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$54+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — MDW
Nov 8 — Nov 151
Sat 11/8
Sat 11/15
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 October 9, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$103
(Cheapflightsfares)

One-way from

$54
(Frontier)

Popular in

March

Cheapest in

September

Average price

$336

Good round-trip deal

$366 or less

Good one-way deal

$198 or less
Provider with most accurate pricing for Oklahoma City Will Rogers World-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Oklahoma City Will Rogers World-Chicago (CHI) flights.
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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. 4% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 9, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:05 pmDFW - MDW
Nonstop2h 23mFrontier
Mon 12/293:27 pmMDW - DFW
Nonstop2h 42mFrontier
Deal found 10/8$103
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/142:57 pmDFW - MDW
Nonstop2h 18mFrontier
Sun 11/1611:21 amMDW - DFW
Nonstop2h 35mFrontier
Deal found 10/7$104
This CheapOair deal was found by Cheapflights users on 10/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:51 pmDFW - MDW
1 stop6h 30mFrontier
Thu 10/309:43 pmMDW - DFW
Nonstop2h 38mFrontier
Deal found 10/7$105
This Trip.com deal was found by Cheapflights users on 10/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:35 amDFW - MDW
1 stop5h 55mFrontier
Thu 10/309:43 pmMDW - DFW
Nonstop2h 38mFrontier
Deal found 10/8$106
This CheapOair deal was found by Cheapflights users on 10/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:10 pmDFW - MDW
1 stop11h 22mFrontier
Thu 11/612:30 pmMDW - DFW
1 stop11h 40mFrontier
Deal found 10/9$108
This CheapOair deal was found by Cheapflights users on 10/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/219:01 pmDFW - MDW
Nonstop2h 19mFrontier
Fri 10/245:20 pmMDW - DFW
Nonstop2h 41mFrontier
Deal found 10/7$109
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/249:01 pmDFW - MDW
Nonstop2h 19mFrontier
Mon 10/275:10 amMDW - DFW
Nonstop2h 35mFrontier
Deal found 10/9$110
This CheapOair deal was found by Cheapflights users on 10/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:15 pmDFW - MDW
Nonstop2h 28mFrontier
Sat 11/111:36 amMDW - DFW
1 stop21h 06mFrontier
Deal found 10/9$112
This Cheapflightsfares deal was found by Cheapflights users on 10/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:45 amDFW - MDW
Nonstop2h 28mFrontier
Tue 10/215:20 pmMDW - DFW
Nonstop2h 41mFrontier
Deal found 10/7$113
This Frontier deal was found by Cheapflights users on 10/8. 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.
Tue 10/219:01 pmDFW - MDW
Nonstop2h 19mFrontier
Wed 10/228:05 amMDW - DFW
1 stop10h 05mFrontier
Deal found 10/8$115
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Thu 11/64:57 pmOKC - MDW
1 stop25h 42mFrontier
Thu 11/1312:30 pmMDW - OKC
1 stop6h 30mFrontier
Deal found 10/9$188
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Mon 11/1710:47 amXNA - MDW
1 stop13h 43mMultiple Airlines
Wed 11/191:56 pmMDW - XNA
2 stops26h 41mMultiple Airlines
Deal found 10/8$221

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 October 9, 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

Sat 11/1

8:59 pm-10:12 am

1 stop13h 13m

Chicago Midway

Sun 11/2

11:21 am-1:56 pm

Nonstop2h 35m

$168

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 11/6

4:57 pm-6:39 pm

1 stop25h 42m

Chicago Midway

Thu 11/13

12:30 pm-7:00 pm

1 stop6h 30m

$188

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 12/18

10:52 am-6:18 pm

1 stop7h 26m

Chicago Midway

Mon 12/22

9:29 am-2:43 pm

1 stop5h 14m

$197

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 12/9

1:37 pm-6:00 pm

1 stop4h 23m

Chicago Midway

Mon 12/15

9:34 am-2:21 pm

1 stop4h 47m

$197

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 12/18

10:52 am-6:18 pm

1 stop7h 26m

Chicago Midway

Mon 1/5

5:25 pm-12:17 am

1 stop6h 52m

$197

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 12/11

11:47 am-6:00 pm

1 stop6h 13m

Chicago Midway

Tue 12/16

9:34 am-2:21 pm

1 stop4h 47m

$197

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 10/28

11:43 am-6:25 pm

1 stop6h 42m

Chicago Midway

Wed 10/29

9:35 am-2:20 pm

1 stop4h 45m

$197

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 12/30

4:20 pm-10:22 pm

1 stop6h 02m

Chicago Midway

Mon 1/5

9:30 am-2:55 pm

1 stop5h 25m

$197

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 12/10

1:37 pm-6:00 pm

1 stop4h 23m

Chicago Midway

Thu 12/11

10:49 am-5:26 pm

1 stop6h 37m

$197

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 12/10

6:21 pm-11:49 pm

1 stop5h 28m

Chicago Midway

Wed 12/17

9:34 am-2:21 pm

1 stop4h 47m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/9

Showing 1-10 of 60 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, June is the cheapest month in which you can book a flight from Oklahoma to Chicago Midway Airport (average of $143). Flying from Oklahoma to Chicago Midway Airport in January is currently the most expensive (average of $339). 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 October 9, 2025.

When flying from Oklahoma 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 evening, which can drop the price by up to 47% versus a flight at noon.

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

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.

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

    There are many flights that can get you from Oklahoma to Chicago Midway Airport in 1h 45m. Fly via Frontier, Delta, or Southwest to get the fastest option. The distance between Oklahoma and Chicago Midway Airport is about 582 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Oklahoma to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Oklahoma to Chicago Midway Airport are Frontier ($54), Southwest ($115), and Delta ($144).

  • 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 $381, our data shows the cheapest flight currently is $131. When looking at the most popular route, (Dallas/Fort Worth - Chicago Midway), you can expect to pay $56 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, June is the cheapest month in which you can book a flight from Oklahoma to Chicago Midway Airport (average of $143). Flying from Oklahoma to Chicago Midway Airport in January is currently the most expensive (average of $339). 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
Porter
Benton Harbor
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.
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Portland to O'Hare Intl flights
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Tampa to O'Hare Intl flights
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Top airline flying from Oklahoma to Midway

Discover the top airline 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 October 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$197Average$362FlexibilityNo cancel feeOn-time63%

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