Winnebago County Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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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

FlightsFlightsHotelsHotels

Rockford

Rockford

Top Winnebago County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,067, price is now CA $747 per person
CA $747
per person
Jun 13 - Jun 15
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Black fast is great

Reviewed on Apr 6, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,938, price is now CA $1,283 per person
CA $1,283
per person
Jun 18 - Jun 21
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
I enjoyed this property and the view is top notch

Reviewed on Apr 6, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
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 room was very clean, great location, and great staff.

Reviewed on Apr 6, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,869, price is now CA $2,016 per person
CA $2,016
per person
May 20 - May 27
found 19 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (1,187 reviews)
Excellent choice for solo or business travelers looking for rooms with a good amount of space and a comfortable desk for working from. Great location.

Reviewed on Apr 6, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $4,872, price is now CA $3,433 per person
CA $3,433
per person
May 20 - May 27
found 19 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.

Reviewed on Mar 27, 2026

Winnebago County Hotel Deals

Baymont by Wyndham Rockford

Baymont by Wyndham Rockford

3 out of 5
662 N Lyford Rd Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Apr 26 to Apr 27
CA $105
CA $120 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (1,575 reviews)
Stay was fair. Average customer service. The elevator bothered me a bit because it wasn’t exactly a smooth ride and walls were paper thin. No way to hook up my Netflix or other streaming channels to the TV. It was only set up for Samsung and I have an iPhone. However, room was clean. I would book ...

Reviewed on Apr 6, 2026

Baymont by Wyndham Rockford
Riverview Inn & Suites, an Ascend Collection Hotel

Riverview Inn & Suites, an Ascend Collection Hotel

3 out of 5
700 W Riverside Blvd Rockford IL
Fully refundable
The price is CA $140 per night from Apr 11 to Apr 12
CA $140
CA $159 total
Apr 11 - Apr 12
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Great, friendly, helpful staff.

Reviewed on Apr 6, 2026

Riverview Inn & Suites, an Ascend Collection Hotel
Holiday Inn Rockford by IHG

Holiday Inn Rockford by IHG

3 out of 5
7550 E State Street Rockford IL
Fully refundable
The price is CA $165 per night from Apr 13 to Apr 14
CA $165
CA $188 total
Apr 13 - Apr 14
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
When booking this room I had specifically asked if there was a hot tub and they had said yes but there is not one. Also had asked if they do rides to the casino also said yes but they don’t. Waited in line for a long time on checking into hotel, need more then one person during “peak hours” otherwise ...

Reviewed on Mar 27, 2026

Holiday Inn Rockford by IHG
See all 364 properties in Winnebago County
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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Frequently asked questions

How much does a Winnebago County vacation package cost?
We make it easy to see the world, with Winnebago County packages starting from as low as CA $747. You'll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate escape, why not add a couple of tours and activities to your travel itinerary?
How do I get a cheap travel package to Winnebago County?
By bundling. Flights, rental cars and hotels — combine whatever you need into a Winnebago County vacation package to save a pile of cash. Score even more discounts when you add extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the freedom to customize your trip your own way. We offer over 550 airlines and 1,000,000 hotel options across the globe, so that everyone has a chance to travel and live out those vacation fantasies.
What are the top hotels in Winnebago County?
Have a look at Courtyard by Marriott Rockford and Baymont by Wyndham Rockford. They're the first choice for many travelers to Rockford. If Loves Park features on your itinerary, La Quinta Inn & Suites by Wyndham Rockford and Holiday Inn Express Hotel & Suites Rockford-Loves Park, an IHG Hotel are two great options.
How far in advance should I book my Winnebago County vacation?
It's difficult to pick the perfect time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available to compare up to 12 months in advance. If you're booking last minute, don't despair. Discounted prices appear from time to time within a few weeks of departure dates.
What should I know before booking a Winnebago County travel package?
Whether it's adventure or relaxation you're seeking, a Winnebago County vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Winnebago County Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to pick from worldwide. With such a big range of choice, finding the perfect carrier to whisk you away to Winnebago County shouldn't be hard.
If I'm not able to travel, can I cancel my Winnebago County vacation package?
It's good to know that you can cancel your Winnebago County booking if your plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.