OKC - CHI

$85 Find Cheap Flights from Oklahoma City to Chicago - Compare and Save

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 10/29. 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

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Everything you should know

Cheapest round-trip
$262
Typical prices: $237-$366
United Airlines
Thu 9/3Sat 9/5
OKC - ORD • Non-stop
Cheapest one-way
$85
Typical prices: $182-$354
Frontier
Thu 10/29
OKC - ORD • 1 stop
Top airlines
Cheapest • from $262 (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 15m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 13% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $197 (round-trip)
Shortest trip • 5h 44m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 59% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 22% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Expert advice
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, Sep 3 - Sat, Sep 5
United Airlines Logo
7:19 am - 9:45 am
OKC
-
ORD
2h 26mnonstop
United Airlines Logo
8:35 pm - 10:56 pm
ORD
-
OKC
2h 21mnonstop
$262United Airlines
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
1:10 pm - 8:05 pm
OKC
-
MDW
6h 55m
1 stop
Southwest Logo
1:05 pm - 10:10 pm
MDW
-
OKC
9h 05m
2 stops
$262Southwest
Wed, Aug 26 - Wed, Sep 2
Southwest Logo
12:05 pm - 8:40 pm
OKC
-
MDW
8h 35m
2 stops
Southwest Logo
3:50 pm - 8:45 pm
MDW
-
OKC
4h 55m
1 stop
$262Southwest
Fri, Sep 11 - Sun, Sep 13
Frontier Logo
8:30 pm - 12:23 am
OKC
-
ORD
27h 53m
1 stop
Frontier Logo
8:55 pm - 1:37 pm
ORD
-
OKC
16h 42m
1 stop
$263Frontier
Fri, Oct 2 - Wed, Oct 7
Frontier Logo
8:30 pm - 12:23 am
OKC
-
ORD
27h 53m
1 stop
Frontier Logo
6:30 am - 7:35 pm
ORD
-
OKC
13h 05m
1 stop
$267Frontier
Thu, Oct 1 - Mon, Oct 5
Multiple Airlines Logo
9:37 am - 10:59 pm
OKC
-
ORD
13h 22m
1 stop
Multiple Airlines Logo
6:30 am - 7:34 pm
ORD
-
OKC
13h 04m
1 stop
$269Multiple Airlines
Thu, Sep 10 - Mon, Sep 14
American Airlines Logo
5:35 pm - 11:30 pm
OKC
-
ORD
5h 55m
1 stop
American Airlines Logo
6:00 pm - 8:22 pm
ORD
-
OKC
2h 22mnonstop
$271American Airlines
Thu, Aug 27 - Sat, Aug 29
American Airlines Logo
4:38 pm - 12:18 am
OKC
-
ORD
7h 40m
1 stop
American Airlines Logo
6:29 pm - 8:49 pm
ORD
-
OKC
2h 20mnonstop
$271American Airlines
Wed, Aug 26 - Sat, Aug 29
Delta Logo
5:12 pm - 11:57 pm
OKC
-
ORD
6h 45m
1 stop
Delta Logo
8:05 am - 2:54 pm
ORD
-
OKC
6h 49m
1 stop
$281Delta
Fri, Sep 25 - Tue, Sep 29
United Airlines Logo
7:15 am - 9:40 am
OKC
-
ORD
2h 25mnonstop
United Airlines Logo
9:16 am - 11:54 am
ORD
-
OKC
2h 38mnonstop
$285United Airlines
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 September.

Flight prices are below average for this route right now.

Flights to Chicago from Oklahoma City usually cost between $282 and $435 in September.
The lowest price found in the past 5 days was $262 on Southwest (Sep 16-Sep 19).

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 $232 on the route between Oklahoma City (OKC) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 13% 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 Thursday, 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 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 $297 (return) on average. On the other hand, the most expensive months are July and June, where the average cost of round-trip tickets is $446 and $432 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 $410, 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 4 weeks before departure, which saves you about 59% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 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.

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.

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.

Good to know

Low season

December

Cheapest flight

$85
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 7% 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 5 days, the lowest price for a flight from Oklahoma City to Chicago was $85 for a one-way ticket and $262 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, JetBlue, and Alaska Airlines 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?

    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 $377 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 $391 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 $223 or less one-way and $386 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 4229 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

We sat on the plane on the tarmac for 4 hours.

Cramped older 737. Noisy passengers nearby. Wish you would change and make KC a hub with a direct from OKC. Best new airport!

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

Late FA meant slow boarding. WiFi did not work. I’m a medium plus sized passenger. The seatbelt was for the first time ever barely fitting. And we delayed on the tarmac 40 min

Some of these FA’s need attitude check. Snarky bitches

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

Nothing, I wont be flying American Airlines again and will not be recommending anyone to fly American Airlines. It was the worst experience flying I've ever had.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

American Airlines is a great dependable airline, on time arrival and departure with polite crew and staff.

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

There was no drink/snack service and the electric outlets were not powered so I couldn’t charge my phone.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

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

We were delayed three times ,and that destroyed my plans, and reservations

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I was unable to check-in on your app at home before the trip. I didn't realize that you charged to get a boarding pass from the couter. I stood in a long line to check-in to be told that I needed to get in another line to get a boarding pass and that it would cost me. When I spoke with the lady at the next counter, she couldn't get me into the check-in on my app so she tried several other ways over about 15 minutes while others were waiting in line. Finally she was able to get into the check-in and then it took a while to click through multiple upsale options to get my pass. I thought it should be easy since I has a personal pack and no seat selection. I was traveling alone to attend a family funeral.

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

Information on your arrival and departure airports