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$100+ Cheap flights from Oklahoma City (OKC) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — MDW
Jan 28 — Feb 41
Wed 1/28
Wed 2/4
1 adult, Economy
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Cheap flight deals from Oklahoma City to Midway

Cheapest flights from Oklahoma City to Midway
Explore the most affordable flight options available from Oklahoma City to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 29, 2025.

This Delta deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:55 amOKC - MDW
1 stop6h 49mDelta
Sun 2/16:14 pmMDW - OKC
1 stop5h 49mDelta
Deal found 12/28$624
This Frontier deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/282:18 pmOKC - MDW
1 stop7h 32mFrontier
Sun 2/16:20 amMDW - OKC
1 stop10h 51mFrontier
Deal found 12/28$690
This Southwest deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:10 pmOKC - MDW
Nonstop1h 55mSouthwest
Sun 1/410:35 pmMDW - OKC
Nonstop2h 15mSouthwest
Deal found 12/28$702
This Southwest deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:10 pmOKC - MDW
Nonstop1h 55mSouthwest
Tue 1/68:15 amMDW - OKC
Nonstop2h 20mSouthwest
Deal found 12/28$743
This Southwest deal was found by Cheapflights users on 12/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:10 pmOKC - MDW
Nonstop1h 55mSouthwest
Mon 12/2910:35 pmMDW - OKC
Nonstop2h 15mSouthwest
Deal found 12/29$753

Find flight deals from Oklahoma City to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Oklahoma City (OKC) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$200
(Priceline)

One-way from

$100
(Priceline)

Popular in

January

Cheapest in

May

Average price

$487

Good round-trip deal

$406 or less

Good one-way deal

$212 or less
Provider with most accurate pricing for Oklahoma City Will Rogers World-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Oklahoma City Will Rogers World-Chicago Midway flights.
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From Oklahoma City Will Rogers World to Chicago Midway
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One-way flight from Oklahoma City Will Rogers World to Chicago Midway
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Highest demand for flights based on searches. 21% potential increase in price ($104 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from Oklahoma City Will Rogers World to Chicago Midway.
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Price to beat on a one-way flight from Oklahoma City Will Rogers World to Chicago Midway.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Oklahoma City to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 29, 2025.
Use the filters below to find and compare flights from Oklahoma City to Chicago Midway Airport that are best for you.

Fly from

Oklahoma City

Fly to

Midway

Route

Depart

Return

Price

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 1/12

8:29 pm-10:34 am

2 stops14h 05m

Chicago Midway

Fri 1/16

9:09 pm-2:24 pm

1 stop17h 15m

$244

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 1/17

7:10 am-4:30 pm

2 stops9h 20m

Chicago Midway

Tue 1/20

12:10 pm-7:10 pm

1 stop7h 00m

$278

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 4/25

5:00 am-6:50 am

Nonstop1h 50m

Chicago Midway

Mon 4/27

10:15 am-12:25 pm

Nonstop2h 10m

$279

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 2/18

5:33 pm-10:31 pm

1 stop4h 58m

Chicago Midway

Sat 2/21

4:13 pm-11:54 pm

1 stop7h 41m

$298

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 1/28

10:10 am-12:05 pm

Nonstop1h 55m

Chicago Midway

Wed 2/4

8:15 am-10:35 am

Nonstop2h 20m

$303

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 1/27

1:00 pm-8:40 pm

2 stops7h 40m

Chicago Midway

Tue 2/3

8:15 am-10:35 am

Nonstop2h 20m

$318

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 2/14

6:00 am-1:10 pm

1 stop7h 10m

$114

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sun 1/18

10:10 am-12:05 pm

Nonstop1h 55m

$127

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 4/11

12:45 pm-5:25 pm

1 stop4h 40m

$128

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 2/7

7:10 am-4:30 pm

1 stop9h 20m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

Showing 1-10 of 14 results
1
2

Compare providers for flights from Oklahoma City to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oklahoma City to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oklahoma City-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Oklahoma City-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Oklahoma City-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oklahoma City-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oklahoma City-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Oklahoma City to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Oklahoma City with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oklahoma City to Chicago Midway Airport

What is the cheapest month to book a flight from Oklahoma City to Chicago Midway Airport?

Currently, June is the cheapest month in which you can book a flight from Oklahoma City to Chicago Midway Airport (average of $143). Flying from Oklahoma City to Chicago Midway Airport in January is currently the most expensive (average of $378). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OKC to MDW?

Find hourly flight availability from Oklahoma City to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oklahoma City to Chicago Midway Airport as you normally would.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated December 29, 2025.
See what other customers who have flown with Southwest from Oklahoma City to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Oklahoma City to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Oklahoma City to Chicago Midway?

    Oklahoma City Will Rogers World (OKC), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Oklahoma City to Chicago Midway. 1 airline have flights from Will Rogers World to Chicago Midway on a regular basis. Booking flights from Oklahoma City Will Rogers World to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • How long is the flight from Oklahoma City to Chicago Midway Airport?

    Airlines like Frontier, Southwest, and Delta fly from Oklahoma City to Chicago Midway Airport in about 4h 58m. The time it takes to get you to your destination can typically vary by up to 9h 07m. Airlines will cover a distance of 690 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Oklahoma City to Chicago Midway Airport round-trip?

    Currently priced at $241, Southwest will fly you from Oklahoma City to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. This flight start at 37% lower than the current average price 3 months from now.

  • What are the cheapest flights from Oklahoma City to Chicago Midway Airport?

    While on average a flight from Oklahoma City to Chicago Midway Airport is generally $352, our data shows the cheapest flight currently is $175. When looking at the most popular route, (Oklahoma City Will Rogers World - Chicago Midway), you can expect to pay $279 for that flight.

  • Can I find deals for flights from Oklahoma City to Midway that include hotel bookings?

    Yes. In addition to deals on Oklahoma City to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oklahoma City to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oklahoma City to Midway.

  • Can I find deals for business class flights from Oklahoma City to Midway?

    Yes. Cheapflights offers flight deals from Oklahoma City to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, June is the cheapest month in which you can book a flight from Oklahoma City to Chicago Midway Airport (average of $143). Flying from Oklahoma City to Chicago Midway Airport in January is currently the most expensive (average of $378). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Oklahoma City to Midway

Discover the top airline that operate flights from Oklahoma City to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$217Average$374FlexibilityNo cancel feeOn-time63%

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