Jefferson County Holidays

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    Save up to S$134 when you book a flight and hotel together*

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Jefferson County Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Price was S$907, price is now S$691 per person
S$691
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
5.8/10 (215 reviews)
Friendly front desk, easy and convenient for my overnight layover in Chicago

Reviewed on 7 Nov, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was S$2,021, price is now S$1,404 per person
S$1,404
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Great stay fir early flights

Reviewed on 8 Jan, 2026

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was S$1,516, price is now S$1,165 per person
S$1,165
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The room and staff were extremely friendly, but I specifically requested a room with a bath so I could soak my leg after a surgery. There was absolutely no water pressure when it came to the bath and the drain wouldn't close all the way. For how much I paid I feel like I should have been able to take a bath

Reviewed on 8 Dec, 2025

DoubleTree by Hilton Chicago - Oak Brook

DoubleTree by Hilton Chicago - Oak Brook

4 out of 5
Price was S$1,245, price is now S$957 per person
S$957
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
6.8/10 (1,000 reviews)
Hotel is old and showing its age. Rooms are old too. Few amenities etc.

Reviewed on 6 Jan, 2026

Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Price was S$984, price is now S$757 per person
S$757
per person
28 Mar - 4 Apr
found 1 day ago
Return direct flight included
Syracuse (SYR) to Chicago (ORD)
6.2/10 (365 reviews)
dated, lamp shade missing, overall dumpy place

Reviewed on 19 Dec, 2025

Top hotels in Jefferson County

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 S$157 per night from 13 Jan to 14 Jan
S$157
13 Jan - 14 Jan
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
Courteous staff, clean room

Reviewed on 11 Jan, 2026

DoubleTree by Hilton Madison East
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 S$252 per night from 20 Jan to 21 Jan
S$252
20 Jan - 21 Jan
includes taxes & fees
8.6/10 Excellent! (3,101 reviews)
The room was excellent. No complaints about the stay, only docking a star because it took 30 minutes to check in due to their being one person at check in. We were glad we arrived to check in early because when 4:00 pm rolled around, the line to check in was 3 times longer. If they could staff check ...

Reviewed on 7 Jan, 2026

Timber Ridge Lodge and Waterpark
Lodge Geneva National

Lodge Geneva National

4 out of 5
W4240 WI-50 Lake Geneva WI
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,369 reviews)
it was great .. everything was as seen on the web site .. Santa pop up very cool .. staff was amazing !!

Reviewed on 5 Jan, 2026

Get rates
Lodge Geneva National
See all 1,184 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 holiday package cost?
Custom make your Jefferson County package from just S$691. 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 holiday package. It's that easy! From hotels and flights to tours and rental cars, Expedia makes travelling 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 Centre 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 holiday?
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 holiday, 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 holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our holiday 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 holiday package?
Don't worry if you're rethinking your Jefferson County holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.