Southern Wisconsin Holidays from £670

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Your Southern Wisconsin Holiday

With a Southern Wisconsin holiday package that can be tailored to your needs, planning your next adventure has never been so simple. If Milwaukee is your first stop, get ready to experience a city with a reputation for its distilleries and craft breweries, dining and plenty more. Begin your trip to Southern Wisconsin with some time in Milwaukee visiting popular sights like American Family Field and Wisconsin State Fair Park. Wisconsin Dells is another top city that draws crowds from near and far. Mt. Olympus Water and Theme Park and Chula Vista Waterparks are two of the leading places to see in this destination. When you're ready to stop dreaming and start packing, Expedia will help turn your Southern Wisconsin holiday into reality.

Top Southern Wisconsin Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,030, price is now £670 per person
£670
per person
5 May - 8 May
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!

Reviewed on 27 Feb 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was £2,462, price is now £1,814 per person
£1,814
per person
17 May - 22 May
found 1 hour ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was amazing. Staff was fantastic. Best Hotel we have ever stayed at

Reviewed on 26 Feb 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,925, price is now £1,488 per person
£1,488
per person
17 May - 22 May
found 1 hour ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
Very beautiful, clean hotel, and the staff was very respectful and nice

Reviewed on 24 Feb 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,343, price is now £1,054 per person
£1,054
per person
5 May - 8 May
found 1 day ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
We had a great stay!

Reviewed on 23 Feb 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £865, price is now £688 per person
£688
per person
2 Apr - 6 Apr
found 5 hours ago
Return direct flight included
Dublin (DUB) 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

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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

Southern Wisconsin Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)

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 £101 per night from 29 Mar to 30 Mar
£101
29 Mar - 30 Mar
includes taxes & fees
9.4/10 Exceptional! (3,518 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 £121 per night from 24 Mar to 25 Mar
£121
24 Mar - 25 Mar
includes taxes & fees
9.6/10 Exceptional! (2,007 reviews)
Beautiful property and excellent staff

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 £145 per night from 11 Mar to 12 Mar
£145
11 Mar - 12 Mar
includes taxes & fees
9.8/10 Exceptional! (2,572 reviews)
Wonderful art everywhere, clean and spacious room. Very convenient self-park without going outside (valet is available too). Can walk indoors to adjacent Pabst Theatre and Milwaukee Rep Theatres. Several dining options.

Reviewed on 26 Feb 2026

Saint Kate - The Arts Hotel
See all 7,438 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Cool street art in Madison, Wisconsin

University of Wisconsin-Madison

Enjoy the student vibe around University of Wisconsin-Madison, a top university in Madison. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Wisconsin-Madison
Harley-Davidson Museum showing 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

Kalahari Indoor Waterpark

Bring the children to Kalahari Indoor Waterpark and have a fun-filled day at this theme park in Baraboo. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.

Kalahari Indoor 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. Flight-inclusive packages are ATOL protected.