Cheap Vacations in Jefferson County

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Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
Price was $433, price is now $332 per person
$332
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,081, price is now $678 per person
$678
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $802, price is now $573 per person
$573
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $854, price is now $623 per person
$623
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $666, price is now $486 per person
$486
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,027, price is now $763 per person
$763
per person
Nov 24 - Nov 26
found 7 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was $783, price is now $591 per person
$591
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $763, price is now $589 per person
$589
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
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 $789, price is now $610 per person
$610
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was $992, price is now $771 per person
$771
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)

3-night Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
Price was $433, price is now $332 per person
$332
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,081, price is now $678 per person
$678
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $802, price is now $573 per person
$573
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $854, price is now $623 per person
$623
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $666, price is now $486 per person
$486
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Price was $783, price is now $591 per person
$591
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was $789, price is now $610 per person
$610
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $533, price is now $414 per person
$414
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Price was $992, price is now $771 per person
$771
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Price was $997, price is now $777 per person
$777
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $655, price is now $513 per person
$513
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $886, price is now $699 per person
$699
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)

4-night Jefferson County vacations

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

Chicago Marriott Midway

3.5 out of 5
Price was $537, price is now $429 per person
$429
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $852, price is now $568 per person
$568
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was $666, price is now $487 per person
$487
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $848, price is now $633 per person
$633
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $898, price is now $681 per person
$681
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $760, price is now $578 per person
$578
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Price was $964, price is now $734 per person
$734
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Villa Christina

Villa Christina

3 out of 5
Price was $880, price is now $673 per person
$673
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was $825, price is now $633 per person
$633
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $637, price is now $499 per person
$499
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $562, price is now $444 per person
$444
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $1,061, price is now $849 per person
$849
per person
Nov 26 - Nov 30
found 14 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)

5-night Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $622, price is now $458 per person
$458
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,069, price is now $637 per person
$637
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $872, price is now $588 per person
$588
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Price was $883, price is now $631 per person
$631
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was $903, price is now $652 per person
$652
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Price was $914, price is now $670 per person
$670
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Price was $798, price is now $585 per person
$585
per person
Dec 13 - Dec 18
found 12 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $1,026, price is now $756 per person
$756
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Price was $799, price is now $591 per person
$591
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Price was $789, price is now $585 per person
$585
per person
Dec 13 - Dec 18
found 12 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $783, price is now $592 per person
$592
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Price was $792, price is now $600 per person
$600
per person
Dec 7 - Dec 12
found 19 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)

6-7 night Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Price was $751, price is now $751 per person
$751
per person
Nov 25 - Dec 2
found 1 hour ago
Roundtrip flight included
Seattle (SEA) to Chicago (ORD)
Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Price was $1,084, price is now $849 per person
$849
per person
Nov 25 - Dec 2
found 1 hour ago
Roundtrip flight included
Seattle (SEA) to Chicago (ORD)
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Price was $1,565, price is now $1,565 per person
$1,565
per person
Nov 25 - Dec 2
found 1 hour ago
Roundtrip flight included
Seattle (SEA) to Chicago (ORD)

Top places to visit in Jefferson County

A stone bridge with multiple arches over a river, surrounded by trees and grassy areas.
FlightsFlightsHotelsHotels

Watertown

Watertown

Flight deals to Jefferson County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Jul 13 - Thu, Jul 15
ATL
Atlanta
MSN
Madison
$282 Roundtrip, found 4 days ago
$282
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Jul 13 from Atlanta to Madison, returning Thu, Jul 15, priced at $282 found 4 days ago
Tue, Nov 10 - Tue, Nov 17
BOS
Boston
MSN
Madison
$298 Roundtrip, found 2 days ago
$298
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Nov 10 from Boston to Madison, returning Tue, Nov 17, priced at $298 found 2 days ago
Fri, Oct 30 - Sun, Nov 1
LAS
Las Vegas
MSN
Madison
$325 Roundtrip, found 6 days ago
$325
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Fri, Oct 30 from Las Vegas to Madison, returning Sun, Nov 1, priced at $325 found 6 days ago

Top rated hotels for your Jefferson County vacation

Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Free Cancellation
26.83 mi from city center
$44 nightly
The price is $51 total per night
$51 total
Nov 8 - Nov 9
Total with taxes and fees
When you stay at Motel 6 Madison, WI - East in Madison, you'll be in a shopping district, within a 15-minute drive of University of Wisconsin-Madison and East Towne Mall.
Pet friendly
Parking included
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
7036 Grand Geneva Wy Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
33.85 mi from city center
$272 nightly
The price is $304 total per night
$304 total
Nov 24 - Nov 25
Total with taxes and fees
Located in Lake Geneva, Grand Geneva Resort & Spa is on a lake, a 4-minute drive from The Mountain Top at Grand Geneva Resort and 7 minutes from Geneva Lake.
Pool
Hot Tub
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
34.41 mi from city center
$172 nightly
The price is $192 total per night
$192 total
Nov 24 - Nov 25
Total with taxes and fees
When you stay at Timber Ridge Lodge and Waterpark in Lake Geneva, you'll be in a regional park, within a 15-minute drive of Geneva Lake and Lake Como.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Jefferson County
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.