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Find cheap flights from Chicago Midway Airport to Wisconsin from $49

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Wisconsin departing on 5/31. 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
0 bags
Sat 6/15
Sat 6/22

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Best Wisconsin Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Green Bay
Green Bay1 stop$412
Wausau
Wausau1 stop$424
Minneapolis
Minneapolisnonstop$107
Duluth
Duluth2 stops$208

Good to know

Cheapest flight

$49
Flight from Chicago Midway Airport to Minneapolis

FAQs - booking Wisconsin flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport 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 Chicago Midway Airport to Wisconsin.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Wisconsin from Chicago Midway Airport 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 Chicago Midway Airport 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 to Wisconsin with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport 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 to Wisconsin from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Wisconsin

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Minneapolis $109 one-way - $247 round-trip
  • Morning departure is around 9% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to Wisconsin

 
Need help choosing which airline to fly with from Midway 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
DeltaOverall score based on 10673 reviews
8.0Entertainment
8.2Boarding
7.9Comfort
8.6Crew
7.4Food
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Book cheap flights from Chicago to Wisconsin

Recent round-trip flight deals

7/4Thu
nonstopDelta
1h 39mMDW-MSP
7/6Sat
nonstopDelta
1h 38mMSP-MDW
$107
6/11Tue
nonstopDelta
1h 37mMDW-MSP
6/16Sun
nonstopDelta
1h 39mMSP-MDW
$117
6/8Sat
nonstopDelta
1h 36mMDW-MSP
6/16Sun
nonstopDelta
1h 39mMSP-MDW
$127
6/14Fri
nonstopSouthwest
1h 25mMDW-MSP
6/15Sat
nonstopSouthwest
1h 25mMSP-MDW
$185
5/28Tue
1 stopSouthwest
3h 55mMDW-MSP
5/30Thu
1 stopSouthwest
7h 05mMSP-MDW
$210
9/14Sat
1 stopFrontier
7h 33mMDW-MSP
9/16Mon
1 stopFrontier
12h 53mMSP-MDW
$241
8/5Mon
1 stopFrontier
9h 11mMDW-MSP
8/6Tue
1 stopFrontier
11h 58mMSP-MDW
$254
6/6Thu
2 stops
24h 29mMDW-MSP
6/10Mon
1 stop
11h 34mMSP-MDW
$301
6/7Fri
2 stops
16h 57mMDW-MSP
6/17Mon
1 stop
12h 08mMSP-MDW
$344
9/13Fri
3 stopsWestJet
20h 23mMDW-GRB
9/16Mon
3 stopsWestJet
19h 17mGRB-MDW
$1,509

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Recent one-way flight deals

5/31Fri
nonstopDelta
1h 33mMDW-MSP
$49
6/11Tue
nonstopDelta
1h 37mMDW-MSP
$59
6/6Thu
nonstopDelta
1h 34mMDW-MSP
$69
7/3Wed
nonstopDelta
1h 38mMDW-MSP
$79
9/14Sat
1 stopFrontier
7h 33mMDW-MSP
$119
6/5Wed
1 stopFrontier
5h 45mMDW-MSP
$129
5/24Fri
1 stop
11h 39mMDW-MSP
$153
7/14Sun
2 stops
25h 04mMDW-MSP
$161
5/21Tue
3 stopsWestJet
25h 17mMDW-MSP
$836
7/14Sun
3 stopsWestJet
25h 14mMDW-GRB
$957

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Last minute flights from Midway to Wisconsin

Last minute flight, train and bus deals

5/18Sat
nonstopDelta
1h 33mMDW-MSP
5/25Sat
nonstopDelta
1h 30mMSP-MDW
$240
5/18Sat
multi-stopDelta
3h 43mMDW-MSP
5/25Sat
nonstopDelta
1h 30mMSP-MDW
$249
5/18Sat
nonstopDelta
1h 33mMDW-MSP
5/22Wed
nonstopDelta
1h 31mMSP-MDW
$281
5/18Sat
nonstopDelta
1h 37mMDW-MSP
5/22Wed
multi-stopDelta
3h 45mMSP-MDW
$290
5/20Mon
nonstopSouthwest
1h 25mMDW-MSP
5/22Wed
nonstopSouthwest
1h 25mMSP-MDW
$297
5/20Mon
multi-stopSouthwest
9h 15mMDW-MSP
5/22Wed
nonstopSouthwest
1h 25mMSP-MDW
$306
5/21Tue
multi-stopFrontier
7h 55mMDW-MSP
5/23Thu
multi-stopFrontier
8h 48mMSP-MDW
$577
5/17Fri
multi-stop
26h 52mMDW-MSP
5/19Sun
multi-stop
14h 05mMSP-MDW
$704
5/18Sat
multi-stopFrontier
17h 59mMDW-MSP
5/25Sat
multi-stopFrontier
11h 24mMSP-MDW
$739
5/21Tue
multi-stop
25h 17mMDW-MSP
6/19Wed
multi-stop
14h 30mMSP-MDW
$1,192

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Chicago Midway Airport - Wisconsin Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Wisconsin - Chicago Midway Airport

Cabin classes: