Leland Holidays

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Leland Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,105, price is now S$1,733 per person
S$1,733
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (2,288 reviews)
Chip painting in shower/tub

Reviewed on 22 Aug, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was S$2,898, price is now S$2,234 per person
S$2,234
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
Proximity to all gates at airport

Reviewed on 23 Aug, 2025

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
Price was S$2,301, price is now S$1,843 per person
S$1,843
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Not worth the price.

Reviewed on 21 Aug, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,224, price is now S$1,802 per person
S$1,802
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,012 reviews)
It was a very nice place. I don’t agree with the parking fees and then the added on three dollar Eco fee when nursing to be parking right beside it that was the cities and didn’t seem like very of secure parking. It wasn’t fenced in or anything just I don’t understand the fee for the parking Other night. It was a stay

Reviewed on 24 Aug, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
O'Hare
Price was S$2,181, price is now S$1,844 per person
S$1,844
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (2,393 reviews)
Pool was extremely chlorinated

Reviewed on 24 Aug, 2025

Top hotels in Leland

Grand Bear Resort at Starved Rock

Grand Bear Resort at Starved Rock

3 out of 5
2643 IL-178, Utica, IL
The price is S$147 per night from 3 Sept to 4 Sept
S$147
3 Sept - 4 Sept
includes taxes & fees
7.2/10 Good! (904 reviews)
"Location"

Reviewed on 7 Aug, 2025

Grand Bear Resort at Starved Rock
Holiday Inn Express & Suites Yorkville by IHG

Holiday Inn Express & Suites Yorkville by IHG

2.5 out of 5
577 E KENDALL DRIVE, Yorkville, IL
Fully refundable
The price is S$148 per night from 14 Sept to 15 Sept
S$148
14 Sept - 15 Sept
includes taxes & fees
8.2/10 Very Good! (586 reviews)
"This was one of the best hotel stays I have had in a very long time. The service we received was very personal and the gentleman, at the front desk, when we checked late, in the evening was accommodating and personable. The 4th floor room #424 was clean, and had sufficient towels, soap, etc. for ..."

Reviewed on 23 Aug, 2025

Holiday Inn Express & Suites Yorkville by IHG
Postcard Cabins Starved Rock

Postcard Cabins Starved Rock

2 out of 5
1879 N 2703rd Rd, Ottawa, IL
The price is S$219 per night from 26 Aug to 27 Aug
S$219
26 Aug - 27 Aug
includes taxes & fees
9.8/10 Exceptional! (57 reviews)
"It was very clean, easy to find and very very quiet. The service was excellent and there were many extra surprises ( firewood, ingredients for s’mores, a lantern) it was a wonderful stay"

Reviewed on 20 Aug, 2025

Postcard Cabins Starved Rock
See all 325 properties in Leland
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$1,733 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?

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