
Stephenson County Vacation Packages
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Top Stephenson County Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Price was CA $904, price is now CA $644 per person
CA $644
per person
May 22 - May 24
found 6 hours ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
We didn’t get the room we thought we booked. Very disappointing. The staff was nice but said this happens a lot because third party reservations. We DO NOT like booking through any place but directly through the hotel. Customer service has definitely changed over the years. We used to like Marriott but because of this we try and book at smaller hotels who answers their phones and makes their own reservations.
Reviewed on Apr 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,812, price is now CA $1,154 per person
CA $1,154
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Excellent staff, beautiful views.
Reviewed on Apr 5, 2026

The Langham, Chicago
Downtown Chicago
Price was CA $1,811, price is now CA $1,227 per person
CA $1,227
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The staff were wonderful, the room was beautiful, and the location was fantastic. I really wanted to love this hotel. Unfortunately, two issues made for a difficult stay.
The noise was severe. Despite being listed as soundproof, our junior suite on the 10th floor was incredibly loud. We’ve stayed in many major cities (and lived in some). But have not experienced this level of disruption from sirens, car alarms, horns, and blasting music from passersby all night. The blackout curtains are thin and don't reach the floor, offering little sound buffering. This is a far cry from the double-glazed windows and heavy drapes you'd expect from a hotel marketing itself as soundproof.
The motion-sensor system controlling all lights and HVAC was also a safety concern. If you're still for too long (say, soaking in the bathtub), the entire room goes pitch black. Even the bathroom night light turns off on a timer. We asked the staff to disable this, and they said they did, but the problem persisted.
For the price of a 5-star hotel, these issues brought the experience down to a 3-star stay. It's a shame, because so much else was genuinely excellent. We’d return, but only if these issues are addressed.
Reviewed on Apr 5, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,067, price is now CA $747 per person
CA $747
per person
Jun 13 - Jun 15
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Cleaning was ok but location was the best. Everything was around the corner
Reviewed on Apr 5, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,434, price is now CA $1,043 per person
CA $1,043
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
Was a little noisy but I think that was just my unit. Facilities were top notch!
Reviewed on Apr 4, 2026
Stephenson County Hotel Deals

Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is CA $159 per night from Apr 19 to Apr 20
CA $159
CA $177 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (877 reviews)
Convenient and safe location
Reviewed on Apr 2, 2026

Hampton Inn Freeport
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Apr 19 to Apr 20
CA $142
CA $157 total
Apr 19 - Apr 20
includes taxes & fees
8.8/10 Excellent! (461 reviews)
The breakfast was excellent. The place was clean. And the staff was very helpful.
Reviewed on Mar 30, 2026

Super 8 by Wyndham Freeport
1551 Sleezer Home Rd Freeport IL
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from Apr 7 to Apr 8
CA $102
CA $113 total
Apr 7 - Apr 8
includes taxes & fees
6.8/10 (351 reviews)
The proerty manager had several rooms on the 2nd floor with unsupervised kids in it who ran in and out of the rooms banging the doors as they ran through the halls, playing.
Reviewed on Mar 15, 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.







