Southern Wisconsin Holidays from £716

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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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was £1,146, price is now £716 per person
£716
per person
16 Oct - 21 Oct
found 20 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Excellent staff very friendly

Reviewed on 29 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,928, price is now £1,178 per person
£1,178
per person
16 Oct - 21 Oct
found 20 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,113, price is now £1,322 per person
£1,322
per person
10 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,244, price is now £783 per person
£783
per person
16 Oct - 21 Oct
found 19 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,100 reviews)
The best hotel for Navy Pier

Reviewed on 28 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,374, price is now £867 per person
£867
per person
16 Oct - 21 Oct
found 20 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

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
Milwaukee

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

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is £37 per night from 2 Sept to 3 Sept
£37
2 Sept - 3 Sept
includes taxes & fees
6.8/10 (2,361 reviews)
"Li"

Reviewed on 26 Aug 2025

Mt. Olympus Water & Theme Park Resort
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
9.4/10 Exceptional! (3,023 reviews)
"I loved the bed"

Reviewed on 26 Aug 2025

Get rates
The Madison Concourse Hotel and Governor's Club
Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is £65 per night from 17 Sept to 18 Sept
£65
17 Sept - 18 Sept
includes taxes & fees
8/10 Very Good! (1,273 reviews)
"My husband and I found this place very pleasant for our two night stay. I'm a very picky clean freak and found this hotel good, even with all the crazy reviews, we didn't find it filthy at all like some are saying. We actually had to stay in two different rooms since I booked two separate reservations ..."

Reviewed on 25 Aug 2025

Sonesta Select Milwaukee Brookfield
See all 7,601 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 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
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

How much does a Southern Wisconsin travel package cost?
From as little as £716, you can tailor make your Southern Wisconsin package. Simply combine hotels, flights and rental cars and be rewarded with discounts.
If I'm not able to travel, can I cancel my Southern Wisconsin travel package?
It's difficult to predict what the future holds, so it's comforting to know that you can change or cancel your Southern Wisconsin travel package. If you made your booking in the last 24 hours, you may be eligible for a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Southern Wisconsin?
Bundle your hotels and flights with Expedia to save on your next exciting adventure. With over 550 air carriers and 1,000,000 properties around the globe, your Southern Wisconsin travel package can be customized exactly to suit your travel style. With all those extra dollars, why not add one or two awesome experiences and tours? It's an easy way to unlock even more bargains. Your dream holiday in Southern Wisconsin is much closer than you thought!
Does Expedia offer Book Now, Pay Later Southern Wisconsin holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has worked out a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a fantastic getaway without drying up your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's easy monthly instalment plans. If paying a little each month sounds right for you, choose this option at checkout.
  • Pay in instalments holidays: If you'd like to pay for your getaway across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.

How far in advance should I book my Southern Wisconsin holiday?
Travellers can normally compare international flights on Expedia up to 12 months prior to departure. Booking last minute? With a bit of luck, it's still possible to nab a cheaper ticket just weeks before your flight.
What does an Expedia Southern Wisconsin travel package include?
Car rentals, flights and hotels — we connect you to the very best deals. All you'll have to do is pick and choose your favourite combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to craft an amazing Southern Wisconsin escape.
What should I know before booking a Southern Wisconsin travel package?
You'll pick up amazing savings when you combine your flights, hotels and rental cars into a package. Not only that, booking everything in one spot makes trip planning easier. So why waste time or money? Whether you're putting together a ritzy city getaway or an affordable family break, check out our package deals today.
Can I choose my airline with a Southern Wisconsin Expedia travel package?
Expedia offers access to more than 550 partner airlines worldwide, so you definitely can. Simply pick the carrier you want and put together your ideal Southern Wisconsin escape.

* 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.