Cheap Vacations in Wisconsin

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Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 2 - Jul 6
just found
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) 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
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
W Chicago - City Center

W Chicago - City Center

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)

3-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
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 14
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 12 - Jul 15
found 23 hours ago
Roundtrip flight included
Orlando (MCO) 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 11 - Jul 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 12 - Jul 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Rand Tower Hotel , Minneapolis, A Tribute Portfolio Hotel

Rand Tower Hotel , Minneapolis, A Tribute Portfolio Hotel

4.5 out of 5
Save 100% on your flight
per person
Jun 28 - Jul 1
found 11 hours ago
Roundtrip flight included
Denver (DEN) to Minneapolis (MSP)
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 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Save 100% on your flight
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)

4-night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 6
just found
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 6
just found
Roundtrip flight included
Denver (DEN) 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 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 6
just found
Roundtrip flight included
Denver (DEN) 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
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 6
just found
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
W Chicago - City Center

W Chicago - City Center

4 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 6
just found
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 26 - Jun 30
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
per person
Jul 2 - Jul 6
just found
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) 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 26 - Jun 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)

5-night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) 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
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Central Loop Hotel

Central Loop Hotel

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
The Talbott Hotel

The Talbott Hotel

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (MDW)
Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

3.5 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Bridgeview Inn Chicago Area

Bridgeview Inn Chicago Area

2 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Save 100% on your flight
per person
Jun 24 - Jun 29
found 12 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)

Flight deals to Wisconsin

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

Sun, May 26 - Sun, May 26
DEN
Denver
MSP
Minneapolis
$58 Roundtrip, found 4 days ago
$58
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, May 26 from Denver to Minneapolis, returning Sun, May 26, priced at $58 found 4 days ago
Tue, Jun 4 - Wed, Jun 12
PHL
Philadelphia
MSP
Minneapolis
$58 Roundtrip, found 2 days ago
$58
Roundtrip
found 2 days ago
Select Sun Country Airlines flight, departing Tue, Jun 4 from Philadelphia to Minneapolis, returning Wed, Jun 12, priced at $58 found 2 days ago
Wed, Jun 5 - Wed, Jun 12
ATL
Atlanta
MSP
Minneapolis
$60 Roundtrip, just found
$60
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Jun 5 from Atlanta to Minneapolis, returning Wed, Jun 12, priced at $60 just found
Sat, Jun 15 - Tue, Jun 18
DFW
Dallas
MSP
Minneapolis
$68 Roundtrip, found 19 hours ago
$68
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Jun 15 from Dallas to Minneapolis, returning Tue, Jun 18, priced at $68 found 19 hours ago
Sat, Jun 8 - Sat, Jun 15
DEN
Denver
MKE
Milwaukee
$78 Roundtrip, found 5 days ago
$78
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Jun 8 from Denver to Milwaukee, returning Sat, Jun 15, priced at $78 found 5 days ago
Sun, Sep 29 - Sun, Sep 29
DFW
Dallas
MKE
Milwaukee
$87 Roundtrip, found 3 days ago
$87
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sun, Sep 29 from Dallas to Milwaukee, returning Sun, Sep 29, priced at $87 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 27 - May 28
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.
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 27 - May 28
Located in Wisconsin Dells, Mt. Olympus Water & Theme Park Resort is within a 5-minute drive of Ghost Outpost and Top Secret.
Pool
Parking available
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 27 - May 28
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.