Winnebago County Vacations & Trips from ￥367,626

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The Latest Winnebago County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥501,426, price is now ￥367,626 per person
￥367,626
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Awesome stay!

Reviewed on Jul 10, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥728,116, price is now ￥544,748 per person
￥544,748
per person
Aug 31 - Sep 9
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on Jul 9, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥692,976, price is now ￥522,384 per person
￥522,384
per person
Aug 31 - Sep 9
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on Jul 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥654,872, price is now ￥496,616 per person
￥496,616
per person
Aug 31 - Sep 9
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on Jul 8, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥726,588, price is now ￥553,021 per person
￥553,021
per person
Aug 31 - Sep 9
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Mediocre all around and for the price point not worth it. Great location. But nothing else compelling. Food was only ok. Service was only ok. Nothing memorable. Will seek somewhere else next time.

Reviewed on Jul 8, 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 ￥14,612 per night from Aug 2 to Aug 3
￥14,612
￥16,655 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (1,701 reviews)
"Nice place to stay and was conveniently located to family in Belvidere."

Reviewed on Jul 10, 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 ￥16,423 per night from Aug 4 to Aug 5
￥16,423
￥18,719 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very Good! (1,012 reviews)
"We stay for day it was just nice"

Reviewed on Jul 9, 2026

Riverview Inn & Suites, an Ascend Collection Hotel
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 ￥20,636 per night from Aug 6 to Aug 7
￥20,636
￥23,522 total
Aug 6 - Aug 7
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
"extremely clean hotel and rooms"

Reviewed on Jul 7, 2026

Embassy Suites by Hilton Rockford Riverfront
See all 370 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 ￥367,626. 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.

Stay near popular Winnebago County attractions

A waterfall cascading over rocks in a forested area with autumn foliage.

Anderson Japanese Gardens

8.6/10 (180 reviews)
Rockford’s iconic gardens may be in the heartland of America, but you’ll feel transported to Japan as you explore the winding paths, ponds and waterfalls.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.