OKC - MDW

$130 Find Cheap Flights from Oklahoma City to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$259
Typical prices: $338-$528
Southwest
Wed 12/5Sun 12/9
OKC - MDW • Non-stop
Cheapest one-way
$130
Typical prices: $137-$329
Southwest
Sun 12/16
OKC - MDW • Non-stop
Nonstop flights
You can fly direct with Southwest. Average duration is 1h 57m
Direct flights
+1
Direct flights
+1
When to travel
Cheapest • 35% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $252 (round-trip)
Shortest trip • 5h 12m (one-way)
Insights
Insights
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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

Sat, Dec 5 - Wed, Dec 9
Southwest Logo
5:00 am - 6:55 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
10:15 am - 12:25 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 10mnonstop
$259Southwest
Wed, Nov 25 - Wed, Dec 2
Southwest Logo
4:10 pm - 6:05 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
8:50 pm - 11:05 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 15mnonstop
$259Southwest
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
5:20 am - 7:20 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
2h 00mnonstop
Southwest Logo
8:50 pm - 11:05 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 15mnonstop
$259Southwest
Wed, Nov 25 - Wed, Dec 2
Southwest Logo
5:15 am - 7:10 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
10:15 am - 12:25 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 10mnonstop
$259Southwest
Sat, Dec 5 - Thu, Dec 10
Southwest Logo
12:40 pm - 2:35 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
8:50 pm - 11:05 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 15mnonstop
$259Southwest
Thu, Nov 26 - Thu, Dec 3
Southwest Logo
10:50 am - 12:45 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
8:50 pm - 11:05 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 15mnonstop
$259Southwest
Sat, Nov 21 - Wed, Nov 25
Southwest Logo
4:00 pm - 5:55 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
9:45 pm - 12:10 amMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 25mnonstop
$259Southwest
Sat, Nov 21 - Wed, Nov 25
Southwest Logo
4:00 pm - 5:55 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
9:45 pm - 12:10 amMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 25mnonstop
$259Southwest
Mon, Nov 23 - Thu, Nov 26
Delta Logo
7:27 am - 11:50 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
4h 23m1 stop Minneapolis St Paul
Delta Logo
11:27 am - 4:32 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
5h 05m1 stop Atlanta Hartsfield-Jackson
$279Delta
Wed, Dec 2 - Sat, Dec 5
Delta Logo
5:25 pm - 10:54 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
5h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:28 am - 6:14 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
6h 46m1 stop Atlanta Hartsfield-Jackson
$279Delta
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 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 typically range from $338 to $528. The lowest price found in the past 5 days was $259, on Southwest.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Oklahoma City to Chicago Midway Airport. It’s 24% cheaper than the average day, while Sunday is the most expensive, with prices 46% higher.

What’s 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.

Key details for Oklahoma City to Chicago Midway Airport flights

Low season

January

Cheapest flight

$130
Beat the crowds with an average 49% drop in travelers.
The most popular month to fly with an average 38% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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 6:57 am
    • Latest: departs at 5:10 pm and lands at 7:07 pm.

    The flight takes about 1h 57m.

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

    A nonstop flight from Oklahoma City to Chicago Midway Airport takes 1h 57m, 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.

  • 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 $338 to $528, with an average of $396 over the past 12 months. Anything below $338 counts as a good deal.

  • 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 $252 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $397 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 Embraer 175 (Enhanced Winglets) family is used most often on this route, operated mainly by United Airlines. Other aircraft seen on the route include Canadair (Bombardier) Regional Jet 700 variants.

  • 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%.

  • 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 $259 to $1,644. That means the highest observed fare was about 6x higher than the lowest one.

  • 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.

  • 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 $146, which is 40% below the typical average for this route.

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

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • 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 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

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

    Yes. Flexible dates can save you up to 48% on flights from Oklahoma City to Chicago Midway Airport. Saturday is the cheapest departure day at $303 round-trip on average, while Sunday is the most expensive at $582, a difference of $279.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Oklahoma City to Chicago Midway Airport?

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

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

    Flying via Denver Intl (DEN) gives the shortest average 1-stop total travel time at 5h 12m, compared with 8h 13m via Atlanta Hartsfield-Jackson (ATL).

  • 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 Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • 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.

  • 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 always check the fare details before booking.

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 are flexible, aim for a Saturday departure and avoid flying on Sunday. On this route, Saturday flights average $303, about $279 less than Sunday fares (48% 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 Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $252 round-trip on this route - about $146 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 Chicago Midway Airport

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

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to Oklahoma City Will Rogers World

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Wednesday

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Thursday

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Friday

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Saturday

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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