Cheap Vacations in Wisconsin

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Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Chicago-Vernon Hills, an IHG Hotel

Hotel Indigo Chicago-Vernon Hills, an IHG Hotel

3.5 out of 5
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Holiday Inn & Suites Chicago - Downtown, an IHG Hotel

Holiday Inn & Suites Chicago - Downtown, an IHG Hotel

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
Save 100% on your flight
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Chez Hotel Arlington Heights

Chez Hotel Arlington Heights

4 out of 5
Save 100% on your flight
per person
Jan 6 - Jan 13
found 15 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hyatt Regency Bloomington - Minneapolis

Hyatt Regency Bloomington - Minneapolis

4 out of 5
East Bloomington
per person
Jan 16 - Jan 20
found 20 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Minneapolis (MSP)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Downtown Chicago
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Dec 27 - Jan 1
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.
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
per person
Jan 1 - Jan 4
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
Jan 1 - Jan 4
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
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
Holiday Inn Chicago North Shore, an IHG Hotel

Holiday Inn Chicago North Shore, an IHG Hotel

3 out of 5
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Marriott Chicago Schaumburg

Marriott Chicago Schaumburg

3.5 out of 5
per person
Jan 17 - Jan 20
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.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hyatt Regency Bloomington - Minneapolis

Hyatt Regency Bloomington - Minneapolis

4 out of 5
per person
Jan 16 - Jan 20
found 20 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Minneapolis (MSP)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
per person
Jan 16 - Jan 20
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
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
Dec 27 - Jan 1
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
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
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
Dec 31 - Jan 5
found 23 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
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
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
InterContinental Chicago Magnificent Mile, an IHG Hotel

InterContinental Chicago Magnificent Mile, an IHG Hotel

4.5 out of 5
Save 100% on your flight
per person
Dec 27 - Jan 1
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.
Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
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
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Holiday Inn & Suites Chicago - Downtown, an IHG Hotel

Holiday Inn & Suites Chicago - Downtown, an IHG Hotel

3 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
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
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Save 100% on your flight
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.

Fri, Dec 6 - Thu, Dec 12
PHX
Phoenix
MSP
Minneapolis
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Dec 6 from Phoenix to Minneapolis, returning Thu, Dec 12, priced at $68 found 2 days ago
Sat, Dec 14 - Wed, Dec 18
DEN
Denver
MSP
Minneapolis
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Dec 14 from Denver to Minneapolis, returning Wed, Dec 18, priced at $68 found 2 days ago
Wed, Dec 4 - Wed, Dec 11
ATL
Atlanta
MSP
Minneapolis
$80 Roundtrip, found 7 hours ago
$80
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Wed, Dec 4 from Atlanta to Minneapolis, returning Wed, Dec 11, priced at $80 found 7 hours ago
Fri, Dec 13 - Sun, Dec 15
DFW
Dallas
MSP
Minneapolis
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Select Sun Country Airlines flight, departing Fri, Dec 13 from Dallas to Minneapolis, returning Sun, Dec 15, priced at $107 found 3 days ago
Wed, Dec 11 - Tue, Dec 17
JFK
New York
MKE
Milwaukee
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Wed, Dec 11 from New York to Milwaukee, returning Tue, Dec 17, priced at $118 found 4 days ago
Wed, Jan 15 - Mon, Jan 27
JFK
New York
MSP
Minneapolis
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jan 15 from New York to Minneapolis, returning Mon, Jan 27, priced at $118 found 2 days ago

Top rated hotels for your Wisconsin vacation

Hilton Milwaukee City Center

Hilton Milwaukee City Center

4 out of 5
509 W Wisconsin Ave, Milwaukee, WI
Free Cancellation
Reserve now, pay when you stay
67.5 mi from city center
The price is $109 per night
$109
includes taxes & fees
$93 per night
Dec 22 - Dec 23
With a stay at Hilton Milwaukee, you'll be centrally located in Milwaukee, just a 3-minute walk from Marquette University and 10 minutes by foot from Fiserv Forum.
Pet friendly
Free WiFi
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 $128 per night
$128
includes taxes & fees
$111 per night
Nov 24 - Nov 25
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
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 $160 per night
$160
includes taxes & fees
$135 per night
Dec 3 - Dec 4
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
Free WiFi
Don't see what you're looking for?
See all available properties in Wisconsin
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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.