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 Naperville/Warrenville

Hilton Garden Inn Naperville/Warrenville

3 out of 5
Save 100% on your flight
Price was $622, price is now $437 per person
$437
per person
Jul 22 - Jul 27
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,252, price is now $730 per person
$730
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,407, price is now $895 per person
$895
per person
Aug 6 - Aug 10
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) 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 $1,004, price is now $645 per person
$645
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,173, price is now $797 per person
$797
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,559, price is now $1,092 per person
$1,092
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,326, price is now $945 per person
$945
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Neighborhood Hotel-New Buffalo

The Neighborhood Hotel-New Buffalo

2 out of 5
Downtown New Buffalo
Save 100% on your flight
Price was $1,254, price is now $901 per person
$901
per person
Jul 28 - Aug 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Garden Inn Hoffman Estates

Hilton Garden Inn Hoffman Estates

3 out of 5
Save 100% on your flight
Price was $634, price is now $456 per person
$456
per person
Jul 22 - Jul 27
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,441, price is now $1,036 per person
$1,036
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,004, price is now $645 per person
$645
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,252, price is now $730 per person
$730
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,173, price is now $797 per person
$797
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,559, price is now $1,092 per person
$1,092
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,326, price is now $945 per person
$945
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,441, price is now $1,036 per person
$1,036
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,735, price is now $1,253 per person
$1,253
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $2,095, price is now $1,515 per person
$1,515
per person
Jul 30 - Aug 2
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,282, price is now $928 per person
$928
per person
Jul 15 - Jul 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,101, price is now $802 per person
$802
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $968, price is now $714 per person
$714
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $1,022, price is now $756 per person
$756
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

4-night Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Save 100% on your flight
Price was $741, price is now $515 per person
$515
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,473, price is now $830 per person
$830
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,122, price is now $701 per person
$701
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,407, price is now $895 per person
$895
per person
Aug 6 - Aug 10
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,336, price is now $855 per person
$855
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,150, price is now $745 per person
$745
per person
Jul 15 - Jul 19
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,244, price is now $821 per person
$821
per person
Aug 6 - Aug 10
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,618, price is now $1,076 per person
$1,076
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,351, price is now $909 per person
$909
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,295, price is now $873 per person
$873
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,672, price is now $1,161 per person
$1,161
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,562, price is now $1,089 per person
$1,089
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-night Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Naperville/Warrenville

Hilton Garden Inn Naperville/Warrenville

3 out of 5
Save 100% on your flight
Price was $622, price is now $437 per person
$437
per person
Jul 22 - Jul 27
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,688, price is now $932 per person
$932
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,566, price is now $932 per person
$932
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $1,169, price is now $736 per person
$736
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,947, price is now $1,237 per person
$1,237
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,594, price is now $1,031 per person
$1,031
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,537, price is now $1,001 per person
$1,001
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,617, price is now $1,062 per person
$1,062
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,258, price is now $847 per person
$847
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,367, price is now $943 per person
$943
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,309, price is now $916 per person
$916
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $1,307, price is now $916 per person
$916
per person
Jul 16 - Jul 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

6-7 night Jefferson County vacations

Price found within the past 48 hours. Click for updated prices.
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 $859, price is now $667 per person
$667
per person
Jul 15 - Jul 21
found 7 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $2,409, price is now $1,632 per person
$1,632
per person
Jul 28 - Aug 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $3,548, price is now $2,442 per person
$2,442
per person
Jul 28 - Aug 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,640, price is now $1,859 per person
$1,859
per person
Jul 28 - Aug 3
found 9 hours 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 $2,478, price is now $1,745 per person
$1,745
per person
Jul 28 - Aug 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,785, price is now $1,321 per person
$1,321
per person
Jul 15 - Jul 21
found 7 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flight
Price was $2,389, price is now $1,782 per person
$1,782
per person
Jul 28 - Aug 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $2,285, price is now $1,728 per person
$1,728
per person
Jul 28 - Aug 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Save 100% on your flight
Price was $2,169, price is now $1,645 per person
$1,645
per person
Jul 28 - Aug 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,988, price is now $2,275 per person
$2,275
per person
Jul 28 - Aug 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,879, price is now $1,438 per person
$1,438
per person
Jul 15 - Jul 21
found 7 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $1,569, price is now $1,206 per person
$1,206
per person
Jul 15 - Jul 21
found 7 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)

Top places to visit in Jefferson County

Tenney Park in the Spring in Madison Wisconsin
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, Oct 1 - Tue, Oct 6
LAS
Las Vegas
MSN
Madison
$272 Roundtrip, found 9 hours ago
$272
Roundtrip
found 9 hours ago
Select Bargain Flight flight, departing Thu, Oct 1 from Las Vegas to Madison, returning Tue, Oct 6, priced at $272 found 9 hours ago
Mon, Aug 17 - Wed, Aug 19
DCA
Washington
MSN
Madison
$274 Roundtrip, found 4 days ago
$274
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Mon, Aug 17 from Washington to Madison, returning Wed, Aug 19, priced at $274 found 4 days ago
Tue, Jul 7 - Thu, Jul 9
DEN
Denver
MSN
Madison
$290 Roundtrip, found 15 hours ago
$290
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Tue, Jul 7 from Denver to Madison, returning Thu, Jul 9, priced at $290 found 15 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
$199 nightly
The price is $225 total per night
$225 total
Jun 14 - Jun 15
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
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
$305 nightly
The price is $340 total per night
$340 total
Jul 6 - Jul 7
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
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
$204 nightly
The price is $228 total per night
$228 total
Jun 15 - Jun 16
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
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.