OKC - MDW

$111 Find Cheap Flights from Oklahoma City 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 from Oklahoma City to Midway departing on 7/13. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oklahoma City to Chicago, 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 Oklahoma City to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Oklahoma City to Midway (OKC-MDW)

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

Sat, Jul 5 - Sat, Jul 12
Frontier Logo
6:05 am - 8:54 pmOKC-MDW
14h 49m1 stop
Frontier Logo
2:44 pm - 10:38 pmMDW-OKC
7h 54m1 stop
$210Frontier
Find Deal
Mon, Jul 7 - Thu, Jul 17
Frontier Logo
6:05 am - 11:41 amOKC-MDW
5h 36m1 stop
Frontier Logo
2:44 pm - 10:17 pmMDW-OKC
7h 33m1 stop
$276Frontier
Find Deal
Mon, Jun 30 - Mon, Jun 30
Southwest Logo
5:10 pm - 7:05 pmOKC-MDW
1h 55mnonstop
Southwest Logo
9:50 pm - 11:55 pmMDW-OKC
2h 05mnonstop
$283Southwest
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Thu, Aug 14 - Sat, Aug 16
Southwest Logo
3:35 pm - 5:30 pmOKC-MDW
1h 55mnonstop
Southwest Logo
7:25 pm - 9:25 pmMDW-OKC
2h 00mnonstop
$285Southwest
Find Deal
Mon, Aug 4 - Thu, Aug 7
Southwest Logo
5:10 pm - 7:05 pmOKC-MDW
1h 55mnonstop
Southwest Logo
7:45 am - 9:45 amMDW-OKC
2h 00mnonstop
$287Southwest
Find Deal
Thu, Aug 14 - Sat, Aug 16
Southwest Logo
5:10 pm - 8:25 pmOKC-MDW
3h 15m1 stop
Southwest Logo
7:25 pm - 9:25 pmMDW-OKC
2h 00mnonstop
$295Southwest
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Sat, Aug 2 - Thu, Aug 7
Delta Logo
7:20 am - 1:06 pmOKC-MDW
5h 46m1 stop
Delta Logo
6:00 am - 1:00 pmMDW-OKC
7h 00m1 stop
$302Delta
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Mon, Aug 4 - Thu, Aug 7
Delta Logo
1:55 pm - 9:42 pmOKC-MDW
7h 47m1 stop
Delta Logo
6:00 am - 1:00 pmMDW-OKC
7h 00m1 stop
$307Delta
Find Deal
Fri, Aug 15 - Mon, Aug 18
Frontier Logo
6:05 am - 11:41 amOKC-MDW
5h 36m1 stop
Frontier Logo
8:35 am - 7:14 pmMDW-OKC
10h 39m1 stop
$308Frontier
Find Deal
Wed, Aug 20 - Sun, Aug 24
Delta Logo
11:25 am - 5:47 pmOKC-MDW
6h 22m1 stop
Delta Logo
6:04 am - 12:55 pmMDW-OKC
6h 51m1 stop
$418Delta
Find Deal
Useful Info

KAYAK's insights & trends for Oklahoma City to Midway flights

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

What’s the cheapest day of the week to fly from Oklahoma City to Chicago Midway Airport?

The average price of all round-trip flights from Oklahoma City to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Thursday and more expensive on a Sunday. On your return trip to Oklahoma City, you should consider flying back on a Wednesday, and avoid Tuesdays for better deals.

What is the cheapest month to fly from Oklahoma City to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oklahoma City to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Oklahoma City to Chicago Midway Airport is May, where tickets cost $224 (return) on average. On the other hand, the most expensive months are January and April, where the average cost of round-trip tickets is $527 and $418 respectively.

Can I save money by flying with a layover from Oklahoma City to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $302 on average.

Good to know

Low seasonFebruary
High seasonJune
Cheapest flight$111
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Oklahoma City to Chicago Midway Airport

When to book flights from Oklahoma City to Midway

Are your dates flexible? Find out the best times to travel from Oklahoma City to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Oklahoma City to Chicago Midway Airport flights

  • What is the cheapest flight from Oklahoma City to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Oklahoma City to Chicago Midway Airport was $111 for a one-way ticket and $210 for a round-trip.

  • Do I need a passport to fly between Oklahoma City and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Oklahoma City to Chicago Midway Airport?

    American Airlines, and Delta offer inflight Wi-Fi service on the Oklahoma City to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Oklahoma City to Chicago Midway Airport?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Oklahoma City to Chicago Midway Airport flight route.

  • On which days can I fly direct from Oklahoma City to Chicago Midway Airport?

    There are nonstop flights from Oklahoma City to Chicago Midway Airport on a daily basis.

  • Which is the best airline for flights from Oklahoma City to Chicago, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Oklahoma City to Chicago are Southwest and Frontier. With an average price for the route of $369 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $202 and an overall rating of 5.9.

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

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oklahoma City 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 Oklahoma City 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 Oklahoma City 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 Oklahoma City with another airline. Booking your flights between Oklahoma City and MDW can sometimes prove cheaper using this method.

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

KAYAK’s top tips for finding a cheap flight from Oklahoma City to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $189 or less one-way and $306 or less round-trip.

Prefer to fly direct from Oklahoma City to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Oklahoma City Will Rogers World to Chicago Midway.
Find which airlines fly direct from Oklahoma City Will Rogers World Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Oklahoma City Will Rogers World to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Oklahoma City Will Rogers World

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Oklahoma City to Midway

 
See real verified KAYAK customer reviews for airlines flying from Oklahoma City to Chicago. 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 Oklahoma City 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 4278 reviews
8.2Boarding
7.1Food
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

They canceled flight. Hard to believe there was even a plane incoming for us to get on

The worst. We never made our connection and they did absolutely nothing to help us at the airport.

Our flight was cancelled. They could do nothing to help us get another flight that was timely. Because the first leg was cancelled we were unable to get to our connection. We had to book on an entirely different airline for today. So we spent more money, lost a day of vacation and will never fly Frontier again, so the 'we are sorry, here is $100 credit' is a joke since we won't be flying on Frontier.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. The flight was delayed due to an attendant forgetting to come to work. On the flight no drinks were offered only for purchase meals.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. On the flight no drinks were offered only for purchase meals.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

Everything you need to know for your flight from Oklahoma City to Midway

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