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$68+ Cheap flights from Oklahoma 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — MDW
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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Cheap flight deals from Oklahoma to Midway

Keep the following information in mind while searching for Oklahoma to Midway flight deals. Data was last updated August 17, 2025.

Round-trip from

$114
(CheapOair)

One-way from

$68
(Cheapflightsfares)

Popular in

March

Cheapest in

February

Average price

$364

Good round-trip deal

$236 or less

Good one-way deal

$152 or less
From Oklahoma to Chicago Midway
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One-way flight from Oklahoma to Chicago Midway
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Highest demand for flights based on searches. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 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 to Chicago Midway.
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Price to beat on a one-way flight from Oklahoma to Chicago Midway.
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Find flight deals from Oklahoma to Midway

Cheapest flights from Oklahoma to Midway
Explore the most affordable flight options available from Oklahoma to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2025.

This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/88:00 amDFW - MDW
1 stop5h 38mFrontier
Tue 10/145:20 pmMDW - DFW
Nonstop2h 41mFrontier
Deal found 8/17$114
This Cheapflightsfares deal was found by Cheapflights users on 8/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:45 pmDFW - MDW
1 stop5h 35mFrontier
Mon 9/87:15 amMDW - DFW
Nonstop2h 31mFrontier
Deal found 8/16$115
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/115:45 pmDFW - MDW
1 stop5h 35mFrontier
Mon 9/157:15 amMDW - DFW
Nonstop2h 31mFrontier
Deal found 8/17$116
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/56:28 pmDFW - MDW
Nonstop2h 24mFrontier
Mon 9/89:47 pmMDW - DFW
Nonstop2h 34mFrontier
Deal found 8/17$117
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:35 amDFW - MDW
1 stop5h 55mFrontier
Mon 11/36:27 pmMDW - DFW
Nonstop2h 35mFrontier
Deal found 8/17$119
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/208:00 amDFW - MDW
Nonstop2h 28mFrontier
Mon 9/229:47 pmMDW - DFW
Nonstop2h 34mFrontier
Deal found 8/17$121
This Gotogate deal was found by Cheapflights users on 8/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:00 amDFW - MDW
Nonstop2h 28mFrontier
Mon 10/66:21 amMDW - DFW
1 stop8h 27mFrontier
Deal found 8/16$122
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1510:41 amDFW - MDW
Nonstop2h 30mFrontier
Thu 9/1810:13 amMDW - DFW
Nonstop2h 38mFrontier
Deal found 8/17$123
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:28 pmDFW - MDW
Nonstop2h 24mFrontier
Mon 9/226:20 amMDW - DFW
1 stop13h 34mFrontier
Deal found 8/16$125
This Southwest deal was found by Cheapflights users on 8/15. 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 10/46:35 amTUL - MDW
Nonstop1h 45mSouthwest
Tue 10/75:30 pmMDW - TUL
Nonstop1h 50mSouthwest
Deal found 8/15$203
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.
Mon 9/86:50 pmOKC - MDW
1 stop5h 15mSouthwest
Wed 9/105:15 pmMDW - OKC
Nonstop2h 00mSouthwest
Deal found 8/14$213
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/64:57 pmOKC - MDW
1 stop25h 42mFrontier
Sun 11/912:30 pmMDW - OKC
1 stop30h 30mFrontier
Deal found 8/16$216

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oklahoma 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 17, 2025.
Use the filters below to find and compare flights from Oklahoma to Chicago Midway Airport that are best for you.

