Southwest Wisconsin Holidays from £822

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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
Price was £1,137, price is now £822 per person
£822
per person
7 May - 11 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Staff were great, clean room, nice shower and breakfast buffet was solid considering its free. Rooftop was closed but probably just until it gets warmer. Would stay again!

Reviewed on 23 Mar 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,000, price is now £2,229 per person
£2,229
per person
16 May - 23 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
You will never look at staying at a hotel the same again. Absolutely the best. The level of standard is unmatched. Not our first go around and definitely will continue visiting.

Reviewed on 21 Mar 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £2,706, price is now £2,096 per person
£2,096
per person
16 May - 23 May
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Truly one of our favorite stays! The staff makes you feel at home & are super accommodating. I will stay here every time! The bellman Michael is quite literally the best ever!! He made our stay so wonderful and special!

Reviewed on 16 Mar 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,640, price is now £2,128 per person
£2,128
per person
12 May - 18 May
found 1 hour ago
Return direct flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (3,230 reviews)
Nice staff very clean

Reviewed on 23 Mar 2026

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Downtown Chicago
Price was £2,003, price is now £1,694 per person
£1,694
per person
28 May - 1 Jun
found 18 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,103 reviews)
Clean spacious my go to vacation spot all year around

Reviewed on 22 Mar 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
Wisconsin State Capitol building, view from Monona Terrace rooftop.; Shutterstock ID 5305432

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 £102 per night from 29 Mar to 30 Mar
£102
29 Mar - 30 Mar
includes taxes & fees
9.4/10 Exceptional! (3,585 reviews)
The room had a smell to it, almost like cigarette smoke. Especially in the bathroom.

Reviewed on 23 Mar 2026

The Madison Concourse Hotel and Governor's Club
Great Wolf Lodge Wisconsin Dells

Great Wolf Lodge Wisconsin Dells

3.5 out of 5
1400 Great Wolf Dr Baraboo WI
Fully refundableReserve now, pay when you stay
The price is £100 per night from 5 Apr to 6 Apr
£100
5 Apr - 6 Apr
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
Smalll resort. Only for those with small kids. Don’t recommend if you have kids over 5

Reviewed on 23 Mar 2026

Great Wolf Lodge Wisconsin Dells
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 £42 per night from 5 Apr to 6 Apr
£42
5 Apr - 6 Apr
includes taxes & fees
Mt. Olympus Water & Theme Park Resort
See all 3,702 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

Cool street art in Madison, Wisconsin

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

Kalahari Indoor Waterpark

Bring the children to Kalahari Indoor Waterpark and have a fun-filled day at this 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

Bring the family to Noah's Ark Waterpark and have a fun-filled day at this theme park in Wisconsin Dells. Stroll along the area's riverfront 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.