Leaf River Vacation Packages
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Leaf River vacation deals
- Swissotel - Chicago
Jan 7 - Jan 11Swissotel - Chicago + Flight
Downtown Chicago4 nights4.5 star property9.0/10 - Wonderful (3,566 reviews)"Breakfast was good"Reviewed November 4, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,051CA $758found 1 day agoper traveller - Sheraton Grand Chicago Riverwalk
Dec 19 - Dec 23Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (1,874 reviews)Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YHM • 1 stopCA $2,730CA $1,208found 1 day agoper traveller - Park Hyatt Chicago
Dec 27 - Jan 2Park Hyatt Chicago + Flight
Downtown Chicago6 nights5.0 star property9.6/10 - Exceptional (1,001 reviews)"Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."Reviewed November 4, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • Nonstop - The Emily Hotel
Jan 7 - Jan 11The Emily Hotel + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (1,357 reviews)"Our stay at The Emily Hotel was outstanding! The entire property was well-maintained and the customer service provided by Leo and his team was excellent! We thoroughly enjoyed the offerings at Flora and were able to experience a Rooftop Cinema event! The hotel is conveniently located in walking distance to great restaurants and the L. I highly recommend The Emily Hotel and look forward to my stay during my next visit to Chicago!"Reviewed November 4, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,190CA $853found 1 day agoper traveller - Level Chicago Fulton Market
Jan 7 - Jan 11Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (602 reviews)"If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."Reviewed November 4, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,044CA $760found 1 day agoper traveller
Leaf River Hotel Deals
"Great place in a great town."
Country Inn & Suites by Radisson, Freeport, IL
Country Inn & Suites by Radisson, Freeport, IL
"Breakfast buffet was good"
Embassy Suites by Hilton Rockford Riverfront
Embassy Suites by Hilton Rockford Riverfront
"Awesome location in the park. Pictures on Expedia makes It look a little less "rural" than reality. Breakfast not available in early morning. Super Top to live the nature, not the best for business travel"
City Express By Marriott Freeport
City Express By Marriott FreeportFrequently Asked Questions
How much does a Leaf River vacation package cost?
You'll find cheap prices from CA $758 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.