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

An aerial view of a park with a lake, a road, and a bridge.
FlightsFlightsHotelsHotels

Rockford

Rockford

Top Winnebago County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,110, price is now CA $797 per person
CA $797
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,079, price is now CA $1,318 per person
CA $1,318
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
All good

Reviewed on Nov 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,806, price is now CA $1,260 per person
CA $1,260
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $1,944, price is now CA $1,379 per person
CA $1,379
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,256, price is now CA $2,339 per person
CA $2,339
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful

Reviewed on Nov 10, 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 $97 per night from Dec 6 to Dec 7
CA $97
CA $111 total
Dec 6 - Dec 7
includes taxes & fees
9/10 Wonderful! (1,818 reviews)
"No problems, nothing outstanding, but 1 night just to sleep for work, everything was good."

Reviewed on Nov 11, 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 $126 per night from Nov 29 to Nov 30
CA $126
CA $144 total
Nov 29 - Nov 30
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"Staff was friendly, dinner was beautiful overlooking river"

Reviewed on Nov 12, 2026

Riverview Inn & Suites, an Ascend Collection Hotel
Holiday Inn Rockford(I-90&Rt 20/State St) by IHG

Holiday Inn Rockford(I-90&Rt 20/State St) by IHG

3 out of 5
7550 E State Street Rockford IL
Fully refundable
The price is CA $146 per night from Dec 13 to Dec 14
CA $146
CA $167 total
Dec 13 - Dec 14
includes taxes & fees
Holiday Inn Rockford(I-90&Rt 20/State St) by IHG
See all 382 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.
All Inclusive Vacations
All Inclusive Vacations
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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 $797. 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.

Stay near popular Winnebago County attractions

A waterfall cascading over rocks in a forested area with autumn foliage.

Anderson Japanese Gardens

8.6/10 (180 reviews)
Rockford’s iconic gardens may be in the heartland of America, but you’ll feel transported to Japan as you explore the winding paths, ponds and waterfalls.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.