Cheap Vacations in Jefferson County

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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
Save 100% on your flight
Price was $738, price is now $541 per person
$541
per person
Aug 28 - Aug 31
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 $1,131, price is now $655 per person
$655
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $876, price is now $617 per person
$617
per person
Sep 11 - Sep 14
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 $1,171, price is now $844 per person
$844
per person
Aug 28 - Aug 31
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 10 hours ago
Roundtrip flight included
Charlotte (CLT) 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 $735, price is now $560 per person
$560
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $819, price is now $638 per person
$638
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $899, price is now $710 per person
$710
per person
Aug 28 - Aug 31
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.
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 $603, price is now $445 per person
$445
per person
Sep 11 - Sep 14
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 $1,131, price is now $655 per person
$655
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
Save 100% on your flight
Price was $876, price is now $617 per person
$617
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
Save 100% on your flight
Price was $1,028, price is now $735 per person
$735
per person
Sep 10 - Sep 13
found 1 hour ago
Roundtrip flight included
Charlotte (CLT) 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 $1,171, price is now $844 per person
$844
per person
Aug 28 - Aug 31
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 16 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $738, price is now $541 per person
$541
per person
Aug 28 - Aug 31
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 10 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)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $735, price is now $560 per person
$560
per person
Sep 11 - Sep 14
found 1 day 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 $1,065, price is now $818 per person
$818
per person
Aug 27 - Aug 30
found 1 day 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.
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
Price was $686, price is now $581 per person
$581
per person
Sep 4 - Sep 8
just found
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,184, price is now $916 per person
$916
per person
Sep 1 - Sep 5
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
Price was $998, price is now $786 per person
$786
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Price was $1,104, price is now $872 per person
$872
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Price was $863, price is now $702 per person
$702
per person
Sep 4 - Sep 8
just found
Roundtrip flight included
Dallas (DFW) 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)
Chicago Marriott Midway

Chicago Marriott Midway

3.5 out of 5
Price was $1,132, price is now $944 per person
$944
per person
Sep 4 - Sep 8
found 1 hour ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
Price was $2,342, price is now $1,966 per person
$1,966
per person
Sep 3 - Sep 7
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
Price was $922, price is now $776 per person
$776
per person
Sep 4 - Sep 8
found 1 hour ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Price was $1,149, price is now $969 per person
$969
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
Price was $766, price is now $652 per person
$652
per person
Sep 4 - Sep 8
just found
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 $843, price is now $722 per person
$722
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)

5-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
Price was $867, price is now $666 per person
$666
per person
Sep 13 - Sep 18
found 1 hour 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 $2,136, price is now $1,294 per person
$1,294
per person
Sep 18 - Sep 23
found 4 hours 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 12 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 4 hours 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 4 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,648, price is now $1,232 per person
$1,232
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop 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)
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Save 100% on your flight
Price was $1,392, price is now $1,081 per person
$1,081
per person
Sep 13 - Sep 18
found 1 hour ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
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 4 hours ago
Roundtrip flight included
Baltimore (BWI) 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 4 hours 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 6 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 6 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 6 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 5 hours ago
$260
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Thu, Dec 31 from Boston to Madison, returning Wed, Jan 6, priced at $260 found 5 hours ago
Tue, Aug 11 - Fri, Aug 14
DCA
Washington
MSN
Madison
$262 Roundtrip, found 1 hour ago
$262
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Tue, Aug 11 from Washington to Madison, returning Fri, Aug 14, priced at $262 found 1 hour 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

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 28 - Jul 29
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
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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.