vibrant city of Sterling is calling your name. Uncover both its hidden gems and highlights with a Sterling vacation package that's custom made for you. If seeing the sights is a priority during your trip to Sterling, be sure to head over to big-name attractions like Sauk Valley Community College and Sinnissippi Park. Your perfect Sterling vacation is a couple of clicks away. Explore accommodations, flights and more on Expedia for a trip that's tailored just for you.
Top Sterling Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Suites Deerfield
Price was CA $828, price is now CA $593 per person
CA $593
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,000 reviews)
Tv in the room didn’t work for local tv or for Netflix. It was rendered useless. The bartender was not very present at the bar because he was busy running room service. I waited at the bar close to 10 min before going to the front desk to ask if there was a bartender because I didn’t see any employee activity and the front desk advised me to just wait a min. The drinks were pretty good. The room was great. Spacious and clean. Tv is kinda vital for some entertainment
Reviewed on May 31, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,701, price is now CA $1,168 per person
CA $1,168
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Great experience and beautiful views
Reviewed on Jun 1, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,515, price is now CA $1,060 per person
CA $1,060
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,126 reviews)
Great and very elegant hotel! I absolutely loved it! The only thing is a little bit noisy but it’s the price you have to pay to be in an excellent location, you have everything you need in a walking distance. I would definitely stay here again.
Reviewed on May 30, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,358, price is now CA $969 per person
CA $969
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,711 reviews)
The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back up to the room
Other than that the front desk and cleaning ladies was very nice.
Reviewed on May 29, 2026
Sterling Hotel Deals
Country Inn & Suites by Radisson, Rock Falls, IL
2106 First Avenue Rock Falls IL
Fully refundable
The price is CA $160 per night from Jun 7 to Jun 8
CA $160
CA $177 total
Jun 7 - Jun 8
includes taxes & fees
7.8/10 Good! (810 reviews)
"Very clean and good place to stay"
Reviewed on Jun 1, 2026
Quality Inn & Suites Dixon near I-88
136 Plaza Dr Dixon IL
Fully refundable
The price is CA $159 per night from Jun 21 to Jun 22
CA $159
CA $177 total
Jun 21 - Jun 22
includes taxes & fees
8/10 Very Good! (669 reviews)
"Was put in an extended stay room. Very Nice. The construction going on makes it difficult to get to any where. I kept getting lost."
Reviewed on May 15, 2026
Tru By Hilton Dixon
1806 S. Galena Ave Dixon IL
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jun 21 to Jun 22
CA $190
CA $211 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (75 reviews)
"Upon checking in there was no body soap in the container in the bathroom. Rooms are very small, with 4 people in the room. The breakfast in the morning was good."
Reviewed on May 25, 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.
