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$42+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Dec 22 — Dec 291
Mon 12/22
Mon 12/29
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 November 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$87
(Kiwi.com)

One-way from

$42
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$346

Good round-trip deal

$306 or less

Good one-way deal

$171 or less
Provider with most accurate pricing for Oklahoma City Will Rogers World-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Oklahoma City Will Rogers World-Chicago (CHI) flights.
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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 ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 22, 2025.

This CheapOair deal was found by Cheapflights users on 11/21. 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 12/1111:47 amDFW - MDW
Nonstop2h 17mFrontier
Sun 12/148:05 amMDW - DFW
Nonstop2h 42mFrontier
Deal found 11/21$89
This Expedia deal was found by Cheapflights users on 11/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:01 pmDFW - ORD
Nonstop2h 38mFrontier
Thu 1/17:57 pmORD - DFW
Nonstop2h 54mFrontier
Deal found 11/20$90
This Super.com deal was found by Cheapflights users on 11/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:01 pmDFW - ORD
Nonstop2h 38mFrontier
Tue 12/3010:22 pmORD - DFW
Nonstop2h 44mFrontier
Deal found 11/20$92
This Super.com deal was found by Cheapflights users on 11/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:47 amDFW - MDW
Nonstop2h 17mFrontier
Sun 12/78:05 amMDW - DFW
Nonstop2h 42mFrontier
Deal found 11/19$93
This Kiwi.com deal was found by Cheapflights users on 11/21. 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.
Wed 12/241:35 pmDFW - ORD
Nonstop2h 25mSpirit Airlines
Wed 12/317:57 pmORD - DFW
Nonstop2h 43mSpirit Airlines
Deal found 11/21$94
This Super.com deal was found by Cheapflights users on 11/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/89:02 amDFW - MDW
Nonstop2h 18mFrontier
Thu 12/118:05 amMDW - DFW
Nonstop2h 42mFrontier
Deal found 11/19$94
This Super.com deal was found by Cheapflights users on 11/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:35 pmDFW - ORD
Nonstop2h 25mSpirit Airlines
Sun 1/47:57 pmORD - DFW
Nonstop2h 43mSpirit Airlines
Deal found 11/21$95
This Super.com deal was found by Cheapflights users on 11/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:47 amDFW - MDW
Nonstop2h 17mFrontier
Sun 12/78:05 amMDW - DFW
Nonstop2h 42mFrontier
Deal found 11/19$95
This Priceline deal was found by Cheapflights users on 11/20. 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.
Thu 12/115:30 amDFW - ORD
Nonstop2h 34mMultiple Airlines
Tue 12/163:26 pmORD - DFW
1 stop7h 46mMultiple Airlines
Deal found 11/20$96
This Cheapflightsfares deal was found by Cheapflights users on 11/21. 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.
Tue 12/95:28 amDFW - ORD
1 stop13h 08mSpirit Airlines
Tue 12/167:20 amORD - DFW
Nonstop2h 38mSpirit Airlines
Deal found 11/21$97
This Kiwi.com deal was found by Cheapflights users on 11/20. 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.
Thu 12/1111:47 amDFW - MDW
Nonstop2h 17mFrontier
Mon 12/158:42 pmMDW - DFW
1 stop26h 12mFrontier
Deal found 11/20$97
This Trip.com deal was found by Cheapflights users on 11/20. 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.
Fri 12/265:56 pmDFW - ORD
Nonstop2h 40mFrontier
Wed 12/313:30 pmORD - DFW
Nonstop2h 58mFrontier
Deal found 11/20$98

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 November 22, 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

Thu 12/11

11:47 am-2:04 pm

Nonstop2h 17m

Chicago Midway

Sun 12/14

8:05 am-10:47 am

Nonstop2h 42m

$89

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 1/8

11:06 am-5:52 pm

1 stop6h 46m

Chicago O'Hare Intl

Sat 1/10

9:15 am-12:11 pm

Nonstop2h 56m

$95

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Fri 1/9

10:07 pm-12:42 am

Nonstop2h 35m

Chicago O'Hare Intl

Sun 1/11

7:30 am-9:13 pm

1 stop13h 43m

$100

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 1/15

7:00 am-9:29 am

Nonstop2h 29m

Chicago O'Hare Intl

Sun 1/18

9:15 am-12:10 pm

Nonstop2h 55m

$117

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 1/9

1:15 pm-3:33 pm

Nonstop2h 18m

Chicago Midway

Sun 1/11

9:15 am-12:05 pm

Nonstop2h 50m

$122

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Fri 12/12

7:27 pm-10:07 pm

Nonstop2h 40m

Chicago O'Hare Intl

Mon 12/15

9:06 pm-11:25 am

1 stop14h 19m

$127

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 1/9

10:36 am-10:21 pm

1 stop11h 45m

Chicago Midway

Sun 1/11

12:41 pm-7:06 am

1 stop18h 25m

$129

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sun 12/21

11:42 am-1:59 pm

Nonstop2h 17m

Chicago Midway

Sun 12/28

8:00 am-10:42 am

Nonstop2h 42m

$132

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 12/19

11:42 am-1:59 pm

Nonstop2h 17m

Chicago Midway

Sun 12/21

8:00 am-10:42 am

Nonstop2h 42m

$132

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 12/24

7:00 am-9:21 am

Nonstop2h 21m

Chicago Midway

Wed 12/31

10:21 am-1:06 pm

Nonstop2h 45m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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, June is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $121). Flying from Oklahoma to Chicago in March is currently the most expensive (average of $304). 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 November 22, 2025.

It’s optimal to fly from Oklahoma to Chicago in the morning. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Oklahoma to Chicago. Price data was last updated on December 16, 2024.

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

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 November 22, 2025.

The most flights from USOK to CHI are scheduled on a Friday (31 on average). You will have fewer flight options on Sunday, 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 2h 17m. Fly via Frontier, United Airlines, or Delta to get the fastest option. There are 797 mi between Oklahoma and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $59 on United Airlines. Other airlines that offer cheap prices include Frontier from $68 and American Airlines from $107 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: Iberia (79%), Air New Zealand (77%), Royal Jordanian (77%).

  • What are the cheapest flights from Oklahoma to Chicago?

    Looking for the cheapest flight from Oklahoma to Chicago? While on average our users pay $1,274, our data indicates the cheapest price to be $148. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $71.

  • 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, June is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $121). Flying from Oklahoma to Chicago in March is currently the most expensive (average of $304). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$238FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$189Average$355FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$367FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$259Average$404FlexibilityNo cancel feeOn-time69%

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