Winnebago County Vacations & Trips from ￥314,217

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The Latest Winnebago County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥374,696, price is now ￥314,217 per person
￥314,217
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Clean perfect view rooms. Convenient to enjoy navy pier.

Reviewed on Mar 28, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥546,288, price is now ￥399,292 per person
￥399,292
per person
Apr 29 - May 5
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was very nice. The room was very clean, amenities great, and staff friendly. Also, a great location less than a block off of Michigan Ave. Perfect for shopping! I would definitely stay here again.

Reviewed on Mar 28, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥446,148, price is now ￥381,583 per person
￥381,583
per person
Apr 29 - May 5
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
This was perfect for a night in the city! Great all around and will stay again. Great staff at check-in!

Reviewed on Mar 27, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥443,372, price is now ￥382,310 per person
￥382,310
per person
Apr 29 - May 5
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Great room and staff

Reviewed on Mar 28, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was ￥369,545, price is now ￥319,390 per person
￥319,390
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Our stay at the Thompson was perfect! Very friendly staff! I strongly recommend a corner room with the city view on the highest floor that you can and trust me you can’t miss

Reviewed on Mar 27, 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 ￥13,331 per night from Apr 5 to Apr 6
￥13,331
￥15,196 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,564 reviews)
Breakfast was good

Reviewed on Mar 28, 2026

Baymont by Wyndham Rockford
Riverview Inn & Suites, an Ascend Collection Hotel

Riverview Inn & Suites, an Ascend Collection Hotel

3 out of 5
700 W Riverside Blvd Rockford IL
Fully refundable
The price is ￥16,409 per night from Apr 5 to Apr 6
￥16,409
￥18,703 total
Apr 5 - Apr 6
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Everything was great

Reviewed on Mar 22, 2026

Riverview Inn & Suites, an Ascend Collection Hotel
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 ￥19,558 per night from Apr 29 to Apr 30
￥19,558
￥22,291 total
Apr 29 - Apr 30
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
When booking this room I had specifically asked if there was a hot tub and they had said yes but there is not one. Also had asked if they do rides to the casino also said yes but they don’t. Waited in line for a long time on checking into hotel, need more then one person during “peak hours” otherwise ...

Reviewed on Mar 27, 2026

Holiday Inn Rockford by IHG
See all 362 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 ￥314,217. 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.