Chicago

$59+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
jul. 6 — jul. 131
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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 Thursday or Saturday 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 julio 1, 2025.

Round-trip from

$214
(Flightnetwork)

One-way from

$59
(Priceline)

Popular in

March

Cheapest in

February

Average price

$364

Good round-trip deal

$337 or less

Good one-way deal

$199 or less
From Oklahoma City Will Rogers World to Chicago (CHI)
One-way flight from Oklahoma City Will Rogers World to Chicago (CHI)
High demand for flights, 0% potential price rise
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Oklahoma City Will Rogers World to Chicago (CHI).
Price to beat on a one-way flight from Oklahoma City Will Rogers World to Chicago (CHI).

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 julio 1, 2025.

This Flightnetwork deal was found by Cheapflights users on 6/30. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/76:05 amOKC - ORD
1 stop18h 27mFrontier
lun. 8/115:40 amORD - OKC
1 stop16h 37mFrontier
Deal found 6/30$214
This Southwest deal was found by Cheapflights users on 6/30. 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.
mié. 10/297:50 amOKC - MDW
1 stop7h 40mSouthwest
lun. 11/38:05 amMDW - OKC
1 stop6h 40mSouthwest
Deal found 6/30$217
This Southwest deal was found by Cheapflights users on 6/30. 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.
mié. 10/291:50 pmOKC - ORD
1 stop8h 30mSouthwest
lun. 11/36:05 amORD - OKC
1 stop8h 40mSouthwest
Deal found 6/30$217
This FlightHub deal was found by Cheapflights users on 7/1. 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.
lun. 8/116:05 amOKC - MDW
1 stop5h 36mFrontier
vie. 8/1512:35 pmMDW - OKC
1 stop9h 42mFrontier
Deal found 7/1$220
This American Airlines deal was found by Cheapflights users on 6/30. 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.
mié. 8/132:02 pmOKC - ORD
Nonstop2h 16mAmerican Airlines
sáb. 8/166:00 amORD - OKC
1 stop5h 16mAmerican Airlines
Deal found 6/30$235
This United Airlines deal was found by Cheapflights users on 6/30. 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.
vie. 8/81:10 pmOKC - ORD
Nonstop2h 23mUnited Airlines
mié. 8/139:15 amORD - OKC
Nonstop2h 39mUnited Airlines
Deal found 6/30$243
This Delta deal was found by Cheapflights users on 6/30. 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.
jue. 8/77:00 amOKC - MDW
1 stop4h 48mDelta
dom. 8/107:07 pmMDW - OKC
1 stop4h 51mDelta
Deal found 6/30$288

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 julio 1, 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

jue. 8/7

6:05 am-12:32 am

1 stop18h 27m

Chicago O'Hare Intl

lun. 8/11

5:40 am-10:17 pm

1 stop16h 37m

$214

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

jue. 9/4

3:50 pm-11:05 pm

1 stop7h 15m

Chicago O'Hare Intl

lun. 9/15

3:10 pm-11:00 pm

1 stop7h 50m

$217

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

lun. 8/11

6:05 am-11:41 am

1 stop5h 36m

Chicago Midway

vie. 8/15

12:35 pm-10:17 pm

1 stop9h 42m

$220

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

mié. 8/13

4:30 pm-9:55 pm

1 stop5h 25m

Chicago Midway

sáb. 8/16

7:25 pm-9:25 pm

Nonstop2h 00m

$223

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

mié. 8/13

2:02 pm-4:18 pm

Nonstop2h 16m

Chicago O'Hare Intl

sáb. 8/16

6:00 am-11:16 am

1 stop5h 16m

$235

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

vie. 8/8

1:10 pm-3:33 pm

Nonstop2h 23m

Chicago O'Hare Intl

mié. 8/13

9:15 am-11:54 am

Nonstop2h 39m

$243

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

jue. 8/7

7:00 am-11:48 am

1 stop4h 48m

Chicago Midway

dom. 8/10

7:07 pm-11:58 pm

1 stop4h 51m

$288

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

lun. 8/4

6:05 am-11:41 am

1 stop5h 36m

$59

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

lun. 8/4

6:00 pm-12:32 am

1 stop6h 32m

$59

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

jue. 8/7

5:33 pm-7:48 pm

Nonstop2h 15m

$98

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 17 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.

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.

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.

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 June 27, 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 julio 1, 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 46% 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 June 29, 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 julio 1, 2025.

The most flights from OKC to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip from Oklahoma City to Chicago?

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 julio 1, 2025.
See what other customers who have flown with Southwest, Delta, and United 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.

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
8.0
Very good

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 17 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 $214. Other airlines that can offer you cheap pricing are Southwest, from $217, and American Airlines, from $235. Users have found that Frontier is 40% 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 Frontier, which is currently one of the cheapest options available, starting at $59. American Airlines flights start at $98 while deals on Southwest start at $99 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: Republic Airways (91%), Emirates (91%), Envoy Air( 87%).

  • 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 $3,716, our data indicates the cheapest price to be $148. The most popular route (Oklahoma City Will Rogers World - Chicago O'Hare Intl), is priced around $182.

  • 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 Oklahoma City?

Book flights to Oklahoma City if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 julio 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$193FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$233Average$354FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$268Average$416FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$303Average$368FlexibilityNo cancel feeOn-time63%

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