OKC - CHI

$72 Find Cheap Flights from Oklahoma City to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oklahoma City to Chicago departing on 10/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oklahoma City to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oklahoma City to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Oklahoma City to Chicago (OKC-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oklahoma City to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oklahoma City to Chicago

Fri, Oct 24 - Mon, Oct 27
Frontier Logo
7:21 pm - 12:59 amOKC-ORD
5h 38m1 stop
Frontier Logo
6:50 am - 6:34 pmORD-OKC
11h 44m1 stop
$144Frontier
Find Deal
Thu, Oct 23 - Mon, Oct 27
Frontier Logo
5:48 pm - 11:39 pmOKC-ORD
5h 51m1 stop
Frontier Logo
10:51 am - 6:34 pmORD-OKC
7h 43m1 stop
$145Frontier
Find Deal
Sat, Oct 4 - Wed, Oct 8
Multiple Airlines Logo
8:00 am - 9:28 pmOKC-ORD
13h 28m1 stop
Multiple Airlines Logo
6:35 am - 6:28 pmORD-OKC
35h 53m2 stops
$239Multiple Airlines
Find Deal
Sat, Oct 18 - Thu, Oct 23
Multiple Airlines Logo
5:33 pm - 11:53 pmOKC-ORD
6h 20m1 stop
Multiple Airlines Logo
7:45 pm - 6:36 pmORD-OKC
22h 51m2 stops
$248Multiple Airlines
Find Deal
Wed, Feb 11 - Wed, Feb 18
Southwest Logo
10:10 am - 12:05 pmOKC-MDW
1h 55mnonstop
Southwest Logo
8:15 am - 10:35 amMDW-OKC
2h 20mnonstop
$284Southwest
Find Deal
Wed, Feb 11 - Wed, Feb 18
United Airlines Logo
1:40 pm - 3:58 pmOKC-ORD
2h 18mnonstop
United Airlines Logo
9:25 am - 11:46 amORD-OKC
2h 21mnonstop
$284United Airlines
Find Deal
Wed, Feb 11 - Wed, Feb 18
American Airlines Logo
4:05 pm - 12:10 amOKC-ORD
8h 05m1 stop
American Airlines Logo
8:20 pm - 10:46 pmORD-OKC
2h 26mnonstop
$294American Airlines
Find Deal
Wed, Feb 11 - Wed, Feb 18
Southwest Logo
10:10 am - 12:05 pmOKC-MDW
1h 55mnonstop
Southwest Logo
8:55 am - 5:00 pmMDW-OKC
8h 05m1 stop
$294Southwest
Find Deal
Sat, Nov 1 - Tue, Nov 4
United Airlines Logo
12:31 pm - 2:44 pmOKC-ORD
2h 13mnonstop
United Airlines Logo
7:35 pm - 10:11 pmORD-OKC
2h 36mnonstop
$297United Airlines
Find Deal
Thu, Oct 23 - Mon, Oct 27
American Airlines Logo
2:03 pm - 4:21 pmOKC-ORD
2h 18mnonstop
American Airlines Logo
6:41 pm - 9:14 pmORD-OKC
2h 33mnonstop
$299American Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Southwest's two free checked bags benefit travelers.
United offers free messaging for better connectivity.
Expert advice
Expert advice
Expert advice
Expert advice
Top routes
OKC-MDW
Cheapest • 11% average savings
OKC-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 43% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 13% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$144
Typical prices: $241-423
Frontier
Fri 10/24Mon 10/27
OKC - ORD • 1 stop
Cheapest non-stop
$284
Typical prices: $293-305
Southwest
Wed 2/11Wed 2/18
OKC - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

Expert advice for your flight from Oklahoma City to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
British Airways

BA offers 31-inch legroom in economy, ensuring comfort on short-haul flights.


BA's free snack includes sour cream and chive pretzels on short-haul flights.

