Leland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Top Leland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,139
per person
Sep 25 - Sep 27
found 14 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The service and rooms were excellent. Beds were comfortable and views were to die for. The food at Terra16 was a good but the wait times and food service took to long. Our fruit platter took over a half hour for breakfast. The spa was nice, but the lockers were hard to use or some worked and some did not lock. Front desk was exceptional and property was gorgeous. I would definitely stay again and was very happy with the staff who generally were attentive and kind.
Reviewed on Aug 13, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,424
per person
Oct 2 - Oct 6
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Pendry Chicago
Downtown Chicago
CA $1,454
per person
Oct 1 - Oct 4
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,145 reviews)
Everyone at the Pendry was super nice. I would definitely recommend this hotel. My friend got sick and they offered to run across the street to get her medicine. Exceptional service.
Reviewed on Aug 12, 2026
Ready to book your vacation to Leland?
Leland Hotel Deals
Grand Bear Resort at Starved Rock
2643 IL-178 Utica IL
CA $164
CA $187 total
Sep 8 - Sep 9
includes taxes & fees
7.2/10 Good! (1,003 reviews)
"Family friendly. Activities are for younger kids mostly."
Reviewed on Aug 12, 2026
Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
CA $124
CA $138 total
Aug 30 - Aug 31
includes taxes & fees
8.4/10 Very good! (468 reviews)
"I purchased the stay for my daughter and son in law’s birthdays. They love the hotel for the location and safety."
Reviewed on Aug 12, 2026
Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy
1879 N 2703rd Rd Ottawa IL
CA $235
CA $323 total
Aug 18 - Aug 19
includes taxes & fees
9.6/10 Exceptional! (250 reviews)
"10/10 experience, would recommend to everyone! room was clean, staff was amazing, and everything was just an overall great experience. Definitely will be coming back!"
Reviewed on Aug 10, 2026
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 vacation package cost?
You'll find cheap prices from CA $1,139 on Expedia for your Leland break. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Leland costs.
What are the cheapest months to go to Leland?
January, February and November are great times to search for cheap Leland vacation packages. Choosing to travel in less busy periods means you can typically find lower prices on flights and accommodations.
How many days is enough for Leland?
The ideal duration of your Leland vacation depends on what you'd like to do. Usually, a few days to a week will give you enough time to visit all the leading attractions and explore some hidden spots along the way.
How to find the best Leland package deals?
Start your search for a Leland package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Leland package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Leland escape underway.
Is it cheaper to book a Leland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights individually. Better still, you can customize your Leland getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Leland?
Enjoy incredible bargains by reserving your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Leland escape.
How to plan a trip to Leland?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Leland.
- Budget wisely: Besides the price of your stay, you'll need to consider other expenses too. These include flights, food and transportation. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Leland.
- Decide your trip length: Consider how much time you want to spend discovering Leland. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Leland 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.
