Sterling 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
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.
Four Seasons Hotel Chicago
Downtown Chicago
CA $5,588
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Perfect location for shopping, beach, and restaurants. Very clean and staff is very friendly… did not disappoint. Everything met the mark and expectations of a Four Seasons.
Reviewed on Sep 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,698
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍
Reviewed on Sep 2, 2026
Freehand Chicago
Downtown Chicago
CA $2,050
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
7.8/10 Good! (3,367 reviews)
Pros - this hotel is conveniently located and its less expensive than some others in the area.
Cons - the first room I was given had water damage in the ceiling and did not smell good. I also checked the AC unit and the filter was completely clogged with dust, this type of washable filter is supposed to be cleaned every month and it looks like it has at least 9+ months of dust on it. I complained about the water damage and they moved me to another room. The next room didn't have soap or shampoo in the bathroom for some reason, and I checked the air filter in this room also and it clearly hasn't been cleaned in forever. In addition to cleaning the air filters, this type of AC unit is supposed to be professionally cleaned once per year. This one has clearly not been cleaned in years.
If you want a well maintained hotel, try somewhere else.
Reviewed on Sep 2, 2026
Ready to book your vacation to Sterling?
Sterling Hotel Deals
Fairfield By Marriott Inn & Suites Dixon
1755 Fulfs Lane Dixon IL
Fully refundableReserve now, pay when you stay
CA $161
CA $178 total
Sep 27 - Sep 28
includes taxes & fees
Country Inn & Suites by Radisson, Rock Falls, IL
2106 First Avenue Rock Falls IL
Fully refundable
CA $136
CA $151 total
Sep 27 - Sep 28
includes taxes & fees
7.8/10 Good! (848 reviews)
"Elevator was out of order. Mold on the walls and ceiling."
Reviewed on Aug 25, 2026
Tru By Hilton Dixon
1806 S. Galena Ave Dixon IL
Fully refundableReserve now, pay when you stay
CA $156
CA $173 total
Sep 20 - Sep 21
includes taxes & fees
8.6/10 Excellent! (97 reviews)
"Appears super clean and modern but was actually pretty cheap. Had no water pressure in the shower and very hard bed. Wasn’t expecting it to be five star by any means but will definitely not stay there again."
Reviewed on Aug 31, 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.
Frequently asked questions
How much does a Sterling vacation package cost?
Offering great value package deals from CA $1,161 on Expedia, you'll be surprised at how little a vacation to Sterling costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Sterling?
If you're hoping to score a cheap Sterling vacation package, consider planning a trip in January, February and November. You're likely to find lower rates on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Sterling?
The ideal duration of your Sterling vacation depends on what you'd like to do and see. Typically, a few days to a week will give you time to tick off all the major sights and discover some hidden spots along the way.
How to find the best Sterling package deals?
Use Expedia's filter tool to find some terrific Sterling package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Sterling package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Sterling vacation as a package?
You can enjoy significant savings on your Sterling retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Sterling?
If you have your Sterling travel dates confirmed, book as early as you can to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Sterling?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Sterling.
- Set a budget: Factor in expenses such as flights, food and transportation when working out how much to save for your trip to Sterling. Then, select a property that fits your budget, whether that's a low-cost stay or a swankier getaway.
- Decide your trip length: Consider how much time you want to spend discovering Sterling. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Sterling vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
