Cheap Vacations in Wisconsin

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Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Sophy Hyde Park

Sophy Hyde Park

4 out of 5
Hyde Park
Save 100% on your flight
per person
Jun 28 - Jul 1
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) 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
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)

3-night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 1
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
Sophy Hyde Park

Sophy Hyde Park

4 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 1
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
per person
Jun 28 - Jul 1
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 4
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
per person
Jul 1 - Jul 4
Roundtrip flight included
Toronto (YYZ) 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 1 - Jul 4
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
per person
Jul 1 - Jul 4
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
per person
Jul 1 - Jul 4
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
W Chicago - City Center

W Chicago - City Center

4 out of 5
per person
Jul 1 - Jul 4
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
per person
Jul 1 - Jul 4
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
per person
Jul 1 - Jul 4
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
per person
Jul 1 - Jul 4
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)

4-night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) 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 9
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 20
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 9
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)

5-night Wisconsin vacations

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

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) 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
Jun 16 - Jun 21
Roundtrip non-stop flight included
Tampa (TPA) to Chicago (ORD)

6-7 night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Dubbel Dutch

Dubbel Dutch

3 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Save 100% on your flight
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
Holiday Inn Milwaukee Brookfield, an IHG Hotel

Holiday Inn Milwaukee Brookfield, an IHG Hotel

3 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
Candlewood Suites Milwaukee Airport, an IHG Hotel

Candlewood Suites Milwaukee Airport, an IHG Hotel

2.5 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
Sonesta Milwaukee West Wauwatosa

Sonesta Milwaukee West Wauwatosa

3.5 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
Hyatt Place Milwaukee West

Hyatt Place Milwaukee West

3 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
Embassy Suites by Hilton Milwaukee Brookfield

Embassy Suites by Hilton Milwaukee Brookfield

3.5 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
Holiday Inn Express Hotel & Suites Milwaukee Airport, an IHG Hotel

Holiday Inn Express Hotel & Suites Milwaukee Airport, an IHG Hotel

2.5 out of 5
per person
Jun 16 - Jun 22
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)

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, May 29 - Wed, Jun 5
ATL
Atlanta
MSP
Minneapolis
$50 Roundtrip, found 17 hours ago
$50
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, May 29 from Atlanta to Minneapolis, returning Wed, Jun 5, priced at $50 found 17 hours ago
Sat, May 18 - Tue, May 21
DEN
Denver
MSP
Minneapolis
$53 Roundtrip, found 6 days ago
$53
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 18 from Denver to Minneapolis, returning Tue, May 21, priced at $53 found 6 days ago
Wed, Jun 5 - Wed, Jun 12
PHL
Philadelphia
MSP
Minneapolis
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
Select Sun Country Airlines flight, departing Wed, Jun 5 from Philadelphia to Minneapolis, returning Wed, Jun 12, priced at $58 found 2 hours ago
Tue, May 14 - Sat, May 18
DFW
Dallas
MSP
Minneapolis
$62 Roundtrip, found 3 days ago
$62
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 14 from Dallas to Minneapolis, returning Sat, May 18, priced at $62 found 3 days ago
Sat, May 18 - Tue, May 21
PHX
Phoenix
MSP
Minneapolis
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 18 from Phoenix to Minneapolis, returning Tue, May 21, priced at $68 found 2 days ago
Wed, Jul 31 - Wed, Aug 7
DEN
Denver
MKE
Milwaukee
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Jul 31 from Denver to Milwaukee, returning Wed, Aug 7, priced at $68 found 3 days 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
Free Cancellation
Reserve now, pay when you stay
57.38 mi from city center
The price is $129 per night
$129
per night
May 12 - May 13
With a stay at The Madison Concourse Hotel and Governor's Club, you'll be centrally located in Madison, within a 5-minute drive of University of Wisconsin-Madison and Camp Randall Stadium.
Pool
Hot Tub
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 12 - May 13
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 12 - May 13
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
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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.