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Cheap flights from Oklahoma City to Chicago from $119

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oklahoma City to Chicago departing on 9/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Oklahoma City to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
1:10 pm - 8:05 pm
OKC
-
MDW
6h 55m
1 stop
Southwest Logo
1:05 pm - 10:10 pm
MDW
-
OKC
9h 05m
2 stops
$262Southwest
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
7:15 am - 4:00 pm
OKC
-
MDW
8h 45m
2 stops
Southwest Logo
12:00 pm - 6:25 pm
MDW
-
OKC
6h 25m
1 stop
$262Southwest
Tue, Sep 22 - Thu, Sep 24
Southwest Logo
12:05 pm - 8:45 pm
OKC
-
MDW
8h 40m
2 stops
Southwest Logo
5:20 pm - 10:45 pm
MDW
-
OKC
5h 25m
1 stop
$262Southwest
Tue, Sep 22 - Wed, Sep 23
Southwest Logo
9:05 am - 3:30 pm
OKC
-
MDW
6h 25m
2 stops
Southwest Logo
5:30 pm - 10:55 pm
MDW
-
OKC
5h 25m
1 stop
$262Southwest
Wed, Sep 16 - Mon, Sep 21
Southwest Logo
7:15 am - 4:05 pm
OKC
-
MDW
8h 50m
2 stops
Southwest Logo
6:50 am - 1:45 pm
MDW
-
OKC
6h 55m
1 stop
$262Southwest
Wed, Sep 16 - Sat, Sep 19
Southwest Logo
5:50 am - 2:15 pm
OKC
-
MDW
8h 25m
2 stops
Southwest Logo
10:55 am - 8:55 pm
MDW
-
OKC
10h 00m
2 stops
$267Southwest
Sat, Sep 26 - Tue, Sep 29
Southwest Logo
7:15 am - 4:00 pm
OKC
-
MDW
8h 45m
2 stops
Southwest Logo
11:10 am - 6:30 pm
MDW
-
OKC
7h 20m
2 stops
$267Southwest
Tue, Sep 22 - Wed, Sep 23
Southwest Logo
7:05 am - 5:05 pm
OKC
-
MDW
10h 00m
2 stops
Southwest Logo
11:05 am - 9:40 pm
MDW
-
OKC
10h 35m
2 stops
$267Southwest
Wed, Nov 11 - Sat, Nov 14
Delta Logo
5:22 pm - 10:44 pm
OKC
-
MDW
5h 22m
1 stop
Delta Logo
6:05 am - 12:22 pm
MDW
-
OKC
6h 17m
1 stop
$281Delta
Wed, Sep 9 - Thu, Sep 10
Delta Logo
5:12 pm - 10:36 pm
OKC
-
MDW
5h 24m
1 stop
Delta Logo
6:11 am - 11:00 am
MDW
-
OKC
4h 49m
1 stop
$281Delta
Wed, Aug 26 - Sat, Aug 29

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Southwest flights from Oklahoma City to Chicago Midway Airport

Our best Southwest deals on Oklahoma City to Chicago Midway Airport flight tickets
Southwest
Sep 16
OKC7:15 amOklahoma City Will Rogers World
8h 50m
2 stops
MDW4:05 pmChicago Midway
Sep 19
MDW6:50 amChicago Midway
6h 55m
1 stop
OKC1:45 pmOklahoma City Will Rogers World
$262
Southwest
Aug 22
OKC12:35 pmOklahoma City Will Rogers World
6h 35m
2 stops
MDW7:10 pmChicago Midway
Aug 25
MDW11:10 amChicago Midway
7h 20m
2 stops
OKC6:30 pmOklahoma City Will Rogers World
$267
Southwest
Sep 5
OKC12:55 pmOklahoma City Will Rogers World
5h 35m
1 stop
MDW6:30 pmChicago Midway
Sep 6
MDW8:10 amChicago Midway
7h 10m
1 stop
OKC3:20 pmOklahoma City Will Rogers World
$269

Delta flights from Oklahoma City to Chicago Midway Airport

Our best Delta deals on Oklahoma City to Chicago Midway Airport flight tickets
Delta
Dec 2
OKC5:30 pmOklahoma City Will Rogers World
5h 26m
1 stop
MDW10:56 pmChicago Midway
Dec 5
MDW11:28 amChicago Midway
6h 46m
1 stop
OKC6:14 pmOklahoma City Will Rogers World
$281
Delta
Aug 27
OKC5:20 amOklahoma City Will Rogers World
6h 31m
1 stop
MDW11:51 amChicago Midway
Aug 29
MDW6:11 amChicago Midway
4h 49m
1 stop
OKC11:00 amOklahoma City Will Rogers World
$305
Delta
Aug 26
OKC5:12 pmOklahoma City Will Rogers World
5h 24m
1 stop
MDW10:36 pmChicago Midway
Aug 29
MDW6:11 amChicago Midway
4h 49m
1 stop
OKC11:00 amOklahoma City Will Rogers World
$317

momondo Fare Finder

 
Customize your flight search to find flights from Oklahoma City to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 2, 2026.
Use the filters below to find and compare flights from Oklahoma City to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 8/20

