Cheap Vacations in Wisconsin

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Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)

3-night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 7
found 21 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
per person
Jul 4 - Jul 7
found 21 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)

4-night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
per person
Jul 6 - Jul 10
found 3 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
per person
Jul 6 - Jul 10
found 3 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
per person
Jul 6 - Jul 10
found 3 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
per person
Jul 6 - Jul 10
found 3 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
per person
Jul 6 - Jul 10
found 3 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
per person
Jul 6 - Jul 10
found 3 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)

5-night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)

6-7 night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)

Top places to visit in Wisconsin

Milwaukee Art Museum featuring art and modern architecture
FlightsFlightsHotelsHotels

Milwaukee

Milwaukee

Flight deals to Wisconsin

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

Wed, Jun 5 - Wed, Jun 12
ATL
Atlanta
MSP
Minneapolis
$60 Roundtrip, found 2 days ago
$60
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jun 5 from Atlanta to Minneapolis, returning Wed, Jun 12, priced at $60 found 2 days ago
Tue, Jun 4 - Tue, Jun 4
DEN
Denver
MSP
Minneapolis
$63 Roundtrip, just found
$63
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jun 4 from Denver to Minneapolis, returning Tue, Jun 4, priced at $63 just found
Tue, Jul 9 - Tue, Jul 16
PHL
Philadelphia
MKE
Milwaukee
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jul 9 from Philadelphia to Milwaukee, returning Tue, Jul 16, priced at $68 just found
Tue, Jun 4 - Wed, Jun 12
PHL
Philadelphia
MSP
Minneapolis
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 4 from Philadelphia to Minneapolis, returning Wed, Jun 12, priced at $68 found 1 day ago
Sat, Jun 15 - Tue, Jun 18
DFW
Dallas
MSP
Minneapolis
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jun 15 from Dallas to Minneapolis, returning Tue, Jun 18, priced at $68 found 4 days ago
Tue, Aug 6 - Tue, Aug 6
DFW
Dallas
MKE
Milwaukee
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 6 from Dallas to Milwaukee, returning Tue, Aug 6, priced at $87 found 1 day ago

Top rated hotels for your Wisconsin vacation

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
57.38 mi from city center
The price is $139 per night
$139
per night
Jun 16 - Jun 17
A stay at The Madison Concourse Hotel and Governor's Club places you in the heart of Madison, just a 3-minute walk from Wisconsin State Capitol and within a 5-minute drive of University of Wisconsin-Madison.
Pool
Pet friendly
Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
Free Cancellation
Reserve now, pay when you stay
51.56 mi from city center
The price is $25 per night
$25
per night
May 29 - May 30
Located in Wisconsin Dells, Mt. Olympus Water & Theme Park Resort is within a 5-minute drive of Ghost Outpost and Top Secret.
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave, Milwaukee, WI
Free Cancellation
Reserve now, pay when you stay
67.55 mi from city center
The price is $132 per night
$132
per night
May 29 - May 30
With a stay at Saint Kate - The Arts Hotel, you'll be centrally located in Milwaukee, within a 10-minute walk of Riverside Theater and Fiserv Forum.
Pet friendly
Breakfast available
Don't see what you're looking for?
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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.