Leaf River 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 Leaf River Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago
Downtown Chicago
CA $684
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (2,711 reviews)
Parking was interesting and expensive, but hey, it’s Chicago. I appreciated the staff’s knowledge on other parking methods. Overall our 1 night stay was great! Room was neat and very clean.
Reviewed on Aug 13, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,001
per person
Sep 21 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 1 day 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
Ready to book your vacation to Leaf River?
Leaf River Hotel Deals
Baymont by Wyndham Rockford
662 N Lyford Rd Rockford IL
Fully refundableReserve now, pay when you stay
CA $98
CA $112 total
Aug 23 - Aug 24
includes taxes & fees
9/10 Wonderful! (1,730 reviews)
"Ease of check-in-my room was ready early, so able to get in 30 minutes before check-in! Nice pool-I enjoyed it!"
Reviewed on Aug 13, 2026
Riverview Inn & Suites, an Ascend Collection Hotel
700 W Riverside Blvd Rockford IL
Fully refundable
CA $129
CA $147 total
Sep 6 - Sep 7
includes taxes & fees
8.4/10 Very good! (1,019 reviews)
"The staff was very helpful and the view from the window of the river and wildlife critters was beautiful."
Reviewed on Aug 12, 2026
Embassy Suites by Hilton Rockford Riverfront
416 S Main Street Rockford IL
Fully refundableReserve now, pay when you stay
CA $170
CA $194 total
Sep 13 - Sep 14
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 Leaf River vacation package cost?
You'll find cheap prices from CA $684 on Expedia for your Leaf River break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Leaf River costs.
What are the cheapest months to go to Leaf River?
January, February and November are the best times to search for cheap Leaf River vacation packages. Opting to travel in quieter months means you can generally find reduced prices on flights and accommodations.
How many days is enough for Leaf River?
With a well-planned itinerary, you can easily visit the most popular Leaf River sights in a few days. But if you prefer to discover hidden spots or go on day tours, consider booking your Leaf River vacation for longer.
How to find the best Leaf River package deals?
Bagging a cheap Leaf River package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most economical Leaf River package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Leaf River vacation as a package?
You can enjoy significant savings on your Leaf River break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Leaf River?
Land incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Leaf River vacation.
How to plan a trip to Leaf River?
- Choose when to get away: Check your schedule and pack your bags. Your favourite season and the type of activities available will also help you decide when to escape to Leaf River.
- Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will likely be the biggest expense during your trip to Leaf River.
- Decide how many days away: Start by listing all the attractions you want to get to in Leaf River. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalized Leaf River vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
