Waterman Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Waterman Vacation

Our vacation packages to Waterman offer countless opportunities to immerse yourself in new sights, sounds and experiences. And with all the finer details taken care of, you can relax and enjoy your city break to the fullest. Fill your trip to Waterman with tours of its most popular attractions. First up? You won't want to miss Shabbona Lake State Park. A couple of quick clicks is all it takes to craft your perfect Waterman vacation on Expedia.

Top Waterman Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,332, price is now CA $999 per person
CA $999
per person
Dec 25 - Dec 28
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $2,559, price is now CA $1,037 per person
CA $1,037
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was CA $2,031, price is now CA $1,315 per person
CA $1,315
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,005 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $2,339, price is now CA $1,641 per person
CA $1,641
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Always the best hotel in Chicago!!!!

Reviewed on Nov 2, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,843, price is now CA $1,417 per person
CA $1,417
per person
Dec 25 - Dec 28
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Amazing property and hospitality!

Reviewed on Nov 2, 2026

Ready to book your vacation to Waterman?

 

Choose your dates

Waterman Hotel Deals

Best Western Sycamore Inn

Best Western Sycamore Inn

2.5 out of 5
1935 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Nov 29 to Nov 30
CA $130
CA $144 total
Nov 29 - Nov 30
includes taxes & fees
Best Western Sycamore Inn
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 CA $154 per night from Nov 8 to Nov 9
CA $154
CA $177 total
Nov 8 - Nov 9
includes taxes & fees
8.4/10 Very good! (756 reviews)
"Nice place"

Reviewed on Nov 1, 2026

Holiday Inn Express & Suites Yorkville by IHG
Country Inn & Suites by Radisson, Sycamore, IL

Country Inn & Suites by Radisson, Sycamore, IL

2.5 out of 5
1450 South Peace Road Sycamore IL
Fully refundable
The price is CA $127 per night from Dec 3 to Dec 4
CA $127
CA $141 total
Dec 3 - Dec 4
includes taxes & fees
8.4/10 Very good! (1,002 reviews)
"Staff was very friendly and helpful to me. The room was clean and the bed was comfortable. Nights are getting chilly and the heating system is working fine. Décor at the hotel is getting old. Flooring in the main entrance or I should say Lobby needs to be replaced."

Reviewed on Nov 1, 2026

Country Inn & Suites by Radisson, Sycamore, IL
See all 53 properties in Waterman
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Waterman vacation package cost?
Offering great value package deals from CA $999 on Expedia, you'll be surprised at how little a vacation to Waterman costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Waterman?
You're likely to find reduced prices and better availability in January, February and April. Explore our cheap Waterman vacation packages and you could get some great off-season deals.
How many days is enough for Waterman?
Usually, a handful of days is enough to visit the main attractions during your Waterman vacation. But if you want to have some time to kick back or take day tours, think about extending your trip.
How to find the best Waterman package deals?
Use Expedia's filters to find some of the best Waterman package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Waterman package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Waterman vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Waterman vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Waterman?
If you've got your Waterman vacation dates confirmed, book as early as you can to snap up some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Waterman?

  1. Pick your dates: The things you'd like to do in Waterman and your favourite season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to cover everything from meals and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Waterman.
  3. Decide how long to go for: Now that you know more about Waterman, you can work out the right length of your break. Pull together a rough plan and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Waterman vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.