OKC - MDW

$55 Find Cheap Flights from Oklahoma City to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oklahoma City to Midway departing on 11/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oklahoma City to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oklahoma City to Chicago, as well as popular online travel agencies
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Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oklahoma City to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oklahoma City to Midway

Wed, Nov 12 - Sun, Nov 16
Frontier Logo
3:42 pm - 11:30 amOKC-MDW
19h 48m1 stop
Frontier Logo
6:15 am - 3:50 pmMDW-OKC
9h 35m1 stop
$152Frontier
Find Deal
Fri, Dec 5 - Mon, Dec 8
Frontier Logo
4:49 pm - 10:12 pmOKC-MDW
5h 23m1 stop
Frontier Logo
12:18 pm - 7:32 pmMDW-OKC
7h 14m1 stop
$163Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
6:19 pm - 10:12 pmOKC-MDW
27h 53m1 stop
Frontier Logo
12:18 pm - 7:32 pmMDW-OKC
7h 14m1 stop
$170Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
8:29 pm - 10:12 pmOKC-MDW
25h 43m2 stops
Frontier Logo
12:18 pm - 7:32 pmMDW-OKC
7h 14m1 stop
$173Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
6:19 pm - 10:12 pmOKC-MDW
27h 53m1 stop
Frontier Logo
12:18 pm - 7:32 pmMDW-OKC
7h 14m1 stop
$175Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
4:49 pm - 10:12 pmOKC-MDW
5h 23m1 stop
Frontier Logo
6:15 am - 3:19 pmMDW-OKC
9h 04m1 stop
$176Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
8:29 pm - 10:12 pmOKC-MDW
25h 43m2 stops
Frontier Logo
12:18 pm - 7:32 pmMDW-OKC
7h 14m1 stop
$177Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
8:29 pm - 10:12 pmOKC-MDW
25h 43m2 stops
Frontier Logo
12:18 pm - 7:32 pmMDW-OKC
7h 14m1 stop
$178Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
3:20 pm - 5:15 pmOKC-MDW
1h 55mnonstop
Southwest Logo
8:15 am - 10:30 amMDW-OKC
2h 15mnonstop
$271Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
7:25 am - 2:30 pmOKC-MDW
7h 05m1 stop
Southwest Logo
8:15 am - 10:30 amMDW-OKC
2h 15mnonstop
$281Southwest
Find Deal

Everything you should know

Top airlines
Frontier
Cheapest • from $152 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
May
Cheapest • 38% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$152
Overall average: $417
Frontier
Wed 11/12Sun 11/16
OKC - MDW • 1 stop
Cheapest non-stop
$271
Typical prices: $217-$354
Southwest
Thu 12/4Mon 12/8
OKC - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Booking Insights

KAYAK's insights & trends for Oklahoma City to Midway flights

Get data-powered insights and trends into flights from Oklahoma City to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Oklahoma City to Chicago Midway Airport?

The average price of all round-trip flights from Oklahoma City to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Thursday and more expensive on a Sunday. On your return trip to Oklahoma City, you should consider flying back on a Wednesday, and avoid Saturdays for better deals.

What is the cheapest month to fly from Oklahoma City to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oklahoma City to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Oklahoma City to Chicago Midway Airport is May, where tickets cost $224 (return) on average. On the other hand, the most expensive months are January and April, where the average cost of round-trip tickets is $527 and $418 respectively.

Can I save money by flying with a layover from Oklahoma City to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $241, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$55
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Oklahoma City to Chicago Midway Airport

When to book flights from Oklahoma City to Midway

Are your dates flexible? Find out the best times to travel from Oklahoma City to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Oklahoma City to Chicago Midway Airport flights

  • What is the cheapest flight from Oklahoma City to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Oklahoma City to Chicago Midway Airport was $55 for a one-way ticket and $152 for a round-trip.

  • Do I need a passport to fly between Oklahoma City and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Oklahoma City to Chicago Midway Airport?

    American Airlines, and Delta offer inflight Wi-Fi service on the Oklahoma City to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Oklahoma City to Chicago Midway Airport?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Oklahoma City to Chicago Midway Airport flight route.

  • On which days can I fly direct from Oklahoma City to Chicago Midway Airport?

    There are nonstop flights from Oklahoma City to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Oklahoma City to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oklahoma City to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oklahoma City to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Oklahoma City is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Oklahoma City to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Oklahoma City with another airline. Booking your flights between Oklahoma City and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oklahoma City to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Oklahoma City up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Oklahoma City to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $135 or less one-way and $389 or less round-trip.

Prefer to fly direct from Oklahoma City to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Oklahoma City Will Rogers World to Chicago Midway.
Find which airlines fly direct from Oklahoma City Will Rogers World Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Oklahoma City Will Rogers World to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Oklahoma City Will Rogers World

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Oklahoma City to Midway

 
See real verified KAYAK customer reviews for airlines flying from Oklahoma City to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Oklahoma City to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4243 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Everything you need to know for your flight from Oklahoma City to Midway

Information on your arrival and departure airports

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