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$52+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
1 adult, Economy
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Cheap 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 February 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Wed 4/296:45 am
DFW
-
ORD
Nonstop2h 25m
Spirit Airlines
Thu 5/77:20 pm
ORD
-
DFW
Nonstop2h 38m
Spirit Airlines
Deal found 2/20$75
This Super.com deal was found by Cheapflights users on 2/17. 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 4/1310:08 pm
DFW
-
ORD
Nonstop2h 35m
Frontier
Thu 4/165:11 am
ORD
-
DFW
Nonstop2h 49m
Frontier
Deal found 2/17$76
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:17 pm
DFW
-
MDW
Nonstop2h 20m
Frontier
Thu 4/234:15 pm
MDW
-
DFW
Nonstop2h 54m
Frontier
Deal found 2/19$76
This Super.com deal was found by Cheapflights users on 2/19. 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 4/1710:17 pm
DFW
-
ORD
Nonstop2h 35m
Frontier
Sun 4/195:11 am
ORD
-
DFW
Nonstop2h 49m
Frontier
Deal found 2/19$77
This Frontier deal was found by Cheapflights users on 2/18. 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 4/178:03 pm
DFW
-
MDW
Nonstop2h 18m
Frontier
Mon 4/204:09 pm
MDW
-
DFW
Nonstop2h 54m
Frontier
Deal found 2/18$77
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:17 pm
DFW
-
ORD
Nonstop2h 35m
Frontier
Sun 5/105:11 am
ORD
-
DFW
Nonstop2h 49m
Frontier
Deal found 2/20$78
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:55 pm
DFW
-
MDW
Nonstop2h 20m
Frontier
Mon 5/44:14 pm
MDW
-
DFW
Nonstop2h 54m
Frontier
Deal found 2/20$78
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 4/306:45 am
DFW
-
ORD
Nonstop2h 25m
Spirit Airlines
Fri 5/17:20 pm
ORD
-
DFW
Nonstop2h 38m
Spirit Airlines
Deal found 2/20$79
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Fri 5/110:17 pm
DFW
-
ORD
Nonstop2h 35m
Multiple Airlines
Thu 5/77:20 pm
ORD
-
DFW
Nonstop2h 38m
Multiple Airlines
Deal found 2/20$80
This Super.com deal was found by Cheapflights users on 2/18. 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 3/269:43 pm
DFW
-
ORD
Nonstop2h 33m
Frontier
Sat 4/47:15 am
ORD
-
DFW
Nonstop2h 55m
Frontier
Deal found 2/18$81
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Sat 3/216:05 pm
DFW
-
MDW
Nonstop2h 16m
Frontier
Wed 3/2511:25 am
MDW
-
DFW
Nonstop2h 43m
Frontier
Deal found 2/16$81
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2512:37 pm
DFW
-
ORD
Nonstop2h 38m
Frontier
Tue 3/314:41 pm
ORD
-
DFW
Nonstop3h 01m
Frontier
Deal found 2/20$82

Find flight deals from Oklahoma to Chicago

Keep the following information in mind while searching for Oklahoma to Chicago flight deals. Data was last updated February 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$75
(Kiwi.com)

One-way from

$52
(Super.com)

Popular in

March

Cheapest in

September

Average price

$347

Good round-trip deal

$353 or less

Good one-way deal

$185 or less
Provider with most accurate pricing for Oklahoma City Will Rogers World-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oklahoma City Will Rogers World-Chicago (CHI) flights.
Search Deals
From Oklahoma to Chicago (CHI)
Search Deals
One-way flight from Oklahoma to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Oklahoma to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Oklahoma to Chicago (CHI).
Search Deals

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 February 20, 2026.
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 - ORD

DFWORD

Dallas/Fort Worth

Mon 3/9

10:17 pm-12:53 am

Nonstop2h 36m

Chicago O'Hare Intl

Wed 3/11

4:28 pm-7:29 pm

Nonstop3h 01m

$94

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Wed 4/22

6:45 am-9:10 am

Nonstop2h 25m

Chicago O'Hare Intl

Wed 5/6

5:30 am-2:00 pm

1 stop8h 30m

$95

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Mon 3/2

2:45 pm-11:15 pm

1 stop8h 30m

Chicago O'Hare Intl

Tue 3/31

4:41 pm-7:42 pm

Nonstop3h 01m

$108

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Wed 5/20

6:45 am-9:10 am

Nonstop2h 25m

Chicago O'Hare Intl

Tue 5/26

7:20 pm-9:58 pm

Nonstop2h 38m

$109

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 5/14

10:17 pm-12:52 am

Nonstop2h 35m

Chicago O'Hare Intl

Sun 5/17

8:24 pm-9:43 pm

1 stop25h 19m

$116

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 5/14

6:05 am-5:51 pm

1 stop11h 46m

Chicago O'Hare Intl

Sat 5/16

4:55 pm-7:57 pm

Nonstop3h 02m

$129

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 2/28

8:42 pm-11:17 pm

Nonstop2h 35m

Chicago O'Hare Intl

Mon 3/2

8:16 pm-9:58 am

1 stop13h 42m

$141

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Wed 3/18

7:35 am-7:51 pm

1 stop12h 16m

Chicago O'Hare Intl

Tue 3/24

9:28 am-5:08 pm

1 stop7h 40m

$147

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Mon 3/2

2:45 pm-11:15 pm

1 stop8h 30m

Chicago O'Hare Intl

Mon 3/16

5:25 am-8:17 am

Nonstop2h 52m

$156

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 5/15

8:46 am-7:31 pm

1 stop10h 45m

Chicago Midway

Wed 5/20

2:20 pm-11:05 pm

1 stop8h 45m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

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 $303). 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 February 20, 2026.

It’s optimal to fly from Oklahoma to Chicago in the morning. By choosing this option you can save up to 30% 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 February 17, 2026.

Travelers seeking maximum savings on their Oklahoma to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday 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 February 20, 2026.

The most flights from USOK to CHI are scheduled on a Thursday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

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 25m. Fly via Frontier, Spirit Airlines, or Delta to get the fastest option. There are 801 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 $115 on American Airlines. Other airlines that offer cheap prices include Southwest from $123 and United Airlines from $125 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: Republic Airways (91%), Envoy Air (88%), Iberia (86%).

  • What are the cheapest flights from Oklahoma to Chicago?

    Looking for the cheapest flight from Oklahoma to Chicago? While on average our users pay $1,039, our data indicates the cheapest price to be $193. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $64.

  • 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 $303). 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
Merrillville
Hammond
Porter
Benton Harbor

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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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Los Angeles to Midway flights
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Dulles Intl to St. Louis flights
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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 February 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$138Average$249FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$182Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$356FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$374FlexibilityNo cancel feeOn-time63%

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