Winnebago County Holidays

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Top destinations in Winnebago County

Rockford featuring general coastal views and a city
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Rockford

Rockford

Top Flight + Hotel Deals in Winnebago County

Price found within the past 48 hours. Click for updated prices.
Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was €1,027, price is now €877 per person
€877
per person
11 Apr - 16 Apr
found 4 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (1,002 reviews)
Second time staying here.

Reviewed on 17 Feb 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was €1,332, price is now €1,065 per person
€1,065
per person
11 Apr - 16 Apr
found 4 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (2,217 reviews)
Had a steak and ribs at the restaurant downstairs and both were delicious

Reviewed on 1 Mar 2026

Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning

Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning

3 out of 5
Price was €2,291, price is now €1,856 per person
€1,856
per person
11 Apr - 16 Apr
found 4 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
No reviews
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4 out of 5
Downtown Chicago
Price was €1,193, price is now €1,012 per person
€1,012
per person
11 Apr - 16 Apr
found 4 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,385 reviews)
We chose this hotel thinking it would be a short drive/uber to the palace theater. Nope it was a 5 block walk that was wonderfully well lit. Many different places to eat close by.

Reviewed on 6 Mar 2026

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was €1,066, price is now €904 per person
€904
per person
11 Apr - 16 Apr
found 4 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
Center of the Loop, easy walk to a majority of landmark sights.

Reviewed on 5 Mar 2026

Top hotels in Winnebago County

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 €70 per night from 5 Apr to 6 Apr
€70
5 Apr - 6 Apr
includes taxes & fees
9/10 Wonderful! (1,544 reviews)
The stay was well worth the money

Reviewed on 7 Mar 2026

Baymont by Wyndham Rockford
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 €108 per night from 5 Apr to 6 Apr
€108
5 Apr - 6 Apr
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
Clean

Reviewed on 3 Mar 2026

Holiday Inn Rockford by IHG
Embassy Suites by Hilton Rockford Riverfront

Embassy Suites by Hilton Rockford Riverfront

3.5 out of 5
416 S Main Street Rockford IL
The price is €152 per night from 22 Mar to 23 Mar
€152
22 Mar - 23 Mar
includes taxes & fees
9.4/10 Exceptional! (944 reviews)
Great location

Reviewed on 5 Mar 2026

Embassy Suites by Hilton Rockford Riverfront
See all 366 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.

Frequently asked questions

How much does a Winnebago County holiday package cost?
We make it easy to see the world, with Winnebago County packages starting from as low as €877. You'll have the flexibility to combine your favourite 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 holiday 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 holiday 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 travellers 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 holiday?
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 holiday package lets you organise 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 holiday 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 holiday 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.