Jefferson County Vacations & Trips from ￥289,144

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The Latest Jefferson County Vacation Packages

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

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ￥366,794, price is now ￥289,144 per person
￥289,144
per person
Nov 12 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
The room was clean and comfortable and the restaurant was good.

Reviewed on Oct 1, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥419,726, price is now ￥294,296 per person
￥294,296
per person
Nov 12 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
The facility is new, clean, hygienic (no carpet), quiet (thick walls). The bathroom is sophisticated. European style breakfast is phenomenal and free. Lobby cocktail bar and rooftop restaurant are nostalgic. Elevators are prompt. What else can I expect? It was outstanding.

Reviewed on Oct 5, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥400,376, price is now ￥319,842 per person
￥319,842
per person
Nov 12 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (352 reviews)
Everything was wonder beside my shower head it was leaking bad

Reviewed on Sep 30, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥409,925, price is now ￥328,220 per person
￥328,220
per person
Nov 12 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
Nice river view, very comfortable beds and linens, central to shopping, restaurants & the beautiful river walk. Great stay for first time in Chicago.

Reviewed on Oct 4, 2025

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 ￥444,085, price is now ￥365,270 per person
￥365,270
per person
Nov 12 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
We stayed at The Sable last weekend and we have a serious complaint: our own home now feels deeply, deeply inadequate. The views of the city were so stunning, they ruined my ability to enjoy the view of my neighbor's fence. And the service was so fantastic, I'm now struggling to readjust to the real world. To make matters worse, the bars and restaurants downstairs were way too convenient and fun—it’s a real problem when the best spot in the city is right in your lobby. It's a dangerous place that sets unrealistic expectations for daily life. 10/10, would have my reality ruined again.

Reviewed on Oct 2, 2025

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
Fully refundableReserve now, pay when you stay
The price is ￥20,647 per night from Oct 15 to Oct 16
￥20,647
￥28,623 total
Oct 15 - Oct 16
includes taxes & fees
8.6/10 Excellent! (3,001 reviews)
"Overall, solid stay with my family. The water park is cool, but not a whole lot to do for all day. You only end up spending a couple hours before you’re bored. Cleanliness of the rooms is alright but the pools could use some cleaning on the bottom. Good time with my family overall though! We liked ..."

Reviewed on Oct 1, 2025

Timber Ridge Lodge and Waterpark
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd, Madison, WI
Fully refundableReserve now, pay when you stay
The price is ￥5,971 per night from Nov 2 to Nov 3
￥5,971
￥6,896 total
Nov 2 - Nov 3
includes taxes & fees
6.6/10 (1,000 reviews)
"Nice"

Reviewed on Sep 29, 2025

Motel 6 Madison, WI - East
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 ￥17,424 per night from Oct 12 to Oct 13
￥17,424
￥20,125 total
Oct 12 - Oct 13
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Very nice"

Reviewed on Oct 1, 2025

DoubleTree by Hilton Madison East
See all 1,218 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 ￥289,144. 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.