฿10,750 Cheap Flights from Oklahoma City (OKC) to Chicago (MDW)

View ฿10,750 flight on Fri, 19 Sep 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 (OKC) to Chicago (MDW)

Prices were available within the past 7 days and start at ฿10,750 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

February is typically the cheapest month to fly

From ฿4,072 - ฿21,357 per traveller.

Graph displaying average flight prices per month

Flight from Oklahoma City to Chicago route information
Origin airport
Will Rogers World
Destination airport
Midway Intl.
Distance
1105 km
Average flight time
2 hours 18 mins

Perfect flights from Oklahoma City to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Oklahoma City to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of Chicago, surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Will Rogers World to Midway Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿10,750 and roundtrip prices . Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Midway Intl. and explore Chicago and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your OKC to MDW travel arrangements today and embark on the journey of a lifetime in Chicago.

Frequently asked questions

How much is a flight from Will Rogers World Airport (OKC) to Midway Intl. Airport (MDW)?
Round-trip journeys between OKC and Midway Airport start from . This figure is based on fares offered within the last 7 days on Expedia for flights departing within the next year — make your booking ASAP to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Will Rogers World Airport (OKC) to MDW?
Most flights can be conveniently cancelled online, but whether you are charged a fee depends on your airline. If you do have to cancel your trip, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from Will Rogers Airport to MDW that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for OKC to Midway Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from OKC to Midway Intl. Airport (MDW)?
That movie you've been wanting to see will just have to wait — the flight distance between Will Rogers Airport (OKC) and Chicago Airport (MDW) is only 1,100 kilometres. The captain will be instructing you to put your seat upright for landing before you know it.
Which airlines fly direct from Will Rogers Airport to Midway Airport?
A popular choice with many savvy travellers, Southwest Airlines (WN) offers 56 flights every month from OKC to Midway Intl. Airport (MDW). Pick the one that fits with your travel schedule and book your fare today.
Are Will Rogers Airport to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can sometimes find a bargain, with some super cheap fares from OKC to Midway Airport appearing a few weeks before the departure date. If you'd rather book ahead of time, Expedia compares and updates the best flight deals regularly — as early as 12 months in advance in some cases. It depends on the carrier though, as not all airlines advertise prices that far in advance.

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