
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.

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,509, price is now CA $1,013 per person
CA $1,013
per person
May 11 - May 15
found 9 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,830, price is now CA $1,190 per person
CA $1,190
per person
Jun 4 - Jun 7
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
We loved everything about this modern hotel, with one exception: the room doors “bang” when closing. These sounds can be heard up and down the hall and woke us up multiple times. Recommendation to the property management to install some form of sound mitigation or softer closing mechanism in the doors.
Reviewed on Mar 27, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,728, price is now CA $1,209 per person
CA $1,209
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
The view is amazing, the staff from the valet to the front desk were very nice and professional. Will be going back.
Reviewed on Mar 26, 2026

Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,761, price is now CA $1,307 per person
CA $1,307
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026

Hotel Arista
Price was CA $1,425, price is now CA $1,058 per person
CA $1,058
per person
Jun 3 - Jun 9
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
Our room was spacious, clean and well appointed. I love a bathroom with good lighting and the tv in the vanity mirror was fantastic to catch the morning news as we got ready!!
The staff was exceptional. From check in, to drinks at the bar, to room service, everyone was incredibly friendly and professional. I highly recommend Hotel Arista.
Reviewed on Mar 24, 2026
Waterman Hotel Deals

Hampton Inn DeKalb, IL
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Apr 8 to Apr 9
CA $173
CA $197 total
Apr 8 - Apr 9
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Clean and professional staff
Reviewed on Mar 24, 2026

Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Mar 29 to Mar 30
CA $131
CA $146 total
Mar 29 - Mar 30
includes taxes & fees
8.2/10 Very Good! (404 reviews)
We really enjoyed our stay at this Best Western. Hot breakfast with protein everyday. Every staff member from desk to housekeeper were the friendliest we have ever encountered at a motel! Comfortable bed in rooms with mood lighting. I can’t say enough good about our stay. The entrance drive into ...
Reviewed on Mar 21, 2026

Country Inn & Suites by Radisson, Sycamore, IL
1450 South Peace Road Sycamore IL
8.6/10 Excellent! (987 reviews)
All good
Reviewed on Mar 26, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







