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$59+ Cheap flights from Oklahoma to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Oklahoma to Chicago

Keep the following information in mind while searching for Oklahoma to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$111
(Kiwi.com)

One-way from

$59
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$298

Good round-trip deal

$303 or less

Good one-way deal

$173 or less
From Oklahoma to Chicago (CHI)
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One-way flight from Oklahoma to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Oklahoma to Chicago (CHI).
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Price to beat on a one-way flight from Oklahoma to Chicago (CHI).
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Find flight deals from Oklahoma to Chicago

Cheapest flights from Oklahoma to Chicago
Explore the most affordable flight options available from Oklahoma to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:24 pmDFW - ORD
Nonstop2h 35mFrontier
Mon 11/106:20 pmORD - DFW
Nonstop2h 49mFrontier
Deal found 9/14$111
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/21:53 pmDFW - MDW
1 stop9h 48mFrontier
Fri 10/39:47 pmMDW - DFW
Nonstop2h 34mFrontier
Deal found 9/13$111
This Priceline deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/159:26 pmDFW - ORD
Nonstop2h 33mFrontier
Tue 10/2111:00 amORD - DFW
1 stop7h 07mFrontier
Deal found 9/12$112
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/179:01 pmDFW - MDW
Nonstop2h 19mFrontier
Mon 10/206:24 pmMDW - DFW
1 stop6h 00mFrontier
Deal found 9/13$112
This Booking.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/159:26 pmDFW - ORD
Nonstop2h 33mMultiple Airlines
Thu 10/2312:28 pmORD - DFW
Nonstop2h 31mMultiple Airlines
Deal found 9/13$113
This Mytrip deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:00 amDFW - MDW
Nonstop2h 28mFrontier
Mon 10/66:21 amMDW - DFW
1 stop8h 27mFrontier
Deal found 9/13$113
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:28 pmDFW - MDW
Nonstop2h 24mFrontier
Sat 10/115:20 pmMDW - DFW
Nonstop2h 41mFrontier
Deal found 9/13$114
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:05 amDFW - ORD
Nonstop2h 28mSpirit Airlines
Thu 10/234:59 pmORD - DFW
1 stop7h 11mSpirit Airlines
Deal found 9/13$115
This CheapOair deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:55 amDFW - MDW
Nonstop2h 23mFrontier
Sun 10/510:13 amMDW - DFW
1 stop21h 36mFrontier
Deal found 9/13$115
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:07 pmDFW - ORD
1 stop5h 52mFrontier
Wed 10/296:25 pmORD - DFW
Nonstop2h 49mFrontier
Deal found 9/13$116
This Frontier deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/149:01 pmDFW - MDW
Nonstop2h 19mFrontier
Wed 10/228:05 amMDW - DFW
1 stop10h 05mFrontier
Deal found 9/12$116
This Frontier deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/159:26 pmDFW - ORD
Nonstop2h 33mFrontier
Mon 10/2712:23 pmORD - DFW
1 stop7h 43mFrontier
Deal found 9/13$117

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oklahoma to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Oklahoma to Chicago that are best for you.

Fly from

Oklahoma

Fly to

Chicago

Route

Depart

Return

Price

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 10/17

9:01 pm-11:20 pm

Nonstop2h 19m

Chicago Midway

Mon 10/20

6:24 pm-12:24 am

1 stop6h 00m

$112

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 10/29

12:05 pm-1:50 pm

Nonstop1h 45m

Chicago Midway

Fri 10/31

8:25 am-10:20 am

Nonstop1h 55m

$133

TulsaChicago

TUL - ORD

TULORD

Tulsa

Tue 10/7

6:16 pm-8:24 pm

Nonstop2h 08m

Chicago O'Hare Intl

Thu 10/9

10:20 pm-12:22 am

Nonstop2h 02m

$133

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 11/13

4:45 pm-6:30 pm

Nonstop1h 45m

Chicago Midway

Sat 11/15

5:15 am-2:05 pm

1 stop8h 50m

$143

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Thu 10/23

5:48 pm-11:39 pm

1 stop5h 51m

Chicago O'Hare Intl

Mon 10/27

5:05 am-4:53 pm

1 stop11h 48m

$144

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Sat 10/25

5:33 pm-11:53 pm

1 stop6h 20m

Chicago O'Hare Intl

Thu 10/30

5:11 am-3:50 pm

1 stop10h 39m

$144

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Fri 10/24

7:21 pm-12:59 am

1 stop5h 38m

Chicago O'Hare Intl

Sun 10/26

6:50 am-7:01 pm

1 stop12h 11m

$144

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 11/12

10:25 pm-11:30 am

1 stop13h 05m

Chicago Midway

Sun 11/16

6:06 pm-7:41 pm

1 stop25h 35m

$150

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 9/26

8:18 pm-9:51 am

1 stop13h 33m

Chicago Midway

Sun 9/28

6:21 am-2:48 pm

1 stop8h 27m

$150

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 10/17

9:01 pm-11:20 pm

Nonstop2h 19m

Chicago Midway

Fri 10/24

12:11 pm-9:46 am

2 stops21h 35m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 results
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Best time to book a flight from Oklahoma to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oklahoma with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oklahoma to Chicago

What is the cheapest month to book a flight from Oklahoma to Chicago?

Currently, August is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $245). Flying from Oklahoma to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OK to CHI?

Find hourly flight availability from Oklahoma to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oklahoma to Chicago as you normally would.

Weekly flight availability from Oklahoma to Chicago

Explore weekly flight availability from Oklahoma to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from USOK to CHI are scheduled on a Monday (33 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (22 on average).

How much does it cost to fly round-trip from Oklahoma to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Oklahoma to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Oklahoma to Chicago?

    There are many flights that can get you from Oklahoma to Chicago in 1h 45m. Fly via Frontier, Southwest, or American Airlines to get the fastest option. There are 582 mi between Oklahoma and Chicago. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Oklahoma to Chicago one-way?

    One-way options have recently been found by users for as low as $68 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $71 and Delta from $99 one-way.

  • What are the most popular routes from Oklahoma to Chicago?

    While some choose either Dallas/Fort Worth - Chicago Midway or Fayetteville Northwest Arkansas - Chicago O'Hare Intl, Dallas/Fort Worth - Chicago O'Hare Intl is the most popular route from Oklahoma to Chicago.

  • What are the most reliable airlines from Oklahoma to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Oklahoma to Chicago on time: Lufthansa (72%), Emirates (71%), Air New Zealand (71%).

  • What are the cheapest flights from Oklahoma to Chicago?

    Looking for the cheapest flight from Oklahoma to Chicago? While on average our users pay $1,084, our data indicates the cheapest price to be $131. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $90.

  • Can I find deals for flights from Oklahoma to Chicago that include hotel bookings?

    Yes. In addition to deals on Oklahoma to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oklahoma to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oklahoma to Chicago.

  • Can I find deals for business class flights from Oklahoma to Chicago?

    Yes. Cheapflights offers flight deals from Oklahoma to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oklahoma to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $245). Flying from Oklahoma to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Oklahoma to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Oklahoma to Chicago

Discover the top 4 airlines that operate flights from Oklahoma to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$195FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$167Average$359FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$189Average$348FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$252Average$420FlexibilityNo cancel feeOn-time69%

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