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$74+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — MDW
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
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 February 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/8. 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 2/204:52 pm
OKC
-
MDW
1 stop5h 33m
Frontier
Mon 2/236:00 am
MDW
-
OKC
1 stop9h 56m
Frontier
Deal found 2/8$151
This Frontier deal was found by Cheapflights users on 2/9. 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 2/274:52 pm
OKC
-
MDW
1 stop5h 45m
Frontier
Mon 3/26:00 am
MDW
-
OKC
1 stop9h 56m
Frontier
Deal found 2/9$154
This Frontier deal was found by Cheapflights users on 2/8. 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 2/234:52 pm
OKC
-
MDW
1 stop5h 37m
Frontier
Fri 2/276:00 am
MDW
-
OKC
1 stop9h 57m
Frontier
Deal found 2/8$181
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Tue 3/108:30 pm
OKC
-
MDW
2 stops25h 49m
Frontier
Tue 3/176:00 am
MDW
-
OKC
1 stop8h 24m
Frontier
Deal found 2/10$199
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 2/204:52 pm
OKC
-
MDW
1 stop5h 33m
Frontier
Sun 2/229:04 pm
MDW
-
OKC
1 stop18h 52m
Frontier
Deal found 2/7$212
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/274:52 pm
OKC
-
MDW
1 stop5h 45m
Frontier
Sun 3/19:04 pm
MDW
-
OKC
1 stop18h 52m
Frontier
Deal found 2/9$216
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Tue 3/173:14 pm
OKC
-
MDW
1 stop5h 40m
Frontier
Mon 3/233:16 pm
MDW
-
OKC
2 stops28h 29m
Frontier
Deal found 2/10$218
This Southwest deal was found by Cheapflights users on 2/9. 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 4/12:55 pm
OKC
-
MDW
Nonstop1h 50m
Southwest
Sun 4/55:55 am
MDW
-
OKC
1 stop8h 05m
Southwest
Deal found 2/9$225

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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$151
(Kiwi.com)

One-way from

$74
(Priceline)

Popular in

December

Cheapest in

May

Average price

$375

Good round-trip deal

$343 or less

Good one-way deal

$214 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
Search Deals
One-way flight from Oklahoma City Will Rogers World to Chicago Midway
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($98 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Oklahoma City Will Rogers World to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Oklahoma City Will Rogers World to Chicago Midway.
Search Deals

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 February 11, 2026.
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

Fri 2/27

4:52 pm-10:37 pm

1 stop5h 45m

Chicago Midway

Mon 3/2

6:00 am-3:56 pm

1 stop9h 56m

$154

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 2/23

8:30 pm-7:07 pm

2 stops22h 37m

Chicago Midway

Thu 2/26

5:16 pm-3:57 pm

1 stop22h 41m

$199

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 4/2

11:05 am-4:35 pm

1 stop5h 30m

Chicago Midway

Sun 4/5

5:05 am-11:55 am

1 stop6h 50m

$235

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 3/23

7:00 am-1:25 pm

1 stop6h 25m

Chicago Midway

Wed 3/25

9:30 am-4:30 pm

1 stop7h 00m

$245

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 3/10

3:14 pm-8:54 pm

1 stop5h 40m

Chicago Midway

Tue 3/17

6:00 am-7:45 pm

2 stops37h 45m

$253

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 3/10

5:00 am-6:50 am

Nonstop1h 50m

Chicago Midway

Tue 3/17

10:05 am-12:20 pm

Nonstop2h 15m

$275

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 3/25

5:00 am-6:50 am

Nonstop1h 50m

Chicago Midway

Tue 3/31

8:40 pm-10:55 pm

Nonstop2h 15m

$275

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 5/30

12:45 pm-2:35 pm

Nonstop1h 50m

$120

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sun 4/12

7:00 am-1:25 pm

1 stop6h 25m

$123

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 4/6

12:20 pm-8:25 pm

2 stops8h 05m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 17 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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 February 11, 2026.

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 12% versus a flight in the evening.

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 February 11, 2026.
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
4,280 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

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 and Southwest fly from Oklahoma City to Chicago Midway Airport in about 5h 30m. The time it takes to get you to your destination can typically vary by up to 15m. 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 35% 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 $313, our data shows the cheapest flight currently is $123. When looking at the most popular route, (Oklahoma City Will Rogers World - Chicago Midway), you can expect to pay $224 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.

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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$241Average$386FlexibilityNo cancel feeOn-time63%

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