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$72+ Cheap flights from Oklahoma City (OKC) 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Oklahoma City Will Rogers World to Chicago are usually found in September or February, booked 76 days in advance, depart on a Saturday or Thursday and return on a Tuesday

Cheap flight deals from Oklahoma City to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Oklahoma City (OKC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 16, 2025.

Round-trip from

$144
(Frontier)

One-way from

$72
(Priceline)

Popular in

March

Cheapest in

September

Average price

$298

Good round-trip deal

$345 or less

Good one-way deal

$173 or less
From Oklahoma City Will Rogers World to Chicago (CHI)
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One-way flight from Oklahoma City Will Rogers World 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 City Will Rogers World to Chicago (CHI).
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Price to beat on a one-way flight from Oklahoma City Will Rogers World to Chicago (CHI).
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Find flight deals from Oklahoma City to Chicago

Cheapest flights from Oklahoma City to Chicago
Explore the most affordable flight options available from Oklahoma City to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:21 pmOKC - ORD
1 stop5h 38mFrontier
Sun 10/266:50 amORD - OKC
1 stop12h 11mFrontier
Deal found 9/14$144
This Frontier deal was found by Cheapflights users on 9/15. 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.
Thu 10/235:48 pmOKC - ORD
1 stop5h 51mFrontier
Mon 10/2710:51 amORD - OKC
1 stop7h 43mFrontier
Deal found 9/15$145
This Frontier deal was found by Cheapflights users on 9/16. 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.
Fri 10/177:21 pmOKC - MDW
1 stop5h 03mFrontier
Mon 10/2712:11 pmMDW - OKC
1 stop6h 23mFrontier
Deal found 9/16$150
This Frontier deal was found by Cheapflights users on 9/15. 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.
Thu 10/235:48 pmOKC - MDW
1 stop5h 58mFrontier
Mon 10/2712:11 pmMDW - OKC
1 stop6h 23mFrontier
Deal found 9/15$152
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:33 pmOKC - ORD
1 stop6h 20mFrontier
Mon 10/205:05 amORD - OKC
1 stop11h 48mFrontier
Deal found 9/14$156
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/18:00 amOKC - ORD
1 stop13h 28mFrontier
Thu 10/25:35 amORD - OKC
1 stop18h 19mFrontier
Deal found 9/15$161
This Priceline deal was found by Cheapflights users on 9/15. 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 9/266:05 amOKC - MDW
1 stop9h 48mFrontier
Mon 9/294:48 pmMDW - OKC
1 stop7h 06mFrontier
Deal found 9/15$163
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 10/2111:16 amOKC - ORD
1 stop12h 37mFrontier
Mon 10/2710:51 amORD - OKC
1 stop7h 43mFrontier
Deal found 9/16$163
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/297:46 pmOKC - ORD
1 stop25h 42mFrontier
Fri 10/310:42 amORD - OKC
1 stop13h 12mFrontier
Deal found 9/14$164
This Priceline deal was found by Cheapflights users on 9/16. 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.
Sat 10/185:33 pmOKC - ORD
1 stop6h 20mFrontier
Fri 10/2410:51 amORD - OKC
1 stop7h 45mFrontier
Deal found 9/16$172
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:05 amOKC - ORD
1 stop27h 32mFrontier
Sat 10/48:25 amORD - OKC
1 stop13h 02mFrontier
Deal found 9/15$175
This Priceline deal was found by Cheapflights users on 9/15. 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 10/107:21 pmOKC - MDW
1 stop5h 03mFrontier
Sat 10/118:35 amMDW - OKC
1 stop10h 49mFrontier
Deal found 9/15$176

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oklahoma City 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 16, 2025.
Use the filters below to find and compare flights from Oklahoma City to Chicago that are best for you.

