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Cheap flights from Oklahoma to Chicago from $49

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 to Chicago departing on 11/29. 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
10:48 pm - 1:05 amDFW-MDW
2h 17mnonstop
Frontier Logo
5:30 am - 8:15 amMDW-DFW
2h 45mnonstop
$92Frontier
Find Deal
Fri, Nov 21 - Sat, Nov 29
Frontier Logo
11:47 am - 2:04 pmDFW-MDW
2h 17mnonstop
Frontier Logo
8:05 am - 10:47 amMDW-DFW
2h 42mnonstop
$93Frontier
Find Deal
Thu, Dec 4 - Sun, Dec 7
Frontier Logo
7:00 am - 9:21 amDFW-MDW
2h 21mnonstop
Frontier Logo
10:21 am - 1:06 pmMDW-DFW
2h 45mnonstop
$94Frontier
Find Deal
Wed, Dec 24 - Wed, Dec 31
Frontier Logo
11:47 am - 2:04 pmDFW-MDW
2h 17mnonstop
Frontier Logo
12:35 pm - 3:05 pmMDW-DFW
2h 30mnonstop
$96Frontier
Find Deal
Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
11:47 am - 2:04 pmDFW-MDW
2h 17mnonstop
Multiple Airlines Logo
6:00 am - 6:47 pmMDW-DFW
12h 47m1 stop
$120Multiple Airlines
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Thu, Dec 4 - Sat, Dec 6
Southwest Logo
3:15 pm - 5:00 pmTUL-MDW
1h 45mnonstop
Southwest Logo
1:55 pm - 3:45 pmMDW-TUL
1h 50mnonstop
$226Southwest
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Wed, Dec 3 - Mon, Dec 8
Delta Logo
10:09 am - 4:18 pmTUL-MDW
6h 09m1 stop
Delta Logo
10:49 am - 6:00 pmMDW-TUL
7h 11m1 stop
$227Delta
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Fri, Dec 5 - Tue, Dec 9
Delta Logo
6:55 pm - 11:47 pmXNA-MDW
4h 52m1 stop
Delta Logo
12:50 pm - 8:28 pmMDW-XNA
7h 38m1 stop
$229Delta
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Thu, Dec 4 - Mon, Dec 8
Southwest Logo
10:10 am - 5:15 pmTUL-MDW
7h 05m1 stop
Southwest Logo
1:55 pm - 3:45 pmMDW-TUL
1h 50mnonstop
$236Southwest
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Wed, Dec 3 - Mon, Dec 8
Multiple Airlines Logo
8:53 am - 7:50 pmXNA-MDW
10h 57m1 stop
Multiple Airlines Logo
8:56 pm - 8:03 amMDW-XNA
11h 07m1 stop
$270Multiple Airlines
Find Deal
Fri, Feb 20 - Sun, Feb 22

Frontier flights from Oklahoma to Chicago Midway Airport

Our best Frontier deals on Oklahoma to Chicago Midway Airport flight tickets
Frontier
Nov 21
DFW10:48 pmDallas/Fort Worth
2h 17m
MDW1:05 amChicago Midway
Nov 29
MDW5:30 amChicago Midway
2h 45m
DFW8:15 amDallas/Fort Worth
$92
Find similar
Frontier
Dec 4
DFW11:47 amDallas/Fort Worth
2h 17m
MDW2:04 pmChicago Midway
Dec 7
MDW8:05 amChicago Midway
2h 42m
DFW10:47 amDallas/Fort Worth
$93
Find similar
Frontier
Dec 24
DFW7:00 amDallas/Fort Worth
2h 21m
MDW9:21 amChicago Midway
Dec 31
MDW10:21 amChicago Midway
2h 45m
DFW1:06 pmDallas/Fort Worth
$94
Find similar

