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
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 4 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Would have liked coffeemaker in the room and some glasses or cups for water. The bathroom was nice, but for the price, we felt the room was cramped and the window small. Location was convenient.
Reviewed on Jun 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,463, price is now CA $1,624 per person
CA $1,624
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $3,213, price is now CA $2,212 per person
CA $2,212
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.
Reviewed on Jun 23, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $2,026, price is now CA $1,407 per person
CA $1,407
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable
Reviewed on Jun 23, 2026
Waterman Hotel Deals
Best Western Sycamore Inn
1935 Dekalb Ave Sycamore IL
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Jun 29 to Jun 30
CA $113
CA $125 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very good! (428 reviews)
"Great"
Reviewed on Jun 19, 2026
The Montcler Hotel - Redberri Luxury Collection
3300 Drew Ave Sandwich IL
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Jul 5 to Jul 6
CA $149
CA $162 total
Jul 5 - Jul 6
includes taxes & fees
5/10 (14 reviews)
"The staff was friendy and thehotel had many upgrades. The room was clean and comfortable. Overall we had a nice quiet stay. We plan to stay there again in the future."
Reviewed on Jun 18, 2026
Super 8 by Wyndham Rochelle
601 E Highway 38 Rochelle IL
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from Jul 7 to Jul 8
CA $93
CA $103 total
Jul 7 - Jul 8
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
"The staff was great! Breakfast was cereal, oatmeal, toast, and juice/coffee. Not the newest fixtures (tub a little rusty, doors a bit splintered, etc), but overall was a decent place to stay when passing through."
Reviewed on Jun 24, 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.