Fly from

Oklahoma City

Fly to

Chicago

Route

Depart

Return

Price

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

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

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 10/20

7:19 pm-12:24 am

1 stop5h 05m

Chicago Midway

Mon 10/27

12:11 pm-6:34 pm

1 stop6h 23m

$150

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 10/20

10:47 am-12:24 am

1 stop13h 37m

Chicago Midway

Fri 10/24

12:11 pm-4:38 pm

1 stop28h 27m

$186

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 10/16

5:48 pm-11:46 pm

1 stop5h 58m

Chicago Midway

Mon 10/27

6:15 am-4:53 pm

1 stop10h 38m

$197

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 10/17

8:30 pm-10:21 am

2 stops13h 51m

Chicago Midway

Mon 10/27

12:11 pm-6:34 pm

1 stop6h 23m

$221

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 10/24

11:02 am-11:46 pm

2 stops12h 44m

Chicago Midway

Sun 10/26

9:26 pm-6:34 pm

2 stops21h 08m

$227

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 9/29

6:05 am-11:20 pm

2 stops17h 15m

Chicago Midway

Fri 10/3

4:48 pm-11:54 pm

1 stop7h 06m

$241

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Thu 10/2

6:05 am-11:39 pm

2 stops17h 34m

Chicago O'Hare Intl

Sat 10/4

8:25 am-9:27 pm

1 stop13h 02m

$255

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 10/16

5:48 pm-8:31 am

1 stop14h 43m

Chicago Midway

Sun 10/19

9:26 pm-4:53 pm

1 stop19h 27m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 41 results
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Best time to book a flight from Oklahoma City to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oklahoma City 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 City to Chicago

How far ahead should I book a flight from Oklahoma City to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Oklahoma City to Chicago. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Oklahoma City to Chicago, you should look to book at least 76 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, August is the cheapest month in which you can book a flight from Oklahoma City to Chicago (average of $245). Flying from Oklahoma City 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 OKC to CHI?

Find hourly flight availability from Oklahoma City 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 16, 2025.

One of the essential ways to save on airfare from Oklahoma City to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 43% on airfare.

What is the cheapest day to fly from Oklahoma City to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Oklahoma City to Chicago. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Oklahoma City to Chicago flight should consider departing on Saturday mornings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Oklahoma City to Chicago

Explore weekly flight availability from Oklahoma City 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 16, 2025.

The most flights from OKC to CHI are scheduled on a Monday (33 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

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

What’s the top layover airport for flights from Oklahoma City to Chicago?

Share of 1-stop round-trip flights from Oklahoma City to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Atlanta (ATL) – chosen by Cheapflights users on 50% of 1-stop itineraries from Oklahoma City to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Oklahoma City to Chicago?

Average round-trip fare for 1-stop flights from Oklahoma City to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $313.

What’s the fastest layover option from Oklahoma City to Chicago?

Shortest average travel time for 1-stop one-way flights from Oklahoma City to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 14m.

Which airport typically offers the quickest layover for flights from Oklahoma City to Chicago?

Average layover duration for 1-stop one-way flights from Oklahoma City to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 3h 04m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 16, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Oklahoma City to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,174 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

  • What airport do you fly from for flights from Oklahoma City to Chicago?

    Oklahoma City Will Rogers World (OKC) is the airport you will fly out of if you book a flight from Oklahoma City to Chicago. You should not have trouble finding flights to Chicago from Will Rogers World; the airport handles an average of 27 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 4 airlines have flights from the Oklahoma City airport to Chicago. It is only a 7.0 mi journey to Will Rogers World (OKC) from Oklahoma City’s city center.

  • How long is the flight from Oklahoma City to Chicago?

    Frontier can get you from Oklahoma City to Chicago in just under 5h 51m. Your travel time can differ by up to . The distance between Oklahoma City and Chicago is about 692 mi.

  • What are the cheapest airlines flying from Oklahoma City to Chicago round-trip?

    Cheapflights users have booked flights from Oklahoma City to Chicago round-trip from $118. Other airlines that can offer you cheap pricing are American Airlines, from $233, and Southwest, from $241. Users have found that Frontier is 65% cheaper than the other options available to this destination.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $72. United Airlines flights start at $136 while deals on Delta start at $146 one-way.

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

    Before booking your flight to Chicago from Oklahoma City, check out the most reliable airlines to get you to your destination on time: Envoy Air (100%), Emirates (85%), Lufthansa( 76%).

  • What are the cheapest flights from Oklahoma City to Chicago?

    Looking for the cheapest flight from Oklahoma City to Chicago? While on average our users pay $563, our data indicates the cheapest price to be $128. The most popular route (Oklahoma City Will Rogers World - Chicago O'Hare Intl), is priced around $206.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oklahoma City 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 City to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Oklahoma City to Chicago (average of $245). Flying from Oklahoma City 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
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Lansing
Hammond
Benton Harbor
Porter
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Alternative routes for Oklahoma City 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 City to Chicago

Discover the top 4 airlines that operate flights from Oklahoma City 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$195FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$233Average$353FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$241Average$363FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$252Average$423FlexibilityNo cancel feeOn-time69%

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