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

Compare Oklahoma City Will Rogers World to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Map with a flight path from Oklahoma City Will Rogers World to Chicago Midway. A plane icon is halfway along the route with a label that says "Direct flight".
Direct flight

Your route at a glance

Cheapest deal$295
Cheapest monthSeptember
Average flight duration1 hour and 56 minutes
Most popular airlineSouthwest Airlines

Flight deals from Oklahoma City Will Rogers World to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Oklahoma City Will Rogers World to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.$295 per passenger.Departing Fri, 5 Sep, returning Mon, 8 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oklahoma City Will Rogers World on Fri, 5 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 8 Sep, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From $295, select.
Chicago.$311 per passenger.Departing Wed, 29 Oct, returning Sat, 1 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oklahoma City Will Rogers World on Wed, 29 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 1 Nov, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From $311, select.
Chicago.$315 per passenger.Departing Wed, 27 Aug, returning Thu, 28 Aug.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oklahoma City Will Rogers World on Wed, 27 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 28 Aug, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From $315, select.
Chicago.$387 per passenger.Departing Sat, 4 Oct, returning Sun, 5 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oklahoma City Will Rogers World on Sat, 4 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 5 Oct, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From $387, select.
Chicago.$447 per passenger.Departing Wed, 17 Dec, returning Sat, 20 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oklahoma City Will Rogers World on Wed, 17 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 20 Dec, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From $447, select.
Chicago.$457 per passenger.Departing Thu, 20 Nov, returning Sun, 23 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oklahoma City Will Rogers World on Thu, 20 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 23 Nov, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From $457, select.
Chicago.$470 per passenger.Departing Sat, 30 Aug, returning Tue, 2 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Oklahoma City Will Rogers World on Sat, 30 Aug, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 2 Sep, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From $470, select.
Chicago.$609 per passenger.Departing Fri, 22 Aug, returning Sun, 24 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oklahoma City Will Rogers World on Fri, 22 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 24 Aug, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From $609, select.

Find the cheapest month to fly from Oklahoma City Will Rogers World to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Oklahoma City Will Rogers World to Chicago Midway flights are currently cheapest in September.
Aug
from $315
Sep
from $295
Oct
from $387
Nov
from $457
Dec
from $447
Jan
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Feb
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Mar
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Apr
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May
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Jun
from $952
Jul
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Direct flights from Oklahoma City Will Rogers World to Chicago Midway

Oklahoma City Will Rogers World to Chicago Midway: Alternative routes

Compare routes from Oklahoma City Will Rogers World to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Finding cheap flights from Oklahoma City Will Rogers World to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Oklahoma City Will Rogers World to Chicago Midway is $295. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 56 minutes is the average flight time from Oklahoma City Will Rogers World to Chicago Midway.
Southwest Airlines flies direct from Oklahoma City Will Rogers World to Chicago Midway.
As of August 2025, there are 10 flights per week flying from Oklahoma City Will Rogers World to Chicago Midway.
The cheapest month to fly from Oklahoma City Will Rogers World to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Oklahoma City Will Rogers World Airport to Chicago Midway Airport on Friday, 5 September 2025.
Yes – the average flight time is 1 hour and 56 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Flying from Will Rogers World Airport (OKC) to Chicago Midway International Airport (MDW): what you need to know

  • The average time for a direct flight from Will Rogers World Airport to Chicago Midway International Airport is 1 hour 55 minutes.

  • Oklahoma City and Chicago are in the UTC-5 timezone. That means you won't need to account for any time differences.

  • Each week, there are seven Will Rogers World Airport to Chicago Midway International Airport flights. To jet off early, go for the 05:00 Southwest Airlines flight. If you're eager to make the most of your day before you fly, the last flight is at 17:45 with Southwest Airlines.

  • Arrive at the airport on time so you don't miss your OKC to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to prevent a last-minute sprint to your gate.

  • Travelling during a peak month like July? Major public holidays and other popular periods can lead to longer queues and delays at check-in and security. Play things extra safe and arrive up to four hours before an international flight and two hours before domestic departures.

  • Southwest Airlines has direct flights from Will Rogers World Airport to Chicago Midway International Airport. Book with this popular carrier, then get ready to discover the sights in Chicago — and maybe even more of United States if you have time.

  • The airline with the highest number of bookings on this route is Southwest Airlines.

  • Southwest Airlines is the most punctual carrier operating OKC to MDW flights, with 76.67% of its services landing on time.

  • If you want to explore another city along the way, just uncheck 'Direct flights only' when searching for your ticket from Will Rogers World Airport to Chicago Midway International Airport. Here are the most popular stopovers between OKC and MDW:

    • Nashville International Airport

    • Dallas/Fort Worth International Airport

    • William P. Hobby Airport

How to find the cheapest flights from Will Rogers World Airport (OKC) to Chicago Midway International Airport (MDW)

  • The lowest price we've found for a one-way Will Rogers World Airport to Chicago Midway International Airport flight is $145. A return fare is currently $295. Depending on the availability when you book, these fares can change.

  • To secure cheap tickets from OKC to MDW, book your trip nine months before your planned departure.

  • Organise your trip for August. That's the cheapest month for flights from Will Rogers World Airport to Chicago Midway International Airport. If you have flexibility with your dates, try out the 'Whole month' tool to see the lowest airfare across each month.

  • You don't need to check back in every day to find out if fares have gone down when you set up a Price Alert. We'll send you an update as soon as there's a new deal on cheap flights from OKC to MDW.

  • Tailor your trip with filters. Pick your departure and arrival times, total journey duration and airlines. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' flights from Will Rogers World Airport to Chicago Midway International Airport.

Handy information about Will Rogers World Airport (OKC)

  • You'll find OKC at 7100 Terminal Drive.

  • 81.65% of flights leaving Will Rogers World Airport arrive at their destination on time. Given its strong performance rating, you're unlikely to experience delays when flying out of OKC.

  • Will Rogers World Airport is around 18 kilometres from central Oklahoma City. If you're driving, catching a cab or ride-sharing from the centre, it'll take 15 minutes or so to arrive, depending on the traffic.

  • Get your travels off to a hassle-free start by staying near OKC. Whether you're boarding an early flight from Will Rogers World Airport to Chicago Midway International Airport or just don't like being rushed, these hotels have you covered:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you need is a long journey to your hotel if you're arriving on a late Will Rogers World Airport to Chicago Midway International Airport flight. Stay at one of these accommodation options near MDW instead:

  • Explore without limits with a Chicago Midway International Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and find adventure across Chicago and beyond.

  • Lock in the best possible rate by booking your ride from Chicago Midway International Airport around four weeks before your departure date.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • The address for MDW is 5700 South Cicero.

  • Chicago Midway International Airport to central Chicago has a drive time of about 20 minutes. It's approximately 19 kilometres away.

  • It typically takes 45 minutes if you're travelling on public transport.

When to fly to Chicago Midway International Airport (MDW)

  • It's time to work out your trip dates for your flight from Will Rogers World Airport to Chicago Midway International Airport. July is the most popular month to visit Chicago. If you're after a more relaxed vibe, go in May.

  • When reserving your flight from Will Rogers World Airport to Chicago Midway International Airport, consider the type of weather you like. July is the warmest month in Chicago, with the temperature ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from OKC to MDW sometime around then if you like cooler conditions.

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be discovered once you've seen Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another favourite destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Oklahoma City to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.