Leland Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Leland Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
S$667
per person
21 Nov - 23 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
Room was standard, close to millennium park, very helpful staff, & yummy restaurant!
Reviewed on 13 Oct, 2026
Top hotels in Leland
Grand Bear Resort at Starved Rock
2643 IL-178 Utica IL
S$144
20 Oct - 21 Oct
includes taxes & fees
Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy
1879 N 2703rd Rd Ottawa IL
S$273
12 Nov - 13 Nov
includes taxes & fees
9.8/10 Exceptional! (289 reviews)
"Bring your own s’more supplies, roasting forks and a broom. The cabin was intimate and overall comfortable. Needed some extra cleaning as there was a large pile of leaves on the entrance into the cabin, so they kept getting tracked in regardless of the no shoes policy. They ran of out s’more supplies ..."
Reviewed on 13 Oct, 2026
Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
S$135
1 Nov - 2 Nov
includes taxes & fees
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 Leland holiday package cost?
You can snap up a holiday package to this top destination from S$614 on Expedia. However, how much your holiday to Leland costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Leland?
January, February and November are great times to search for cheap Leland holiday packages. Travelling in quieter periods means you'll typically find lower prices on flights and accommodation.
How many days is enough for Leland?
Usually, a handful of days is enough to tick off the top sights during your Leland holiday. However, if you want to have some time to rest or go on day trips, think about extending your trip.
How to find the best Leland package deals?
Landing a cheap Leland package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most affordable Leland package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Leland holiday as a package?
You can enjoy significant savings on your Leland getaway by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to browse some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Leland?
If you've got your Leland travel dates locked in, book as early as you can to grab some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Leland?
- Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Leland.
- Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to activities and airfares. Your hotel will probably be the biggest expense during your trip to Leland.
- Decide how many days away: Start by compiling a list of the sights and activities you want to get to in Leland. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your airfare and accommodation: After you've nailed down your trip dates and duration, lock in the ideal Leland holiday package for you.
* 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.
