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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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — MDW
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$116
(Kiwi.com)

One-way from

$54
(Frontier)

Popular in

March

Cheapest in

April

Average price

$287

Good round-trip deal

$326 or less

Good one-way deal

$189 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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High demand for flights, 5% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/62:40 pmDFW - MDW
Nonstop2h 23mFrontier
Sat 8/98:05 amMDW - DFW
Nonstop2h 27mFrontier
Deal found 4/17$116
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/104:17 pmDFW - MDW
1 stop4h 57mDelta
Tue 5/134:15 pmMDW - DFW
1 stop7h 44mDelta
Deal found 4/17$197
This Southwest deal was found by Cheapflights users on 4/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/183:15 pmTUL - MDW
Nonstop1h 40mSouthwest
Sat 6/216:00 pmMDW - TUL
Nonstop1h 45mSouthwest
Deal found 4/17$263
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2010:01 amTUL - MDW
1 stop5h 19mDelta
Tue 5/2710:25 amMDW - TUL
1 stop7h 35mDelta
Deal found 4/15$267
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/174:35 pmXNA - MDW
1 stop5h 12mDelta
Wed 7/231:00 pmMDW - XNA
1 stop4h 05mDelta
Deal found 4/16$280
This Southwest deal was found by Cheapflights users on 4/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/33:05 pmOKC - MDW
Nonstop1h 55mSouthwest
Sat 6/79:50 pmMDW - OKC
Nonstop2h 05mSouthwest
Deal found 4/17$287
This Delta deal was found by Cheapflights users on 4/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/31:47 pmOKC - MDW
1 stop7h 40mDelta
Sat 6/71:55 pmMDW - OKC
1 stop6h 39mDelta
Deal found 4/17$307
This Frontier deal was found by Cheapflights users on 4/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/238:59 amOKC - MDW
1 stop11h 18mFrontier
Tue 5/276:35 amMDW - OKC
1 stop7h 42mFrontier
Deal found 4/17$311

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 April 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

Wed 8/6

2:40 pm-5:03 pm

Nonstop2h 23m

Chicago Midway

Sat 8/9

8:05 am-10:32 am

Nonstop2h 27m

$116

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sat 5/10

4:17 pm-9:14 pm

1 stop4h 57m

Chicago Midway

Tue 5/13

4:15 pm-11:59 pm

1 stop7h 44m

$197

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 6/18

3:15 pm-4:55 pm

Nonstop1h 40m

Chicago Midway

Sat 6/21

6:00 pm-7:45 pm

Nonstop1h 45m

$263

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 5/20

10:01 am-3:20 pm

1 stop5h 19m

Chicago Midway

Tue 5/27

10:25 am-6:00 pm

1 stop7h 35m

$267

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 6/3

3:05 pm-5:00 pm

Nonstop1h 55m

Chicago Midway

Sat 6/7

9:50 pm-11:55 pm

Nonstop2h 05m

$287

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Wed 4/30

11:40 am-5:19 pm

1 stop5h 39m

Chicago Midway

Sat 5/3

6:04 am-11:24 am

1 stop5h 20m

$290

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 6/3

1:47 pm-9:27 pm

1 stop7h 40m

Chicago Midway

Sat 6/7

1:55 pm-8:34 pm

1 stop6h 39m

$307

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 5/23

8:59 am-8:17 pm

1 stop11h 18m

Chicago Midway

Tue 5/27

6:35 am-2:17 pm

1 stop7h 42m

$311

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sat 6/7

11:19 am-1:42 pm

Nonstop2h 23m

$57

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 6/3

3:24 pm-10:44 pm

1 stop7h 20m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 19 results
1
2

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 April 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 17, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Oklahoma to Chicago have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Comfort

8.0

Overall

8.0

Food

7.1

Crew

8.6

Boarding

8.2

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 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), Delta ($99), and Southwest ($116).

  • 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, Oklahoma City Will Rogers World - Chicago Midway or Tulsa - 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 $299, our data shows the cheapest flight currently is $167. When looking at the most popular route, (Dallas/Fort Worth - Chicago Midway), you can expect to pay $115 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 Oklahoma?

Book flights to Oklahoma if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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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John F Kennedy Intl to Midway flights
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Los Angeles to Midway 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$278Average$368FlexibilityNo cancel feeOn-time63%

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