Jefferson County Holidays

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Jefferson County Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Downtown Chicago
Price was S$2,686, price is now S$2,396 per person
S$2,396
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,197 reviews)
Room was clean and everything was good. Front desk could be a little more friendly especially one of the afternoon girls.

Reviewed on 5 Mar, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was S$3,187, price is now S$2,412 per person
S$2,412
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) 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 9 Mar, 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was S$2,970, price is now S$2,593 per person
S$2,593
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.4/10 Exceptional! (1,993 reviews)
Friendly staff, very helpful and approachable. The rooms were clean and I pay attention to these things, the room was immaculate upon checkin. I appreciated the lovely in-room espresso machine too. Good breakfast from the onsite restaurant. There’s also coffee, donuts and bubble tea cafes right across Michigan ave. Close to the art institute, the orange and red lines, and more I am sure. Highly recommend the Arlo for your stay in downtown Chicago.

Reviewed on 9 Mar, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Price was S$2,896, price is now S$2,583 per person
S$2,583
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 9 Mar, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was S$2,908, price is now S$2,595 per person
S$2,595
per person
29 May - 31 May
found 1 hour ago
Return flight included
Singapore (SIN) 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 9 Mar, 2026

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Top hotels in Jefferson County

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 S$248 per night from 17 Mar to 18 Mar
S$248
17 Mar - 18 Mar
includes taxes & fees
8.6/10 Excellent! (3,166 reviews)
Yes but very crowded weekend stay

Reviewed on 8 Mar, 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 S$156 per night from 15 Mar to 16 Mar
S$156
15 Mar - 16 Mar
includes taxes & fees
9.4/10 Exceptional! (1,017 reviews)
Fabulous

Reviewed on 9 Mar, 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 S$174 per night from 11 Mar to 12 Mar
S$174
11 Mar - 12 Mar
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 9 Mar, 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 holiday package cost?
Custom make your Jefferson County package from just S$2,396. 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.