$77 Cheap Flights from Oklahoma City (OKC) to Chicago (MDW)

View $77 flight on Fri, Dec 12, 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 $77 for one-way flights and $154 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Nov 3 - Thu, Nov 13
OKC
Oklahoma City
MDW
Chicago
$154 Roundtrip, found 5 hours ago
$154
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Oklahoma City to Chicago, returning Thu, Nov 13, priced at $154 found 5 hours ago
Frontier Airlines
Thu, Nov 6 - Mon, Nov 10
OKC
Oklahoma City
MDW
Chicago
$156 Roundtrip, found 5 hours ago
$156
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Oklahoma City to Chicago, returning Mon, Nov 10, priced at $156 found 5 hours ago
Frontier Airlines
Sat, Dec 6 - Thu, Dec 11
OKC
Oklahoma City
MDW
Chicago
$160 Roundtrip, found 16 hours ago
$160
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sat, Dec 6 from Oklahoma City to Chicago, returning Thu, Dec 11, priced at $160 found 16 hours ago
Frontier Airlines
Sun, Oct 19 - Fri, Oct 24
OKC
Oklahoma City
MDW
Chicago
$166 Roundtrip, just found
$166
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Oct 19 from Oklahoma City to Chicago, returning Fri, Oct 24, priced at $166 just found
Frontier Airlines
Thu, Nov 6 - Mon, Nov 10
OKC
Oklahoma City
MDW
Chicago
$168 Roundtrip, found 5 hours ago
$168
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, Nov 6 from Oklahoma City to Chicago, returning Mon, Nov 10, priced at $168 found 5 hours ago
Frontier Airlines
Wed, Nov 12 - Mon, Nov 17
OKC
Oklahoma City
MDW
Chicago
$170 Roundtrip, found 16 hours ago
$170
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Wed, Nov 12 from Oklahoma City to Chicago, returning Mon, Nov 17, priced at $170 found 16 hours ago
Frontier Airlines
Sun, Oct 19 - Thu, Oct 23
OKC
Oklahoma City
MDW
Chicago
$178 Roundtrip, just found
$178
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Oct 19 from Oklahoma City to Chicago, returning Thu, Oct 23, priced at $178 just found
Frontier Airlines
Thu, Oct 30 - Sun, Nov 9
OKC
Oklahoma City
MDW
Chicago
$196 Roundtrip, found 6 days ago
$196
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Oklahoma City to Chicago, returning Sun, Nov 9, priced at $196 found 6 days ago
Southwest Airlines
Sat, Dec 13 - Sun, Dec 14
OKC
Oklahoma City
MDW
Chicago
$213 Roundtrip, found 4 hours ago
$213
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Dec 13 from Oklahoma City to Chicago, returning Sun, Dec 14, priced at $213 found 4 hours ago
Delta
Sat, Nov 8 - Mon, Nov 10
OKC
Oklahoma City
MDW
Chicago
$223 Roundtrip, found 4 hours ago
$223
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Nov 8 from Oklahoma City to Chicago, returning Mon, Nov 10, priced at $223 found 4 hours ago

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

February is typically the cheapest month to fly

From $125 - $658 per traveler.

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 $287
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $287

Frequently asked questions

How much does a flight from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $77 or cheap return flight from $154 from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
November is the least expensive month to fly from OKC to MDW. Timing your trip outside of the busy season is often the key to finding better fares.
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 Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll fly you from OKC to MDW. Then, sort your results by "Price (lowest to highest)" to score the best deal available.
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.

Travel information

Origin airport
Will Rogers World
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$154
Distance
690 mi
Average flight time
1 hour 55 mins

Book with confidence

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 November. 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 $77 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.

 

Oklahoma City to Chicago Flights

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