OKC - MDW

$90 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 4/16. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$180
Frontier
Thu 4/16Sun 4/19
OKC - MDW • 1 stop
Cheapest non-stop
$303
Typical prices: $383-$638
Southwest
Tue 3/31Wed 4/1
OKC - MDW • Non-stop
Top airlines
Frontier
Cheapest • from $180 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 50m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
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

Thu, Apr 16 - Sun, Apr 19
Frontier Logo
5:05 pm - 10:19 pm
OKC
-
MDW
5h 14m
1 stop
Frontier Logo
6:00 am - 4:19 pm
MDW
-
OKC
10h 19m
1 stop
$180Frontier
Thu, Apr 23 - Sun, Apr 26
Frontier Logo
5:05 pm - 10:19 pm
OKC
-
MDW
5h 14m
1 stop
Frontier Logo
10:53 am - 4:19 pm
MDW
-
OKC
5h 26m
1 stop
$201Frontier
Thu, Apr 23 - Sun, Apr 26
Frontier Logo
5:05 pm - 10:19 pm
OKC
-
MDW
5h 14m
1 stop
Frontier Logo
6:00 am - 4:19 pm
MDW
-
OKC
10h 19m
1 stop
$255Frontier
Tue, Mar 31 - Wed, Apr 1
Southwest Logo
2:55 pm - 4:45 pm
OKC
-
MDW
1h 50mnonstop
Southwest Logo
10:05 am - 12:20 pm
MDW
-
OKC
2h 15mnonstop
$303Southwest
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
5:00 am - 6:50 am
OKC
-
MDW
1h 50mnonstop
Southwest Logo
10:20 am - 12:30 pm
MDW
-
OKC
2h 10mnonstop
$309Southwest
Tue, Mar 31 - Wed, Apr 1
Southwest Logo
7:45 pm - 5:00 am
OKC
-
MDW
9h 15m
1 stop
Southwest Logo
10:05 am - 12:20 pm
MDW
-
OKC
2h 15mnonstop
$313Southwest
Sat, Apr 11 - Sat, Apr 18
Southwest Logo
5:00 am - 6:50 am
OKC
-
MDW
1h 50mnonstop
Southwest Logo
6:30 pm - 8:40 pm
MDW
-
OKC
2h 10mnonstop
$315Southwest
Tue, Mar 31 - Wed, Apr 1
Southwest Logo
5:00 am - 6:50 am
OKC
-
MDW
1h 50mnonstop
Southwest Logo
10:30 am - 6:00 pm
MDW
-
OKC
7h 30m
2 stops
$318Southwest
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
5:00 am - 6:50 am
OKC
-
MDW
1h 50mnonstop
Southwest Logo
10:10 am - 6:05 pm
MDW
-
OKC
7h 55m
1 stop
$319Southwest
Mon, Apr 13 - Mon, Apr 20
Frontier Logo
8:30 pm - 7:31 pm
OKC
-
MDW
23h 01m
2 stops
Frontier Logo
6:00 am - 2:21 pm
MDW
-
OKC
8h 21m
1 stop
$323Frontier
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 Tuesday 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.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $376 on average.

Find deals

Good to know

Low seasonMay
Cheapest flight$90
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly and prices are also 3% lower on average.
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 $90 for a one-way ticket and $180 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, Delta, and JetBlue 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 $209 or less one-way and $383 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 4318 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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

Information on your arrival and departure airports

Oklahoma City (OKC)
Midway (MDW)