Southwest Wisconsin Holidays from £982

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Your Southwest Wisconsin Holiday

Set off on your next big adventure with a Southwest Wisconsin holiday package, and leave relaxed knowing all the details are already organised. And with the ability to tailor your escape, it'll be one to remember! A trip to Southwest Wisconsin wouldn't be complete without exploring some of its most well-known cities, starting with Wisconsin Dells. A couple of the most popular attractions here include Mt. Olympus Water and Theme Park and Chula Vista Waterparks. Lake Delton is another favourite city with Southwest Wisconsin travellers. Visitors to this exciting city enjoy Mt. Olympus Water and Theme Park and Chula Vista Waterparks. Quit dreaming and get packing, because your Southwest Wisconsin holiday is just clicks away with Expedia.

Top Southwest 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
per person
8 Sept - 12 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Great helpful staff! Very clean! Wonderful experience! Breakfast buffet is a must! So delicious

Reviewed on 31 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
The stay so far has been great, but we attempted to order in room dining which, according to the menu, is available until 5AM, but were advised by the front desk staff that we would not be able to order food for at least 40 minutes while the kitchen was “cleaned”. No other solutions were provided and we were very disappointed in this interaction.

Reviewed on 30 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Sept - 30 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (229 reviews)
Room was clean, balcony had a nice view, bed were comfortable, shower was nice

Reviewed on 31 Jul 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
20 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

Where to stay in Southwest Wisconsin

Find the best Southwest Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Wisconsin
Madison featuring flowers, a house and a garden

Downtown Madison

The ample dining options and fantastic lake views are top of the list for many visitors to Downtown Madison. A stop by Orpheum Theater or Overture Center for the Arts might round out your trip.

Find hotels in Downtown Madison

Southwest Wisconsin Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)

Top hotels in Southwest 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 £76 per night from 17 Aug to 18 Aug
£76
17 Aug - 18 Aug
includes taxes & fees
6.8/10 (2,284 reviews)
"Food options , nearby attractions"

Reviewed on 30 Jul 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! (2,907 reviews)
"Very comfortable and convenient, and very nice staff."

Reviewed on 30 Jul 2025

Get rates
The Madison Concourse Hotel and Governor's Club
Days Inn & Suites by Wyndham Wisconsin Dells

Days Inn & Suites by Wyndham Wisconsin Dells

2.5 out of 5
2504 Wisconsin Dells Parkway, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
The price is £40 per night from 1 Sept to 2 Sept
£40
1 Sept - 2 Sept
includes taxes & fees
7/10 Good! (1,482 reviews)
"Good location"

Reviewed on 30 Jul 2025

Days Inn & Suites by Wyndham Wisconsin Dells
See all 3,783 properties in Southwest 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

5/5(2 reviews)

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
Top Secret

Top Secret

Enjoy a stop at Top Secret, an entertaining place to visit in Wisconsin Dells. Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants.

Top Secret

Kalahari Indoor Waterpark

Enjoy the rides and games at Kalahari Indoor Waterpark and see why this is a favourite theme park in Lake Delton. Stroll along the riverfront or experience the entertainment choices in this family-friendly area.

Kalahari Indoor Waterpark

Frequently asked questions

How much does a Southwest Wisconsin travel package cost?
Starting from as low as £982, a travel package is your ticket to affordable travel. Create your own Southwest Wisconsin trip by picking from our great range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Southwest Wisconsin travel package?
You can. We totally understand that life doesn't always go to plan, so we're here to help if you need to make changes to your Southwest Wisconsin travel package. You may be able to amend or cancel your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Southwest Wisconsin?
Bundle your flights and hotels with Expedia to save on your next adventure. With more than 550 partner airlines and 1,000,000 hotels across the world, your Southwest Wisconsin travel package can be tailored exactly to suit your travel style. With all those extra dollars, why not throw in a few interesting experiences and tours? It's an easy way to unlock even more discounts. Your dream getaway to Southwest Wisconsin is closer than you thought!
Does Expedia offer Book Now, Pay Later Southwest Wisconsin holidays?
We sure do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply select the payment plan that suits best during checkout and take the stress out of budgeting for your trip. Remember to bundle your flights, accommodation and activities with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your holiday across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan from Klarna.

How far in advance should I book my Southwest Wisconsin holiday?
Smart travellers will likely want to book early. You can generally look up international fares on Expedia up to a year before your intended flight. If you're purchasing your ticket at the last minute, don't worry. Bargain prices occasionally occur in the last weeks prior to departure.
What does an Expedia Southwest Wisconsin travel package include?
It comes down to what kind of getaway you have in the works. Southwest Wisconsin holiday deals can include car rentals, hotels and flights. You can mix and match to find the travel package that suits your budget and style. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Southwest Wisconsin travel package?
Design deals that suit your budget with an Expedia package. Hotels, airfares, rental cars — we've got them all. You'll save loads just by combining your bookings. Whether you're taking off on an adventure in the snow or drinking cocktails on a beach, your dream getaway is only clicks away.
Can I choose my airline with a Southwest Wisconsin Expedia travel package?
Yes, you're in charge. We offer more than 550 partner airlines worldwide, so you can customize your Southwest Wisconsin escape according to your budget and travel needs.

* 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.