Jefferson County Vacations & Trips from ￥322,754
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top destinations in Jefferson County
Fairfield
Brighton
Libertyville
Maharishi Vedic City
Batavia
Lockridge
Packwood
Pleasant Plain
The Latest Jefferson County Vacation Packages
- LondonHouse Chicago, Curio Collection by Hilton
Dec 24 - Dec 30LondonHouse Chicago, Curio Collection by Hilton + Flight
Downtown Chicago6 nights4.5 star property9.4/10 - Exceptional (3,896 reviews)Roundtrip • Tokyo (TYO) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥371,021￥322,754found 3 hours agoper traveler - Hotel Riu Plaza Chicago
Dec 24 - Dec 30Hotel Riu Plaza Chicago + Flight
Downtown Chicago6 nights4.0 star property9.4/10 - Exceptional (5,663 reviews)Roundtrip • Tokyo (TYO) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥440,563￥343,515found 3 hours agoper traveler - Eurostars Magnificent Mile
Dec 24 - Dec 30Eurostars Magnificent Mile + Flight
Downtown Chicago6 nights4.0 star property9.0/10 - Wonderful (3,991 reviews)"I would say the best part was the view from the 20th floor looking right at the Magnificent Mile! The windows from ceiling to floor were awesome! The view at night was amazing! Everything was AMAZING!!"Reviewed November 8, 2026Roundtrip • Tokyo (TYO) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥405,868￥332,054found 3 hours agoper traveler - Swissotel - Chicago
Dec 24 - Dec 30Swissotel - Chicago + Flight
Downtown Chicago6 nights4.5 star property9.0/10 - Wonderful (3,579 reviews)"Had an amazing time celebrating my wife’s birthday I will return ou room was so clean and had all the things that we needed"Reviewed November 8, 2026Roundtrip • Tokyo (TYO) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥397,070￥331,151found 3 hours agoper traveler - Kimpton Gray Hotel by IHG
Dec 24 - Dec 30Kimpton Gray Hotel by IHG + Flight
Downtown Chicago6 nights4.5 star property9.4/10 - Exceptional (1,005 reviews)Roundtrip • Tokyo (TYO) - Chicago (ORD)NRT - ORD • 1 stop ORD - NRT • 1 stop￥396,881￥331,043found 3 hours agoper traveler
Discover the most popular places to visit in Jefferson County
Jefferson County Hotel Deals
AmericInn by Wyndham Fairfield
AmericInn by Wyndham Fairfield
"Unfortunately, the television had cable that included nothing local. NO news, local info, etc. No regular channels. All together a big waste!!!"
Frequently Asked Questions
How much does a Jefferson County vacation package cost?
Custom make your Jefferson County package from a low ￥322,754. Choose from any combination of hotels, flights and rental cars to craft the getaway you've long been dreaming about. Don't forget to add on one or two experiences!
How do I get a cheap travel package to Jefferson County?
Bundle your hotel and flight bookings, add extras such as a rental car or activities, and save with a Jefferson County vacation package. You won't just score wonderful discounts on your getaway — you'll have plenty of choice within your reach too. When you book with Expedia, you'll have your pick of over 550 air carriers and 1,000,000 properties around the world. Your next big adventure starts right here, right now!
How far in advance should I book my Jefferson County vacation?
Get rewarded with the biggest variety and the lowest prices by booking your adventure to Jefferson County early. Air carriers generally sell tickets anywhere up to a year prior to departure, so start locking things in as soon as you can. That said, Expedia is committed to providing you with the best bargains around, so there's never a bad time to book your dream vacation!
What does an Expedia Jefferson County travel package include?
Packages include rental cars, hotels and flights, but you can mix and match them to create your ideal Jefferson County escape. You can also add on some experiences and activities once you've made your booking. You're the boss! When you combine your bookings with Expedia, you'll get access to discounts you won't find anywhere else.
What should I know before booking a Jefferson County travel package?
So many places to travel to, so many things to do. With a travel package, you'll be able to afford more of them. Bundle your hotels, flights and rental cars and enjoy big savings.
Can I choose my airline with a Jefferson County Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you sure can! Simply pick your preferred carrier and put together the perfect Jefferson County trip.
If I'm not able to travel, can I cancel my Jefferson County vacation package?
Whether it's your hotel, flight or rental car, yes, you can amend or cancel it. Booked your Jefferson County vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings older than that, you may incur a charge from your hotel, airline or car rental company. For more information, browse our Customer Service Portal. We're here to help you each step of the way.