OKC - CHI

$84 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 5/20. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$180
Frontier
Thu 4/30Mon 5/4
OKC - MDW • 1 stop
Cheapest non-stop
$319
Typical prices: $373-$442
Southwest
Tue 4/7Tue 4/14
OKC - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags benefit travelers.
United offers free messaging for better connectivity.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $180 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 10m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 3% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $138 (round-trip)
Shortest trip • 5h 03m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 36% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 25% price drop
Most popular
Good to know
Good to know
+1
+1
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+1
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Flight Deals
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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

Thu, Apr 30 - Mon, May 4
Frontier Logo
5:05 pm - 10:19 pm
OKC
-
MDW
5h 14m
1 stop
Frontier Logo
6:00 am - 2:21 pm
MDW
-
OKC
8h 21m
1 stop
$180Frontier
Thu, Apr 23 - Mon, Apr 27
Frontier Logo
5:05 pm - 10:39 pm
OKC
-
ORD
5h 34m
1 stop
Frontier Logo
5:50 am - 2:21 pm
ORD
-
OKC
8h 31m
1 stop
$180Frontier
Tue, Jun 2 - Wed, Jun 3
Frontier Logo
1:56 pm - 7:51 pm
OKC
-
ORD
5h 55m
1 stop
Frontier Logo
9:42 pm - 11:56 am
ORD
-
OKC
14h 14m
1 stop
$189Frontier
Thu, Apr 16 - Thu, Apr 23
Frontier Logo
5:05 pm - 10:19 pm
OKC
-
MDW
5h 14m
1 stop
Frontier Logo
6:00 am - 4:20 pm
MDW
-
OKC
10h 20m
1 stop
$201Frontier
Mon, Apr 13 - Thu, Apr 16
Frontier Logo
7:25 pm - 6:20 am
OKC
-
ORD
10h 55m
1 stop
Frontier Logo
5:50 am - 4:10 pm
ORD
-
OKC
10h 20m
1 stop
$201Frontier
Fri, May 8 - Mon, May 11
Multiple Airlines Logo
1:55 pm - 9:12 pm
OKC
-
ORD
31h 17m
2 stops
Multiple Airlines Logo
9:42 pm - 11:56 am
ORD
-
OKC
14h 14m
1 stop
$237Multiple Airlines
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
3:05 pm - 4:55 pm
OKC
-
MDW
1h 50mnonstop
Southwest Logo
10:20 am - 12:30 pm
MDW
-
OKC
2h 10mnonstop
$319Southwest
Tue, Apr 28 - Sat, May 2
Southwest Logo
3:05 pm - 4:55 pm
OKC
-
MDW
1h 50mnonstop
Southwest Logo
10:30 am - 12:40 pm
MDW
-
OKC
2h 10mnonstop
$327Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
3:05 pm - 4:55 pm
OKC
-
MDW
1h 50mnonstop
Southwest Logo
12:35 pm - 8:50 pm
MDW
-
OKC
8h 15m
1 stop
$329Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
3:05 pm - 4:55 pm
OKC
-
MDW
1h 50mnonstop
Southwest Logo
9:40 am - 4:10 pm
MDW
-
OKC
6h 30m
2 stops
$334Southwest
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Oklahoma City to Chicago departing in April.

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 $279 on the route between Oklahoma City (OKC) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 3% 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, Monday is the most expensive day to fly from Oklahoma City to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Mondays 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 $264 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $410 and $386 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.

No, with an average price for the route of $440, prices are generally cheapest when you fly direct.

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 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Expert advice

Expert advice for your flight from Oklahoma City to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Duncan Madden

Duncan Madden

Expert on British Airways

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.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Blane Bachelor

Blane Bachelor

Expert on Southwest

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

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.

Good to know

Low seasonDecember
Cheapest flight$84
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 3% 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 $84 for a one-way ticket and $180 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 Canadair (Bombardier) Regional Jet 700 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Oklahoma City and Chicago, with Star Alliance 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 $350 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 $373 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 $246 or less one-way and $436 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 4320 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

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

Information on your arrival and departure airports