Southwest Wisconsin Holidays from £1,210

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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.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was £1,475, price is now £1,210 per person
£1,210
per person
10 Sept - 16 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,033 reviews)
The room was large, clean, and comfortable. The blackout shades and space were highlights. There are only two things that would make me question staying here again… 1. We arrived early and our room wasn’t ready, which is no big deal, but they wouldn’t even let us use the pool while we waited on our room. In my extensive travels, I’ve never experienced that and it was a bummer for my daughter. 2. The price for parking is really high… $65 a day! I understand it’s located in Chicago, but it’s not even located within walking distance to downtown. If you figure in the room rate, with the parking fee, and Uber fees, it makes the nightly rate very high compared to other hotels located in the heart of downtown.

Reviewed on 21 Jun 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £2,134, price is now £1,673 per person
£1,673
per person
10 Sept - 16 Sept
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,241 reviews)
My fave Chicago stay

Reviewed on 19 Jun 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,469, price is now £1,948 per person
£1,948
per person
30 Jul - 3 Aug
found 12 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
hotel was immaculate and the people were amazing.

Reviewed on 20 Jun 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £2,049, price is now £1,665 per person
£1,665
per person
30 Jul - 3 Aug
found 12 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,384 reviews)
I truly enjoyed my stay at this hotel. From the moment I arrived, the staff made me feel welcome and valued. Everyone was so friendly, attentive, and genuinely eager to help, which made the experience even more enjoyable. The hotel was clean, comfortable, and had everything I needed for a relaxing stay. I especially loved the location—it was convenient to restaurants, shopping, and local attractions, making it easy to get around and enjoy the area without any hassle.

Reviewed on 21 Jun 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was £1,888, price is now £1,547 per person
£1,547
per person
30 Jul - 3 Aug
found 12 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
The hotel is fresh and clean. Very nice facility. Staff anre wonderful. Only comment is there should be free water in the rooms, at least for Marriott members. For the rates charged, water should be included. Water pressure is a bit low.

Reviewed on 21 Jun 2026

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
A large domed building surrounded by modern cityscape and a body of water.

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

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 £103 per night from 28 Jun to 29 Jun
£103
28 Jun - 29 Jun
includes taxes & fees
9.4/10 Exceptional! (3,891 reviews)
"Microwaves in the"

Reviewed on 21 Jun 2026

The Madison Concourse Hotel and Governor's Club
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 £81 per night from 22 Jul to 23 Jul
£81
22 Jul - 23 Jul
includes taxes & fees
7/10 Good! (2,821 reviews)
"Very spacious room, what I didn’t like was the guest above us running and jumping around at 12:30/1:00am in the morning for 2 nights straight other than that it was nice."

Reviewed on 22 Jun 2026

Mt. Olympus Water & Theme Park Resort
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is £58 per night from 29 Jun to 30 Jun
£58
29 Jun - 30 Jun
includes taxes & fees
8/10 Very good! (1,323 reviews)
"Room was clean"

Reviewed on 21 Jun 2026

Baymont by Wyndham Madison West/Middleton WI West
See all 3,734 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
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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

Kalahari Indoor Waterpark

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

Kalahari Indoor Waterpark

Noah's Ark Waterpark

Have a fun-filled day at Noah's Ark Waterpark and find out why this is a popular theme park in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.

Noah's Ark Waterpark

Frequently asked questions

Can I cancel my flight booking to Southwest Wisconsin due to COVID-19?
Our Customer Service Portal is where you can get important information about changing or cancelling your flight due to COVID-19. Before you reserve a seat, it's a good idea to look over the terms and conditions of your preferred carrier too.
What's the best way to find cheap flights to Southwest Wisconsin that have flexible change policies?
It's as easy as counting to three with Expedia. First, enter your preferred travel dates and press "Search." Step 2: Check the "No change fee" box below the "Flexible change policies" subheading on the left-hand side of your screen. Step 3. Reserve your flexible and cheap ticket to Southwest Wisconsin.
What are some of the general tips for travellers to Southwest Wisconsin during the COVID-19 outbreak?
With new rules, restrictions and safety measures to follow, travel looks a bit different these days. These are some helpful things to know before you hop on that plane to Southwest Wisconsin:
  • Investigate if any travel restrictions apply to your origin and destination before locking in a flight. Also check if there are any requirements you'll need to follow on arrival, such as taking a COVID-19 test.
  • When you pass through airport screening, do not remove your face mask. You will be asked to lower it briefly for identification purposes. Travellers who refuse to wear a mask may face civil penalties and may also be escorted from the terminal.
  • Rather than handing a TSA agent your boarding pass, position it directly on the scanner yourself. Once that's done, hold it up for inspection.
  • One container of liquid hand sanitizer is now allowed in your carry-on bag. It must be no larger than 12 oz (350 ml), and you'll need to take it out of your bag at the X-ray machine for scanning.
  • To minimize handling during the screening process, put items such as your belt, phone and wallet into your carry-on instead of into the bins.
  • Transport all food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on makes it less likely that a TSA agent will need to touch and open your bag for inspection.

Which airlines fly to Southwest Wisconsin?
Arrange your airfare with United Airlines and then start piecing together your Southwest Wisconsin to-do list. This leading airline provides 238 flights every month to Dane County Regional Airport (MSN), a major gateway.
How can I find cheap tickets to Southwest Wisconsin?
In the last seven days, was the best price for a flight to Southwest Wisconsin. If you want to save even more, book ahead of time and be flexible with your travel dates. Search for your flight to Southwest Wisconsin, then see prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Southwest Wisconsin?
The cost of a round-trip flight to Southwest Wisconsin in the last seven days fluctuated between and . If you were heading one way from (), you could have landed a cheap fare from only .
What are the most popular airports to fly into in Southwest Wisconsin?
Jet into Dane County Regional Airport (MSN) and enjoy all that Southwest Wisconsin has to offer. As the region's main entry point, around 1068 flights touch down here each month.
When is the cheapest time to fly to Southwest Wisconsin?
If you can be flexible with what date you travel to Southwest Wisconsin, try to fly out earlier in the week. The most economical day to take off is usually Tuesday, followed by Monday. Saturday is typically the costliest day, with many holiday makers opting to take off on the weekend.
How much is a plane ticket to Southwest Wisconsin?
In the last seven days, fares varied between and . Have a look at our fantastic deals to Southwest Wisconsin, pick your favourite and then start packing your bags.
Which airlines with flights to Southwest Wisconsin employ COVID-19 cleanliness policies?
In response to the current pandemic, many airlines have adopted extra rules and standards to help their passengers fly with peace of mind. Check out what these carriers are doing:
  • 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.
  • United 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.