Fly from

Oklahoma

Fly to

Midway

Route

Depart

Return

Price

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 9/11

5:45 pm-11:20 pm

1 stop5h 35m

Chicago Midway

Sat 9/13

11:23 am-1:59 pm

Nonstop2h 36m

$114

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 10/8

8:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Tue 10/14

5:20 pm-8:01 pm

Nonstop2h 41m

$114

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 10/31

2:57 pm-5:15 pm

Nonstop2h 18m

Chicago Midway

Mon 11/3

1:37 pm-8:00 pm

1 stop6h 23m

$115

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 9/25

5:45 pm-11:20 pm

1 stop5h 35m

Chicago Midway

Fri 10/3

9:47 pm-12:21 am

Nonstop2h 34m

$115

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Mon 11/3

2:57 pm-5:15 pm

Nonstop2h 18m

Chicago Midway

Thu 11/6

1:37 pm-8:00 pm

1 stop6h 23m

$115

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 11/14

2:57 pm-5:15 pm

Nonstop2h 18m

Chicago Midway

Mon 11/17

1:37 pm-8:00 pm

1 stop6h 23m

$116

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 10/22

8:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Sat 10/25

5:20 pm-8:01 pm

Nonstop2h 41m

$116

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 9/5

10:41 am-1:11 pm

Nonstop2h 30m

Chicago Midway

Fri 9/5

4:48 pm-12:23 am

1 stop7h 35m

$116

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 9/4

5:45 pm-11:20 pm

1 stop5h 35m

Chicago Midway

Sat 9/6

11:23 am-1:59 pm

Nonstop2h 36m

$116

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 9/11

5:45 pm-11:20 pm

1 stop5h 35m

Chicago Midway

Mon 9/15

7:15 am-9:46 am

Nonstop2h 31m

$116

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 58 results
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Best time to book a flight from Oklahoma to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Oklahoma 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 to Chicago Midway Airport

What is the cheapest month to book a flight from Oklahoma to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Oklahoma to Chicago Midway Airport (average of $160). Flying from Oklahoma 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 OK to MDW?

Find hourly flight availability from Oklahoma 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 17, 2025.

When flying from Oklahoma to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Oklahoma to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most popular routes from Oklahoma to Chicago Midway Airport?

    When deciding which route to take from Oklahoma to Chicago Midway Airport consider Dallas/Fort Worth - Chicago Midway, Fayetteville Northwest Arkansas - Chicago Midway or Oklahoma City Will Rogers World - Chicago Midway as they are the most popular.

  • What are the cheapest flights from Oklahoma to Chicago Midway Airport?

    While on average a flight from Oklahoma to Chicago Midway Airport is generally $290, our data shows the cheapest flight currently is $106. When looking at the most popular route, (Dallas/Fort Worth - Chicago Midway), you can expect to pay $76 for that flight.

  • Can I find deals for flights from Oklahoma to Midway that include hotel bookings?

    Yes. In addition to deals on Oklahoma to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oklahoma to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oklahoma to Midway.

  • Can I find deals for business class flights from Oklahoma to Midway?

    Yes. Cheapflights offers flight deals from Oklahoma 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 to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Oklahoma to Chicago Midway Airport (average of $160). Flying from Oklahoma 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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Alternative routes for Oklahoma to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Boston to O'Hare Intl flights
Ontario to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Newark to Midway flights
Charlotte to O'Hare Intl flights
Austin to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to Midway flights
Santa Ana to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Baltimore to Midway flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Orlando to O'Hare Intl flights
Dulles Intl to Midway flights
Burbank to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hobby to O'Hare Intl flights
San Diego to O'Hare Intl flights
Raleigh to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Portland to O'Hare Intl flights
Denver to Midway flights
San Francisco to Midway flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Tampa to O'Hare Intl flights
Love Field to Midway flights
Boston to Midway flights
Philadelphia to Midway flights
Fort Lauderdale to O'Hare Intl flights
Seattle to Midway flights
Tampa to Midway flights
Las Vegas to O'Hare Intl flights
Miami to O'Hare Intl flights
Austin to Midway flights

Top 2 airlines flying from Oklahoma to Midway

Discover the top 2 airlines that operate flights from Oklahoma 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$197Average$360FlexibilityNo cancel feeOn-time63%
FrontierCheapest$202Average$202FlexibilityNo cancel feeOn-time62%

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