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Cheap flights from Oklahoma City to Chicago from $66

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 2/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
4:49 pm - 10:12 pmOKC-MDW
5h 23m1 stop
Frontier Logo
6:15 am - 3:19 pmMDW-OKC
9h 04m1 stop
$138Frontier
Find Deal
Fri, Dec 12 - Sun, Dec 14
Frontier Logo
4:37 pm - 10:12 pmOKC-MDW
5h 35m1 stop
Frontier Logo
6:12 am - 3:37 pmMDW-OKC
9h 25m1 stop
$141Frontier
Find Deal
Thu, Dec 18 - Thu, Dec 25
Frontier Logo
6:07 pm - 11:45 amOKC-MDW
17h 38m1 stop
Frontier Logo
6:20 am - 5:11 pmMDW-OKC
10h 51m1 stop
$181Frontier
Find Deal
Thu, Feb 5 - Sun, Feb 8
Frontier Logo
8:29 pm - 3:49 pmOKC-MDW
19h 20m2 stops
Frontier Logo
6:20 am - 5:11 pmMDW-OKC
10h 51m1 stop
$188Frontier
Find Deal
Thu, Feb 5 - Sun, Feb 8
Frontier Logo
4:49 pm - 10:12 pmOKC-MDW
5h 23m1 stop
Frontier Logo
6:12 am - 3:37 pmMDW-OKC
9h 25m1 stop
$198Frontier
Find Deal
Fri, Dec 5 - Thu, Dec 25
Frontier Logo
4:49 pm - 10:12 pmOKC-MDW
5h 23m1 stop
Frontier Logo
6:15 am - 3:19 pmMDW-OKC
9h 04m1 stop
$204Frontier
Find Deal
Fri, Dec 12 - Sun, Dec 14
Frontier Logo
8:29 pm - 9:22 pmOKC-MDW
24h 53m2 stops
Frontier Logo
6:15 am - 3:19 pmMDW-OKC
9h 04m1 stop
$211Frontier
Find Deal
Fri, Dec 12 - Sun, Dec 14
Frontier Logo
2:18 pm - 1:59 pmOKC-MDW
23h 41m2 stops
Frontier Logo
10:50 pm - 1:23 pmMDW-OKC
14h 33m1 stop
$227Frontier
Find Deal
Sat, Dec 20 - Sun, Jan 4
Frontier Logo
4:49 pm - 10:12 pmOKC-MDW
5h 23m1 stop
Frontier Logo
12:18 pm - 7:37 pmMDW-OKC
7h 19m1 stop
$252Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
4:37 pm - 10:12 pmOKC-MDW
5h 35m1 stop
Frontier Logo
10:50 pm - 1:23 pmMDW-OKC
14h 33m1 stop
$258Frontier
Find Deal
Thu, Jan 1 - Sun, Jan 4

Frontier flights from Oklahoma City to Chicago Midway Airport

Our best Frontier deals on Oklahoma City to Chicago Midway Airport flight tickets
Frontier
Dec 12
OKC4:49 pmOklahoma City Will Rogers World
5h 23m
1 stop
MDW10:12 pmChicago Midway
Dec 14
MDW6:15 amChicago Midway
9h 04m
1 stop
OKC3:19 pmOklahoma City Will Rogers World
$138
Find similar
Frontier
Dec 18
OKC4:37 pmOklahoma City Will Rogers World
5h 35m
1 stop
MDW10:12 pmChicago Midway
Dec 25
MDW6:12 amChicago Midway
9h 25m
1 stop
OKC3:37 pmOklahoma City Will Rogers World
$141
Find similar
Frontier
Feb 5
OKC6:07 pmOklahoma City Will Rogers World
17h 38m
1 stop
MDW11:45 amChicago Midway
Feb 8
MDW6:20 amChicago Midway
10h 51m
1 stop
OKC5:11 pmOklahoma City Will Rogers World
$181
Find similar

