Southern Wisconsin Holidays from £934

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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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,506, price is now £934 per person
£934
per person
5 Sept - 10 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Friendly competent staff at checkin. The room and the view were spectacular. Wish we would have had time to use more of the amenities. I’d stay again if the opportunity arises.

Reviewed on 16 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,433, price is now £948 per person
£948
per person
5 Sept - 10 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)

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 £2,421, price is now £1,635 per person
£1,635
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,107, price is now £1,433 per person
£1,433
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Awful experience will not be going back ever again

Reviewed on 16 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,977, price is now £1,349 per person
£1,349
per person
5 Sept - 10 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)

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
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

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 £91 per night from 12 Aug to 13 Aug
£91
12 Aug - 13 Aug
includes taxes & fees
7/10 Good! (2,880 reviews)
"Water park was amazing"

Reviewed on 16 Jul 2026

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
The price is £123 per night from 2 Aug to 3 Aug
£123
2 Aug - 3 Aug
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is £167 per night from 19 Jul to 20 Jul
£167
19 Jul - 20 Jul
includes taxes & fees
9.2/10 Wonderful! (1,361 reviews)
"Nice, clean and comfortable. They had everything we wanted for a great family reunion. We actually had 3 rooms and would do it again in a heartbeat. Staff very friendly also."

Reviewed on 16 Jul 2026

Harbor Shores on Lake Geneva
See all 7,703 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

Stay near popular Southern Wisconsin attractions

A baseball game in a stadium with a person holding a hot dog and a drink.
Photo by Tim Ard
Open Photo by Tim Ard

American Family Field

9.0/10 (2,832 reviews)
Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.
See properties

Frequently asked questions

How much does a Southern Wisconsin travel package cost?
From as little as £934, 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.

Explore a world of travel with Expedia

* 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.