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Jefferson County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,345, price is now CA $940 per person
CA $940
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,579, price is now CA $1,040 per person
CA $1,040
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,707, price is now CA $1,146 per person
CA $1,146
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,574, price is now CA $1,063 per person
CA $1,063
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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 CA $1,502, price is now CA $1,042 per person
CA $1,042
per person
Jul 28 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.

Top Jefferson County hotels deals

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
The price is CA $170 per night
CA $170
CA $224 total
May 25 - May 26
includes taxes & fees
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Gary Gygax Memorial and Lake Geneva Cruise Line are located nearby.
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
The price is CA $233 per night
CA $233
CA $314 total
May 26 - May 27
includes taxes & fees
Book a stay at this spa aparthotel in Lake Geneva. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Moose Mountain Falls Waterpark and Dan Patch Stables are located nearby.
Pool
Hot tub
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Free cancellation
Reserve now, pay when you stay
The price is CA $134 per night
CA $134
CA $155 total
May 24 - May 25
includes taxes & fees
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions East Towne Mall and Olbrich Botanical Gardens are located nearby.
Pool
Pet-friendly
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
The price is CA $160 per night
CA $160
CA $216 total
May 25 - May 26
includes taxes & fees
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy an outdoor pool, 2 hot tubs, and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Gary Gygax Memorial and Lake Geneva Cruise Line are located nearby.
Pool
Hot tub
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
7036 Grand Geneva Way Lake Geneva WI
Free cancellation
The price is CA $205 per night
CA $205
CA $229 total
May 26 - May 27
includes taxes & fees
Book a stay at this spa resort in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions The Highlands Golf Course and The Brute Golf Course are located nearby.
Pool
Hot tub
Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
2400 E Geneva St Delavan WI
Free cancellation
Reserve now, pay when you stay
The price is CA $151 per night
CA $151
CA $214 total
May 31 - Jun 1
includes taxes & fees
Book a stay at this beach resort in Delavan. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lake Lawn Resort Marina and Delavan Historical Society are located nearby.
Pool
Hot tub
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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.

Photos of local treasures

Browse Jefferson County vacation photos for more inspiration

Historic Jefferson County Courthouse and Clock Tower Victorian style old historical building in Port Townsend, Olympic Peninsula, Washington State
Mid-May in Wisconsin, a large oak tree leafs out as its branches create a border for a distant lone oak, both growing in a farm field.
Jefferson County
Jefferson County
Jefferson County

Frequently asked questions

How much are vacation packages to Jefferson County?
You can pick up an awesome flight and hotel bundle from just CA $940. With a Travelocity vacation package, a getaway to Jefferson County has never looked so enticing! Save some time and money and get an early start with packing your suitcases.
Where can I get the best vacation package deals for Jefferson County?
No matter your style, Travelocity can help you score the best Jefferson County package deal. The only thing you have to do is select a combination from our 400 air carriers and 1,000,000 properties worldwide.
Why should I book my Jefferson County vacation bundle via Travelocity?
Because we believe in crafting special vacation experiences. From hotels and flights to car rentals and activities, our packages make it a breeze to save. Our support team is available 24/7 to ensure you'll never wander alone. We also have a Price Match Guarantee, so you can lock in your vacation knowing you've scored the best deal around. How? If you find a lower price, we'll match it!
Can I save money on my Jefferson County car rental if I bundle it with a hotel or flight?
You sure can with our Jefferson County vacation packages. With one of these, there are lots of ways to stretch your budget further. Bundle any two or more car, flight, hotel and tour bookings and see the savings pile up. With a rental car, all the landmarks in and around Jefferson County are within reach.
Which airport is best for Jefferson County?
That depends on where you're taking off from and where you're going — General Mitchell Intl. Airport (MKE), Dane County Regional Airport (MSN) or Rockford, IL (RFD-Greater Rockford) are where you'll most likely touch down.
What is there to do in Jefferson County?
A diverse and lively destination, Jefferson County offers some terrific landmarks. Lake Koshkonong and Glacial River Bike Trail are a couple of the top picks.