Cheap Vacations in Jefferson County

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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
Downtown Chicago
Save 100% on your flight
Price was $848, price is now $603 per person
$603
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,407, price is now $775 per person
$775
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,435, price is now $839 per person
$839
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,162, price is now $1,310 per person
$1,310
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 $1,490, price is now $932 per person
$932
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,041, price is now $718 per person
$718
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay One Chicago

Stay One Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,176, price is now $817 per person
$817
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,191, price is now $853 per person
$853
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,412, price is now $1,024 per person
$1,024
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,155, price is now $843 per person
$843
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)

3-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
Save 100% on your flight
Price was $848, price is now $603 per person
$603
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,407, price is now $775 per person
$775
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $2,162, price is now $1,310 per person
$1,310
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 $1,490, price is now $932 per person
$932
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,041, price is now $718 per person
$718
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay One Chicago

Stay One Chicago

4 out of 5
Save 100% on your flight
Price was $1,176, price is now $817 per person
$817
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Save 100% on your flight
Price was $1,191, price is now $853 per person
$853
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $1,412, price is now $1,024 per person
$1,024
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,155, price is now $843 per person
$843
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,549, price is now $1,133 per person
$1,133
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 $1,112, price is now $817 per person
$817
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $1,320, price is now $971 per person
$971
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)

4-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
Save 100% on your flight
Price was $1,051, price is now $731 per person
$731
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,588, price is now $919 per person
$919
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,435, price is now $839 per person
$839
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 $1,496, price is now $924 per person
$924
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 $1,157, price is now $738 per person
$738
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Save 100% on your flight
Price was $1,152, price is now $773 per person
$773
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,276, price is now $862 per person
$862
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Wade

The Wade

4.5 out of 5
Save 100% on your flight
Price was $1,398, price is now $946 per person
$946
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 $1,400, price is now $969 per person
$969
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Save 100% on your flight
Price was $1,183, price is now $822 per person
$822
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Ohio House Motel

Ohio House Motel

3 out of 5
Save 100% on your flight
Price was $1,112, price is now $779 per person
$779
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Freehand Chicago

Freehand Chicago

4 out of 5
Save 100% on your flight
Price was $1,184, price is now $835 per person
$835
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Denver (DEN) 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
Save 100% on your flight
Price was $1,222, price is now $868 per person
$868
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,840, price is now $1,034 per person
$1,034
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) 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 $1,841, price is now $1,119 per person
$1,119
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Save 100% on your flight
Price was $1,624, price is now $1,062 per person
$1,062
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,643, price is now $1,076 per person
$1,076
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) 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 $1,491, price is now $983 per person
$983
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,692, price is now $1,133 per person
$1,133
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Save 100% on your flight
Price was $1,564, price is now $1,053 per person
$1,053
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,114, price is now $1,429 per person
$1,429
per person
Oct 14 - Oct 19
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,807, price is now $1,222 per person
$1,222
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
Save 100% on your flight
Price was $1,589, price is now $1,131 per person
$1,131
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
Price was $1,766, price is now $1,265 per person
$1,265
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) 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 $1,237, price is now $816 per person
$816
per person
Oct 22 - Oct 29
found 7 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,284, price is now $1,287 per person
$1,287
per person
Oct 22 - Oct 29
found 7 hours ago
Roundtrip flight included
Houston (IAH) 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 $2,103, price is now $1,266 per person
$1,266
per person
Oct 14 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $2,795, price is now $1,705 per person
$1,705
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $2,071, price is now $1,321 per person
$1,321
per person
Oct 22 - Oct 29
found 7 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,533, price is now $1,643 per person
$1,643
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,823, price is now $1,196 per person
$1,196
per person
Oct 14 - Oct 20
found 8 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $2,978, price is now $2,081 per person
$2,081
per person
Oct 16 - Oct 23
just found
Roundtrip flight included
Philadelphia (PHL) 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 $2,525, price is now $1,776 per person
$1,776
per person
Oct 16 - Oct 23
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $2,401, price is now $1,707 per person
$1,707
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,579, price is now $1,125 per person
$1,125
per person
Oct 22 - Oct 29
found 7 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Save 100% on your flight
Price was $1,603, price is now $1,185 per person
$1,185
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
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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
$282 Roundtrip, found 4 days ago
$282
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Thu, Oct 1 from Las Vegas to Madison, returning Tue, Oct 6, priced at $282 found 4 days ago
Sat, Oct 10 - Tue, Oct 13
PDX
Portland
MSN
Madison
$299 Roundtrip, found 4 days ago
$299
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Sat, Oct 10 from Portland to Madison, returning Tue, Oct 13, priced at $299 found 4 days ago
Fri, Sep 11 - Sun, Sep 13
BOS
Boston
MSN
Madison
$305 Roundtrip, found 1 day ago
$305
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Sep 11 from Boston to Madison, returning Sun, Sep 13, priced at $305 found 1 day 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
$146 nightly
The price is $166 total per night
$166 total
Sep 15 - Sep 16
Total with taxes and fees
With a stay at Harbor Shores on Lake Geneva, you'll be centrally located in Lake Geneva, steps from Geneva Lake and 3 minutes by foot from Riviera Ballroom.
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
$184 nightly
The price is $205 total per night
$205 total
Oct 7 - Oct 8
Total with taxes and fees
With a stay at Timber Ridge Lodge and Waterpark in Lake Geneva, you'll be in a regional park, within a 5-minute drive of Geneva Lake and Moose Mountain Falls Waterpark.
Pool
Hot Tub
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
$311 nightly
The price is $346 total per night
$346 total
Oct 5 - Oct 6
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
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.