Cheap Vacations in Jefferson County

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Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was $595, price is now $473 per person
$473
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,142, price is now $700 per person
$700
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $809, price is now $547 per person
$547
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $851, price is now $620 per person
$620
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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
Save 100% on your flight
Price was $779, price is now $571 per person
$571
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,027, price is now $755 per person
$755
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,134, price is now $835 per person
$835
per person
Aug 28 - Aug 31
found 7 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,065, price is now $818 per person
$818
per person
Aug 27 - Aug 30
found 22 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $777, price is now $614 per person
$614
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Save 100% on your flight
Price was $1,918, price is now $1,521 per person
$1,521
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

3-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
Save 100% on your flight
Price was $809, price is now $547 per person
$547
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,142, price is now $700 per person
$700
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $851, price is now $620 per person
$620
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,000, price is now $729 per person
$729
per person
Sep 3 - Sep 6
found 13 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $779, price is now $571 per person
$571
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,027, price is now $755 per person
$755
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,134, price is now $835 per person
$835
per person
Aug 28 - Aug 31
found 7 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,396, price is now $1,034 per person
$1,034
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Price was $989, price is now $739 per person
$739
per person
Aug 25 - Aug 28
found 8 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $1,687, price is now $1,274 per person
$1,274
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $1,065, price is now $818 per person
$818
per person
Aug 27 - Aug 30
found 22 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $925, price is now $715 per person
$715
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)

4-night Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Price was $872, price is now $676 per person
$676
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,839, price is now $1,279 per person
$1,279
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Freehand Chicago

Freehand Chicago

4 out of 5
Save 100% on your flight
Price was $1,378, price is now $1,013 per person
$1,013
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Price was $1,080, price is now $831 per person
$831
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Save 100% on your flight
Price was $1,236, price is now $954 per person
$954
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,915, price is now $1,513 per person
$1,513
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Chicago Marriott Midway

Chicago Marriott Midway

3.5 out of 5
Price was $1,096, price is now $889 per person
$889
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 $922, price is now $759 per person
$759
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Ohio House Motel

Ohio House Motel

3 out of 5
Price was $1,038, price is now $866 per person
$866
per person
Sep 2 - Sep 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $2,303, price is now $1,927 per person
$1,927
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
Price was $1,001, price is now $844 per person
$844
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Fairfield Inn and Suites by Marriott Chicago Midway Airport

Fairfield Inn and Suites by Marriott Chicago Midway Airport

3 out of 5
Price was $981, price is now $832 per person
$832
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

5-night Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Price was $1,142, price is now $893 per person
$893
per person
Sep 18 - Sep 23
found 1 hour ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,136, price is now $1,294 per person
$1,294
per person
Sep 18 - Sep 23
found 1 hour ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $2,323, price is now $1,497 per person
$1,497
per person
Sep 4 - Sep 9
found 9 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,472, price is now $1,002 per person
$1,002
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 $1,629, price is now $1,112 per person
$1,112
per person
Sep 18 - Sep 23
found 1 hour ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $1,375, price is now $1,022 per person
$1,022
per person
Sep 18 - Sep 23
found 1 hour ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Save 100% on your flight
Price was $1,313, price is now $1,009 per person
$1,009
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,178, price is now $906 per person
$906
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $2,119, price is now $1,631 per person
$1,631
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Save 100% on your flight
Price was $1,918, price is now $1,521 per person
$1,521
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $1,409, price is now $1,123 per person
$1,123
per person
Sep 18 - Sep 23
found 1 hour ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $1,329, price is now $1,066 per person
$1,066
per person
Sep 18 - Sep 23
found 1 hour ago
Roundtrip flight included
Baltimore (BWI) 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
Save 100% on your flight
Price was $1,396, price is now $900 per person
$900
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $6,369, price is now $3,662 per person
$3,662
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,885, price is now $1,758 per person
$1,758
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $2,273, price is now $1,395 per person
$1,395
per person
Sep 1 - Sep 7
found 3 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $2,290, price is now $1,452 per person
$1,452
per person
Sep 1 - Sep 7
found 3 hours ago
Roundtrip flight included
New York (NYC) 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 $2,301, price is now $1,556 per person
$1,556
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $2,921, price is now $2,003 per person
$2,003
per person
Sep 1 - Sep 7
found 3 hours ago
Roundtrip flight included
New York (NYC) 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 $1,756, price is now $1,244 per person
$1,244
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $2,299, price is now $1,671 per person
$1,671
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,390, price is now $1,015 per person
$1,015
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $3,737, price is now $2,747 per person
$2,747
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $1,438, price is now $1,069 per person
$1,069
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Top places to visit in Jefferson County

A serene lake with a clear reflection of trees and a building, under a bright sun.
FlightsFlightsHotelsHotels

Fort Atkinson

Fort Atkinson

Flight deals to Jefferson County

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

Thu, Dec 31 - Wed, Jan 6
BOS
Boston
MSN
Madison
$260 Roundtrip, found 2 hours ago
$260
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Thu, Dec 31 from Boston to Madison, returning Wed, Jan 6, priced at $260 found 2 hours ago
Fri, Sep 4 - Tue, Sep 8
DEN
Denver
MSN
Madison
$279 Roundtrip, found 3 days ago
$279
Roundtrip
found 3 days ago
Select United flight, departing Fri, Sep 4 from Denver to Madison, returning Tue, Sep 8, priced at $279 found 3 days ago
Wed, Aug 19 - Mon, Aug 24
PDX
Portland
MSN
Madison
$298 Roundtrip, found 3 hours ago
$298
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Wed, Aug 19 from Portland to Madison, returning Mon, Aug 24, priced at $298 found 3 hours ago

Top rated hotels for your Jefferson County vacation

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
34.22 mi from city center
$219 nightly
The price is $248 total per night
$248 total
Jul 27 - Jul 28
Total with taxes and fees
With a stay at Harbor Shores on Lake Geneva, you'll be centrally located in Lake Geneva, a 1-minute drive from Geneva Lake and 6 minutes from Lake Como.
Pool
Parking included
The Cove Of Lake Geneva

The Cove Of Lake Geneva

3.5 out of 5
111 Center St Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
34.2 mi from city center
$279 nightly
The price is $314 total per night
$314 total
Aug 10 - Aug 11
Total with taxes and fees
The Cove Of Lake Geneva is in the heart of Lake Geneva, within a 5-minute walk of Riviera Ballroom and Lake Geneva Cruise Line.
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
$277 nightly
The price is $309 total per night
$309 total
Aug 25 - Aug 26
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.