$165 Find Cheap Flights from Midland to Wisconsin

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midland to Wisconsin departing on 1/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Wisconsin

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Midland to Wisconsin, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Midland to Wisconsin, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midland to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$257
Madison
Madison1 stop$317
Milwaukee
Milwaukee1 stop$257
Madison
Madison1 stop$317

Book Cheap Midland to Wisconsin Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midland to Wisconsin that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midland to Wisconsin

Wed, Jan 28 - Thu, Jan 29
American Airlines Logo
12:41 pm - 10:38 pmMAF-ORD
9h 57m1 stop
American Airlines Logo
6:54 am - 12:11 pmORD-MAF
5h 17m1 stop
$165American Airlines
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Wed, Jan 28 - Thu, Jan 29
Southwest Logo
7:05 am - 1:00 pmMAF-ORD
5h 55m2 stops
Southwest Logo
7:15 am - 3:25 pmORD-MAF
8h 10m1 stop
$246Southwest
Find Deal
Sat, Jan 17 - Wed, Jan 21
American Airlines Logo
12:41 pm - 5:05 pmMAF-MKE
4h 24m1 stop
American Airlines Logo
3:53 pm - 10:54 pmMKE-MAF
7h 01m1 stop
$257American Airlines
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Sat, Jan 17 - Wed, Jan 21
American Airlines Logo
7:00 am - 3:57 pmMAF-MKE
8h 57m2 stops
American Airlines Logo
3:53 pm - 10:54 pmMKE-MAF
7h 01m1 stop
$262American Airlines
Find Deal
Sat, Feb 21 - Tue, Feb 24
American Airlines Logo
9:11 am - 3:07 pmMAF-ORD
5h 56m1 stop
American Airlines Logo
6:54 pm - 1:53 pmORD-MAF
18h 59m2 stops
$304American Airlines
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Wed, Jan 28 - Thu, Jan 29
Southwest Logo
7:05 am - 1:00 pmMAF-ORD
5h 55m2 stops
Southwest Logo
2:15 pm - 10:15 pmORD-MAF
8h 00m2 stops
$305Southwest
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Sat, Jan 17 - Wed, Jan 21
United Airlines Logo
7:20 am - 2:22 pmMAF-MKE
7h 02m1 stop
United Airlines Logo
3:45 pm - 9:54 pmMKE-MAF
6h 09m1 stop
$313United Airlines
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Wed, Jan 21 - Sat, Jan 24
United Airlines Logo
7:20 am - 1:15 pmMAF-MSN
5h 55m1 stop
United Airlines Logo
8:15 am - 4:35 pmMSN-MAF
8h 20m1 stop
$317United Airlines
Find Deal
Sat, Jan 17 - Wed, Jan 21
United Airlines Logo
7:20 am - 2:22 pmMAF-MKE
7h 02m1 stop
United Airlines Logo
10:30 am - 7:49 pmMKE-MAF
9h 19m2 stops
$318United Airlines
Find Deal
Fri, Jan 9 - Mon, Jan 12
Southwest Logo
6:40 am - 1:00 pmMAF-ORD
6h 20m1 stop
Southwest Logo
2:15 pm - 9:35 pmORD-MAF
7h 20m1 stop
$354Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Midland to Wisconsin flights

Get data-powered insights and trends into flights from Midland to Wisconsin to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between Midland and Wisconsin?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Midland to Wisconsin.

There is just one airline that flies from Midland to Wisconsin direct and that is Southwest. The best round-trip deal found from Southwest for the route is to Milwaukee (MKE) and costs $381.

Which airlines provide the cheapest flights from Midland to Wisconsin?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Midland to Wisconsin were found on American Airlines ($165) and Southwest ($246).

Good to know

Cheapest flight$165
Flight from Midland to Chicago

FAQs - booking Wisconsin flights

  • How does KAYAK find such low prices on flights from Midland to Wisconsin?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Midland to Wisconsin.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Midland to Wisconsin?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Midland to Wisconsin is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Midland to Wisconsin?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Midland to Wisconsin with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Midland to Wisconsin?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Midland to Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Wisconsin?

    The cheapest time of day to fly to Wisconsin is generally in the morning, when round-trip flights cost $426 on average. Morning departures are around 4% cheaper than evening flights, on average. The most expensive time of day to fly to Wisconsin is generally in the evening, which is peak travel time and where the average cost of a ticket is $446.

Reviews of the top airline flying from Midland to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from Midland to Wisconsin. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midland to Wisconsin? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4254 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Everything you need to know for your flight from Midland to Wisconsin

Information on your arrival and departure airports