Sterling Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*
  • Find the right fit

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

    Plan, book, and manage your trip all in one place

Sterling Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
S$678
per person
4 Dec - 8 Dec
found 1 day ago
Return flight included
Vancouver (YVR) to Chicago (ORD)
8.2/10 Very good! (3,012 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
S$853
per person
4 Dec - 8 Dec
found 1 day ago
Return flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Only the wall outlet near the beds didn't work ...just that...everything was great !! Excelent hotel

Reviewed on 21 Sept, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
S$713
per person
4 Dec - 8 Dec
found 1 day ago
Return flight included
Vancouver (YVR) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
M

Reviewed on 21 Sept, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
S$875
per person
4 Dec - 8 Dec
found 1 day ago
Return flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
S$841
per person
4 Dec - 8 Dec
found 1 day ago
Return flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Good location, close to everything

Reviewed on 21 Sept, 2026

Top hotels in Sterling

Fairfield By Marriott Inn & Suites Dixon

Fairfield By Marriott Inn & Suites Dixon

1755 Fulfs Lane Dixon IL
Fully refundableReserve now, pay when you stay
S$177
8 Oct - 9 Oct
includes taxes & fees
Fairfield By Marriott Inn & Suites Dixon
Country Inn & Suites by Radisson, Rock Falls, IL

Country Inn & Suites by Radisson, Rock Falls, IL

2106 First Avenue Rock Falls IL
Fully refundable
S$144
27 Sept - 28 Sept
includes taxes & fees
Country Inn & Suites by Radisson, Rock Falls, IL
Tru By Hilton Dixon

Tru By Hilton Dixon

1806 S. Galena Ave Dixon IL
Fully refundableReserve now, pay when you stay
S$161
27 Sept - 28 Sept
includes taxes & fees
8.6/10 Excellent! (105 reviews)
"Our room was spotless and we enjoyed relaxing in there. The added hooks on the wall were definitely convenient for hanging up our things. The bathroom vanity was spacious and allowed both of us to spread out our toiletries. The shower water pressure was amazing and we enjoyed having the body wash, ..."

Reviewed on 14 Sept, 2026

Tru By Hilton Dixon
See all 52 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.

Frequently asked questions

How much does a Sterling holiday package cost?
Offering excellent value package deals from S$678 on Expedia, you'll be thrilled with how little a holiday to Sterling costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Sterling?
If you're hoping to book a cheap Sterling holiday package, consider planning a trip in January, February and November. You'll usually find better prices on flights and accommodation during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Sterling?
The ideal length of your Sterling holiday depends on what you'd like to do. Typically, a few days to a week will give you plenty of time to go to all the top attractions and discover some hidden treasures along the way.
How to find the best Sterling package deals?
Use Expedia's filters to help you find some fabulous Sterling package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Sterling package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Sterling holiday as a package?
You can enjoy significant savings on your next Sterling break by booking a tailored holiday package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Sterling?
Land incredible discounts by booking your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Sterling escape.
How to plan a trip to Sterling?
  1. Choose your travel dates: What you'd like to do in Sterling and your preferred season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your hotel will probably be the largest expense during your trip to Sterling.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you'd like to get to in Sterling. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Sterling holiday package that brings all your bookings together.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.