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Cheap flights from Oklahoma to Chicago from $60

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 10/18. 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

Frontier Logo
9:10 am - 11:30 amDFW-MDW
2h 20mnonstop
Frontier Logo
6:15 pm - 8:59 pmMDW-DFW
2h 44mnonstop
$109Frontier
Find Deal
Thu, Nov 20 - Tue, Nov 25
Frontier Logo
9:10 am - 11:30 amDFW-MDW
2h 20mnonstop
Frontier Logo
6:15 pm - 8:59 pmMDW-DFW
2h 44mnonstop
$110Frontier
Find Deal
Thu, Nov 20 - Tue, Nov 25
Frontier Logo
6:28 pm - 8:52 pmDFW-MDW
2h 24mnonstop
Frontier Logo
5:20 pm - 8:01 pmMDW-DFW
2h 41mnonstop
$111Frontier
Find Deal
Fri, Oct 3 - Tue, Oct 7
Frontier Logo
9:06 am - 8:21 pmDFW-MDW
11h 15m1 stop
Frontier Logo
5:20 pm - 8:01 pmMDW-DFW
2h 41mnonstop
$112Frontier
Find Deal
Thu, Oct 16 - Tue, Oct 21
Multiple Airlines Logo
5:15 pm - 1:38 pmDFW-MDW
20h 23m2 stops
Multiple Airlines Logo
5:20 pm - 8:01 pmMDW-DFW
2h 41mnonstop
$155Multiple Airlines
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Tue, Oct 14 - Sat, Oct 18
Delta Logo
5:42 pm - 10:14 pmXNA-MDW
4h 32m1 stop
Delta Logo
6:00 am - 11:31 amMDW-XNA
5h 31m1 stop
$229Delta
Find Deal
Sat, Nov 8 - Wed, Nov 12
Delta Logo
12:27 pm - 5:35 pmXNA-MDW
5h 08m1 stop
Delta Logo
1:08 pm - 4:58 pmMDW-XNA
3h 50m1 stop
$249Delta
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Wed, Oct 1 - Sat, Oct 4
Southwest Logo
6:55 pm - 12:05 amTUL-MDW
5h 10m1 stop
Southwest Logo
5:30 pm - 7:20 pmMDW-TUL
1h 50mnonstop
$264Southwest
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Wed, Oct 15 - Wed, Oct 22
Multiple Airlines Logo
10:47 am - 12:30 amXNA-MDW
13h 43m1 stop
Multiple Airlines Logo
12:30 pm - 6:41 pmMDW-XNA
6h 11m1 stop
$264Multiple Airlines
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Mon, Nov 10 - Thu, Nov 13
Southwest Logo
6:35 am - 8:20 amTUL-MDW
1h 45mnonstop
Southwest Logo
3:45 pm - 5:30 pmMDW-TUL
1h 45mnonstop
$269Southwest
Find Deal
Sat, Oct 25 - Mon, Oct 27

Frontier flights from Oklahoma to Chicago Midway Airport

Our best Frontier deals on Oklahoma to Chicago Midway Airport flight tickets
Frontier
Nov 20
DFW9:10 amDallas/Fort Worth
2h 20m
MDW11:30 amChicago Midway
Nov 25
MDW6:15 pmChicago Midway
2h 44m
DFW8:59 pmDallas/Fort Worth
$109
Find similar
Frontier
Nov 20
DFW9:10 amDallas/Fort Worth
2h 20m
MDW11:30 amChicago Midway
Nov 25
MDW6:15 pmChicago Midway
2h 44m
DFW8:59 pmDallas/Fort Worth
$110
Find similar
Frontier
Oct 3
DFW6:28 pmDallas/Fort Worth
2h 24m
MDW8:52 pmChicago Midway
Oct 7
MDW5:20 pmChicago Midway
2h 41m
DFW8:01 pmDallas/Fort Worth
$111
Find similar

Delta flights from Oklahoma to Chicago Midway Airport

Our best Delta deals on Oklahoma to Chicago Midway Airport flight tickets
Delta
Nov 8
XNA5:42 pmFayetteville Northwest Arkansas
4h 32m
1 stop
MDW10:14 pmChicago Midway
Nov 12
MDW6:00 amChicago Midway
5h 31m
1 stop
XNA11:31 amFayetteville Northwest Arkansas
$229
Find similar
Delta
Oct 1
XNA12:27 pmFayetteville Northwest Arkansas
5h 08m
1 stop
MDW5:35 pmChicago Midway
Oct 4
MDW1:08 pmChicago Midway
3h 50m
1 stop
XNA4:58 pmFayetteville Northwest Arkansas
$249
Find similar
Delta
Jan 17
TUL5:15 pmTulsa
4h 31m
1 stop
MDW9:46 pmChicago Midway
Jan 28
MDW5:25 pmChicago Midway
5h 01m
1 stop
TUL10:26 pmTulsa
$251
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 September 18, 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

Thu 11/20

9:10 am-11:30 am

Nonstop2h 20m

Chicago Midway

Tue 11/25

6:15 pm-8:59 pm

Nonstop2h 44m

$109

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 11/20

9:10 am-11:30 am

Nonstop2h 20m

Chicago Midway

Tue 11/25

6:15 pm-8:59 pm

Nonstop2h 44m

$110

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 10/3

6:28 pm-8:52 pm

Nonstop2h 24m

Chicago Midway

Tue 10/7

5:20 pm-8:01 pm

Nonstop2h 41m

$111

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 10/16

9:06 am-8:21 pm

1 stop11h 15m

Chicago Midway

Tue 10/21

5:20 pm-8:01 pm

Nonstop2h 41m

$112

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 10/14

5:15 pm-1:38 pm

2 stops20h 23m

Chicago Midway

Sat 10/18

5:20 pm-8:01 pm

Nonstop2h 41m

$155

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Sat 11/8

5:42 pm-10:14 pm

1 stop4h 32m

Chicago Midway

Wed 11/12

6:00 am-11:31 am

1 stop5h 31m

$229

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Wed 10/1

12:27 pm-5:35 pm

1 stop5h 08m

Chicago Midway

Sat 10/4

1:08 pm-4:58 pm

1 stop3h 50m

$249

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 10/15

6:55 pm-12:05 am

1 stop5h 10m

Chicago Midway

Wed 10/22

5:30 pm-7:20 pm

Nonstop1h 50m

$264

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Mon 11/10

10:47 am-12:30 am

1 stop13h 43m

Chicago Midway

Thu 11/13

12:30 pm-6:41 pm

1 stop6h 11m

$264

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 10/25

6:35 am-8:20 am

Nonstop1h 45m

Chicago Midway

Mon 10/27

3:45 pm-5:30 pm

Nonstop1h 45m

$269

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 February is also very affordable. Most momondo users find prices during this month for around $299.

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 $385. 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 $393 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $398. 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.

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

$220

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 $220. The best round-trip flight deal from Oklahoma to Chicago Midway Airport found on momondo in the last 72 hours is $303.
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 $167Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
FrontierPriceFrom $202Free CancellationRating
5.8
3,171 reviews
Search Frontier flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Portage
Schererville
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Crown Point
Munster
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Porter
Griffith
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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