Cheap Vacations in Wisconsin

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Wisconsin vacations

Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Downtown Chicago
Price was $718, price is now $538 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $753, price is now $578 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
Price was $718, price is now $555 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flightPrice was $1,455, price is now $1,129 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was $755, price is now $587 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was $1,276, price is now $996 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was $803, price is now $635 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Downtown Chicago
Price was $792, price is now $628 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,203, price is now $964 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was $1,517, price is now $1,220 per person
per person
Jul 16 - Jul 19
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)

3-night Wisconsin vacations

Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Price was $718, price is now $538 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $753, price is now $578 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Price was $718, price is now $555 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Price was $755, price is now $587 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Price was $1,276, price is now $996 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $803, price is now $635 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was $1,203, price is now $964 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Price was $1,517, price is now $1,220 per person
per person
Jul 16 - Jul 19
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Kimpton Gray Hotel, an IHG Hotel

Kimpton Gray Hotel, an IHG Hotel

4.5 out of 5
Price was $689, price is now $563 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Kimpton Hotel Monaco Chicago, an IHG Hotel

Kimpton Hotel Monaco Chicago, an IHG Hotel

4.5 out of 5
Price was $701, price is now $576 per person
per person
Jul 6 - Jul 9
Roundtrip non-stop flight included
Charlotte (CLT) 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
Price was $1,114, price is now $920 per person
per person
Jul 16 - Jul 19
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
Thompson Chicago

Thompson Chicago

4.5 out of 5
Price was $1,107, price is now $916 per person
per person
Jul 16 - Jul 19
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)

4-night Wisconsin vacations

The Langham, Chicago

The Langham, Chicago

5 out of 5
Save 100% on your flightPrice was $1,839, price is now $1,319 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Price was $971, price is now $709 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Price was $970, price is now $727 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $1,005, price is now $769 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Price was $995, price is now $762 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $923, price is now $720 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flightPrice was $1,798, price is now $1,418 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Thompson Chicago

Thompson Chicago

4.5 out of 5
Price was $1,120, price is now $885 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Price was $792, price is now $628 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Price was $1,336, price is now $1,061 per person
per person
Jul 20 - Jul 24
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
Price was $752, price is now $598 per person
per person
Jul 22 - Jul 26
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $1,015, price is now $814 per person
per person
Jul 6 - Jul 10
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)

5-night Wisconsin vacations

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Save 100% on your flightPrice was $1,185, price is now $745 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Save 100% on your flightPrice was $951, price is now $628 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Save 100% on your flightPrice was $2,110, price is now $1,463 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flightPrice was $930, price is now $646 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
Hyatt Rosemont Near O'Hare

Hyatt Rosemont Near O'Hare

3.5 out of 5
Save 100% on your flightPrice was $1,071, price is now $757 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flightPrice was $1,242, price is now $884 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Save 100% on your flightPrice was $1,007, price is now $735 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flightPrice was $895, price is now $662 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
Save 100% on your flightPrice was $909, price is now $678 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
Price was $720, price is now $546 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flightPrice was $1,715, price is now $1,327 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)
Thompson Chicago

Thompson Chicago

4.5 out of 5
Save 100% on your flightPrice was $927, price is now $720 per person
per person
Jul 26 - Jul 31
Roundtrip non-stop flight included
New Orleans (MSY) to Chicago (ORD)

6-7 night Wisconsin vacations

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Save 100% on your flightPrice was $1,572, price is now $1,039 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flightPrice was $1,451, price is now $987 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Save 100% on your flightPrice was $1,220, price is now $833 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Save 100% on your flightPrice was $2,542, price is now $1,789 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flightPrice was $1,232, price is now $877 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop 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 flightPrice was $2,239, price is now $1,604 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
Price was $1,004, price is now $728 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Save 100% on your flightPrice was $1,300, price is now $956 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flightPrice was $2,553, price is now $1,885 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) 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 flightPrice was $1,437, price is now $1,066 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Save 100% on your flightPrice was $1,259, price is now $949 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $1,188, price is now $898 per person
per person
Jul 22 - Jul 29
Roundtrip non-stop 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

Wisconsin Vacation Deal FAQ's

Where to find Wisconsin package deals?

On CheapTickets, you can find package deals in Wisconsin and save up to $287.

When is peak season in Wisconsin?

are very popular times to visit Wisconsin.

When is the best time to visit Wisconsin?

If you're looking for cheap vacations to Wisconsin, is the best time to visit Wisconsin.

When is the worst time time to visit Wisconsin?

Prices for Wisconsin vacations can peak during .

When is low season in Wisconsin?

We have found to be the least-crowded time of the year to visit Wisconsin.

Flight deals to Wisconsin

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

Tue, Jul 4 - Wed, Jul 19
DEN
Denver
MSP
Minneapolis
$88 Roundtrip, found 4 hours ago
$88
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Jul 4 from Denver to Minneapolis, returning Wed, Jul 19, priced at $88 found 4 hours ago
Sat, Aug 19 - Sat, Aug 26
DEN
Denver
MKE
Milwaukee
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 19 from Denver to Milwaukee, returning Sat, Aug 26, priced at $98 found 1 day ago
Sun, Jul 2 - Mon, Jul 3
ATL
Atlanta
MSP
Minneapolis
$106 Roundtrip, found 4 days ago
$106
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sun, Jul 2 from Atlanta to Minneapolis, returning Mon, Jul 3, priced at $106 found 4 days ago
Wed, Aug 30 - Sat, Sep 16
DEN
Denver
MSN
Madison
$128 Roundtrip, found 9 hours ago
$128
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Aug 30 from Denver to Madison, returning Sat, Sep 16, priced at $128 found 9 hours ago
Thu, Nov 30 - Mon, Dec 11
AZA
Mesa
MSP
Minneapolis
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Thu, Nov 30 from Mesa to Minneapolis, returning Mon, Dec 11, priced at $134 found 1 day ago
Wed, Nov 1 - Mon, Nov 13
PHX
Phoenix
MSP
Minneapolis
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Wed, Nov 1 from Phoenix to Minneapolis, returning Mon, Nov 13, priced at $154 found 1 day ago

Top rated hotels for your Wisconsin vacation

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 $35 per night
$35
per night
Jun 4 - Jun 5
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 $182 per night
$182
per night
Jun 11 - Jun 12
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.
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, 53703
Free Cancellation
Reserve now, pay when you stay
57.38 mi from city center
The price is $149 per night
$149
per night
Jul 3 - Jul 4
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 Capitol Square.
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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.