$80 Cheap Flights from Oklahoma City (OKC) to Chicago (MDW)

View $80 flight on Sun, Nov 9, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $80 for one-way flights and $160 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Sep 29 - Fri, Oct 10
OKC
Oklahoma City
MDW
Chicago
$160 Roundtrip, found 11 hours ago
$160
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Oklahoma City to Chicago, returning Fri, Oct 10, priced at $160 found 11 hours ago
Frontier Airlines
Mon, Nov 3 - Fri, Nov 7
OKC
Oklahoma City
MDW
Chicago
$162 Roundtrip, found 5 days ago
$162
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Oklahoma City to Chicago, returning Fri, Nov 7, priced at $162 found 5 days ago
Frontier Airlines
Fri, Oct 3 - Fri, Oct 10
OKC
Oklahoma City
MDW
Chicago
$173 Roundtrip, found 12 hours ago
$173
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Oct 3 from Oklahoma City to Chicago, returning Fri, Oct 10, priced at $173 found 12 hours ago
Frontier Airlines
Fri, Oct 10 - Mon, Oct 27
OKC
Oklahoma City
MDW
Chicago
$186 Roundtrip, found 22 hours ago
$186
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Fri, Oct 10 from Oklahoma City to Chicago, returning Mon, Oct 27, priced at $186 found 22 hours ago
Frontier Airlines
Mon, Oct 6 - Fri, Oct 10
OKC
Oklahoma City
MDW
Chicago
$193 Roundtrip, found 12 hours ago
$193
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Mon, Oct 6 from Oklahoma City to Chicago, returning Fri, Oct 10, priced at $193 found 12 hours ago
Frontier Airlines
Mon, Oct 20 - Fri, Oct 24
OKC
Oklahoma City
MDW
Chicago
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Oklahoma City to Chicago, returning Fri, Oct 24, priced at $196 found 1 day ago
Southwest Airlines
Wed, Oct 1 - Fri, Oct 3
OKC
Oklahoma City
MDW
Chicago
$200 Roundtrip, found 3 hours ago
$200
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Oct 1 from Oklahoma City to Chicago, returning Fri, Oct 3, priced at $200 found 3 hours ago
Frontier Airlines
Fri, Oct 3 - Sat, Oct 11
OKC
Oklahoma City
MDW
Chicago
$206 Roundtrip, found 12 hours ago
$206
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Oct 3 from Oklahoma City to Chicago, returning Sat, Oct 11, priced at $206 found 12 hours ago
Frontier Airlines
Fri, Sep 5 - Fri, Sep 12
OKC
Oklahoma City
MDW
Chicago
$207 Roundtrip, just found
$207
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Sep 5 from Oklahoma City to Chicago, returning Fri, Sep 12, priced at $207 just found
Delta
Wed, Dec 17 - Wed, Jan 21
OKC
Oklahoma City
MDW
Chicago
$259 Roundtrip, just found
$259
Roundtrip
just found
Select Delta flight, departing Wed, Dec 17 from Oklahoma City to Chicago, returning Wed, Jan 21, priced at $259 just found

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 $406
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $406
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
$160
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 September. 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 $80 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?
Grab a cheap one-way flight from $80 or cheap return flight from $160 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)?
September 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.

Explore a world of travel with Expedia

*Available to One Key members.