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Cheap flights from Oklahoma City to Chicago from $90

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 5/14. 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
0 bags

Find the cheapest flights from Oklahoma City to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
1:56 pm - 10:02 pm
OKC
-
MDW
8h 06m
1 stop
Frontier Logo
6:00 am - 1:01 pm
MDW
-
OKC
7h 01m
1 stop
$140Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
5:05 pm - 10:19 pm
OKC
-
MDW
5h 14m
1 stop
Frontier Logo
6:00 am - 2:21 pm
MDW
-
OKC
8h 21m
1 stop
$180Frontier
Thu, Apr 30 - Mon, May 4
Frontier Logo
1:56 pm - 10:02 pm
OKC
-
MDW
8h 06m
1 stop
Frontier Logo
6:00 am - 12:56 pm
MDW
-
OKC
6h 56m
1 stop
$201Frontier
Thu, Jun 4 - Tue, Jun 9
Frontier Logo
1:56 pm - 10:02 pm
OKC
-
MDW
8h 06m
1 stop
Frontier Logo
6:00 am - 1:01 pm
MDW
-
OKC
7h 01m
1 stop
$222Frontier
Thu, May 28 - Thu, Jun 4
Frontier Logo
1:56 pm - 10:02 pm
OKC
-
MDW
8h 06m
1 stop
Frontier Logo
6:00 am - 1:01 pm
MDW
-
OKC
7h 01m
1 stop
$225Frontier
Tue, May 26 - Sun, May 31
Frontier Logo
1:56 pm - 10:11 pm
OKC
-
MDW
8h 15m
1 stop
Frontier Logo
6:00 am - 12:53 pm
MDW
-
OKC
6h 53m
1 stop
$270Frontier
Thu, Jul 30 - Sun, Aug 2
Frontier Logo
1:56 pm - 10:02 pm
OKC
-
MDW
8h 06m
1 stop
Frontier Logo
6:00 am - 1:01 pm
MDW
-
OKC
7h 01m
1 stop
$278Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
5:04 pm - 10:19 pm
OKC
-
MDW
5h 15m
1 stop
Frontier Logo
6:00 am - 1:01 pm
MDW
-
OKC
7h 01m
1 stop
$280Frontier
Sun, May 3 - Thu, May 7
Multiple Airlines Logo
12:41 pm - 11:09 am
OKC
-
MDW
22h 28m
2 stops
Multiple Airlines Logo
9:30 pm - 12:14 pm
MDW
-
OKC
14h 44m
1 stop
$285Multiple Airlines
Tue, May 26 - Mon, Jun 1
Multiple Airlines Logo
12:41 pm - 11:09 am
OKC
-
MDW
22h 28m
2 stops
Multiple Airlines Logo
9:30 pm - 12:14 pm
MDW
-
OKC
14h 44m
1 stop
$293Multiple Airlines
Tue, May 26 - Mon, Jun 1

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Frontier flights from Oklahoma City to Chicago Midway Airport

Our best Frontier deals on Oklahoma City to Chicago Midway Airport flight tickets
Frontier
May 7
OKC1:56 pmOklahoma City Will Rogers World
8h 06m
1 stop
MDW10:02 pmChicago Midway
May 10
MDW6:00 amChicago Midway
7h 01m
1 stop
OKC1:01 pmOklahoma City Will Rogers World
$140
Frontier
Apr 30
OKC5:05 pmOklahoma City Will Rogers World
5h 14m
1 stop
MDW10:19 pmChicago Midway
May 4
MDW6:00 amChicago Midway
8h 21m
1 stop
OKC2:21 pmOklahoma City Will Rogers World
$180
Frontier
Apr 30
OKC5:05 pmOklahoma City Will Rogers World
5h 14m
1 stop
MDW10:19 pmChicago Midway
May 3
MDW6:00 amChicago Midway
10h 19m
1 stop
OKC4:19 pmOklahoma City Will Rogers World
$201

Delta flights from Oklahoma City to Chicago Midway Airport

Our best Delta deals on Oklahoma City to Chicago Midway Airport flight tickets
Delta
Jun 3
OKC7:09 amOklahoma City Will Rogers World
4h 47m
1 stop
MDW11:56 amChicago Midway
Jun 10
MDW6:05 amChicago Midway
6h 06m
1 stop
OKC12:11 pmOklahoma City Will Rogers World
$339
Delta
Jun 3
OKC5:40 amOklahoma City Will Rogers World
6h 16m
1 stop
MDW11:56 amChicago Midway
Jun 8
MDW5:11 pmChicago Midway
6h 44m
1 stop
OKC11:55 pmOklahoma City Will Rogers World
$347
Delta
Apr 24
OKC2:57 pmOklahoma City Will Rogers World
7h 31m
1 stop
MDW10:28 pmChicago Midway
May 3
MDW6:00 amChicago Midway
7h 51m
1 stop
OKC1:51 pmOklahoma City Will Rogers World
$594

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 April 19, 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 5/7

1:56 pm-10:02 pm

1 stop8h 06m

Chicago Midway

Sun 5/10

6:00 am-1:01 pm

1 stop7h 01m

$140

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 4/30

5:05 pm-10:19 pm

1 stop5h 14m

Chicago Midway

Mon 5/4

6:00 am-2:21 pm

1 stop8h 21m

$180

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 6/4

1:56 pm-10:02 pm

1 stop8h 06m

Chicago Midway

Tue 6/9

6:00 am-12:56 pm

1 stop6h 56m

$201

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 5/28

1:56 pm-10:02 pm

1 stop8h 06m

Chicago Midway

Thu 6/4

6:00 am-1:01 pm

1 stop7h 01m

$222

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 5/26

1:56 pm-10:02 pm

1 stop8h 06m

Chicago Midway

Sun 5/31

6:00 am-1:01 pm

1 stop7h 01m

$225

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 7/30

1:56 pm-10:11 pm

1 stop8h 15m

Chicago Midway

Sun 8/2

6:00 am-12:53 pm

1 stop6h 53m

$270

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 5/7

1:56 pm-10:02 pm

1 stop8h 06m

Chicago Midway

Sun 5/10

6:00 am-1:01 pm

1 stop7h 01m

$278
Quickest round-trip

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sun 5/3

5:04 pm-10:19 pm

1 stop5h 15m

Chicago Midway

Thu 5/7

6:00 am-1:01 pm

1 stop7h 01m

$280

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 5/26

12:41 pm-11:09 am

2 stops22h 28m

Chicago Midway

Mon 6/1

9:30 pm-12:14 pm

1 stop14h 44m

$285

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 5/26

12:41 pm-11:09 am

2 stops22h 28m

Chicago Midway

Mon 6/1

9:30 pm-12:14 pm

1 stop14h 44m

$293

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?

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 $379. 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 $459.

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 $409 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $416. 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?

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

$223

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 $223. The best round-trip flight deal from Oklahoma City to Chicago Midway Airport found on momondo in the last 72 hours is $403.
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

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 $240Free CancellationRating
8.0
4,328 reviews
Search Southwest flights

  • Southwest Flights From Oklahoma City to Chicago Midway Airport

    Southwest operates around 11 flights from Oklahoma City to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $393, but momondo users have found Southwest deals from Oklahoma City to Chicago Midway Airport from as low as $240 round-trip. Southwest has been scored 8.0/10 in 4,328 reviews.

Traveling to a place near Chicago?

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