Jefferson County Vacations & Trips from ￥368,190

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Jefferson County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥495,657, price is now ￥368,190 per person
￥368,190
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (414 reviews)
This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back.

Reviewed on Mar 8, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥640,345, price is now ￥417,190 per person
￥417,190
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Great location right off of Michigan Ave. They have a very good breakfast, that included almost everything you could want. It was very popular and packed with people. One negative, it felt like it was a cafeteria and not a relaxing place to sit down, relax and enjoy.

Reviewed on Mar 9, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥624,805, price is now ￥463,414 per person
￥463,414
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
Every thing was amazing the staff was friendly and helpful shops and everything was close by I loved it thank you again

Reviewed on Mar 9, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥653,618, price is now ￥488,172 per person
￥488,172
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,839 reviews)
One of the best hotels I've ever stayed at

Reviewed on Mar 10, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥573,854, price is now ￥430,932 per person
￥430,932
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Great stay. Staff was slightly inattentive at times with requests for things to room.

Reviewed on Mar 9, 2026

Jefferson County Hotel Deals

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
The price is ￥21,973 per night from Mar 17 to Mar 18
￥21,973
￥30,659 total
Mar 17 - Mar 18
includes taxes & fees
8.6/10 Excellent! (3,166 reviews)
Yes but very crowded weekend stay

Reviewed on Mar 8, 2026

Timber Ridge Lodge and Waterpark
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is ￥16,690 per night from Mar 29 to Mar 30
￥16,690
￥19,276 total
Mar 29 - Mar 30
includes taxes & fees
9.4/10 Exceptional! (1,017 reviews)
Fabulous

Reviewed on Mar 9, 2026

DoubleTree by Hilton Madison East
The Cove Of Lake Geneva

The Cove Of Lake Geneva

3.5 out of 5
111 Center St Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is ￥15,462 per night from Mar 12 to Mar 13
￥15,462
￥21,494 total
Mar 12 - Mar 13
includes taxes & fees
9/10 Wonderful! (1,411 reviews)
Great place to stay at! It’s walking distance to downtown and the Lake is right across the street from the hotel!

Reviewed on Mar 9, 2026

The Cove Of Lake Geneva
See all 1,199 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 ￥368,190. 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.