Southern Wisconsin Holidays from £1,128

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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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,511, price is now £1,128 per person
£1,128
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Helpful staff, great location, adequate rooms!

Reviewed on 14 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £2,126, price is now £1,495 per person
£1,495
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,225 reviews)
Great location, service wasn’t the greatest, fees are high, crib was outdated.

Reviewed on 13 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,717, price is now £1,219 per person
£1,219
per person
17 Jun - 22 Jun
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Yessss it’s was amazing

Reviewed on 13 Apr 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,030, price is now £1,451 per person
£1,451
per person
29 May - 2 Jun
just found
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included

Reviewed on 12 Apr 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £2,344, price is now £1,744 per person
£1,744
per person
29 May - 2 Jun
just found
Return flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Nice hotel I would stay here again

Reviewed on 15 Apr 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 Pabst Theater 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 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 £167 per night from 11 May to 12 May
£167
11 May - 12 May
includes taxes & fees
9.6/10 Exceptional! (2,073 reviews)
Hotel was lovely. Blu has such amazing view.

Reviewed on 15 Apr 2026

The Pfister Hotel
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 £106 per night from 19 Apr to 20 Apr
£106
19 Apr - 20 Apr
includes taxes & fees
9.4/10 Exceptional! (3,642 reviews)
.

Reviewed on 14 Apr 2026

The Madison Concourse Hotel and Governor's Club
Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
1400 Great Wolf Dr Baraboo WI
Fully refundableReserve now, pay when you stay
The price is £99 per night from 3 May to 4 May
£99
3 May - 4 May
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
Easy Parking. Fun for our family with teenagers but we saw group activities with little ones as well. Lots of food options and nice gift shop. Prices comparable to others. We bought a pizza for $20. Water park is great even with it being too cold to go outside. 10/10 would recommend to anyone!

Reviewed on 15 Apr 2026

Great Wolf Lodge Wisconsin Dells
See all 7,492 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

University of Wisconsin-Madison

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

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
EAA Aviation Museum

EAA Aviation Museum

You can spend an afternoon exploring the galleries in EAA Aviation Museum during your travels in Oshkosh. Visit the area's shops or attend a sporting event.

EAA Aviation Museum

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.