American Airlines

AA's Main Cabin Extra offers early boarding and complimentary drinks.


AA provides 20 minutes of free Wi-Fi by watching an ad.

Southwest

Southwest offers free carry-on and personal item, but checked bags now incur fees.


Southwest's cancellation policy allows changes up to 10 minutes before departure with travel credit or refund.

Read more about Southwestby Blane Bachelor
United Airlines

United's Economy Plus offers up to 6 inches more legroom than standard economy.


United provides free messaging on most flights, enhancing connectivity.

Our travel experts
Duncan Madden

Duncan Madden

Expert on British Airways

Duncan Madden

Duncan Madden

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Read more
Harriet Baskas

Harriet Baskas

Expert on American 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
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Booking Insights

KAYAK's insights & trends for Oklahoma City to Chicago flights

Get data-powered insights and trends into flights from Oklahoma City to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Oklahoma City to Chicago?

What is the cheapest Oklahoma City to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Oklahoma City to Chicago costs $203 on the route between Oklahoma City (OKC) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 11% cheaper than other Oklahoma City-Chicago routes. The most popular route is between Oklahoma City (OKC) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Oklahoma City to Chicago?

The average price of all round-trip flights from Oklahoma City to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Oklahoma City to Chicago. For your return ticket, we recommend flying on a Saturday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Oklahoma City to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oklahoma City to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Oklahoma City to Chicago is September, where tickets cost $298 (return) on average. On the other hand, the most expensive months are March and July, where the average cost of round-trip tickets is $391 and $364 respectively.

Can I save money by flying with a layover from Oklahoma City to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $308 on average.

How far in advance should I book a flight from Oklahoma City to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Oklahoma City to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Oklahoma City to Chicago, you should book around 3 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$72
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Oklahoma City to Chicago O'Hare Airport

When to book flights from Oklahoma City to Chicago

Are your dates flexible? Find out the best times to travel from Oklahoma City to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Oklahoma City to Chicago

  • What is the cheapest flight from Oklahoma City to Chicago?

    In the last 3 days, the lowest price for a flight from Oklahoma City to Chicago was $72 for a one-way ticket and $144 for a round-trip.

  • Do I need a passport to fly between Oklahoma City and Chicago?

    No

  • Which airports will I be using when flying from Oklahoma City to Chicago?

    Oklahoma City is served by only 1 airport and there are 2 airports in Chicago. You will leave Oklahoma City from Oklahoma City Will Rogers World and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Oklahoma City to Chicago?

    American Airlines, Delta, Alaska Airlines, and JetBlue offer inflight Wi-Fi service on the Oklahoma City to Chicago flight route.

  • Which aircraft models fly most regularly from Oklahoma City to Chicago?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Oklahoma City to Chicago flight route.

  • Which airline alliances offer flights from Oklahoma City to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Oklahoma City and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Oklahoma City to Chicago?

    There are nonstop flights from Oklahoma City to Chicago on a daily basis.

  • Which is the best airline for flights from Oklahoma City to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Oklahoma City to Chicago are Southwest and United Airlines. With an average price for the route of $353 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $420 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Oklahoma City to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oklahoma City to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oklahoma City to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Oklahoma City is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Oklahoma City to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Oklahoma City with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oklahoma City to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Oklahoma City up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Oklahoma City to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $226 or less one-way and $369 or less round-trip.

Prefer to fly direct from Oklahoma City to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Oklahoma City Will Rogers World to Chicago.
Find which airlines fly direct from Oklahoma City Will Rogers World Airport to Chicago, which days they fly and book direct flights.

Direct departures

Oklahoma City Will Rogers World to Chicago

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Direct returns

Chicago to Oklahoma City Will Rogers World

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Reviews of the top 4 airlines serving from Oklahoma City to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Oklahoma City to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Oklahoma City to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Everything you need to know for your flight from Oklahoma City to Chicago

Information on your arrival and departure airports

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