A lake surrounded by lush green hills and a rocky cliff.
Photo by Inbal Arieh
Open Photo by Inbal Arieh

Southwest Wisconsin Holiday Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages with flights are ATOL protected

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.

The Latest Southwest Wisconsin Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 20 Jan - 24 Jan

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,771 reviews)
    "Amazing view, but basic room"
    Reviewed November 7, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LGW • 1 stop
    £1,019
    £797
    per traveller
    found 21 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 20 Jan - 24 Jan

    Pendry Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,162 reviews)
    "Beautiful rooms and service."
    Reviewed November 5, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LGW • 1 stop
    £1,082
    £814
    per traveller
    found 21 hours ago
    Pendry Chicago
  • 25 Dec - 30 Dec

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,077 reviews)
    "Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint"
    Reviewed November 6, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £2,018
    £1,529
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 25 Dec - 30 Dec

    The Peninsula Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,008 reviews)
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £2,673
    £2,123
    per traveller
    found 1 day ago
    The Peninsula Chicago
  • 25 Dec - 30 Dec

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,004 reviews)
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,348
    £1,075
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG

Discover the most popular places to visit in Southwest Wisconsin

Southwest Wisconsin Hotel Deals

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.

Frequently Asked Questions

How much does a Southwest Wisconsin travel package cost?

Starting from as low as £797, 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.