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$75+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — MDW
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$161
(Mytrip)

One-way from

$75
(Priceline)

Popular in

January

Cheapest in

May

Average price

$395

Good round-trip deal

$355 or less

Good one-way deal

$299 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. 7% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 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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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 September 29, 2025.

This Mytrip deal was found by Cheapflights users on 9/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/237:13 pmOKC - MDW
1 stop5h 23mFrontier
Mon 10/2712:11 pmMDW - OKC
1 stop6h 23mFrontier
Deal found 9/28$161
This Frontier deal was found by Cheapflights users on 9/27. 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 10/125:48 pmOKC - MDW
1 stop5h 58mFrontier
Thu 10/166:20 amMDW - OKC
1 stop10h 33mFrontier
Deal found 9/27$163
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:05 amOKC - MDW
1 stop9h 48mFrontier
Sun 10/126:20 amMDW - OKC
1 stop10h 33mFrontier
Deal found 9/29$183
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/107:21 pmOKC - MDW
1 stop5h 03mFrontier
Sat 10/118:35 amMDW - OKC
1 stop10h 49mFrontier
Deal found 9/29$197
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:21 pmOKC - MDW
2 stops15h 00mFrontier
Mon 10/2712:11 pmMDW - OKC
1 stop6h 23mFrontier
Deal found 9/29$207
This Booking.com deal was found by Cheapflights users on 9/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1711:02 amOKC - MDW
1 stop13h 22mFrontier
Sun 10/266:20 amMDW - OKC
1 stop10h 33mFrontier
Deal found 9/28$209
This Booking.com deal was found by Cheapflights users on 9/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/104:37 pmOKC - MDW
1 stop22h 34mFrontier
Mon 10/1310:31 amMDW - OKC
1 stop24h 00mFrontier
Deal found 9/26$223
This Frontier deal was found by Cheapflights users on 9/26. 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.
Fri 10/177:21 pmOKC - MDW
1 stop5h 03mFrontier
Mon 10/206:15 amMDW - OKC
1 stop10h 38mFrontier
Deal found 9/26$224
This Priceline deal was found by Cheapflights users on 9/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/207:19 pmOKC - MDW
1 stop5h 05mFrontier
Fri 10/2412:11 pmMDW - OKC
1 stop6h 25mFrontier
Deal found 9/29$235
This Southwest deal was found by Cheapflights users on 9/27. 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.
Wed 10/222:55 pmOKC - MDW
Nonstop1h 55mSouthwest
Wed 10/225:55 pmMDW - OKC
1 stop5h 00mSouthwest
Deal found 9/27$245

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 September 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

Thu 10/23

7:13 pm-12:36 am

1 stop5h 23m

Chicago Midway

Mon 10/27

12:11 pm-6:34 pm

1 stop6h 23m

$161

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 10/10

7:21 pm-12:24 am

1 stop5h 03m

Chicago Midway

Sat 10/11

8:35 am-7:24 pm

1 stop10h 49m

$197

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 10/24

7:21 pm-10:21 am

2 stops15h 00m

Chicago Midway

Mon 10/27

12:11 pm-6:34 pm

1 stop6h 23m

$207

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 10/10

4:37 pm-3:11 pm

1 stop22h 34m

Chicago Midway

Mon 10/13

10:31 am-10:31 am

1 stop24h 00m

$223

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 10/22

2:55 pm-4:50 pm

Nonstop1h 55m

Chicago Midway

Tue 10/28

7:40 am-9:40 am

Nonstop2h 00m

$235

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 10/22

5:50 am-10:35 am

1 stop4h 45m

Chicago Midway

Wed 10/22

2:45 pm-10:00 pm

1 stop7h 15m

$255

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 12/4

3:20 pm-5:15 pm

Nonstop1h 55m

Chicago Midway

Mon 12/8

8:15 am-10:30 am

Nonstop2h 15m

$269

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 10/21

1:20 pm-10:25 pm

1 stop9h 05m

Chicago Midway

Thu 10/23

9:20 am-2:35 pm

1 stop5h 15m

$272

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sun 10/12

5:48 pm-11:46 pm

1 stop5h 58m

Chicago Midway

Thu 10/16

5:20 pm-10:17 am

2 stops16h 57m

$281

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sun 10/12

7:46 pm-9:31 am

1 stop13h 45m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 19 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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oklahoma City-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, April is the cheapest month in which you can book a flight from Oklahoma City to Chicago Midway Airport (average of $160). Flying from Oklahoma City to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 29, 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 afternoon, which can drop the price by up to 2% 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 September 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
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Boarding

8.1

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 3h 28m. 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 34% 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. Southwest flights start at $118 while deals on Delta start at $128 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 $198. When looking at the most popular route, (Oklahoma City Will Rogers World - Chicago Midway), you can expect to pay $252 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, April is the cheapest month in which you can book a flight from Oklahoma City to Chicago Midway Airport (average of $160). Flying from Oklahoma City to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Oklahoma City to Midway

Discover the top 2 airlines 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$202Average$202FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$241Average$363FlexibilityNo cancel feeOn-time63%

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