Find cheap flights from Chicago Midway Airport to Wisconsin

Find cheap flights from Chicago Midway Airport to Wisconsin

Search hundreds of travel sites at once for deals on flights to Wisconsin. Bundle your flight + hotel and save!

Round-trip
Economy
Chicago (MDW)
Wisconsin
Sun 10/24
Sun 10/31
Any month
Bundle with KAYAK |
Include hotels

Top tips for finding cheap flights to Wisconsin

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Wisconsin is August.
  • Morning departure is around 43% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Wisconsin flights

How long is the flight to Wisconsin from Chicago Midway?

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Top airline flying Chicago Midway to Wisconsin

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,976 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "Great flight. No issues."

Pros: "Nassau security line was quick. US Customs line was quick."
Cons: "The Delta line to drop my bags was long and unorganized. The ticket agents were moving in slow motion. I waited over an hour to drop my bag. I thought I was going to miss my flight."

Cons: "No mechanical failures or delays would be nice"

Cons: "The cabin temperature was very hot"

Cons: "Miniature candy bars are not sufficient for an hour and a half flight."

Cons: "Was not offered a drink in first class prior to take off."

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Cons: "The flight attendants were quick with the pick up of drinks. I had only been served my drink for five minutes and they were already coming around to pick up trash."

Cons: "WiFi didn't work"

Pros: "Good food, entertainment and Delta Comfort section worth the extra cost."
Cons: "Boarding at JFK a nightmare."

Cons: "At least one hour late"

Pros: "Very good check in and customs, etc at both airports especially RDU."
Cons: "Only fair to good in flight service."

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Pros: "It was on time"
Cons: "Plane too cold."

Pros: "Quick boarding, great seats and everything went on schedule."

Pros: "The whole crew was great and very accommodating"

Pros: "Friendly greeting and goodbye.goog entertainment."
Cons: "Too hot, attendant did not know plane."

Pros: "Complimentary beverages."
Cons: "Chicken and pasta for dinner"

Pros: "The pilot was extremely informative The stewardesses were helpful It was a delayed flight and they made it relax"
Cons: "Bad weather at LGA"

Pros: "Upgrade to ComfortPlus"

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Pros: "We boarded quickly, in zones. Staff were professional and courteous."
Cons: "Perhaps more than just 2 episodes of some TV programs eg Goldrush. Also more current shows."

Pros: "flight was on time..arrived early..friendly staff.."

Cons: "The airport and boarding process at SJD was disorganized. There were no sandwiches available to purchase on the flight."

Cons: "Bullshit seating...will happily put frequent flyers next to the freaking toilets."

Pros: "Punctual departures. Adequate overheard space."
Cons: "Food was mediocre for a 5-6 hour flight. I expected a little bit more."

Cons: "You had me check my hand luggage with expensive items that did not arrive."

Pros: "We had the best flight attendant ever! Her name was Sharon on Eandeavor / Delta Cnx, and she made the experience the best flight I've experienced. Thanks Sharon for being awesome!"
Cons: "window seat in back didn't have window"

Pros: "The flight was good. It crashed zero times. I was pleased not to check my carry-on bags. They were attentive in calling for wheelchair assistance for me."
Cons: "Seats are consistently too small."

Pros: "Movie helped to pass the time this was the longest flight ever I was glad when it was over"
Cons: "I have nothing to complain about"

Pros: "Good entertainment options, on-time departure and arrival."
Cons: "Had to stow backpack under seat due to full flight. How is this still the norm? Wi-fi not working."

Pros: "The two Flight Attendants were very attentive, personable, and funny, and interacted well with the passengers."
Cons: "Nothing, everything was good."

Pros: "Airport was being remodeled so there was a bit of confusion and lack of accommodation but other than that the flight was good"

Cons: "The flight got delayed by 3 hours or more. I missed my flight from LA to FL"

Pros: "Fantastic SFO-based crew serving Delta One cabin. They are attentive, and constantly walk around the cabin to provide service."
Cons: "Delay at JFK (first, the inbound aircraft coming late, then 2.5 hrs taxing at JFK, finally landed in SFO but the gate was occupied)."

Pros: "The crew from MSP to LSE onboard were incredibly pleasant and nice"
Cons: "They wanted me to check my bag from MSP to LSE. They weren't as nice as they could have been about it. But in the end I didn't need to check it."

Cons: "When I was transferred to Delta's website to book, the date was reset to 6 months in the future. It happened to be the same Monday the 26th so that's why I didn't notice. Delta refused to refund my money. This was a terrible experience and I plan not to use Kayak or Delta again!"

Cons: "Why can't all the Delta gates be near each other. My connecting flight was very far."

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "Like the online check in and advanced seat assignment"
Cons: "It's only a 45 min flight so no ptoblems"

Cons: "Everything that could have gone wrong with my flights, went wrong. On my way from LA to Raleigh (through Atlanta), I was affected by the weather conditions at Atlanta. I understand that the weather is beyond Delta's scope of control, but customer service is not. I had to wait in line at LAX for 8 hours to even get information on what had happened, and what solutions were available. The customer service call center was collapsed, and at the airport counters at one point there was ONLY ONE DELTA REPRESENTATIVE serving a line of more than 100 upset customers. This IS Delta's fault, and it is unacceptable. This definitely was under Delta's control, but in order to save a few dollars in overtime for emergency staff Delta was willing to let its customers make terribly long lines, miss their flights, their connections and consequently their commitments. It is disappointing to observe how Delta believes that a few dollars saved on extra staff and emergency measures can offset the irreparable long term damage to its business due to upset customers. My way back from Raleigh to Los Angeles was also a disaster. Without any type of explanation and nothing more than an email announcing the change, the nonstop flight I bought was replaced by a 1-stop flight with connection in Atlanta. This was NOT THE PRODUCT I PURCHASED. There is a reason I paid a premium for a nonstop flight, and Delta did not hesitate in providing me with a less valuable product without any explanation or refund. Delta prioritizes its operational metrics - an obsession to fill and overbook its capacity - over its customers' experience, one again under the foolish belief that short term savings in any way offset the long term damage of disappointed and alienated customers. I will NEVER FLY DELTA AGAIN. I will do whatever I can to transmit my experience to everyone I know. At a time where major airline carriers are in the spotlight due to abusive practices (i.e. the United passenger case), I still find hope in knowing that alternatives such as Southwest still put their customers first, over the ethereal benefits that a few-dollar savings in operational expenses can provide."

Pros: "nothing"
Cons: "it took 7hours due to storms"

Pros: "I liked the in-flight entertainment and the crew was very pleasant"
Cons: "The seats are awful. If you're 6 ft or taller, your legs barely fit if at all. Boarding is ridiculous."

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "I've never seen such a modern and easy to use entertainment system before. All the movies are complimentary."

Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Pros: "Flight took off on time and arrived about 30 minutes early."

Cons: "The flight was delayed by inbound aircraft."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago Midway Airport to Wisconsin

Airlines flying from Chicago Midway Airport to Wisconsin have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago Midway Airport to Wisconsin

Mandatory masks

Masks required on board, masks provided on flights from Chicago Midway Airport to Wisconsin

Social distancing seating

Middle seats unavailable to book on flights from Chicago Midway Airport to Wisconsin

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago Midway Airport to Wisconsin

