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$76+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
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 August 14, 2025.

Round-trip from

$203
(Southwest)

One-way from

$76
(Priceline)

Popular in

January

Cheapest in

May

Average price

$372

Good round-trip deal

$253 or less

Good one-way deal

$158 or less
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. 8% potential increase in price ($32 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 August 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/14. 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 11/113:20 pmOKC - MDW
Nonstop1h 55mSouthwest
Thu 11/139:40 pmMDW - OKC
Nonstop2h 10mSouthwest
Deal found 8/14$203
This Delta deal was found by Cheapflights users on 8/14. 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.
Tue 9/94:02 pmOKC - MDW
1 stop5h 24mDelta
Tue 9/166:00 amMDW - OKC
1 stop6h 55mDelta
Deal found 8/14$209
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/304:05 pmOKC - MDW
Nonstop1h 55mSouthwest
Mon 11/38:15 amMDW - OKC
Nonstop2h 15mSouthwest
Deal found 8/13$217
This Frontier deal was found by Cheapflights users on 8/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/208:00 amOKC - MDW
2 stops15h 17mFrontier
Mon 9/224:48 pmMDW - OKC
1 stop7h 06mFrontier
Deal found 8/13$219
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/204:05 pmOKC - MDW
Nonstop1h 55mSouthwest
Fri 10/248:40 pmMDW - OKC
Nonstop2h 05mSouthwest
Deal found 8/12$223
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/57:05 amOKC - MDW
2 stops10h 10mSouthwest
Sun 11/99:40 pmMDW - OKC
Nonstop2h 10mSouthwest
Deal found 8/12$224
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/204:20 pmOKC - MDW
1 stop7h 05mSouthwest
Mon 9/228:25 pmMDW - OKC
Nonstop2h 00mSouthwest
Deal found 8/13$227
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:50 amOKC - MDW
Nonstop1h 55mSouthwest
Wed 10/81:25 pmMDW - OKC
2 stops9h 15mSouthwest
Deal found 8/12$232

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 August 14, 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 10/6

6:50 am-8:45 am

Nonstop1h 55m

Chicago Midway

Wed 10/8

7:40 am-9:40 am

Nonstop2h 00m

$203

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 11/11

3:20 pm-5:15 pm

Nonstop1h 55m

Chicago Midway

Thu 11/13

9:40 pm-11:50 pm

Nonstop2h 10m

$203

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 9/9

4:02 pm-9:26 pm

1 stop5h 24m

Chicago Midway

Tue 9/16

6:30 pm-11:58 pm

1 stop5h 28m

$209

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 9/23

1:40 pm-9:36 pm

1 stop7h 56m

Chicago Midway

Tue 9/30

6:00 am-12:55 pm

1 stop6h 55m

$209

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 11/5

3:20 pm-5:15 pm

Nonstop1h 55m

Chicago Midway

Sun 11/9

9:40 pm-11:50 pm

Nonstop2h 10m

$209

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 9/23

7:15 am-1:03 pm

1 stop5h 48m

Chicago Midway

Wed 9/24

6:30 pm-11:58 pm

1 stop5h 28m

$209

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 10/21

2:55 pm-4:50 pm

Nonstop1h 55m

Chicago Midway

Fri 10/24

8:40 pm-10:45 pm

Nonstop2h 05m

$209

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 9/22

5:10 pm-8:25 pm

1 stop3h 15m

Chicago Midway

Wed 9/24

5:15 pm-7:15 pm

Nonstop2h 00m

$213

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 10/10

7:25 pm-12:24 am

1 stop4h 59m

$80

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 10/3

6:05 am-3:53 pm

1 stop9h 48m

$82

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 18 results
1
2

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 August 14, 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 in the morning.

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 August 14, 2025.
See what other customers who have flown with Southwest and Frontier 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
4,244 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,217 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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. 2 airlines 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.

  • What are the cheapest airlines flying from Oklahoma City to Chicago Midway Airport round-trip?

    Currently priced at $202, Frontier will fly you from Oklahoma City to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Southwest for as low as $253. These flights start at 44% 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 $290, our data shows the cheapest flight currently is $106. When looking at the most popular route, (Oklahoma City Will Rogers World - Chicago Midway), you can expect to pay $185 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

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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$202Average$202FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$253Average$363FlexibilityNo cancel feeOn-time63%

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