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$57+ 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 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
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 January, booked 49 days in advance, depart on a Saturday or Thursday and return on a Tuesday

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 October 23, 2025.

This Priceline deal was found by Cheapflights users on 10/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/94:44 pmOKC - MDW
1 stop5h 19mFrontier
Thu 11/1312:30 pmMDW - OKC
1 stop6h 30mFrontier
Deal found 10/21$179
This Frontier deal was found by Cheapflights users on 10/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/94:44 pmOKC - ORD
1 stop7h 27mFrontier
Thu 11/135:11 amORD - OKC
1 stop10h 39mFrontier
Deal found 10/21$179
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:10 amOKC - MDW
1 stop5h 58mDelta
Sun 12/76:00 amMDW - OKC
1 stop7h 14mDelta
Deal found 10/23$180
This Delta deal was found by Cheapflights users on 10/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:50 amOKC - ORD
1 stop5h 16mDelta
Sun 12/75:30 amORD - OKC
1 stop7h 44mDelta
Deal found 10/23$180
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Mon 11/178:15 pmOKC - ORD
2 stops14h 59mFrontier
Tue 11/186:05 pmORD - OKC
1 stop20h 06mFrontier
Deal found 10/21$181
This Priceline deal was found by Cheapflights users on 10/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:49 pmOKC - MDW
1 stop5h 23mFrontier
Mon 12/812:18 pmMDW - OKC
1 stop7h 14mFrontier
Deal found 10/21$183
This Delta deal was found by Cheapflights users on 10/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:22 amOKC - ORD
1 stop7h 21mDelta
Mon 12/86:45 amORD - OKC
1 stop6h 29mDelta
Deal found 10/21$183
This Trip.com deal was found by Cheapflights users on 10/22. 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 10/317:45 pmOKC - ORD
1 stop27h 44mFrontier
Mon 11/105:05 amORD - OKC
1 stop11h 07mFrontier
Deal found 10/22$184
This American Airlines deal was found by Cheapflights users on 10/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:00 pmOKC - ORD
Nonstop2h 20mAmerican Airlines
Thu 12/44:05 pmORD - OKC
1 stop7h 18mAmerican Airlines
Deal found 10/22$190
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:27 pmOKC - ORD
Nonstop2h 13mUnited Airlines
Mon 12/87:39 pmORD - OKC
Nonstop2h 36mUnited Airlines
Deal found 10/21$198
This Trip.com deal was found by Cheapflights users on 10/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/47:51 pmOKC - ORD
1 stop19h 48mFrontier
Fri 11/76:00 amORD - OKC
1 stop13h 00mFrontier
Deal found 10/21$207
This Frontier deal was found by Cheapflights users on 10/22. 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
Mon 10/275:05 amORD - OKC
1 stop11h 48mFrontier
Deal found 10/22$208

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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$179
(Priceline)

One-way from

$57
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$353

Good round-trip deal

$374 or less

Good one-way deal

$171 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.
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From Oklahoma City Will Rogers World to Chicago (CHI)
Search Deals
One-way flight from Oklahoma City Will Rogers World to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Oklahoma City Will Rogers World to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Oklahoma City Will Rogers World to Chicago (CHI).
Search Deals

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 October 23, 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 11/13

4:57 pm-12:11 am

1 stop7h 14m

Chicago O'Hare Intl

Sun 11/16

5:01 am-3:50 pm

1 stop10h 49m

$179

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 12/6

7:10 am-1:08 pm

1 stop5h 58m

Chicago Midway

Sun 12/7

6:00 am-1:14 pm

1 stop7h 14m

$180

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Sat 12/6

6:50 am-12:06 pm

1 stop5h 16m

Chicago O'Hare Intl

Sun 12/7

5:30 am-1:14 pm

1 stop7h 44m

$180

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Sat 1/17

5:55 am-1:23 pm

1 stop7h 28m

Chicago O'Hare Intl

Mon 1/19

5:55 pm-11:59 pm

1 stop6h 04m

$180

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Sat 12/13

6:50 am-12:06 pm

1 stop5h 16m

Chicago O'Hare Intl

Sun 12/14

5:30 am-1:14 pm

1 stop7h 44m

$180

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Fri 12/5

11:22 am-6:43 pm

1 stop7h 21m

Chicago O'Hare Intl

Mon 12/8

6:45 am-1:14 pm

1 stop6h 29m

$183

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Wed 12/3

5:00 pm-7:20 pm

Nonstop2h 20m

Chicago O'Hare Intl

Thu 12/4

4:05 pm-11:23 pm

1 stop7h 18m

$190

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Fri 12/5

4:27 pm-6:40 pm

Nonstop2h 13m

Chicago O'Hare Intl

Mon 12/8

7:39 pm-10:15 pm

Nonstop2h 36m

$198

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 1/17

3:15 pm-8:25 pm

1 stop5h 10m

Chicago Midway

Mon 1/19

7:55 am-10:15 am

Nonstop2h 20m

$207

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Sat 12/6

8:29 pm-11:08 am

1 stop14h 39m

Chicago Midway

Sun 12/7

7:27 pm-7:32 pm

2 stops24h 05m

$212

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 42 results
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Compare providers for flights from Oklahoma City to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oklahoma City to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oklahoma City-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oklahoma City-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oklahoma City-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oklahoma City-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oklahoma City-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 17, 2025.

To ensure you get the cheapest price possible for a flight from Oklahoma City to Chicago, you should look to book at least 48 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, February is the cheapest month in which you can book a flight from Oklahoma City to Chicago (average of $125). Flying from Oklahoma City 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 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 October 23, 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 23% 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 October 19, 2025.

Travelers seeking maximum savings on their Oklahoma City 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 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 October 23, 2025.

The most flights from OKC to CHI are scheduled on a Thursday (32 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 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 October 23, 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
4,237 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
8,991 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
11,028 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
3,128 reviews
Southwest
8.0
Very good
4,237 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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 20 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, Delta, and Southwest can get you from Oklahoma City to Chicago in just under 5h 10m. Your travel time can differ by up to 2h 04m. The distance between Oklahoma City and Chicago is about 690 mi. This flight may include one or multiple stops.

  • 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 Southwest, from $241, and United Airlines, from $252. 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 United Airlines, which is currently one of the cheapest options available, starting at $64. American Airlines flights start at $64 while deals on Southwest start at $88 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%), Air New Zealand (79%), 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 $869, our data indicates the cheapest price to be $158. The most popular route (Oklahoma City Will Rogers World - Chicago O'Hare Intl), is priced around $145.

  • 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, February is the cheapest month in which you can book a flight from Oklahoma City to Chicago (average of $125). Flying from Oklahoma City 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$188FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$241Average$366FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$252Average$422FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$262Average$353FlexibilityNo cancel feeOn-time71%

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