OKC - MDW

$129 Find Cheap Flights from Oklahoma City to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$268
Typical prices: $335-$528
Southwest
Sat 10/20Sat 10/27
OKC - MDW • Non-stop
Cheapest non-stop
$325
Typical prices: $339-$547
Southwest
Sat 2/17Thu 2/22
OKC - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 56m
Direct flights
+1
Direct flights
+1
When to travel
February
Cheapest • 34% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Denver Intl (DEN)
Cheapest • Avg $167 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 8h 13m (one-way)
Insights
Insights
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 Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oklahoma City to Midway

Tue, Oct 20 - Tue, Oct 27
Southwest Logo
3:05 pm - 5:00 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
10:00 am - 3:20 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
5h 20m1 stop Austin Bergstrom
$268Southwest
Sat, Oct 31 - Sat, Nov 7
Southwest Logo
5:30 am - 7:25 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
5:05 am - 12:00 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
6h 55m1 stop Phoenix Sky Harbor Intl
$268Southwest
Tue, Oct 20 - Tue, Oct 27
Southwest Logo
3:05 pm - 5:00 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
1:05 pm - 8:40 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
7h 35m2 stops Detroit Metropolitan Wayne County Denver Intl
$273Southwest
Sat, Oct 31 - Sat, Nov 7
Southwest Logo
10:40 am - 12:35 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
11:05 am - 9:45 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
10h 40m2 stops Omaha Eppley Airfield Phoenix Sky Harbor Intl
$273Southwest
Sat, Oct 31 - Sat, Nov 7
Southwest Logo
9:50 am - 4:45 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
6h 55m2 stops Dallas Love Field Nashville Intl
Southwest Logo
2:55 pm - 9:30 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
6h 35m1 stop Houston Hobby
$283Southwest
Tue, Oct 20 - Tue, Oct 27
Southwest Logo
1:20 pm - 9:00 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
7h 40m1 stop Denver Intl
Southwest Logo
3:30 pm - 10:10 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
6h 40m2 stops Omaha Eppley Airfield Dallas Love Field
$283Southwest
Sat, Oct 31 - Sat, Nov 7
Southwest Logo
9:50 am - 4:35 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
6h 45m2 stops Dallas Love Field Austin Bergstrom
Southwest Logo
11:05 am - 9:45 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
10h 40m2 stops Omaha Eppley Airfield Phoenix Sky Harbor Intl
$288Southwest
Tue, Oct 27 - Thu, Oct 29
Southwest Logo
3:05 pm - 5:00 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
10:25 pm - 12:35 amMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 10mnonstop
$289Southwest
Tue, Oct 20 - Thu, Oct 29
Delta Logo
7:25 am - 11:47 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
4h 22m1 stop Minneapolis St Paul
Delta Logo
12:49 pm - 8:30 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
7h 41m1 stop Atlanta Hartsfield-Jackson
$345Delta
Thu, Nov 12 - Wed, Nov 18
Delta Logo
5:30 am - 11:59 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
6h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:13 pm - 11:59 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
6h 46m1 stop Atlanta Hartsfield-Jackson
$345Delta
Booking Insights

Price, demand and travel trends for Oklahoma City to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Oklahoma City to Chicago Midway Airport with more confidence.

How much is a round-trip flight from Oklahoma City to Chicago Midway Airport?

Round-trip flights from Oklahoma City to Chicago Midway Airport start at $268. Prices are below average for this route right now, with typical round-trip fares ranging from $335 to $528. The lowest price found in the past 5 days was $268 on Southwest.

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

Tuesday is the cheapest day of the week to fly from Oklahoma City to Chicago Midway Airport, it is 19% cheaper than the average day. Sunday is the most expensive day with flight prices 49% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • February is the cheapest month to fly from Oklahoma City to Chicago Midway Airport at $257 round-trip.
  • April ($614) and December ($582) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 138% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Oklahoma City to Chicago Midway Airport flights

Low season

January

Cheapest flight

$129
Best time to beat the crowds with an average 1% 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

Your Oklahoma City to Chicago Midway Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines offer extra legroom and free seat selection on Oklahoma City to Chicago Midway Airport flights?

