Southwest Wisconsin Holidays

Photo by Inbal Arieh

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Southwest Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,785, price is now €1,273 per person
€1,273
per person
26 Jul - 31 Jul
found 6 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Terrible attitude of the front desk clerk. Room smelled bad, dirty carpet.

Reviewed on 24 Jun 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,960, price is now €2,051 per person
€2,051
per person
26 Jul - 31 Jul
found 6 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,744 reviews)
Excelente, ubicación perfecta cerca de todo

Reviewed on 23 Jun 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €2,178, price is now €1,560 per person
€1,560
per person
26 Jul - 31 Jul
found 6 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Great location, great space in the rooms!!

Reviewed on 21 Jun 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €3,025, price is now €2,181 per person
€2,181
per person
26 Jul - 31 Jul
found 6 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.

Reviewed on 24 Jun 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €3,435, price is now €2,554 per person
€2,554
per person
26 Jul - 31 Jul
found 6 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
We love the Peninsula! The staff, location, room, and the Shanghai restaurant top tier.

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

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 €104 per night from 22 Jul to 23 Jul
€104
22 Jul - 23 Jul
includes taxes & fees
7/10 Good! (2,830 reviews)
"After driving over 6 1/2 hours to get here, we struggled to find where to check in. Also, we finally get to the main building to check in and we go to our room only to find standing water on the floor in the room. Called the front desk which is not even on the site on the building. “They” say they ..."

Reviewed on 24 Jun 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 €120 per night from 28 Jun to 29 Jun
€120
28 Jun - 29 Jun
includes taxes & fees
9.4/10 Exceptional! (3,889 reviews)
"Great location in Madison."

Reviewed on 24 Jun 2026

The Madison Concourse Hotel and Governor's Club
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 €67 per night from 12 Jul to 13 Jul
€67
12 Jul - 13 Jul
includes taxes & fees
8/10 Very good! (1,328 reviews)
"If you are planning on staying and taking the shuttle to the airport in the morning, make sure the shuttle is available for the time you will need it."

Reviewed on 24 Jun 2026

Baymont by Wyndham Madison West/Middleton WI West
See all 3,735 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.

Popular places to visit

Casino hotel and convention center by Upper Mississippi on calm misty morning at Dubuque Iowa

Q Casino

Why not roll the dice with a visit to Q Casino during your visit to Dubuque? Make time to visit the area's casinos or simply enjoy its top-notch restaurants.

Q Casino

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

Witches Gulch

Explore the great outdoors at Witches Gulch, a lovely green space in Wisconsin Dells. Stroll along the area's lakeside or experience its entertainment choices.

Witches Gulch

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.

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.