Winnebago County Vacation Packages
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Your Winnebago County Vacation
Make planning your next big getaway a piece of cake with a Winnebago County vacation package. Whether it's the history, cuisine or something else entirely that brings you to this destination, our package deals will help you discover it all. Can't decide what should come first? Rockford is one of the most well-known cities to explore during your trip to Winnebago County. When it's time to stop dreaming and start doing, Expedia will help turn your Winnebago County vacation into a reality.
Top vacation destinations in Winnebago County
Rockford
Top Winnebago County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,389, price is now CA $921 per person
CA $921
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The room was small, but fine. The bed was comfortable. The TV was too big so it covered the thermostat control panel, and the remote Guide button didn’t work. Also, the water pressure in the shower was super weak… glad I didn’t need to wash my hair.
But location, general vibe, and staff were great.
Reviewed on Jul 8, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
We came to the property for my wife’s 40th birthday celebration. From the moment we walked in through the doors, we felt pampered. Everyone on staff was friendly, high energy, and always willing to help. The housekeeping staff was top notch as they went above and beyond with expectation on not only keeping things clean, but organizing our clutter, leaving thoughtful birthday treats, and making us feel comfortable. I now do not want to travel without staying at a 4 seasons property. They made our experience 10 times better!
Reviewed on Jul 6, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,047, price is now CA $1,235 per person
CA $1,235
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.
Reviewed on Jul 8, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $2,110, price is now CA $1,436 per person
CA $1,436
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
I enjoyed my stay with my toddler , the location was wonderful . However I did notice a lot of mosquitos , to my surprise the window in room was left open . Other than that it was nice and comfortable .
Reviewed on Jul 8, 2026
Pendry Chicago
Downtown Chicago
Price was CA $2,153, price is now CA $1,484 per person
CA $1,484
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Great location can get a bit noisy but really nice hotel.
Reviewed on Jul 8, 2026
Winnebago County Hotel Deals
Baymont by Wyndham Rockford
662 N Lyford Rd Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jul 12 to Jul 13
CA $127
CA $144 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (1,693 reviews)
"The hotel itself was fine, but not great. The front desk staff was very polite and generally helpful. The room was cleaned the first day after we arrived, but then not at all the next 3 days. Our garbages were overflowing, we had no clean towels, and the body wash dispenser was empty in our shower. ..."
Reviewed on Jul 8, 2026
Riverview Inn & Suites, an Ascend Collection Hotel
700 W Riverside Blvd Rockford IL
The price is CA $144 per night from Jul 29 to Jul 30
CA $144
CA $164 total
Jul 29 - Jul 30
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
"Cooks didnt come in one morning. So no hot breakfast before our tournament, and we counted on hotel breakfast in our plans. No hand soap in the rooms. Asked at front desk, and they didnt have any. We needed towels & washcloths and front desk said they would bring me some when she could. Never ..."
Reviewed on Jul 6, 2026
Embassy Suites by Hilton Rockford Riverfront
416 S Main Street Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Jul 28 to Jul 29
CA $198
CA $226 total
Jul 28 - Jul 29
includes taxes & fees
9.4/10 Exceptional! (1,008 reviews)
"extremely clean hotel and rooms"
Reviewed on Jul 7, 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.
Frequently asked questions
Stay near popular Winnebago County attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
