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Cheap flights from Oklahoma to Chicago from $89

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 8/8. 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 to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:05 am - 6:45 am
TUL
-
MDW
1h 40mnonstop
Southwest Logo
10:30 am - 12:15 pm
MDW
-
TUL
1h 45mnonstop
$177Southwest
Sat, Aug 8 - Tue, Aug 11
Frontier Logo
3:01 pm - 5:26 pm
DFW
-
MDW
2h 25mnonstop
Frontier Logo
6:17 pm - 8:54 pm
MDW
-
DFW
2h 37mnonstop
$184Frontier
Sat, Aug 15 - Mon, Aug 17
Frontier Logo
6:08 pm - 8:32 pm
DFW
-
MDW
2h 24mnonstop
Frontier Logo
4:45 pm - 7:20 pm
MDW
-
DFW
2h 35mnonstop
$186Frontier
Thu, Aug 6 - Wed, Aug 12
Southwest Logo
5:05 am - 6:45 am
TUL
-
MDW
1h 40mnonstop
Southwest Logo
5:20 pm - 10:30 pm
MDW
-
TUL
5h 10m
1 stop
$187Southwest
Sat, Aug 8 - Tue, Aug 11
Frontier Logo
2:30 pm - 4:51 pm
DFW
-
MDW
2h 21mnonstop
Frontier Logo
9:27 pm - 11:59 pm
MDW
-
DFW
2h 32mnonstop
$187Frontier
Tue, Aug 4 - Thu, Aug 13
Frontier Logo
3:01 pm - 5:26 pm
DFW
-
MDW
2h 25mnonstop
Frontier Logo
5:46 pm - 8:20 pm
MDW
-
DFW
2h 34mnonstop
$188Frontier
Sat, Jul 25 - Tue, Jul 28
Delta Logo
6:00 am - 11:51 am
TUL
-
MDW
5h 51m
1 stop
Delta Logo
10:54 am - 4:57 pm
MDW
-
TUL
6h 03m
1 stop
$197Delta
Tue, Aug 4 - Tue, Aug 11
Delta Logo
4:44 pm - 10:36 pm
TUL
-
MDW
5h 52m
1 stop
Delta Logo
10:54 am - 4:57 pm
MDW
-
TUL
6h 03m
1 stop
$201Delta
Mon, Aug 10 - Tue, Aug 11
Allegiant Air Logo
9:36 pm - 8:30 pm
XNA
-
MDW
22h 54m
1 stop
Allegiant Air Logo
9:21 pm - 8:52 pm
MDW
-
XNA
23h 31m
1 stop
$312Allegiant Air
Sun, Jul 19 - Fri, Jul 24
Allegiant Air Logo
9:36 pm - 8:30 pm
XNA
-
MDW
22h 54m
1 stop
Allegiant Air Logo
9:21 pm - 8:52 pm
MDW
-
XNA
23h 31m
1 stop
$318Allegiant Air
Sun, Jul 19 - Fri, Jul 24

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Frontier flights from Oklahoma to Chicago Midway Airport

Our best Frontier deals on Oklahoma to Chicago Midway Airport flight tickets
Frontier
Aug 6
DFW6:08 pmDallas/Fort Worth
2h 24m
MDW8:32 pmChicago Midway
Aug 8
MDW6:41 pmChicago Midway
2h 40m
DFW9:21 pmDallas/Fort Worth
$186
Frontier
Aug 4
DFW2:30 pmDallas/Fort Worth
2h 21m
MDW4:51 pmChicago Midway
Aug 13
MDW9:27 pmChicago Midway
2h 32m
DFW11:59 pmDallas/Fort Worth
$187
Frontier
Jul 25
DFW3:01 pmDallas/Fort Worth
2h 25m
MDW5:26 pmChicago Midway
Jul 28
MDW5:46 pmChicago Midway
2h 34m
DFW8:20 pmDallas/Fort Worth
$188

Southwest flights from Oklahoma to Chicago Midway Airport

Our best Southwest deals on Oklahoma to Chicago Midway Airport flight tickets
Southwest
Aug 8
TUL5:05 amTulsa
1h 40m
MDW6:45 amChicago Midway
Aug 11
MDW10:30 amChicago Midway
1h 45m
TUL12:15 pmTulsa
$177
Southwest
Aug 8
TUL5:05 amTulsa
1h 40m
MDW6:45 amChicago Midway
Aug 12
MDW11:10 amChicago Midway
6h 45m
1 stop
TUL5:55 pmTulsa
$187
Southwest
Aug 5
TUL5:50 amTulsa
1h 40m
MDW7:30 amChicago Midway
Aug 10
MDW8:55 pmChicago Midway
1h 50m
TUL10:45 pmTulsa
$190

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 June 28, 2026.
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

Cheapest round-trip
Quickest round-trip

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 8/8

5:05 am-6:45 am

Nonstop1h 40m

Chicago Midway

Tue 8/11

10:30 am-12:15 pm

Nonstop1h 45m

$177

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sat 8/15

3:01 pm-5:26 pm

Nonstop2h 25m

Chicago Midway

Mon 8/17

6:17 pm-8:54 pm

Nonstop2h 37m

$184

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 8/6

6:08 pm-8:32 pm

Nonstop2h 24m

Chicago Midway

Wed 8/12

4:45 pm-7:20 pm

Nonstop2h 35m

$186

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 8/8

5:05 am-6:45 am

Nonstop1h 40m

Chicago Midway

Tue 8/11

5:20 pm-10:30 pm

1 stop5h 10m

$187

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 8/4

2:30 pm-4:51 pm

Nonstop2h 21m

Chicago Midway

Thu 8/13

9:27 pm-11:59 pm

Nonstop2h 32m

$187

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sat 7/25

3:01 pm-5:26 pm

Nonstop2h 25m

Chicago Midway

Tue 7/28

5:46 pm-8:20 pm

Nonstop2h 34m

$188

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 8/4

6:00 am-11:51 am

1 stop5h 51m

Chicago Midway

Tue 8/11

10:54 am-4:57 pm

1 stop6h 03m

$197

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Mon 8/10

4:44 pm-10:36 pm

1 stop5h 52m

Chicago Midway

Tue 8/11

10:54 am-4:57 pm

1 stop6h 03m

$201

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Sun 7/19

9:36 pm-8:30 pm

1 stop22h 54m

Chicago Midway

Fri 7/24

9:21 pm-8:52 pm

1 stop23h 31m

$312

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Sun 7/19

9:36 pm-8:30 pm

1 stop22h 54m

Chicago Midway

Fri 7/24

9:21 pm-8:52 pm

1 stop23h 31m

$318

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 October is, on average, the cheapest month to fly to Chicago Midway Airport from Oklahoma, with most prices found around $155. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Oklahoma during the month May is also very affordable. Most momondo users find prices during this month for around $177.

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. 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 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 at noon is the least expensive time of day to depart. momondo users have found prices as low as $413 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $444. 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 Tulsa to Chicago Midway for the best Oklahoma - Chicago Midway flight prices

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

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

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

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

$233

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 $233. The best round-trip flight deal from Oklahoma to Chicago Midway Airport found on momondo in the last 72 hours is $380.
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

Frequently asked questions about flying from Oklahoma to Chicago Midway Airport

  • 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 $217Free CancellationRating
7.9
4,246 reviews
Search Southwest flights

Traveling to a place near Chicago?

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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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