Waterman Vacation Packages

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,189, price is now CA $853 per person
CA $853
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The staff was very helpful. There were issues with the use of the TV but the staff was helpful with this.

Reviewed on Jul 5, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,565, price is now CA $1,710 per person
CA $1,710
per person
Sep 16 - Sep 20
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on Jun 26, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,891, price is now CA $1,331 per person
CA $1,331
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
The location of the hotel at Navy pier is excellent for views, sightseeing, boat rides , Hope on Hop off bus rides, 4th of July fireworks.

Reviewed on Jul 5, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,760, price is now CA $1,278 per person
CA $1,278
per person
Aug 19 - Aug 23
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.

Reviewed on Jul 2, 2026

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Downtown Chicago
Price was CA $1,228, price is now CA $894 per person
CA $894
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,343 reviews)
Room where clean and ideal location !

Reviewed on Jul 5, 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 $119 per night from Jul 9 to Jul 10
CA $119
CA $132 total
Jul 9 - Jul 10
includes taxes & fees
8.4/10 Very good! (437 reviews)
"Amazing staff! And amazing hospitality!"

Reviewed on Jul 4, 2026

Best Western Sycamore Inn
The Montcler Hotel - Redberri Luxury Collection

The Montcler Hotel - Redberri Luxury Collection

3 out of 5
3300 Drew Ave Sandwich IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Jul 12 to Jul 13
CA $167
CA $182 total
Jul 12 - Jul 13
includes taxes & fees
4.8/10 (16 reviews)
"No one attended to us at check in for 15 minutes - my wife finally found someone cleaning the rooms to come to the front desk - none of the amenities listed online were open - no restaurant or bar. Would never stay at again"

Reviewed on Jul 2, 2026

The Montcler Hotel - Redberri Luxury Collection
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 $168 per night from Jul 19 to Jul 20
CA $168
CA $193 total
Jul 19 - Jul 20
includes taxes & fees
8.4/10 Very good! (709 reviews)
"My experience with the check in host was terrible the hotel itself was a terrible experience to where I left a day earlier I booked a wheelchair accessible room not only did I not get that the fridge air and TV didn't work I didn't get a new room until 2 a.m in the morning the front desk man was ..."

Reviewed on Jul 5, 2026

Holiday Inn Express & Suites Yorkville by IHG
See all 51 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
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Family Vacations
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Frequently asked questions

How much does a Waterman vacation package cost?
Offering great value package deals from CA $853 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.

Explore a world of travel with Expedia

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