Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Oklahoma to Chicago from $58

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 2/14. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Oklahoma to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:03 pm - 10:21 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
4:09 pm - 7:03 pm
MDW
-
DFW
2h 54mnonstop
$81Frontier
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
8:03 pm - 10:21 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
4:09 pm - 7:03 pm
MDW
-
DFW
2h 54mnonstop
$82Frontier
Fri, Apr 17 - Mon, Apr 20
Frontier Logo
6:56 pm - 9:12 pm
DFW
-
MDW
2h 16mnonstop
Frontier Logo
3:00 pm - 5:46 pm
MDW
-
DFW
2h 46mnonstop
$84Frontier
Thu, Feb 26 - Thu, Mar 5
Frontier Logo
6:56 pm - 9:12 pm
DFW
-
MDW
2h 16mnonstop
Frontier Logo
5:13 pm - 8:00 pm
MDW
-
DFW
2h 47mnonstop
$85Frontier
Thu, Mar 5 - Mon, Mar 9
Frontier Logo
10:44 am - 9:39 pm
DFW
-
MDW
10h 55m
1 stop
Frontier Logo
9:16 pm - 11:59 pm
MDW
-
DFW
2h 43mnonstop
$87Frontier
Sat, Feb 28 - Sat, Mar 7
Delta Logo
5:59 pm - 10:31 pm
XNA
-
MDW
4h 32m
1 stop
Delta Logo
1:10 pm - 5:06 pm
MDW
-
XNA
3h 56m
1 stop
$229Delta
Mon, Mar 2 - Mon, Mar 9
Southwest Logo
3:10 pm - 4:50 pm
TUL
-
MDW
1h 40mnonstop
Southwest Logo
6:15 pm - 8:10 pm
MDW
-
TUL
1h 55mnonstop
$236Southwest
Wed, Apr 8 - Sat, Apr 11
Southwest Logo
10:45 am - 3:25 pm
TUL
-
MDW
4h 40m
1 stop
Southwest Logo
6:15 pm - 8:10 pm
MDW
-
TUL
1h 55mnonstop
$246Southwest
Wed, Apr 8 - Sat, Apr 11
Delta Logo
1:10 pm - 5:45 pm
XNA
-
MDW
4h 35m
1 stop
Delta Logo
6:00 am - 1:34 pm
MDW
-
XNA
7h 34m
1 stop
$249Delta
Thu, Feb 19 - Tue, Feb 24
Multiple Airlines Logo
9:48 pm - 1:08 pm
XNA
-
MDW
15h 20m
2 stops
Multiple Airlines Logo
8:43 pm - 8:28 pm
MDW
-
XNA
23h 45m
1 stop
$344Multiple Airlines
Sun, Mar 8 - Thu, Mar 12

Delta flights from Oklahoma to Chicago Midway Airport

Our best Delta deals on Oklahoma to Chicago Midway Airport flight tickets
Delta
Apr 4
XNA11:46 amFayetteville Northwest Arkansas
6h 54m
1 stop
MDW6:40 pmChicago Midway
Apr 10
MDW1:10 pmChicago Midway
3h 56m
1 stop
XNA5:06 pmFayetteville Northwest Arkansas
$229
Delta
Feb 19
XNA1:10 pmFayetteville Northwest Arkansas
4h 35m
1 stop
MDW5:45 pmChicago Midway
Feb 24
MDW6:00 amChicago Midway
7h 34m
1 stop
XNA1:34 pmFayetteville Northwest Arkansas
$249
Delta
Feb 25
TUL5:26 amTulsa
6h 33m
1 stop
MDW11:59 amChicago Midway
Feb 28
MDW6:00 amChicago Midway
6h 02m
1 stop
TUL12:02 pmTulsa
$269

Frontier flights from Oklahoma to Chicago Midway Airport

Our best Frontier deals on Oklahoma to Chicago Midway Airport flight tickets
Frontier
Apr 17
DFW8:03 pmDallas/Fort Worth
2h 18m
MDW10:21 pmChicago Midway
Apr 20
MDW4:09 pmChicago Midway
2h 54m
DFW7:03 pmDallas/Fort Worth
$81
Frontier
Apr 17
DFW8:03 pmDallas/Fort Worth
2h 18m
MDW10:21 pmChicago Midway
Apr 20
MDW4:09 pmChicago Midway
2h 54m
DFW7:03 pmDallas/Fort Worth
$82
Frontier
Feb 26
DFW6:56 pmDallas/Fort Worth
2h 16m
MDW9:12 pmChicago Midway
Mar 5
MDW3:00 pmChicago Midway
2h 46m
DFW5:46 pmDallas/Fort Worth
$84

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 February 3, 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

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 4/17

8:03 pm-10:21 pm

Nonstop2h 18m

Chicago Midway

Mon 4/20

4:09 pm-7:03 pm

Nonstop2h 54m

$81

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 4/17

8:03 pm-10:21 pm

Nonstop2h 18m

Chicago Midway

Mon 4/20

4:09 pm-7:03 pm

Nonstop2h 54m

$82

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 2/26

6:56 pm-9:12 pm

Nonstop2h 16m

Chicago Midway

Thu 3/5

3:00 pm-5:46 pm

Nonstop2h 46m

$84

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 3/5

6:56 pm-9:12 pm

Nonstop2h 16m

Chicago Midway

Mon 3/9

5:13 pm-8:00 pm

Nonstop2h 47m

$85

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sat 2/28

10:44 am-9:39 pm

1 stop10h 55m

Chicago Midway

Sat 3/7

9:16 pm-11:59 pm

Nonstop2h 43m

$87

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Mon 3/2

5:59 pm-10:31 pm

1 stop4h 32m

Chicago Midway

Mon 3/9

1:10 pm-5:06 pm

1 stop3h 56m

$229

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 4/8

3:10 pm-4:50 pm

Nonstop1h 40m

Chicago Midway

Sat 4/11

6:15 pm-8:10 pm

Nonstop1h 55m

$236

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 4/8

10:45 am-3:25 pm

1 stop4h 40m

Chicago Midway

Sat 4/11

6:15 pm-8:10 pm

Nonstop1h 55m

$246

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Thu 2/19

1:10 pm-5:45 pm

1 stop4h 35m

Chicago Midway

Tue 2/24

6:00 am-1:34 pm

1 stop7h 34m

$249

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Sun 3/8

9:48 pm-1:08 pm

2 stops15h 20m

Chicago Midway

Thu 3/12

8:43 pm-8:28 pm

1 stop23h 45m

$344

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $274.

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 $365. 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 $456.

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 $390 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $422. 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 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 46% 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

$185

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 $185. The best round-trip flight deal from Oklahoma to Chicago Midway Airport found on momondo in the last 72 hours is $353.
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
4,272 reviews
Search Southwest flights

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
Munster
Crown Point
Chesterton
Monticello
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 3/5
Thu 3/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago