
Winnebago County Vacations & Trips from ¥309,498
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.

Level Chicago – Old Town
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
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
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
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
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
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

Holiday Inn Rockford by IHG
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

Embassy Suites by Hilton Rockford Riverfront
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
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
