Cheap Vacations in Wisconsin

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Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Nicollet Island Inn

Nicollet Island Inn

2.5 out of 5
Nicollet Island
Save 100% on your flight
Price was $450, price is now $326 per person
$326
per person
Jan 9 - Jan 11
found 15 hours ago
Roundtrip flight included
Denver (DEN) to Minneapolis (MSP)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $790, price is now $434 per person
$434
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,417, price is now $946 per person
$946
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $794, price is now $534 per person
$534
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,173, price is now $1,479 per person
$1,479
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Save 100% on your flight
Price was $564, price is now $386 per person
$386
per person
Jan 9 - Jan 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was $685, price is now $475 per person
$475
per person
Jan 17 - Jan 19
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Four Points by Sheraton Chicago Schaumburg

Four Points by Sheraton Chicago Schaumburg

3 out of 5
Save 100% on your flight
Price was $616, price is now $444 per person
$444
per person
Jan 9 - Jan 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
Save 100% on your flight
Price was $485, price is now $352 per person
$352
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Save 100% on your flight
Price was $985, price is now $719 per person
$719
per person
Jan 9 - Jan 17
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.
SpringHill Suites by Marriott Chicago Naperville/Warrenville

SpringHill Suites by Marriott Chicago Naperville/Warrenville

3 out of 5
Price was $325, price is now $239 per person
$239
per person
Jan 16 - Jan 19
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $794, price is now $534 per person
$534
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Save 100% on your flight
Price was $521, price is now $360 per person
$360
per person
Jan 23 - Jan 26
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Save 100% on your flight
Price was $482, price is now $345 per person
$345
per person
Jan 16 - Jan 19
found 10 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Aloft Bolingbrook

Aloft Bolingbrook

3 out of 5
Save 100% on your flight
Price was $332, price is now $245 per person
$245
per person
Jan 16 - Jan 19
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Hilton Minneapolis

Hilton Minneapolis

4 out of 5
Price was $538, price is now $398 per person
$398
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Minneapolis (MSP)
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Save 100% on your flight
Price was $334, price is now $249 per person
$249
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hilton Garden Inn Rockford

Hilton Garden Inn Rockford

3 out of 5
Price was $319, price is now $240 per person
$240
per person
Jan 16 - Jan 19
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rockford (RFD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $345, price is now $260 per person
$260
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
Price was $417, price is now $317 per person
$317
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3 out of 5
Save 100% on your flight
Price was $356, price is now $270 per person
$270
per person
Jan 9 - Jan 12
found 13 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $356, price is now $272 per person
$272
per person
Jan 21 - Jan 24
found 24 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)

4-night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was $406, price is now $300 per person
$300
per person
Jan 22 - Jan 26
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
Price was $1,154, price is now $801 per person
$801
per person
Jan 29 - Feb 2
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Price was $672, price is now $475 per person
$475
per person
Jan 29 - Feb 2
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $447, price is now $324 per person
$324
per person
Jan 29 - Feb 2
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
Save 100% on your flight
Price was $485, price is now $352 per person
$352
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Emery, Autograph Collection Hotel

Emery, Autograph Collection Hotel

4.5 out of 5
Save 100% on your flight
Price was $605, price is now $441 per person
$441
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Minneapolis (MSP)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $551, price is now $402 per person
$402
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Save 100% on your flight
Price was $428, price is now $316 per person
$316
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $514, price is now $382 per person
$382
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Austin (AUS) 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
Save 100% on your flight
Price was $723, price is now $540 per person
$540
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Price was $520, price is now $389 per person
$389
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
The Westin Minneapolis

The Westin Minneapolis

4 out of 5
Price was $447, price is now $335 per person
$335
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Minneapolis (MSP)

5-night Wisconsin vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $437, price is now $270 per person
$270
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $866, price is now $463 per person
$463
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $790, price is now $434 per person
$434
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $569, price is now $316 per person
$316
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $743, price is now $414 per person
$414
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $675, price is now $377 per person
$377
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $730, price is now $418 per person
$418
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Save 100% on your flight
Price was $576, price is now $356 per person
$356
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Save 100% on your flight
Price was $556, price is now $354 per person
$354
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,301, price is now $830 per person
$830
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Save 100% on your flight
Price was $751, price is now $484 per person
$484
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Save 100% on your flight
Price was $683, price is now $442 per person
$442
per person
Jan 30 - Feb 4
found 5 hours ago
Roundtrip flight included
Dallas (DFW) 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.

Mon, Feb 2 - Tue, Feb 3
DEN
Denver
MSP
Minneapolis
$69 Roundtrip, found 4 days ago
$69
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Feb 2 from Denver to Minneapolis, returning Tue, Feb 3, priced at $69 found 4 days ago
Thu, Jan 8 - Fri, Jan 9
DFW
Dallas
MSP
Minneapolis
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Dallas to Minneapolis, returning Fri, Jan 9, priced at $113 found 1 day ago
Fri, Feb 6 - Tue, Feb 10
PHL
Philadelphia
RFD
Rockford
$139 Roundtrip, found 5 days ago
$139
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Feb 6 from Philadelphia to Rockford, returning Tue, Feb 10, priced at $139 found 5 days ago
Sat, Jan 10 - Tue, Jan 20
LGA
New York
RFD
Rockford
$139 Roundtrip, found 7 hours ago
$139
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Jan 10 from New York to Rockford, returning Tue, Jan 20, priced at $139 found 7 hours ago
Tue, Jan 13 - Thu, Jan 15
DFW
Dallas
RFD
Rockford
$142 Roundtrip, found 5 days ago
$142
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jan 13 from Dallas to Rockford, returning Thu, Jan 15, priced at $142 found 5 days ago
Mon, Jan 12 - Tue, Jan 13
ATL
Atlanta
RFD
Rockford
$142 Roundtrip, found 6 days ago
$142
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Jan 12 from Atlanta to Rockford, returning Tue, Jan 13, priced at $142 found 6 days ago

Top rated hotels for your Wisconsin vacation

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Free Cancellation
Reserve now, pay when you stay
67.87 mi from city center
$169 nightly
The price is $199 total per night
$199 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
With a stay at The Pfister Hotel, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and Fiserv Forum.
Pool
Spa
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
$139 nightly
The price is $161 total per night
$161 total
Dec 14 - Dec 15
Total with taxes and fees
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
Oneida Casino Hotel

Oneida Casino Hotel

3.5 out of 5
2040 Airport Dr Green Bay WI
Free Cancellation
Reserve now, pay when you stay
59.22 mi from city center
$98 nightly
The price is $113 total per night
$113 total
Dec 14 - Dec 15
Total with taxes and fees
Located in Green Bay, Oneida Casino Hotel is a 1-minute drive from Oneida Casino and 7 minutes from Bay Park Square.
Pool
Hot Tub
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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.