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$75+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Oklahoma City Will Rogers World to Chicago are usually found in February or December, booked 78 days in advance, depart on a Saturday or Thursday and return on a Saturday

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 August 14, 2025.

Round-trip from

$203
(Southwest)

One-way from

$75
(Priceline)

Popular in

March

Cheapest in

February

Average price

$364

Good round-trip deal

$253 or less

Good one-way deal

$158 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. 0% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/113:20 pmOKC - MDW
Nonstop1h 55mSouthwest
Thu 11/139:40 pmMDW - OKC
Nonstop2h 10mSouthwest
Deal found 8/14$203
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/114:29 pmOKC - ORD
Nonstop2h 13mUnited Airlines
Thu 11/137:35 pmORD - OKC
Nonstop2h 36mUnited Airlines
Deal found 8/14$203
This Booking.com deal was found by Cheapflights users on 8/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:46 pmOKC - ORD
1 stop25h 42mFrontier
Sun 9/286:00 amORD - OKC
1 stop17h 49mFrontier
Deal found 8/13$204
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/94:02 pmOKC - MDW
1 stop5h 24mDelta
Tue 9/166:00 amMDW - OKC
1 stop6h 55mDelta
Deal found 8/14$209
This Delta deal was found by Cheapflights users on 8/13. 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.
Tue 9/94:02 pmOKC - ORD
1 stop6h 35mDelta
Tue 9/167:20 amORD - OKC
1 stop5h 35mDelta
Deal found 8/13$209
This Priceline deal was found by Cheapflights users on 8/13. 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.
Mon 8/186:00 pmOKC - ORD
1 stop6h 32mFrontier
Mon 8/2511:44 amORD - OKC
1 stop7h 57mFrontier
Deal found 8/13$211
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/178:00 amOKC - ORD
1 stop13h 28mFrontier
Fri 9/1910:42 amORD - OKC
1 stop13h 12mFrontier
Deal found 8/14$212
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/68:00 amOKC - ORD
1 stop13h 28mFrontier
Tue 9/97:20 amORD - OKC
1 stop13h 18mFrontier
Deal found 8/14$213
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/138:00 amOKC - ORD
2 stops13h 58mMultiple Airlines
Tue 9/167:20 amORD - OKC
1 stop13h 18mMultiple Airlines
Deal found 8/14$215
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:00 amOKC - ORD
1 stop15h 53mFrontier
Thu 11/135:10 amORD - OKC
1 stop8h 54mFrontier
Deal found 8/13$216
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/304:05 pmOKC - MDW
Nonstop1h 55mSouthwest
Mon 11/38:15 amMDW - OKC
Nonstop2h 15mSouthwest
Deal found 8/13$217
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Sat 9/203:23 pmOKC - ORD
Nonstop2h 18mAmerican Airlines
Mon 9/227:01 amORD - OKC
Nonstop2h 14mAmerican Airlines
Deal found 8/13$217

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 August 14, 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 - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 10/6

6:50 am-8:45 am

Nonstop1h 55m

Chicago Midway

Wed 10/8

7:40 am-9:40 am

Nonstop2h 00m

$203

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Mon 10/6

4:07 pm-6:26 pm

Nonstop2h 19m

Chicago O'Hare Intl

Wed 10/8

1:00 pm-3:26 pm

Nonstop2h 26m

$203

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Fri 10/10

7:30 pm-12:51 am

1 stop5h 21m

Chicago O'Hare Intl

Mon 10/13

5:05 am-4:53 pm

1 stop11h 48m

$203

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Tue 11/11

6:46 am-9:10 am

Nonstop2h 24m

Chicago O'Hare Intl

Thu 11/13

7:15 pm-9:45 pm

Nonstop2h 30m

$203

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 11/11

3:20 pm-5:15 pm

Nonstop1h 55m

Chicago Midway

Thu 11/13

9:40 pm-11:50 pm

Nonstop2h 10m

$203

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Tue 11/11

12:31 pm-2:44 pm

Nonstop2h 13m

Chicago O'Hare Intl

Thu 11/13

7:35 pm-10:11 pm

Nonstop2h 36m

$203

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Sat 10/18

12:28 pm-2:47 pm

Nonstop2h 19m

Chicago O'Hare Intl

Tue 10/21

1:00 pm-3:26 pm

Nonstop2h 26m

$203

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Fri 9/26

7:46 pm-9:28 pm

1 stop25h 42m

Chicago O'Hare Intl

Sun 9/28

6:00 am-11:49 pm

1 stop17h 49m

$204

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 9/9

4:02 pm-9:26 pm

1 stop5h 24m

Chicago Midway

Tue 9/16

6:30 pm-11:58 pm

1 stop5h 28m

$209

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 9/23

1:40 pm-9:36 pm

1 stop7h 56m

Chicago Midway

Tue 9/30

6:00 am-12:55 pm

1 stop6h 55m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 40 results
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The best insider tips for Oklahoma City to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Oklahoma City to Chicago trip
Airlines
Japan Airlines

JAL's economy seats offer 34 inches of legroom and seat-back screens on international flights.


JAL's Wi-Fi is available on international flights, but streaming is not supported.

Read more about Japan Airlinesby Emily Zemler
Southwest

Southwest offers two free checked bags, including oversized items like skis or golf clubs.


Southwest's Early Bird check-in provides priority boarding 36 hours before departure.

Read more about Southwestby Marisa Garcia
United Airlines

United's Economy Plus offers extra legroom and priority boarding for MileagePlus Premier members.


Prepay for checked bags on United to save fees 24 hours before your flight.

Read more about United Airlinesby Harriet Baskas
Our travel experts
Emily Zemler

Emily Zemler

Expert on Japan Airlines

Emily Zemler

Emily Zemler

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more

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 August 8, 2025.

To ensure you get the cheapest price possible for a flight from Oklahoma City to Chicago, you should look to book at least 77 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 August 14, 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 44% 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 August 10, 2025.

Travelers seeking maximum savings on their Oklahoma City to Chicago flight should consider departing on Thursday 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 August 14, 2025.

The most flights from OKC to CHI are scheduled on a Thursday (31 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (12 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 August 14, 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
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,217 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 23 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.

  • 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 United Airlines, from $243. Users have found that Frontier is 66% cheaper than the other options available to this destination.

  • 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: Republic Airways (100%), Envoy Air (83%), Emirates( 81%).

  • 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 $969, our data indicates the cheapest price to be $118. The most popular route (Oklahoma City Will Rogers World - Chicago O'Hare Intl), is priced around $203.

  • 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$195FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$233Average$353FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$243Average$422FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$253Average$363FlexibilityNo cancel feeOn-time63%

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