1:10 pm-8:05 pm

1 stop6h 55m

Chicago Midway

Mon 8/24

1:05 pm-10:10 pm

2 stops9h 05m

$262

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 9/22

7:15 am-4:00 pm

2 stops8h 45m

Chicago Midway

Thu 9/24

12:00 pm-6:25 pm

1 stop6h 25m

$262

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 9/22

12:05 pm-8:45 pm

2 stops8h 40m

Chicago Midway

Wed 9/23

5:20 pm-10:45 pm

1 stop5h 25m

$262

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 9/16

9:05 am-3:30 pm

2 stops6h 25m

Chicago Midway

Mon 9/21

5:30 pm-10:55 pm

1 stop5h 25m

$262

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 9/16

7:15 am-4:05 pm

2 stops8h 50m

Chicago Midway

Sat 9/19

6:50 am-1:45 pm

1 stop6h 55m

$262

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 9/26

5:50 am-2:15 pm

2 stops8h 25m

Chicago Midway

Tue 9/29

10:55 am-8:55 pm

2 stops10h 00m

$267

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 9/22

7:15 am-4:00 pm

2 stops8h 45m

Chicago Midway

Wed 9/23

11:10 am-6:30 pm

2 stops7h 20m

$267

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 11/11

7:05 am-5:05 pm

2 stops10h 00m

Chicago Midway

Sat 11/14

11:05 am-9:40 pm

2 stops10h 35m

$267

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 9/9

5:22 pm-10:44 pm

1 stop5h 22m

Chicago Midway

Thu 9/10

6:05 am-12:22 pm

1 stop6h 17m

$281
Quickest round-trip

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 8/26

5:12 pm-10:36 pm

1 stop5h 24m

Chicago Midway

Sat 8/29

6:11 am-11:00 am

1 stop4h 49m

$281

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Oklahoma City to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Oklahoma City and Chicago Midway Airport?

Prices are currently typical for flights on this route.

Typical prices usually range from $253 to $356.
The lowest price recently found on this route was $262.

What is the cheapest month to fly to Chicago Midway Airport?

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Oklahoma City, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Oklahoma City during the month January is also very affordable. Most momondo users find prices during this month for around $0.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Oklahoma City. The lowest ticket price found for a Tuesday departure recently was $386. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Oklahoma City because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $508.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Oklahoma City at noon is the least expensive time of day to depart. momondo users have found prices as low as $436 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $460. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Oklahoma City Will Rogers World to Chicago Midway flight route?

Fly from Oklahoma City Will Rogers World to Chicago Midway for the best Oklahoma City Will Rogers World - Chicago Midway flight prices

What cabin class options are available on Oklahoma City to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Oklahoma City to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Oklahoma City to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Oklahoma City to Chicago Midway Airport.

When to book flights from Oklahoma City to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Oklahoma City to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Oklahoma City to Chicago Midway Airport (OKC to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oklahoma City to Chicago Midway Airport

Best Price Found

$187

Fastest flight time

1h 50m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Oklahoma City in the past 72 hours is $187. The best round-trip flight deal from Oklahoma City to Chicago Midway Airport found on momondo in the last 72 hours is $349.
The fastest flight from Oklahoma City to Chicago Midway Airport takes 1h 50m
Direct flights go from Oklahoma City to Chicago Midway Airport on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Oklahoma City to Chicago Midway Airport

  • How far is Oklahoma City Will Rogers World to Chicago Midway by plane?

    The straight-line distance from Oklahoma City Will Rogers World to Chicago Midway is 683.4 mi. 1h 50m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Oklahoma City Will Rogers World Airport to Chicago Midway Airport?

    Prices for flights from Oklahoma City Will Rogers World Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Oklahoma City Will Rogers World Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Oklahoma City Will Rogers World Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Oklahoma City Will Rogers World Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Oklahoma City to Chicago Midway Airport?

  • What is the most popular airline from Oklahoma City to Chicago Midway Airport?

Best airlines flying from Oklahoma City to Chicago Midway Airport

Compare and see reviews for airlines that fly from Oklahoma City to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $241Free CancellationRating
8.0
4,229 reviews
Search Southwest flights

  • Southwest Flights From Oklahoma City to Chicago Midway Airport

    Southwest operates around 6 flights from Oklahoma City to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $473, but momondo users have found Southwest deals from Oklahoma City to Chicago Midway Airport from as low as $241 round-trip. Southwest has been scored 8.0/10 in 4,229 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Oklahoma City to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Oklahoma City.

Can I find flights from Oklahoma City to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Oklahoma City which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Oklahoma City to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Oklahoma City to Chicago.

I’m not ready to book a flight from Oklahoma City to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Oklahoma City. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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