Winnebago County Vacations & Trips from $389
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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 destinations in Winnebago County
Rockford
Loves Park
The Latest Winnebago County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $633, price is now $389 per person
$389
per person
Mar 31 - Apr 4
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $817, price is now $450 per person
$450
per person
Mar 31 - Apr 4
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
We always stay at RIU when we’re in Chicago. Best hotel in the city!
Reviewed on Jan 4, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $780, price is now $457 per person
$457
per person
Mar 31 - Apr 4
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Best hotel ive ever stayed in. Perfect location for moving around Chicago. Everyone helpful, had a great time.
Reviewed on Jan 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,048, price is now $647 per person
$647
per person
Mar 26 - Mar 29
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,053, price is now $657 per person
$657
per person
Mar 31 - Apr 5
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
Find the Best Winnebago County Vacation Packages
Winnebago County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rockford, IL (RFD-Greater Rockford) |
Population | 3,000 |
Top Sights | Anderson Japanese Gardens, Rock Cut State Park and Kishwaukee River Forest Preserve |
Winnebago County Hotel Deals
Baymont by Wyndham Rockford
662 N Lyford Rd Rockford IL
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $75 total per night from Jan 12 to Jan 13
$75 total
Jan 12 - Jan 13
Total with taxes and fees
9/10 Wonderful! (1,461 reviews)
Nicely dne
Reviewed on Jan 2, 2026
Holiday Inn Rockford by IHG
7550 E State Street Rockford IL
Fully refundable
$82 nightly
The price is $93 total per night from Feb 4 to Feb 5
$93 total
Feb 4 - Feb 5
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
Great stay
Reviewed on Jan 3, 2026
Embassy Suites by Hilton Rockford Riverfront
416 S Main Street Rockford IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $158 total per night from Jan 18 to Jan 19
$158 total
Jan 18 - Jan 19
Total with taxes and fees
9.4/10 Exceptional! (899 reviews)
The hotel itself is so cool but the game simulator was a bit of a rip off at $40/hr. The supplies/balls were dirty and it was clear the room hadn’t been cleaned up after the last people used it. The room was really good looking but half of the lights didn’t work and the strings to pull the curtains ...
Reviewed on Jan 3, 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.
