Cheap Vacations in Jefferson County

Choose two or more items and save on your trip:

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
Downtown Chicago
Price was $622, price is now $458 per person
$458
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,069, price is now $637 per person
$637
per person
Dec 7 - Dec 12
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
Downtown Chicago
Save 100% on your flight
Price was $872, price is now $588 per person
$588
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,065, price is now $753 per person
$753
per person
Dec 7 - Dec 12
found 4 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Destination Geneva National

Destination Geneva National

4 out of 5
Save 100% on your flight
Price was $1,152, price is now $818 per person
$818
per person
Dec 4 - Dec 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was $883, price is now $631 per person
$631
per person
Dec 7 - Dec 12
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
Downtown Chicago
Price was $903, price is now $652 per person
$652
per person
Dec 7 - Dec 12
found 1 day 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 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Villa Christina

Villa Christina

3 out of 5
Greater Grand Crossing
Price was $1,115, price is now $819 per person
$819
per person
Nov 26 - Nov 30
found 4 hours 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
Downtown Chicago
Price was $1,026, price is now $756 per person
$756
per person
Dec 7 - Dec 12
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.
The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

The RIVVY, Chicago Downtown, a Tribute Portfolio Hotel

4 out of 5
Price was $562, price is now $477 per person
$477
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Villa Christina

Villa Christina

3 out of 5
Price was $982, price is now $722 per person
$722
per person
Nov 27 - Nov 30
found 4 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $836, price is now $641 per person
$641
per person
Dec 19 - Dec 22
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Price was $639, price is now $492 per person
$492
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Price was $1,014, price is now $795 per person
$795
per person
Nov 27 - Nov 30
found 4 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
Price was $1,015, price is now $807 per person
$807
per person
Dec 19 - Dec 22
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Price was $601, price is now $498 per person
$498
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Price was $629, price is now $523 per person
$523
per person
Dec 11 - Dec 14
found 10 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $784, price is now $656 per person
$656
per person
Nov 25 - Nov 28
found 2 hours ago
Roundtrip flight included
Washington (DCA) to Chicago (ORD)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Price was $649, price is now $547 per person
$547
per person
Dec 18 - Dec 21
found 4 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
Price was $561, price is now $480 per person
$480
per person
Dec 4 - Dec 7
found 18 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

4 out of 5
Price was $653, price is now $559 per person
$559
per person
Dec 2 - Dec 5
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

4-night Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
Price was $592, price is now $481 per person
$481
per person
Dec 8 - Dec 12
found 15 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Villa Christina

Villa Christina

3 out of 5
Price was $1,115, price is now $819 per person
$819
per person
Nov 26 - Nov 30
found 4 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Price was $756, price is now $560 per person
$560
per person
Dec 8 - Dec 12
found 15 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Price was $1,003, price is now $758 per person
$758
per person
Dec 16 - Dec 20
found 16 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was $1,614, price is now $1,227 per person
$1,227
per person
Dec 16 - Dec 20
found 16 hours ago
Roundtrip non-stop 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 $774, price is now $598 per person
$598
per person
Dec 8 - Dec 12
found 15 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 $884, price is now $688 per person
$688
per person
Dec 16 - Dec 20
found 16 hours ago
Roundtrip non-stop 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 $855, price is now $667 per person
$667
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was $633, price is now $507 per person
$507
per person
Dec 8 - Dec 12
found 15 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Price was $743, price is now $603 per person
$603
per person
Dec 8 - Dec 12
found 15 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Price was $647, price is now $526 per person
$526
per person
Dec 8 - Dec 12
found 15 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Price was $668, price is now $550 per person
$550
per person
Dec 18 - Dec 22
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 1 day 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 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
Save 100% on your flight
Price was $872, price is now $588 per person
$588
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,065, price is now $753 per person
$753
per person
Dec 7 - Dec 12
found 4 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 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 $903, price is now $652 per person
$652
per person
Dec 7 - Dec 12
found 1 day 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 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 $1,026, price is now $756 per person
$756
per person
Dec 7 - Dec 12
found 1 day 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 1 day ago
Roundtrip flight included
Austin (AUS) 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 1 day 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 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
Price was $4,043, price is now $3,070 per person
$3,070
per person
Dec 7 - Dec 12
found 4 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was $850, price is now $616 per person
$616
per person
Dec 9 - Dec 16
found 10 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 $1,318, price is now $808 per person
$808
per person
Dec 9 - Dec 16
found 10 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 $1,006, price is now $655 per person
$655
per person
Dec 9 - Dec 16
found 10 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,286, price is now $862 per person
$862
per person
Dec 9 - Dec 16
found 10 hours 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
Save 100% on your flight
Price was $1,229, price is now $876 per person
$876
per person
Dec 9 - Dec 16
found 10 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
Save 100% on your flight
Price was $1,097, price is now $809 per person
$809
per person
Dec 9 - Dec 16
found 10 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,094, price is now $818 per person
$818
per person
Dec 9 - Dec 16
found 10 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 $1,015, price is now $771 per person
$771
per person
Dec 9 - Dec 16
found 10 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $1,048, price is now $805 per person
$805
per person
Dec 9 - Dec 16
found 10 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Price was $968, price is now $750 per person
$750
per person
Dec 9 - Dec 16
found 10 hours ago
Roundtrip flight included
Austin (AUS) 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 $792, price is now $617 per person
$617
per person
Dec 9 - Dec 16
found 10 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Price was $959, price is now $753 per person
$753
per person
Dec 9 - Dec 16
found 10 hours ago
Roundtrip flight included
Austin (AUS) 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 5 days ago
$282
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Tue, Jul 13 from Atlanta to Madison, returning Thu, Jul 15, priced at $282 found 5 days ago
Tue, Nov 10 - Tue, Nov 17
BOS
Boston
MSN
Madison
$298 Roundtrip, found 3 days ago
$298
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Nov 10 from Boston to Madison, returning Tue, Nov 17, priced at $298 found 3 days ago
Fri, Apr 2 - Mon, Apr 5
BOS
Boston
MSN
Madison
$408 Roundtrip, found 2 days ago
$408
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Fri, Apr 2 from Boston to Madison, returning Mon, Apr 5, priced at $408 found 2 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
$273 nightly
The price is $305 total per night
$305 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
$171 nightly
The price is $191 total per night
$191 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
View all properties
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.