$88 Cheap Flights from Oklahoma City (OKC) to Chicago (MDW)

View $88 flight on Thu, Nov 13, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $88 for one-way flights and $130 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Aug 20 - Fri, Aug 22
OKC
Oklahoma City
MDW
Chicago
$130 Roundtrip, found 6 days ago
$130
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Oklahoma City to Chicago, returning Fri, Aug 22, priced at $130 found 6 days ago
Southwest Airlines
Sat, Aug 9 - Tue, Aug 12
OKC
Oklahoma City
MDW
Chicago
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Aug 9 from Oklahoma City to Chicago, returning Tue, Aug 12, priced at $137 found 6 days ago
Southwest Airlines
Wed, Aug 20 - Fri, Aug 22
OKC
Oklahoma City
MDW
Chicago
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Oklahoma City to Chicago, returning Fri, Aug 22, priced at $140 found 6 days ago
Southwest Airlines
Tue, Nov 4 - Wed, Nov 12
OKC
Oklahoma City
MDW
Chicago
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Oklahoma City to Chicago, returning Wed, Nov 12, priced at $143 found 6 days ago
Southwest Airlines
Wed, Aug 20 - Fri, Aug 22
OKC
Oklahoma City
MDW
Chicago
$145 Roundtrip, found 6 days ago
$145
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Oklahoma City to Chicago, returning Fri, Aug 22, priced at $145 found 6 days ago
Southwest Airlines
Tue, Nov 4 - Wed, Nov 12
OKC
Oklahoma City
MDW
Chicago
$148 Roundtrip, found 6 days ago
$148
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Nov 4 from Oklahoma City to Chicago, returning Wed, Nov 12, priced at $148 found 6 days ago
Southwest Airlines
Wed, Nov 5 - Thu, Nov 13
OKC
Oklahoma City
MDW
Chicago
$149 Roundtrip, found 6 days ago
$149
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Nov 5 from Oklahoma City to Chicago, returning Thu, Nov 13, priced at $149 found 6 days ago
Southwest Airlines
Thu, Nov 13 - Sun, Nov 16
OKC
Oklahoma City
MDW
Chicago
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Nov 13 from Oklahoma City to Chicago, returning Sun, Nov 16, priced at $159 found 6 days ago
Frontier Airlines
Thu, Aug 14 - Mon, Aug 18
OKC
Oklahoma City
MDW
Chicago
$234 Roundtrip, found 21 hours ago
$234
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Oklahoma City to Chicago, returning Mon, Aug 18, priced at $234 found 21 hours ago
Delta
Sat, Sep 13 - Tue, Sep 23
OKC
Oklahoma City
MDW
Chicago
$237 Roundtrip, found 1 hour ago
$237
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Sep 13 from Oklahoma City to Chicago, returning Tue, Sep 23, priced at $237 found 1 hour ago

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

February is typically the cheapest month to fly

From $125 - $655 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $238
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $238
Flights from Oklahoma City (OKC) to Chicago (MDW)
Origin airport
Will Rogers World
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$130
Distance
690 mi
Average flight time
1 hour 55 mins

Oklahoma City to Chicago Flights

The cheapest times to fly from Oklahoma City to Chicago

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 Oklahoma City to Chicago are during the month of August. You can find some of the cheapest flights from Oklahoma City to Chicago with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Oklahoma City to Chicago: 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 Oklahoma City to Chicago

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 Oklahoma City to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $88 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 Oklahoma City to Chicago 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 Oklahoma City to Chicago 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 Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW) cost?
Cheap return fares from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW) start at $113. 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 flight leaving OKC on August 6 2025 and touching down at MDW. The price was last updated on July 14 2025 and has not changed since.
What is the cheapest month to fly from OKC to MDW?
The cheapest flights from OKC to MDW 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 Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
Fly nonstop from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from OKC to MDW?
With prices starting from $57 for a one-way flight from OKC to MDW, Southwest Airlines is currently the cheapest carrier flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from OKC on August 4 2025. Prices were last updated on July 14 2025 and have not changed since.
How many flights per day from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
On average, there is just 1 direct flight leaving from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW) per day. If this isn't convenient for you, think about flights with layovers. Simply filter your search results on Expedia to include one stop or more to discover the next best option.
What are the most popular departure times for flights from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
The 7 AM departures from OKC to MDW see the highest demand. They can also be more expensive. If you're hoping to save money, choose a less crowded time to fly.
What day of the week has the most flights from OKC to MDW?
If you jet off on a Friday, you'll get the largest range of options for flights from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW).
What is the earliest flight from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
Catch the earliest flight at around 5:40AM UTC-6, leaving from Will Rogers World Airport (OKC). You'll be flying for approximately 1h 55m, coming in to land at Midway Intl. Airport (MDW) at approximately 7:35AM UTC-6.
How long does it take to fly from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
It takes approximately 1 hour and 55 minutes to fly the 690 mi from OKC to MDW.
What airline has the least delays from OKC to MDW?
Southwest Airlines has the best track record for on-time direct flights from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW), with an on-time score of 94%. Use the Expedia App to check your flight schedule before you leave and receive notifications about any trip changes.
What is the best time to fly from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) without delays, pick a flight that takes off from Will Rogers World Airport (OKC) before 3 PM. The chance 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 Chicago from Will Rogers World Airport (OKC)?
Take a direct flight from Will Rogers World Airport (OKC) to Chicago and arrive at O'Hare Intl. Airport (ORD). Another convenient arrival point to the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from OKC to MDW just before your trip is usually more expensive. But if you're flexible with your schedule, you could grab a cheap last-minute fare.
Is it cheaper to book an OKC to MDW flight and hotel package?
You'll typically save money by booking an OKC to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one place. After selecting your preferred flights and accommodations, consider adding extras including tours, activities and car rentals.
Can I cancel or change the date of my flight from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
If you booked your OKC to MDW flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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