Winnebago County Vacations & Trips from ￥309,498

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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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥421,916, price is now ￥309,498 per person
￥309,498
per person
Apr 30 - May 6
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥481,245, price is now ￥312,264 per person
￥312,264
per person
Apr 30 - May 6
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Everything was amazing, specially the breakfast buffet.

Reviewed on Feb 7, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥579,324, price is now ￥388,004 per person
￥388,004
per person
Apr 30 - May 6
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥478,193, price is now ￥332,532 per person
￥332,532
per person
Apr 30 - May 6
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥543,532, price is now ￥396,136 per person
￥396,136
per person
Apr 30 - May 6
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.

Reviewed on Feb 3, 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 ￥10,037 per night from Feb 26 to Feb 27
￥10,037
￥11,440 total
Feb 26 - Feb 27
includes taxes & fees
9/10 Wonderful! (1,494 reviews)
The room was one of the cleanest I have ever stayed in and so quiet. The front desk was so friendly and helpful. We would definitely come back again. Thank you for the perfect stay!!

Reviewed on Jan 30, 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 ￥13,364 per night from Feb 15 to Feb 16
￥13,364
￥15,232 total
Feb 15 - Feb 16
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
The hotel was nice, really liked the attached restaurant. The hot water was luke warm at best. Plan ahead for a hot shower.

Reviewed on Jan 24, 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
Fully refundableReserve now, pay when you stay
The price is ￥23,012 per night from Feb 17 to Feb 18
￥23,012
￥26,229 total
Feb 17 - Feb 18
includes taxes & fees
9.4/10 Exceptional! (916 reviews)
Room was clean and staff was excellent.

Reviewed on Feb 1, 2026

Embassy Suites by Hilton Rockford Riverfront
See all 367 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 ￥309,498. 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.