Delta flights from Oklahoma to Chicago Midway Airport

Our best Delta deals on Oklahoma to Chicago Midway Airport flight tickets
Delta
Dec 5
TUL10:09 amTulsa
6h 09m
1 stop
MDW4:18 pmChicago Midway
Dec 9
MDW10:49 amChicago Midway
7h 11m
1 stop
TUL6:00 pmTulsa
$227
Find similar
Delta
Dec 4
XNA6:55 pmFayetteville Northwest Arkansas
4h 52m
1 stop
MDW11:47 pmChicago Midway
Dec 8
MDW12:50 pmChicago Midway
7h 38m
1 stop
XNA8:28 pmFayetteville Northwest Arkansas
$229
Find similar
Delta
Dec 6
TUL4:28 pmTulsa
7h 19m
1 stop
MDW11:47 pmChicago Midway
Dec 10
MDW6:00 amChicago Midway
6h 13m
1 stop
TUL12:13 pmTulsa
$249
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Oklahoma 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 6, 2025.
Use the filters below to find and compare flights from Oklahoma to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 11/21

10:48 pm-1:05 am

Nonstop2h 17m

Chicago Midway

Sat 11/29

5:30 am-8:15 am

Nonstop2h 45m

$92

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 12/4

11:47 am-2:04 pm

Nonstop2h 17m

Chicago Midway

Sun 12/7

8:05 am-10:47 am

Nonstop2h 42m

$93

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 12/24

7:00 am-9:21 am

Nonstop2h 21m

Chicago Midway

Wed 12/31

10:21 am-1:06 pm

Nonstop2h 45m

$94

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 12/12

11:47 am-2:04 pm

Nonstop2h 17m

Chicago Midway

Mon 12/15

12:35 pm-3:05 pm

Nonstop2h 30m

$96

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 12/4

11:47 am-2:04 pm

Nonstop2h 17m

Chicago Midway

Sat 12/6

6:00 am-6:47 pm

1 stop12h 47m

$120

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 12/3

3:15 pm-5:00 pm

Nonstop1h 45m

Chicago Midway

Mon 12/8

1:55 pm-3:45 pm

Nonstop1h 50m

$226

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Fri 12/5

10:09 am-4:18 pm

1 stop6h 09m

Chicago Midway

Tue 12/9

10:49 am-6:00 pm

1 stop7h 11m

$227

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Thu 12/4

6:55 pm-11:47 pm

1 stop4h 52m

Chicago Midway

Mon 12/8

12:50 pm-8:28 pm

1 stop7h 38m

$229

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 12/3

10:10 am-5:15 pm

1 stop7h 05m

Chicago Midway

Mon 12/8

1:55 pm-3:45 pm

Nonstop1h 50m

$236

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Fri 2/20

8:53 am-7:50 pm

1 stop10h 57m

Chicago Midway

Sun 2/22

8:56 pm-8:03 am

1 stop11h 07m

$270

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 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, with most prices found around $224. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Oklahoma during the month October is also very affordable. Most momondo users find prices during this month for around $298.

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. 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 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 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 to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Oklahoma 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 to Chicago Midway Airport flights?

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

Cheap Oklahoma to Chicago Midway Airport flight deals and tips

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

Best Price Found

$171

Fastest flight time

1h 40m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Oklahoma in the past 72 hours is $171. The best round-trip flight deal from Oklahoma to Chicago Midway Airport found on momondo in the last 72 hours is $306.
The fastest flight from Oklahoma to Chicago Midway Airport takes 1h 40m
Direct flights go from Oklahoma to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Oklahoma to Chicago Midway Airport are updated daily.

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

  • How old do you have to be to fly from Oklahoma 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 to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

Best airlines flying from Oklahoma to Chicago Midway Airport

Compare and see reviews for airlines that fly from Oklahoma to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $197Free CancellationRating
8.0
4,240 reviews
Search Southwest flights

Traveling to a place near Chicago?

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Porter
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Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Oklahoma to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. All flights to Chicago from Oklahoma on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Oklahoma.

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

Yes. momondo can track prices for Oklahoma to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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