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Cheap flights from Oklahoma to Chicago from $73

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 6/3. 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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Find the cheapest flights from Oklahoma to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:00 pm - 2:27 pm
DFW
-
MDW
2h 27mnonstop
Frontier Logo
3:22 pm - 5:56 pm
MDW
-
DFW
2h 34mnonstop
$137Frontier
Thu, Aug 6 - Sun, Aug 9
Frontier Logo
11:44 am - 2:07 pm
DFW
-
MDW
2h 23mnonstop
Frontier Logo
3:02 pm - 5:39 pm
MDW
-
DFW
2h 37mnonstop
$140Frontier
Fri, Sep 4 - Sun, Sep 6
Frontier Logo
11:44 am - 2:07 pm
DFW
-
MDW
2h 23mnonstop
Frontier Logo
3:02 pm - 5:39 pm
MDW
-
DFW
2h 37mnonstop
$141Frontier
Fri, Sep 4 - Sun, Sep 6
Frontier Logo
2:25 pm - 4:42 pm
DFW
-
MDW
2h 17mnonstop
Frontier Logo
4:10 pm - 6:53 pm
MDW
-
DFW
2h 43mnonstop
$147Frontier
Sat, Jun 6 - Thu, Jun 11
Frontier Logo
12:00 pm - 2:27 pm
DFW
-
MDW
2h 27mnonstop
Frontier Logo
3:22 pm - 5:56 pm
MDW
-
DFW
2h 34mnonstop
$148Frontier
Mon, Jul 27 - Thu, Jul 30
Southwest Logo
5:00 am - 6:45 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
11:45 am - 1:30 pm
MDW
-
TUL
1h 45mnonstop
$237Southwest
Tue, Jun 9 - Wed, Jun 17
Southwest Logo
5:10 am - 6:55 am
TUL
-
MDW
1h 45mnonstop
Southwest Logo
9:40 am - 11:35 am
MDW
-
TUL
1h 55mnonstop
$240Southwest
Mon, Jun 1 - Wed, Jun 3
Delta Logo
4:43 pm - 10:15 pm
TUL
-
MDW
5h 32m
1 stop
Delta Logo
6:00 am - 11:56 am
MDW
-
TUL
5h 56m
1 stop
$257Delta
Tue, Jul 14 - Wed, Jul 15
Allegiant Air Logo
9:12 pm - 8:40 pm
OKC
-
MDW
23h 28m
1 stop
Allegiant Air Logo
9:30 pm - 12:14 pm
MDW
-
OKC
14h 44m
1 stop
$266Allegiant Air
Thu, May 28 - Mon, Jun 1
Delta Logo
6:00 am - 11:56 am
XNA
-
MDW
5h 56m
1 stop
Delta Logo
1:00 pm - 5:09 pm
MDW
-
XNA
4h 09m
1 stop
$289Delta
Sat, Oct 17 - Wed, Oct 28

Southwest flights from Oklahoma to Chicago Midway Airport

Our best Southwest deals on Oklahoma to Chicago Midway Airport flight tickets
Southwest
Jun 9
TUL5:00 amTulsa
1h 45m
MDW6:45 amChicago Midway
Jun 17
MDW11:45 amChicago Midway
1h 45m
TUL1:30 pmTulsa
$237
Southwest
Jun 1
TUL5:10 amTulsa
1h 45m
MDW6:55 amChicago Midway
Jun 3
MDW9:40 amChicago Midway
1h 55m
TUL11:35 amTulsa
$240
Southwest
May 28
TUL3:55 pmTulsa
1h 45m
MDW5:40 pmChicago Midway
Jun 1
MDW9:50 pmChicago Midway
1h 55m
TUL11:45 pmTulsa
$243

Frontier flights from Oklahoma to Chicago Midway Airport

Our best Frontier deals on Oklahoma to Chicago Midway Airport flight tickets
Frontier
Aug 6
DFW12:00 pmDallas/Fort Worth
2h 27m
MDW2:27 pmChicago Midway
Aug 9
MDW3:22 pmChicago Midway
2h 34m
DFW5:56 pmDallas/Fort Worth
$137
Frontier
Jun 6
DFW2:25 pmDallas/Fort Worth
2h 17m
MDW4:42 pmChicago Midway
Jun 11
MDW4:10 pmChicago Midway
2h 43m
DFW6:53 pmDallas/Fort Worth
$147
Frontier
Jul 27
DFW12:00 pmDallas/Fort Worth
2h 27m
MDW2:27 pmChicago Midway
Jul 30
MDW3:22 pmChicago Midway
2h 34m
DFW5:56 pmDallas/Fort Worth
$148

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 May 10, 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

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 8/6

12:00 pm-2:27 pm

Nonstop2h 27m

Chicago Midway

Sun 8/9

3:22 pm-5:56 pm

Nonstop2h 34m

$137

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 9/4

11:44 am-2:07 pm

Nonstop2h 23m

Chicago Midway

Sun 9/6

3:02 pm-5:39 pm

Nonstop2h 37m

$140

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 9/4

11:44 am-2:07 pm

Nonstop2h 23m

Chicago Midway

Sun 9/6

3:02 pm-5:39 pm

Nonstop2h 37m

$141

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sat 6/6

2:25 pm-4:42 pm

Nonstop2h 17m

Chicago Midway

Thu 6/11

4:10 pm-6:53 pm

Nonstop2h 43m

$147

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Mon 7/27

12:00 pm-2:27 pm

Nonstop2h 27m

Chicago Midway

Thu 7/30

3:22 pm-5:56 pm

Nonstop2h 34m

$148
Quickest round-trip

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 6/9

5:00 am-6:45 am

Nonstop1h 45m

Chicago Midway

Wed 6/17

11:45 am-1:30 pm

Nonstop1h 45m

$237

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Mon 6/1

5:10 am-6:55 am

Nonstop1h 45m

Chicago Midway

Wed 6/3

9:40 am-11:35 am

Nonstop1h 55m

$240

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 7/14

4:43 pm-10:15 pm

1 stop5h 32m

Chicago Midway

Wed 7/15

6:00 am-11:56 am

1 stop5h 56m

$257

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 5/28

9:12 pm-8:40 pm

1 stop23h 28m

Chicago Midway

Mon 6/1

9:30 pm-12:14 pm

1 stop14h 44m

$266

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Sat 10/17

6:00 am-11:56 am

1 stop5h 56m

Chicago Midway

Wed 10/28

1:00 pm-5:09 pm

1 stop4h 09m

$289

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 June is, on average, the cheapest month to fly to Chicago Midway Airport from Oklahoma, with most prices found around $137. If you are unable to visit Chicago Midway Airport during the month of June, then departing from Oklahoma during the month October is also very affordable. Most momondo users find prices during this month for around $155.

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 $374. 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 $481.

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 morning because they tend to be around $425. 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

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

$190

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 $190. The best round-trip flight deal from Oklahoma to Chicago Midway Airport found on momondo in the last 72 hours is $377.
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 $197Free CancellationRating
8.0
4,304 reviews
Search Southwest flights

Traveling to a place near Chicago?

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