Leland Vacations from $352

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The Latest Leland vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $735, price is now $352 per person
$352
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Customer service was great and the property was bright and shiny. You could tell that employees cared about the way the property looked and how they interacted with guests.

Reviewed on Oct 27, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $785, price is now $359 per person
$359
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
Great accommodation, staff really nice, room was spacious and very clean. Perfect location to walk just about anywhere,

Reviewed on Oct 27, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,020, price is now $483 per person
$483
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,050, price is now $518 per person
$518
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $726, price is now $375 per person
$375
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

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Leland Hotel Deals

Grand Bear Resort at Starved Rock

Grand Bear Resort at Starved Rock

3 out of 5
2643 IL-178, Utica, IL
$103 nightly
The price is $114 total per night from Oct 28 to Oct 29
$114 total
Oct 28 - Oct 29
Total with taxes and fees
7.2/10 Good! (980 reviews)
parking lot was ok and husband loved the gym . We had fun miniature golfing and really just enjoyed ourselfs . The place is older and a little outdated but we just enjoyed ourselves away.

Reviewed on Oct 18, 2025

Grand Bear Resort at Starved Rock
Hampton Inn DeKalb, IL

Hampton Inn DeKalb, IL

3 out of 5
663 S. Annie Glidden Road, DeKalb, IL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $127 total per night from Nov 12 to Nov 13
$127 total
Nov 12 - Nov 13
Total with taxes and fees
9.2/10 Wonderful! (983 reviews)
none

Reviewed on Oct 24, 2025

Hampton Inn DeKalb, IL
Comfort Inn Ottawa Starved Rock Area

Comfort Inn Ottawa Starved Rock Area

2.5 out of 5
120 W. Stevenson Road, Ottawa, IL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $104 total per night from Nov 3 to Nov 4
$104 total
Nov 3 - Nov 4
Total with taxes and fees
8.2/10 Very Good! (741 reviews)
Love it

Reviewed on Oct 23, 2025

Comfort Inn Ottawa Starved Rock Area
See all 327 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.

Find the Best Leland Vacation Packages

Leland Essential Information

Language
English
Currency
U.S dollars
Population
940

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Frequently asked questions

How much does a Leland vacation package cost?
You can snap up a vacation package to this top destination from $352 on Expedia. However, how much your vacation to Leland costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Leland?
You're likely to find reduced prices and better availability in November, December and January. Explore our cheap Leland vacation packages and you could get some excellent off-season deals.
How many days is enough for Leland?
The ideal length for your Leland vacation depends on what you'd like to see. Generally, a few days to a week will give you plenty of time to tick off all the top attractions and explore some hidden spots along the way.
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," "Traveler 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Leland vacation as a package?
You can enjoy significant savings on your Leland getaway by booking a personalized vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Leland vacation packages?
Your Leland trip should be an escape from your busy life, not a source of money worries. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.