Southwest flights from Oklahoma City to Chicago Midway Airport

Our best Southwest deals on Oklahoma City to Chicago Midway Airport flight tickets
Southwest
Jan 14
OKC10:10 amOklahoma City Will Rogers World
1h 55m
MDW12:05 pmChicago Midway
Jan 17
MDW7:00 amChicago Midway
7h 40m
1 stop
OKC2:40 pmOklahoma City Will Rogers World
$297
Find similar
Southwest
Dec 18
OKC6:45 amOklahoma City Will Rogers World
1h 55m
MDW8:40 amChicago Midway
Dec 25
MDW8:15 amChicago Midway
2h 15m
OKC10:30 amOklahoma City Will Rogers World
$299
Find similar
Southwest
Dec 18
OKC12:10 pmOklahoma City Will Rogers World
6h 20m
1 stop
MDW6:30 pmChicago Midway
Dec 25
MDW8:15 amChicago Midway
2h 15m
OKC10:30 amOklahoma City Will Rogers World
$309
Find similar

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 November 20, 2025.
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

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 12/12

4:49 pm-10:12 pm

1 stop5h 23m

Chicago Midway

Sun 12/14

6:15 am-3:19 pm

1 stop9h 04m

$138

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 12/18

4:37 pm-10:12 pm

1 stop5h 35m

Chicago Midway

Thu 12/25

6:12 am-3:37 pm

1 stop9h 25m

$141

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 2/5

6:07 pm-11:45 am

1 stop17h 38m

Chicago Midway

Sun 2/8

6:20 am-5:11 pm

1 stop10h 51m

$181

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 2/5

8:29 pm-3:49 pm

2 stops19h 20m

Chicago Midway

Sun 2/8

6:20 am-5:11 pm

1 stop10h 51m

$188

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 12/5

4:49 pm-10:12 pm

1 stop5h 23m

Chicago Midway

Thu 12/25

6:12 am-3:37 pm

1 stop9h 25m

$198

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 12/12

4:49 pm-10:12 pm

1 stop5h 23m

Chicago Midway

Sun 12/14

6:15 am-3:19 pm

1 stop9h 04m

$204

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 12/12

8:29 pm-9:22 pm

2 stops24h 53m

Chicago Midway

Sun 12/14

6:15 am-3:19 pm

1 stop9h 04m

$211

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 12/20

2:18 pm-1:59 pm

2 stops23h 41m

Chicago Midway

Sun 1/4

10:50 pm-1:23 pm

1 stop14h 33m

$227

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 12/5

4:49 pm-10:12 pm

1 stop5h 23m

Chicago Midway

Sun 12/7

12:18 pm-7:37 pm

1 stop7h 19m

$252

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 1/1

4:37 pm-10:12 pm

1 stop5h 35m

Chicago Midway

Sun 1/4

10:50 pm-1:23 pm

1 stop14h 33m

$258

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 cheapest month to fly to Chicago Midway Airport?

The month of May is, on average, the cheapest month to fly to Chicago Midway Airport from Oklahoma City, with most prices found around $224. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Oklahoma City during the month October is also very affordable. Most momondo users find prices during this month for around $274.

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Oklahoma City. The lowest ticket price found for a Thursday 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 $451.

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

Flying to Chicago Midway Airport from Oklahoma City in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $396 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $402. 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 Will Rogers World to Chicago Midway flights?

There is only 1 cabin class available to choose from on Oklahoma City Will Rogers World to Chicago Midway 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?

You could potentially save up to 38% on your flight if you consider stops on a Oklahoma City to Chicago Midway Airport flight.

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

$225

Fastest flight time

1h 50m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oklahoma City in the past 72 hours is $225. The best round-trip flight deal from Oklahoma City to Chicago Midway Airport found on momondo in the last 72 hours is $396.
The fastest flight from Oklahoma City to Chicago Midway Airport takes 1h 50m
Direct flights go from Oklahoma City to Chicago Midway Airport every day.
Search flight deals

  • 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 55m 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 $217Free CancellationRating
8.0
4,251 reviews
Search Southwest flights

  • Southwest Flights From Oklahoma City to Chicago Midway Airport

    Southwest operates around 2 flights from Oklahoma City to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $378, but momondo users have found Southwest deals from Oklahoma City to Chicago Midway Airport from as low as $217 round-trip. Southwest has been scored 8.0/10 in 4,251 reviews.

Traveling to a place near Chicago?

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