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 Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Price was €898, price is now €706 per person
€706
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (3,812 reviews)
Clean room and good stuff

Reviewed on 7 Sep 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,559, price is now €1,040 per person
€1,040
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service

Reviewed on 4 Sep 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,387, price is now €1,035 per person
€1,035
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The hotel was beautiful and clean. In a great location and great views.

Reviewed on 7 Sep 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,378, price is now €1,076 per person
€1,076
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
Beautiful property close to the Fulton Market and night life. The room was eccentric in a way that made our stay cool. It was clean and stocked with a bar & snacks for additional purchase. We enjoyed the Rooftop Cinema on the 6th floor, it was playing my favorite movie! And the restaurant Fora had a delicious breakfast. We definitely recommend this property.

Reviewed on 6 Sep 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,304, price is now €1,021 per person
€1,021
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (347 reviews)
Pool area was great

Reviewed on 4 Sep 2025

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 €74 per night from 10 Sept to 11 Sept
€74
10 Sept - 11 Sept
includes taxes & fees
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 €94 per night from 14 Sept to 15 Sept
€94
14 Sept - 15 Sept
includes taxes & fees
Holiday Inn Rockford by IHG
Econo Lodge

Econo Lodge

2 out of 5
7712 Potawatomi Trail, Rockford, IL
Fully refundableReserve now, pay when you stay
The price is €57 per night from 14 Sept to 15 Sept
€57
14 Sept - 15 Sept
includes taxes & fees
Econo Lodge
See all 351 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 €706. 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.