Southern Wisconsin Holidays

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Top Flight + Hotel Deals in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was €1,174, price is now €919 per person
€919
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
Room was very clean would return again

Reviewed on 23 Feb 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €1,471, price is now €992 per person
€992
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!

Reviewed on 27 Feb 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,284, price is now €919 per person
€919
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on 16 Feb 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was €1,264, price is now €960 per person
€960
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Everything was great, I really enjoyed my stay!

Reviewed on 25 Feb 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,250, price is now €962 per person
€962
per person
7 Apr - 13 Apr
found 1 day ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
amazing stay 10/10 would recommend

Reviewed on 26 Feb 2026

Where to stay in Southern Wisconsin

Find the best Southern Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southern Wisconsin
Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

Downtown Milwaukee

Lake Michigan and Milwaukee City Hall are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee

Top hotels in Southern Wisconsin

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
Fully refundableReserve now, pay when you stay
The price is €116 per night from 29 Mar to 30 Mar
€116
29 Mar - 30 Mar
includes taxes & fees
9.4/10 Exceptional! (3,519 reviews)
Clean room - very busy lobby. Needed another person at the desk during the busy checkin/checkout times. 2 is not enough.

Reviewed on 27 Feb 2026

The Madison Concourse Hotel and Governor's Club
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is €169 per night from 1 Mar to 2 Mar
€169
1 Mar - 2 Mar
includes taxes & fees
9.6/10 Exceptional! (2,009 reviews)
All was great.

Reviewed on 27 Feb 2026

The Pfister Hotel
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is €166 per night from 11 Mar to 12 Mar
€166
11 Mar - 12 Mar
includes taxes & fees
9.8/10 Exceptional! (2,573 reviews)
This room was particularly lovely. The bed was one of the most comfortable I've encountered in any hotel. The room has individual decor that is charming, along with a ukulele and turntable (with vinyl available for your listening pleasure!) Saint Kate has a beautiful bar, with plenty of comfortable ...

Reviewed on 27 Feb 2026

Saint Kate - The Arts Hotel
See all 7,454 properties in Southern Wisconsin
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.

Popular places to visit

Harley-Davidson Museum which includes interior views

Harley-Davidson Museum

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

Harley-Davidson Museum
Milwaukee County Zoo which includes interior views and zoo animals as well as a small group of people

Milwaukee County Zoo

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo

Noah's Ark Waterpark

Bring the family to Noah's Ark Waterpark and have a fun-filled day at this theme park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.

Noah's Ark Waterpark

Frequently asked questions

Can I cancel my flight booking to Southern Wisconsin due to COVID-19?
Our helpful Customer Service Portal is your one-stop shop for almost every travel question, including about flight changes related to COVID-19. For more peace of mind, we recommend looking over the terms and conditions of your airfare before booking a seat.
What's the best way to find cheap flights to Southern Wisconsin that have flexible change policies?
By using our clever "No change fee" filter, that's how. All you have to do is enter your preferred dates and destination, click "Search," then click the checkbox directly under the "Flexible change policies" heading (it's on the left of your screen). Expedia makes it a snap to find inexpensive, flexible tickets to Southern Wisconsin.
What are some of the general tips for travellers to Southern Wisconsin during the COVID-19 outbreak?
In the face of the COVID-19 outbreak, travelling now comes with some extra challenges. Make a note of these valuable tips before jumping on your flight to Southern Wisconsin:
  • Understand what, if any, restrictions or rules apply to both your origin and destination. You may not be able to travel depending on local circumstances, so check before you book your flight.
  • Wear a face mask during airport screening. A TSA employee will ask you to temporarily lower your mask for ID purposes.
  • Instead of handing a TSA employee your boarding pass, position it straight on the reader yourself. After that, hold it up for inspection.
  • One container of liquid hand sanitizer is now permitted in your carry-on bag. It must not be larger than 12 oz (350 ml), and you'll have to remove it from your bag for X-ray screening.
  • Put any personal items (like your phone, wallet and keys) in your carry-on rather than a bin to minimize handling during the screening process.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on means it's less likely a TSA agent will need to open your bag for inspection.

Which airlines fly to Southern Wisconsin?
Delta offers flights into or near Southern Wisconsin, including 573 that arrive at General Mitchell Intl. Airport (MKE) each month. Figure out your travel dates and then book your fare early for the best deal.
How can I find cheap tickets to Southern Wisconsin?
Book ahead of time, fly to or from nearby airports, avoid school holiday time — there are lots of ways! Another one is to take advantage of Expedia's "flexible dates" function. Search for your Southern Wisconsin flight, then check out the cheapest prices for nearby dates. In the last seven days, the lowest price for a flight to Southern Wisconsin was .
How much is a flight to Southern Wisconsin?
One-way flights leaving () sold for as low as in the last seven days. During this period, the cost of a round-trip journey to Southern Wisconsin ranged between and . If you find a fantastic deal, book fast — these prices don't wait around for long.
What are the most popular airports to fly into in Southern Wisconsin?
Get ready to pack your bags and fly into General Mitchell Intl. Airport (MKE), Southern Wisconsin's leading flight hub. Book one of the 2400 flights that touch down at this popular destination each month.
When is the cheapest time to fly to Southern Wisconsin?
Leave for Southern Wisconsin early on in the week and you'll usually be rewarded with cheaper fares. Tuesday is known for being the cheapest day to get on a plane, closely followed by Monday. If you're hoping to avoid the costliest flights, stay away from Saturdays.
How much is a plane ticket to Southern Wisconsin?
In the last seven days, airfares to Southern Wisconsin ranged between and . Prices depend on multiple things, particularly the departure time, airline, seating class and when you make your booking.
Which airlines with flights to Southern Wisconsin employ COVID-19 cleanliness policies?
As lockdowns and restrictions start to lift, airlines are back in the skies with new strategies including physical distancing and an increased supply of face masks, gloves and sanitizer. Here's what some carriers are doing to help stop the spread of COVID-19:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.