Winnebago County Vacations & Trips from ￥242,386

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

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

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Winnebago County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
Downtown Chicago
Price was ￥272,044, price is now ￥242,386 per person
￥242,386
per person
Oct 5 - Oct 10
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,825 reviews)
It was just decent.

Reviewed on Sep 5, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was ￥481,088, price is now ￥378,840 per person
￥378,840
per person
Oct 5 - Oct 10
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug 31, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ￥328,690, price is now ￥269,942 per person
￥269,942
per person
Oct 5 - Oct 10
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (286 reviews)
The staff were excellent

Reviewed on Aug 21, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was ￥542,698, price is now ￥463,804 per person
￥463,804
per person
Oct 5 - Oct 10
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug 12, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥519,605, price is now ￥452,942 per person
￥452,942
per person
Oct 5 - Oct 10
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Truly enjoyed our experience at this hotel. Staff very kind and helpful. Location was perfect because of its location on the Magnificent Mile and getting to other areas of interest in Chicago. The room was very comfortable and clean. Definitely recommend this hotel!

Reviewed on Sep 4, 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 ￥11,358 per night from Sep 10 to Sep 11
￥11,358
￥12,947 total
Sep 10 - Sep 11
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 ￥14,657 per night from Sep 14 to Sep 15
￥14,657
￥16,707 total
Sep 14 - Sep 15
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 ￥8,683 per night from Sep 14 to Sep 15
￥8,683
￥9,899 total
Sep 14 - Sep 15
includes taxes & fees
Econo Lodge
See all 347 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 ￥242,386. 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.