Winnebago County Vacations & Trips from ￥186,871

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Winnebago County Vacation Packages

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 ￥237,250, price is now ￥186,871 per person
￥186,871
per person
Feb 22 - Feb 27
found 2 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Location is the best.

Reviewed on Dec 23, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥368,052, price is now ￥259,596 per person
￥259,596
per person
Feb 22 - Feb 27
found 2 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Loved it here and would stay again! Everything was perfect!

Reviewed on Dec 21, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥488,478, price is now ￥388,768 per person
￥388,768
per person
Jan 22 - Jan 27
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Service and clean room - paying attention to the details

Reviewed on Dec 22, 2025

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
Downtown Chicago
Price was ￥334,192, price is now ￥268,350 per person
￥268,350
per person
Jan 22 - Jan 27
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The room was spotless and the bed super comfy. The staff was very helpful and extremely courteous.

Reviewed on Dec 15, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥363,475, price is now ￥308,896 per person
￥308,896
per person
Jan 22 - Jan 27
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
It was ok. Wouldn’t want to stay longer than a night. Food was pretty bad, room cramped

Reviewed on Dec 23, 2025

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 ￥10,544 per night from Jan 7 to Jan 8
￥10,544
￥12,018 total
Jan 7 - Jan 8, 2026
includes taxes & fees
9/10 Wonderful! (1,442 reviews)
This hotel is lovely! It’s clean, comfortable, and quiet. The staff were so nice and helpful. The breakfast was delicious and had lots of choices. We’re definitely coming back!

Reviewed on Dec 16, 2025

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 ￥12,936 per night from Dec 30 to Dec 31
￥12,936
￥14,745 total
Dec 30 - Dec 31
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Clean hotel. Friendly staff.

Reviewed on Dec 16, 2025

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
Fully refundableReserve now, pay when you stay
The price is ￥20,457 per night from Dec 29 to Dec 30
￥20,457
￥23,317 total
Dec 29 - Dec 30
includes taxes & fees
9.4/10 Exceptional! (893 reviews)
This hotel is nice and clean definitely would recommend anyone in Rockford to stay here! Rooms 10/10 . The staff was very helpful and friendly. The housekeeping comes quick. And the breakfast 10/10.

Reviewed on Dec 21, 2025

Embassy Suites by Hilton Rockford Riverfront
See all 356 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 vacation package cost?
We make it easy to see the world, with Winnebago County packages starting from as low as ￥186,871. 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.