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$60+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 17, 2025.

Round-trip from

$109
(Priceline)

One-way from

$60
(Priceline)

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 17, 2025.

This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/49:27 pmDFW - ORD
Nonstop2h 31mFrontier
Sat 10/1812:05 pmORD - DFW
Nonstop2h 30mFrontier
Deal found 9/17$109
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/249:01 pmDFW - MDW
Nonstop2h 19mFrontier
Mon 10/2712:03 pmMDW - DFW
1 stop8h 03mFrontier
Deal found 9/15$109
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2010:56 pmDFW - ORD
Nonstop2h 35mMultiple Airlines
Fri 10/243:36 pmORD - DFW
Nonstop2h 36mMultiple Airlines
Deal found 9/15$110
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1410:24 pmDFW - ORD
Nonstop2h 35mMultiple Airlines
Tue 11/1810:05 pmORD - DFW
Nonstop2h 29mMultiple Airlines
Deal found 9/15$111
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:45 amDFW - MDW
Nonstop2h 28mFrontier
Mon 10/205:20 pmMDW - DFW
Nonstop2h 41mFrontier
Deal found 9/15$111
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/158:00 amDFW - ORD
1 stop5h 47mFrontier
Wed 10/225:28 pmORD - DFW
Nonstop2h 48mFrontier
Deal found 9/15$112
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:01 pmDFW - MDW
Nonstop2h 19mFrontier
Sun 10/266:24 pmMDW - DFW
1 stop15h 07mFrontier
Deal found 9/15$112
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:24 pmDFW - ORD
Nonstop2h 35mFrontier
Sun 11/911:43 amORD - DFW
1 stop25h 54mFrontier
Deal found 9/17$113
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/149:01 pmDFW - MDW
Nonstop2h 19mFrontier
Tue 10/215:20 pmMDW - DFW
Nonstop2h 41mFrontier
Deal found 9/16$113
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/79:26 pmDFW - ORD
Nonstop2h 33mFrontier
Tue 10/213:12 pmORD - DFW
1 stop6h 20mFrontier
Deal found 9/17$114
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/79:01 pmDFW - MDW
Nonstop2h 19mFrontier
Fri 10/175:10 amMDW - DFW
Nonstop2h 35mFrontier
Deal found 9/17$114
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:05 amDFW - ORD
Nonstop2h 28mSpirit Airlines
Mon 10/2711:55 amORD - DFW
1 stop12h 15mSpirit Airlines
Deal found 9/15$115

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 17, 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 - ORD

DFWORD

Dallas/Fort Worth

Thu 10/16

9:05 am-11:33 am

Nonstop2h 28m

Chicago O'Hare Intl

Tue 10/21

5:05 am-3:31 pm

1 stop10h 26m

$116

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Thu 10/2

6:05 am-9:37 am

1 stop27h 32m

Chicago O'Hare Intl

Sat 10/4

8:25 am-9:27 pm

1 stop13h 02m

$175

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 10/18

5:15 am-10:10 am

1 stop4h 55m

Chicago O'Hare Intl

Sat 10/18

2:20 pm-7:51 pm

1 stop5h 31m

$177

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Fri 10/10

4:37 pm-3:11 pm

1 stop22h 34m

Chicago Midway

Mon 10/13

6:15 am-4:53 pm

1 stop10h 38m

$195

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Tue 12/16

7:01 am-12:05 pm

1 stop5h 04m

Chicago O'Hare Intl

Thu 12/18

5:32 am-1:10 pm

1 stop7h 38m

$197

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sun 10/12

7:00 am-9:37 am

Nonstop2h 37m

Chicago O'Hare Intl

Wed 10/15

7:25 am-10:04 am

Nonstop2h 39m

$197

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 10/25

6:50 am-11:28 am

1 stop4h 38m

Chicago O'Hare Intl

Sat 10/25

4:09 pm-9:52 pm

1 stop5h 43m

$197

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 11/15

5:20 am-12:06 pm

1 stop6h 46m

Chicago O'Hare Intl

Sat 11/15

6:22 pm-11:58 pm

1 stop5h 36m

$197

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

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 11/8

5:55 am-12:40 pm

1 stop6h 45m

Chicago O'Hare Intl

Sat 11/8

4:56 pm-9:48 pm

1 stop4h 52m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

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, 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 17, 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 17, 2025.

The most flights from USOK 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).

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 28m. Fly via Spirit Airlines, Frontier, or United Airlines 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 $66 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $70 and United Airlines from $116 one-way.

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

    While some choose either Dallas/Fort Worth - Chicago Midway or Oklahoma City Will Rogers World - 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: Envoy Air (100%), Emirates (85%), Lufthansa (76%).

  • What are the cheapest flights from Oklahoma to Chicago?

    Looking for the cheapest flight from Oklahoma to Chicago? While on average our users pay $563, our data indicates the cheapest price to be $128. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $89.

  • 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 17, 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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