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$55+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — MDW
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find 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 November 13, 2025.

This Priceline deal was found by Cheapflights users on 11/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/184:37 pmOKC - MDW
1 stop5h 35mFrontier
Sun 12/216:00 amMDW - OKC
1 stop10h 19mFrontier
Deal found 11/13$193
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/124:49 pmOKC - MDW
1 stop5h 23mFrontier
Fri 12/198:00 amMDW - OKC
2 stops29h 23mFrontier
Deal found 11/12$195
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2312:07 pmOKC - MDW
1 stop10h 26mFrontier
Tue 11/254:03 pmMDW - OKC
2 stops19h 18mFrontier
Deal found 11/11$200
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2711:39 amOKC - MDW
1 stop11h 04mFrontier
Mon 12/15:30 amMDW - OKC
2 stops38h 02mFrontier
Deal found 11/12$228
This Frontier deal was found by Cheapflights users on 11/11. 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.
Thu 11/2011:39 amOKC - MDW
1 stop11h 04mFrontier
Fri 11/2112:12 pmMDW - OKC
1 stop6h 21mFrontier
Deal found 11/11$246
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:49 pmOKC - MDW
1 stop5h 23mFrontier
Tue 12/92:49 pmMDW - OKC
2 stops49h 18mFrontier
Deal found 11/10$263
This Frontier deal was found by Cheapflights users on 11/11. 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 12/285:04 pmOKC - MDW
1 stop5h 08mFrontier
Tue 12/306:14 amMDW - OKC
1 stop11h 15mFrontier
Deal found 11/11$272
This Southwest deal was found by Cheapflights users on 11/10. 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.
Sat 12/136:35 amOKC - MDW
Nonstop1h 55mSouthwest
Tue 12/168:15 amMDW - OKC
Nonstop2h 15mSouthwest
Deal found 11/10$303

Cheap 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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$193
(Priceline)

One-way from

$55
(Priceline)

Popular in

January

Cheapest in

May

Average price

$442

Good round-trip deal

$396 or less

Good one-way deal

$225 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
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
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 November 13, 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

Sun 11/23

12:07 pm-10:33 pm

1 stop10h 26m

Chicago Midway

Tue 11/25

4:03 pm-11:21 am

2 stops19h 18m

$200

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 11/27

11:39 am-10:43 pm

1 stop11h 04m

Chicago Midway

Mon 12/1

3:31 pm-7:32 pm

1 stop28h 01m

$239

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 12/3

3:20 pm-5:15 pm

Nonstop1h 55m

Chicago Midway

Sat 12/6

7:30 pm-9:40 pm

Nonstop2h 10m

$303

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 12/13

6:35 am-8:30 am

Nonstop1h 55m

Chicago Midway

Tue 12/16

8:15 am-10:30 am

Nonstop2h 15m

$303

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 12/10

7:10 am-1:10 pm

1 stop6h 00m

Chicago Midway

Wed 12/17

12:50 pm-8:31 pm

1 stop7h 41m

$323

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 12/13

7:10 am-1:10 pm

1 stop6h 00m

Chicago Midway

Tue 12/16

6:00 am-1:14 pm

1 stop7h 14m

$323

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 2/6

8:29 pm-11:45 am

2 stops39h 16m

$100

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 12/11

6:19 pm-2:04 pm

2 stops19h 45m

$133

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 1/17

11:25 am-4:31 pm

1 stop5h 06m

$146

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 1/20

7:00 am-1:09 pm

1 stop6h 09m

$146

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 16 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 November.
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 $348). 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 November 13, 2025.

When flying from Oklahoma City to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 40% versus a flight at noon.

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 November 13, 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
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 and Southwest fly from Oklahoma City to Chicago Midway Airport in about 1h 55m. The time it takes to get you to your destination can typically vary by up to 8h 31m. 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 $217, 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 38% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Oklahoma City to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $100. Delta flights start at $146 while deals on Southwest start at $152 one-way.

  • 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 $382, our data shows the cheapest flight currently is $135. When looking at the most popular route, (Oklahoma City Will Rogers World - Chicago Midway), you can expect to pay $288 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 $348). 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
Hammond
Porter
Benton Harbor
Merrillville

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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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$217Average$378FlexibilityNo cancel feeOn-time63%

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