Jefferson County Vacations & Trips from ￥287,961

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The Latest Jefferson 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 ￥336,865, price is now ￥287,961 per person
￥287,961
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,914 reviews)
Very nice ,very clean ,frienly staff, fresh breakfast

Reviewed on Apr 28, 2026

Hampton Inn Chicago Downtown/N Loop/Michigan Ave

Hampton Inn Chicago Downtown/N Loop/Michigan Ave

3 out of 5
Downtown Chicago
Price was ￥594,252, price is now ￥499,868 per person
￥499,868
per person
Jun 8 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (1,170 reviews)
Everything was 10/10

Reviewed on Apr 27, 2026

Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown

3 out of 5
Downtown Chicago
Price was ￥574,171, price is now ￥485,269 per person
￥485,269
per person
Jun 8 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,178 reviews)
Breakfast was very good. Rooms are pretty clean, they changed sheets daily. Overall good experience

Reviewed on Apr 25, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥369,741, price is now ￥314,786 per person
￥314,786
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (466 reviews)
Great spot for small families that may need a space for than just sleeping

Reviewed on Apr 27, 2026

Freehand Chicago

Freehand Chicago

4 out of 5
Downtown Chicago
Price was ￥495,214, price is now ￥429,018 per person
￥429,018
per person
Jun 8 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8/10 Very Good! (2,893 reviews)
The property was located literally in the center of downtown. Everything was accessible and walkable. All the major attractions were within 2 to 5 km of what Chicago is really advertise to be. Staff was great open bar was amazing. Vibes were nice and other guests were on the same vibe levels.

Reviewed on Apr 28, 2026

Jefferson County Hotel Deals

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is ￥14,554 per night from Apr 30 to May 1
￥14,554
￥20,053 total
Apr 30 - May 1
includes taxes & fees
9.2/10 Wonderful! (1,331 reviews)
Hotel was very nice and convenient location

Reviewed on Apr 28, 2026

Harbor Shores on Lake Geneva
The Cove Of Lake Geneva

The Cove Of Lake Geneva

3.5 out of 5
111 Center St Lake Geneva WI
9/10 Wonderful! (1,449 reviews)
The pool and hot tub were nice and big. The staff was very friendly and helpful. Having two parking passes was great since this was a meetup with family. The location was ideal - easy walking to shopping, restaurants etc

Reviewed on Apr 26, 2026

Get rates
The Cove Of Lake Geneva
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is ￥22,922 per night from May 12 to May 13
￥22,922
￥31,786 total
May 12 - May 13
includes taxes & fees
8.6/10 Excellent! (3,240 reviews)
Whole thing was a nice experience my family’s first time there very nice property

Reviewed on Apr 28, 2026

Timber Ridge Lodge and Waterpark
See all 1,196 properties in Jefferson 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 Jefferson County vacation package cost?
Custom make your Jefferson County package from just ￥287,961. Choose from any combination of rental cars, flights and hotels to craft the getaway you've been dreaming about for ages. Be sure to add on a few experiences or tours!
How do I get a cheap travel package to Jefferson County?
Track down flights that fit your busy schedule, add a hotel room to your booking and watch the savings rack up with a Jefferson County vacation package. It's that easy! From hotels and flights to tours and rental cars, Expedia makes traveling cheaply a cinch. And with more than 550 air carriers and 1,000,000 hotel options throughout the world to choose from, you won't be short of choice.
What are the top hotels in Jefferson County?
When it comes to properties in Fort Atkinson, Comfort Suites Johnson Creek Conference Center and Best Western Watertown are two popular options. If you're also spending time in Watertown, AmericInn by Wyndham Fort Atkinson and Days Inn by Wyndham Johnson Creek will make you feel right at home.
How far in advance should I book my Jefferson County vacation?
Reserving your flights early with Expedia means one less thing to have to worry about. Most carriers advertise tickets up to 12 months prior to departure dates. This is typically the cheapest time to book. If circumstances have left you booking late, incredible deals to Jefferson County sometimes become available just a few weeks before departure.
What does an Expedia Jefferson County travel package include?
Hotels, flights and a cool car for all your fun road trip adventures. Simply select your preferred bundle and gain access to great discounts. Once you've made your booking, add on a few tours and experiences and watch your savings grow. When it comes to creating your Jefferson County vacation, you're in charge!
What should I know before booking a Jefferson County travel package?
So many places to go, so many things to see. With a travel package, you'll be able to cross more of them off your list. Bundle your flights, hotels and rental cars and score big savings.
Can I choose my airline with a Jefferson County Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Jefferson County vacation package?
Don't worry if you're rethinking your Jefferson County vacation package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that life can throw the occasional spanner in the works, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.