    Among airlines operating Oklahoma City to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Oklahoma City to Chicago Midway Airport?

    Only Southwest operates flights between Oklahoma City and Chicago Midway Airport.

  • Which airports can I use when flying from Oklahoma City to Chicago Midway Airport?

    Flights from Oklahoma City to Chicago Midway Airport usually depart from Oklahoma City Will Rogers World (OKC) and arrive at Chicago Midway (MDW).

  • Which airlines include bags at no extra cost on Oklahoma City to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Oklahoma City to Chicago Midway Airport?

    Only Economy Class is available on flights from Oklahoma City to Chicago Midway Airport.

  • How much can I save by taking a layover when flying from Oklahoma City to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $167 round-trip via Denver Intl (DEN), compared to $393 for nonstop.

  • What is the standard checked-bag allowance on flights from Oklahoma City to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Oklahoma City to Chicago Midway Airport?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest. Other aircraft seen on the route include Embraer 175 (Enhanced Winglets) variants.

  • Which airports do connecting flights from Oklahoma City to Chicago Midway Airport pass through?

    Connecting flights from Oklahoma City to Chicago Midway Airport most commonly pass through:

    • Atlanta Hartsfield-Jackson (ATL) - 75% of one-stop connections
    • Denver Intl (DEN) - 25% of one-stop connections
    Together, these airports account for 100% of one-stop bookings on this route.

  • Can I save money by using flexible dates for flights from Oklahoma City to Chicago Midway Airport?

    Yes. Being flexible with your travel dates can save you up to 46% on the Oklahoma City to Chicago Midway Airport route. Tuesday is the cheapest departure day at $319 round-trip on average, while Sunday is the most expensive at $582, a difference of $263. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How are flight departures from Oklahoma City to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Oklahoma City to Chicago Midway Airport flights, with 50% of flights leaving in that window. Afternoon departures account for 50%, evening flights for 0%, and night flights for 0%.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • What are the earliest and latest flights from Oklahoma City to Chicago Midway Airport?

    These are the earliest and latest flight times available from Oklahoma City to Chicago Midway Airport:

    • Earliest: departs at 5:00 am and lands at 6:56 am
    • Latest: departs at 4:10 pm and lands at 6:06 pm.

    The flight takes about 1h 56m.

  • How long is a flight from Oklahoma City to Chicago Midway Airport?

    A nonstop flight from Oklahoma City to Chicago Midway Airport takes 1h 56m, covering 690 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Oklahoma City to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $268 to $1,550. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Oklahoma City to Chicago Midway Airport looking right now?

    One-way fares from Oklahoma City to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $143, which is 48% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Oklahoma City to Chicago Midway Airport?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 8h 13m, compared with 9h 03m via Denver Intl (DEN).

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • How much should I expect to pay for a Oklahoma City to Chicago Midway Airport flight?

    Round-trip flights from Oklahoma City to Chicago Midway Airport range from $335 to $528, with an average of $390 over the past 12 months. Anything below $335 counts as a good deal.

  • Which airlines offer Wi-Fi on Oklahoma City to Chicago Midway Airport flights?

    JetBlue is the only airline on the Oklahoma City to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

Your guide to booking Oklahoma City to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Tuesday departure instead of Sunday. On this route, Tuesday flights average $319 - about $263 less than Sunday (45% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Oklahoma City to Chicago Midway Airport trip for February. Fares historically average $257 round-trip in that month - typically $357 less than the most expensive month, which is April (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Denver Intl Airport (DEN) can be cheaper than flying direct. The cheapest layover option averages $167 round-trip on this route - about $226 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

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

 
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

More options for your flight from Oklahoma City to Midway

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago