$33 Find Cheap Flights from North America to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 10/13. 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.
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1 adult, Economy

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Cheap Flights from North America to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from North America to Midway 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 North America to Midway

Thu, Sep 4 - Thu, Sep 11
Frontier Logo
7:00 am - 9:23 amDFW-MDW
2h 23mnonstop
Frontier Logo
10:18 am - 12:56 pmMDW-DFW
2h 38mnonstop
$67Frontier
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Sat, Aug 9 - Mon, Aug 11
Frontier Logo
11:27 am - 1:50 pmDFW-MDW
2h 23mnonstop
Frontier Logo
6:00 am - 8:33 amMDW-DFW
2h 33mnonstop
$72Frontier
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Tue, Jul 29 - Thu, Aug 7
Frontier Logo
2:40 pm - 5:03 pmDFW-MDW
2h 23mnonstop
Frontier Logo
7:40 am - 10:09 amMDW-DFW
2h 29mnonstop
$73Frontier
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Wed, Aug 27 - Wed, Sep 3
Southwest Logo
4:10 pm - 5:05 pmATL-MDW
1h 55mnonstop
Southwest Logo
6:05 pm - 9:00 pmMDW-ATL
1h 55mnonstop
$88Southwest
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Tue, Aug 12 - Wed, Aug 20
Southwest Logo
4:10 pm - 5:05 pmATL-MDW
1h 55mnonstop
Southwest Logo
1:00 pm - 3:55 pmMDW-ATL
1h 55mnonstop
$91Southwest
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Wed, Aug 6 - Sat, Aug 9
Delta Logo
7:09 am - 8:45 amMSP-MDW
1h 36mnonstop
Delta Logo
9:24 am - 10:58 amMDW-MSP
1h 34mnonstop
$91Delta
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Sat, Aug 9 - Tue, Aug 19
Delta Logo
7:09 am - 8:45 amMSP-MDW
1h 36mnonstop
Delta Logo
9:31 am - 1:43 pmMDW-MSP
4h 12m1 stop
$122Delta
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Mon, Aug 18 - Mon, Aug 25
Allegiant Air Logo
1:22 pm - 6:17 pmIAD-MDW
5h 55m1 stop
Allegiant Air Logo
9:32 am - 3:23 pmMDW-IAD
4h 51m1 stop
$180Allegiant Air
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Fri, Aug 15 - Tue, Aug 19
 Logo
1:22 pm - 6:17 pmIAD-MDW
5h 55m1 stop
 Logo
9:16 am - 9:34 pmMDW-IAD
11h 18m1 stop
Sun, Aug 17 - Thu, Aug 21
Allegiant Air Logo
9:12 pm - 2:04 pmIAD-MDW
17h 52m2 stops
Allegiant Air Logo
11:03 am - 6:20 pmMDW-IAD
6h 17m1 stop
$229Allegiant Air
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Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$33
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Atlanta to Chicago Midway Airport

Flights from North America to Midway: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from North America to Midway 
SheenaFlew with SouthwestLGA-MDWJun 2024
Get to the airport early. NY airports are always busy, even when you have TSA pre check
CindyFlew with SouthwestTPA-MDWMar 2024
Don’t check a bag. Chicago takes forever to get your baggage.
MoFlew with SouthwestOKC-MDWFeb 2024
Eat before you go. No ggod food at Midway.

FAQs for booking North America to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from North America to Chicago Midway Airport?

    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 North America to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from North America 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 North America to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to North America with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from North America to Chicago Midway Airport?

    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 Chicago Midway Airport from North America up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from North America to Midway

 
Need help choosing which airline to fly with from North America to Midway? 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 4250 reviews
8.1Boarding
8.6Crew
7.6Entertainment
8.0Comfort
7.0Food
Airline reviews

It was one and half hour late... Not sure if any other experience matters.

4.0 OkaySudhir, Jul 2025LGA - MCI
Read more Southwest reviews

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Leaving on time and having my luggage on my connecting flight

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

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