Book cheap flights from Chicago Midway Airport to Wisconsin

Recent round-trip flight deals

1/20
Thu
1 stop
Delta
5h 16m
MDW - LSE
1/23
Sun
1 stop
Delta
6h 23m
LSE - MDW
11/6
Sat
1 stop
Delta
4h 36m
MDW - GRB
11/9
Tue
1 stop
Delta
3h 36m
GRB - MDW
2/9
Wed
1 stop
Delta
5h 15m
MDW - GRB
2/23
Wed
1 stop
Delta
6h 07m
GRB - MDW
11/11
Thu
1 stop
Delta
3h 35m
MDW - LSE
11/15
Mon
1 stop
Delta
3h 51m
LSE - MDW
1/13
Thu
1 stop
Delta
5h 16m
MDW - LSE
1/17
Mon
1 stop
Delta
6h 23m
LSE - MDW
2/9
Wed
1 stop
Delta
5h 15m
MDW - GRB
2/23
Wed
1 stop
Delta
4h 03m
GRB - MDW
1/13
Thu
1 stop
Delta
5h 21m
MDW - LSE
1/17
Mon
2 stops
Delta
7h 12m
LSE - MDW
2/9
Wed
1 stop
Delta
5h 15m
MDW - GRB
2/23
Wed
1 stop
Delta
6h 07m
GRB - MDW
1/20
Thu
2 stops
Delta
5h 25m
MDW - LSE
1/23
Sun
1 stop
Delta
6h 23m
LSE - MDW
2/20
Sun
1 stop
Delta
5h 54m
MDW - RHI
3/13
Sun
1 stop
Delta
3h 52m
RHI - MDW
11/11
Thu
1 stop
Delta
5h 27m
MDW - LSE
11/15
Mon
2 stops
Delta
7h 08m
LSE - MDW
11/15
Mon
1 stop
Delta
3h 57m
MDW - CWA
11/16
Tue
1 stop
Delta
6h 03m
CWA - MDW
11/12
Fri
1 stop
Delta
4h 35m
MDW - GRB
11/14
Sun
1 stop
Delta
6h 18m
GRB - MDW
2/20
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1 stop
Delta
5h 54m
MDW - RHI
3/13
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2 stops
Delta
6h 45m
RHI - MDW
11/21
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1 stop
Delta
4h 40m
MDW - GRB
11/28
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1 stop
Delta
6h 18m
GRB - MDW
11/10
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1 stop
Delta
4h 35m
MDW - GRB
11/12
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1 stop
Delta
5h 48m
GRB - MDW
11/13
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Delta
4h 13m
MDW - GRB
11/17
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1 stop
Delta
4h 36m
GRB - MDW
12/12
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1 stop
Delta
4h 48m
MDW - GRB
12/13
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1 stop
Delta
5h 48m
GRB - MDW
11/15
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Delta
5h 06m
MDW - CWA
11/16
Tue
2 stops
Delta
10h 16m
CWA - MDW
11/13
Sat
1 stop
Linear Air Taxi
4h 14m
MDW - GRB
11/15
Mon
1 stop
Linear Air Taxi
4h 13m
GRB - MDW
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Recent one-way flight deals

10/28
Thu
2 stops
Multiple Airlines
29h 44m
MDW - MKE
12/19
Sun
2 stops
Multiple Airlines
26h 02m
MDW - MKE
11/14
Sun
1 stop
Delta
4h 13m
MDW - GRB
11/14
Sun
1 stop
Delta
4h 13m
MDW - GRB
1/3
Mon
1 stop
Delta
4h 27m
MDW - GRB
1/2
Sun
1 stop
Delta
5h 02m
MDW - GRB
11/20
Sat
1 stop
Delta
3h 57m
MDW - CWA
10/29
Fri
1 stop
Delta
18h 48m
MDW - MSN
1/1
Sat
1 stop
Delta
6h 00m
MDW - GRB
10/28
Thu
3 stops
Multiple Airlines
27h 04m
MDW - MKE
10/31
Sun
1 stop
Delta
3h 32m
MDW - LSE
11/11
Thu
1 stop
Delta
6h 12m
MDW - GRB
11/28
Sun
1 stop
Delta
4h 35m
MDW - GRB
11/28
Sun
2 stops
Multiple Airlines
36h 01m
MDW - MKE
10/28
Thu
1 stop
Delta
3h 32m
MDW - LSE
10/29
Fri
1 stop
Delta
5h 25m
MDW - GRB
10/28
Thu
2 stops
Delta
9h 30m
MDW - LSE
12/11
Sat
1 stop
Delta
4h 33m
MDW - GRB
11/28
Sun
3 stops
Multiple Airlines
43h 36m
MDW - MKE
11/28
Sun
1 stop
Linear Air Taxi
4h 09m
MDW - MKE
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