Sterling Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, 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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $927, price is now CA $680 per person
CA $680
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,957 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,453, price is now CA $1,031 per person
CA $1,031
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Super clean. Super views. Super amenities. Will stay again.

Reviewed on Oct 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $2,045, price is now CA $1,478 per person
CA $1,478
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $952, price is now CA $704 per person
CA $704
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
Staff was great and the room was clean!

Reviewed on Oct 29, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,417, price is now CA $1,050 per person
CA $1,050
per person
Jan 22 - Jan 25
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Ready to book your vacation to Sterling?

 

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Sterling Hotel Deals

Fairfield By Marriott Inn & Suites Dixon

Fairfield By Marriott Inn & Suites Dixon

3 out of 5
1755 Fulfs Lane Dixon IL
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Nov 8 to Nov 9
CA $175
CA $194 total
Nov 8 - Nov 9
includes taxes & fees
Fairfield By Marriott Inn & Suites Dixon
Holiday Inn Express Dixon By Ihg

Holiday Inn Express Dixon By Ihg

2.5 out of 5
136 Plaza Dr Suite B Dixon IL
Fully refundable
The price is CA $169 per night from Nov 26 to Nov 27
CA $169
CA $188 total
Nov 26 - Nov 27
includes taxes & fees
8.8/10 Excellent! (15 reviews)
"Clean & Quiet Room. Always friendly staff employees. The rooms could use a little bit more air circulation. , But I'm satisfied staying there when I'm Deer or Turkey Hunting Lee & Ogle Counties. Dan"

Reviewed on Oct 26, 2026

Holiday Inn Express Dixon By Ihg
Candlewood Suites Dixon by IHG

Candlewood Suites Dixon by IHG

2.5 out of 5
136 Plaza Dr Dixon IL
Fully refundable
The price is CA $182 per night from Nov 5 to Nov 6
CA $182
CA $202 total
Nov 5 - Nov 6
includes taxes & fees
8.6/10 Excellent! (12 reviews)
"Clean big rooms. Well kept property and a very helpful staff. I would definitely recommend someone staying at Candlewood suits"

Reviewed on Oct 11, 2026

Candlewood Suites Dixon by IHG
See all 51 properties in Sterling
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Sterling vacation package cost?
Offering great value package deals from CA $680 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.