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Midway

$95+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — MDW
Jun 12 — Jun 191
Fri 6/12
Fri 6/19
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 May 13, 2026.

This Priceline deal was found by Cheapflights users on 5/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Thu 6/46:00 am
MDW
-
OKC
1 stop7h 01m
Frontier
Deal found 5/12$210
This Frontier deal was found by Cheapflights users on 5/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Tue 6/96:00 am
MDW
-
OKC
1 stop6h 56m
Frontier
Deal found 5/12$230
This Frontier deal was found by Cheapflights users on 5/11. 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 5/281:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Thu 6/46:00 am
MDW
-
OKC
1 stop7h 01m
Frontier
Deal found 5/11$234
This Trip.com deal was found by Cheapflights users on 5/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:51 pm
OKC
-
MDW
1 stop8h 20m
Frontier
Thu 6/186:00 am
MDW
-
OKC
1 stop6h 56m
Frontier
Deal found 5/11$246
This Trip.com deal was found by Cheapflights users on 5/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Tue 6/26:00 am
MDW
-
OKC
1 stop7h 01m
Frontier
Deal found 5/12$249
This Priceline deal was found by Cheapflights users on 5/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/71:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Sun 6/146:00 am
MDW
-
OKC
1 stop6h 56m
Frontier
Deal found 5/10$250
This Trip.com deal was found by Cheapflights users on 5/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/41:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Sun 6/76:00 am
MDW
-
OKC
1 stop7h 01m
Frontier
Deal found 5/10$265
This Priceline deal was found by Cheapflights users on 5/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Sun 5/316:00 am
MDW
-
OKC
1 stop7h 01m
Frontier
Deal found 5/11$270
This Priceline deal was found by Cheapflights users on 5/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Sun 6/146:00 am
MDW
-
OKC
1 stop6h 56m
Frontier
Deal found 5/12$310

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 May 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$210
(Priceline)

One-way from

$95
(Frontier)

Popular in

March

Cheapest in

October

Average price

$202

Good round-trip deal

$393 or less

Good one-way deal

$223 or less
Provider with most accurate pricing for Oklahoma City Will Rogers World-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oklahoma City Will Rogers World-Chicago Midway flights.
Search Deals
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. 25% potential increase in price ($133 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 13, 2026.
Use the filters below to find and compare flights from Oklahoma City to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 6/1

6:10 pm-11:55 pm

1 stop5h 45m

Chicago Midway

Tue 6/9

10:30 am-12:30 pm

Nonstop2h 00m

$343
Quickest round-trip

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 7/17

5:00 am-6:55 am

Nonstop1h 55m

Chicago Midway

Tue 7/21

9:55 pm-11:55 pm

Nonstop2h 00m

$362

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 6/10

11:57 am-6:18 pm

1 stop6h 21m

Chicago Midway

Thu 6/11

5:11 pm-11:55 pm

1 stop6h 44m

$364

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 6/6

11:45 am-7:45 pm

1 stop8h 00m

Chicago Midway

Mon 6/8

9:30 pm-11:30 pm

Nonstop2h 00m

$367

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 6/10

2:55 pm-4:50 pm

Nonstop1h 55m

Chicago Midway

Thu 6/11

5:15 am-10:50 am

1 stop5h 35m

$372

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 7/17

5:12 pm-10:15 pm

1 stop5h 03m

Chicago Midway

Tue 7/21

5:10 pm-11:51 pm

1 stop6h 41m

$382

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 6/5

7:10 pm-12:10 am

1 stop5h 00m

Chicago Midway

Tue 6/9

9:55 pm-11:55 pm

Nonstop2h 00m

$383

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sun 6/28

6:45 am-2:40 pm

2 stops7h 55m

Chicago Midway

Wed 7/1

6:30 am-11:40 am

1 stop5h 10m

$387

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 7/29

11:20 am-4:55 pm

2 stops5h 35m

Chicago Midway

Mon 8/3

5:05 pm-12:25 am

1 stop7h 20m

$387
Cheapest one-way

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 6/1

8:40 pm-5:00 am

1 stop8h 20m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/8

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 May.
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 May 13, 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 at noon, which can drop the price by up to 7% versus a flight in the evening.

How much does it cost to fly round-trip from Oklahoma City to Chicago Midway Airport?

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 May 13, 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
7.9
Good
4,296 reviews

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,296 reviews
Southwest
7.9
Good
4,296 reviews

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 1 outbound flight to Chicago Midway per day.

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

    Airlines like Southwest and Delta fly from Oklahoma City to Chicago Midway Airport in about 5h 45m. The time it takes to get you to your destination can typically vary by up to 36m. 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 $240, 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 40% 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 $369, 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 $271 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 May 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$240Average$397FlexibilityNo cancel feeOn-time63%

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