Winnebago Vacation Packages 2026 from ￥348,264

Add multiple dates or destinations

Plan, book, travel with confidence
Better together
Save up to ￥109,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Winnebago Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Aug 23 - Aug 27
Level Chicago - River North + Flight
Downtown Chicago
4 nights
4.0 star property
9.2/10 - Wonderful (1,038 reviews)
"One of the best places we’ve ever stayed. We had an amazing view of downtown Chicago from our floor, and our executive suite was clean and comfortable. We thoroughly enjoyed our stay and would definitely come back. The customer service and our room were excellent."
Reviewed July 20, 2026
Roundtrip • Tokyo (TYO) - Chicago (ORD)
NRT - ORD • 1 stop ORD - NRT • 1 stop
~~￥411,575~~
￥348,264
per traveler
found 1 day ago
Level Chicago - River North
Oct 10 - Oct 13
Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago
3 nights
4.0 star property
9.4/10 - Exceptional (2,609 reviews)
Roundtrip • Fukuoka (FUK) - Chicago (ORD)
FUK - ORD • 1 stop ORD - FUK • 2 stops
~~￥484,061~~
￥399,850
per traveler
found 1 day ago
Sable at Navy Pier Chicago, Curio Collection by Hilton
Aug 23 - Aug 27
Hotel Riu Plaza Chicago + Flight
Downtown Chicago
4 nights
4.0 star property
9.4/10 - Exceptional (4,770 reviews)
"Very well located hotel, just steps away from the magnificent mile. Very nice breakfast buffet. Helpful and attentive staff. Comfortable room."
Reviewed July 21, 2026
Roundtrip • Tokyo (TYO) - Chicago (ORD)
NRT - ORD • 1 stop ORD - NRT • 1 stop
~~￥424,244~~
￥351,057
per traveler
found 1 day ago
Hotel Riu Plaza Chicago
Oct 10 - Oct 13
Eurostars Magnificent Mile + Flight
Downtown Chicago
3 nights
4.0 star property
9.0/10 - Wonderful (3,754 reviews)
"The staff and breakfast was amazing! We had a corner king room and it was ok but definitely needs to be updated. The toilet paper holder was hanging off the wall, corners near the baseboard were crumbly with wall debris and it ooked like needed to be repaired. The fridge worked but the top of it was completely broken off. There is a blacony but the door to it was locked, so laying in bed you are looking out at a cement block. The curtains you have to lift by string and they were all ripped..."
Reviewed July 21, 2026
Roundtrip • Fukuoka (FUK) - Chicago (ORD)
FUK - ORD • 1 stop ORD - FUK • 2 stops
~~￥495,654~~
￥417,180
per traveler
found 1 day ago
Eurostars Magnificent Mile
Aug 23 - Aug 27
Trump International Hotel & Tower Chicago + Flight
Downtown Chicago
4 nights
5.0 star property
9.6/10 - Exceptional (1,951 reviews)
Roundtrip • Tokyo (TYO) - Chicago (ORD)
NRT - ORD • 1 stop ORD - NRT • 1 stop
~~￥502,806~~
￥427,414
per traveler
found 1 day ago
Trump International Hotel & Tower Chicago

Winnebago Hotel Deals

Embassy Suites by Hilton Rockford Riverfront

11.7 km from Winnebago

￥25,732 total

includes taxes & fees

Aug 6 - Aug 7

Alpine Inn Rockford

17.2 km from Winnebago

"We booked a group of five rooms for two nights. Of the five rooms, during the first night and morning we found bed bugs in two of them and promptly checked out and scrambled to find another hotel in the area. The front staff was very kind and understanding. I hope the management will send in a crew to check their rooms."

￥10,829 total

includes taxes & fees

Aug 16 - Aug 17