$109 Cheap Flights from Chicago (MDW) to Oklahoma City (OKC)

View $109 flight on Wed, Nov 5, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Will Rogers World Airport (OKC)

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Cheap Flights from Chicago to Oklahoma City (MDW-OKC)

Prices were available within the past 7 days and start at $109 for one-way flights and $217 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Nov 5 - Tue, Nov 11
MDW
Chicago
OKC
Oklahoma City
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Chicago to Oklahoma City, returning Tue, Nov 11, priced at $217 found 1 hour ago
Southwest Airlines
Fri, Sep 19 - Mon, Sep 22
MDW
Chicago
OKC
Oklahoma City
$223 Roundtrip, found 2 hours ago
$223
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Fri, Sep 19 from Chicago to Oklahoma City, returning Mon, Sep 22, priced at $223 found 2 hours ago
Southwest Airlines
Wed, Nov 5 - Tue, Nov 11
MDW
Chicago
OKC
Oklahoma City
$227 Roundtrip, found 1 hour ago
$227
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Chicago to Oklahoma City, returning Tue, Nov 11, priced at $227 found 1 hour ago
Delta
Wed, Aug 13 - Sat, Aug 16
MDW
Chicago
OKC
Oklahoma City
$228 Roundtrip, found 19 hours ago
$228
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Aug 13 from Chicago to Oklahoma City, returning Sat, Aug 16, priced at $228 found 19 hours ago
Southwest Airlines
Fri, Aug 29 - Sun, Aug 31
MDW
Chicago
OKC
Oklahoma City
$229 Roundtrip, just found
$229
Roundtrip
just found
Select Southwest Airlines flight, departing Fri, Aug 29 from Chicago to Oklahoma City, returning Sun, Aug 31, priced at $229 just found
Southwest Airlines
Wed, Nov 5 - Tue, Nov 11
MDW
Chicago
OKC
Oklahoma City
$232 Roundtrip, found 1 hour ago
$232
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Chicago to Oklahoma City, returning Tue, Nov 11, priced at $232 found 1 hour ago
Southwest Airlines
Wed, Nov 5 - Tue, Nov 11
MDW
Chicago
OKC
Oklahoma City
$233 Roundtrip, found 1 hour ago
$233
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Chicago to Oklahoma City, returning Tue, Nov 11, priced at $233 found 1 hour ago
Delta
Tue, Aug 26 - Sun, Aug 31
MDW
Chicago
OKC
Oklahoma City
$234 Roundtrip, found 21 hours ago
$234
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Aug 26 from Chicago to Oklahoma City, returning Sun, Aug 31, priced at $234 found 21 hours ago
Delta
Tue, Nov 4 - Tue, Nov 11
MDW
Chicago
OKC
Oklahoma City
$237 Roundtrip, found 1 hour ago
$237
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Nov 4 from Chicago to Oklahoma City, returning Tue, Nov 11, priced at $237 found 1 hour ago
Frontier Airlines
Fri, Nov 7 - Mon, Nov 10
MDW
Chicago
OKC
Oklahoma City
$241 Roundtrip, found 5 days ago
$241
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Chicago to Oklahoma City, returning Mon, Nov 10, priced at $241 found 5 days ago

Find the cheapest month to fly from Chicago (MDW) to Oklahoma City (OKC)

February is typically the cheapest month to fly

From $125 - $620 per traveler.

Graph displaying average flight prices per month

Alternative airports near Oklahoma City

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Will Rogers World OKC. Cheapest and Closest option available. Average driving time to city center is 14 minutes. Flights from $475
OKC
Will Rogers World
CheapestClosest
Average driving time to city center14 min
Flights from $475
Flights from Chicago (MDW) to Oklahoma City (OKC)
Origin airport
Midway Intl.
Destination airport
Will Rogers World
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$217
Distance
690 mi
Average flight time
2 hours 5 mins

Chicago to Oklahoma City Flights

The cheapest times to fly from Chicago to Oklahoma City

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Oklahoma City are during the month of November. You can find some of the cheapest flights from Chicago to Oklahoma City with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Oklahoma City

Sunday is one of the best days to book for cheap flights from Chicago to Oklahoma City: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Oklahoma City

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Oklahoma City in 2025. You can also book with separate airlines for your outbound and return journeys, from $109 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Oklahoma City flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Oklahoma City airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC) cost?
Cheap round-trip flights from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC) start at $217. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and American Airlines flight leaving MDW on August 13 2025 and touching down at OKC. The price was last updated on July 19 2025 and has not changed since.
What is the cheapest month to fly from MDW to OKC?
The cheapest flights from MDW to OKC are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC)?
Fly nonstop from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC) on a Southwest Airlines flight.
What is the cheapest airline that flies from MDW to OKC?
With tickets starting at $109 for a one-way flight from MDW to OKC, Southwest Airlines is currently the cheapest carrier operating this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 9 2025. Prices were last updated on July 19 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC)?
On average, only 1 direct flight departs each day from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC). Need more options? Use Expedia's filters to find flights with layovers and squeeze another destination into your itinerary.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC)?
More travelers fly between MDW and OKC at 8 PM than at any other time. Rather go when it's quieter? Try choosing a quieter departure window and it's possible you'll save on your ticket as well.
What day of the week has the most flights from MDW to OKC?
Friday has the most flights from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC). Consider leaving on this day and you'll have the best chance of finding a departure that fits your plans.
What is the earliest flight from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC)?
Catch the earliest flight at around 9:15AM UTC-6, departing from Midway Intl. Airport (MDW). You'll be in the air for around 2h 15m, landing at Will Rogers World Airport (OKC) at approximately 11:30AM UTC-6.
How long does it take to fly from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC)?
It takes approximately 2 hours and 15 minutes to travel the 690 mi from MDW to OKC.
What is the best time to fly from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC)?
To arrive at Will Rogers World Airport (OKC) on time, opt for a flight that leaves Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Oklahoma City from Midway Intl. Airport (MDW)?
Check out your flight options from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC). This is the only Oklahoma City airport you can land at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC) last-minute?
Last-minute bookings from MDW to OKC are usually more expensive. To secure the lowest prices, start looking for flights early. That said, if you can play around with your travel dates, it's possible to score a cheap fare right before you leave.
Is it cheaper to book a MDW to OKC flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to OKC flight and hotel package with Expedia could lead to significant savings. Better still, having it all in one place takes the hassle out of travel planning. Simply pick your flights and choose from our extensive range of hotels, then tailor your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Will Rogers World Airport (OKC)?
You can usually reschedule or cancel your MDW to OKC flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.