OKC - CHI

$78 Find Cheap Flights from Oklahoma City to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$132
Typical prices: $331-$518
Frontier
Sun 12/2Fri 12/14
OKC - ORD • 1 stop
Cheapest non-stop
$259
Typical prices: $336-$524
American Airlines
Mon 11/26Mon 12/3
OKC - ORD • Non-stop
Nonstop flights
You can fly direct with American Airlines, United Airlines and Southwest. Average duration is 2h 19m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 16 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 16% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $245 (round-trip)
Shortest trip • 5h 20m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Expert advice
Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oklahoma City to Chicago

Wed, Dec 2 - Mon, Dec 14
Frontier Logo
8:29 pm - 12:53 amOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
28h 24m1 stop Denver Intl
Frontier Logo
7:25 am - 7:33 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
12h 08m1 stop Denver Intl
$132Frontier
Sat, Dec 5 - Wed, Dec 9
Frontier Logo
8:29 pm - 12:54 amOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
28h 25m1 stop Denver Intl
Frontier Logo
7:25 am - 7:33 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
12h 08m1 stop Denver Intl
$140Frontier
Sat, Dec 5 - Tue, Dec 8
Frontier Logo
8:29 pm - 12:54 amOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
28h 25m1 stop Denver Intl
Frontier Logo
7:25 am - 7:33 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
12h 08m1 stop Denver Intl
$140Frontier
Thu, Nov 26 - Thu, Dec 3
American Airlines Logo
7:15 am - 9:45 amOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
2h 30mnonstop
American Airlines Logo
6:14 pm - 8:54 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
2h 40mnonstop
$259American Airlines
Thu, Nov 19 - Mon, Nov 23
American Airlines Logo
7:15 am - 9:45 amOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
2h 30mnonstop
American Airlines Logo
4:15 pm - 6:59 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
2h 44mnonstop
$259American Airlines
Thu, Dec 10 - Mon, Dec 14
United Airlines Logo
6:00 pm - 8:23 pmOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
2h 23mnonstop
United Airlines Logo
7:55 pm - 10:24 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
2h 29mnonstop
$259United Airlines
Sat, Dec 5 - Tue, Dec 8
United Airlines Logo
7:00 am - 9:18 amOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
2h 18mnonstop
United Airlines Logo
1:34 pm - 4:14 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
2h 40mnonstop
$259United Airlines
Sat, Dec 5 - Wed, Dec 9
Southwest Logo
5:00 am - 6:55 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
10:15 am - 12:25 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 10mnonstop
$259Southwest
Wed, Nov 25 - Wed, Dec 2
Southwest Logo
4:10 pm - 6:05 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
8:50 pm - 11:05 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 15mnonstop
$259Southwest
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
5:20 am - 7:20 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
2h 00mnonstop
Southwest Logo
8:50 pm - 11:05 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 15mnonstop
$259Southwest
Booking Insights

Price, demand and travel trends for Oklahoma City to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Oklahoma City to Chicago typically range from $331 to $518. The lowest price found in the past 5 days was $132, on Frontier.

What is the cheapest Oklahoma City to Chicago flight route?

There's little price difference between Oklahoma City to Chicago routes. They average around $395 round-trip, based on KAYAK data over the past 12 months.

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

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Oklahoma City to Chicago. It’s 9% cheaper than the average day, while Sunday is the most expensive, with prices 22% higher.

What’s the cheapest month to fly from Oklahoma City to Chicago?

•February is the cheapest month to fly from Oklahoma City to Chicago at $333 round-trip.
•July ($459) and March ($458) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 37% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Oklahoma City to Chicago the cheapest?

Flights from Oklahoma City to Chicago are cheapest 16 weeks before departure. Booking in this window typically costs about 50% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Oklahoma City to Chicago

 
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.

Key details for Oklahoma City to Chicago flights

Low season

February

Cheapest flight

$78
Beat the crowds with an average 33% drop in travelers.
The most popular month to fly with an average 38% increase in travelers.
One-way flight from Oklahoma City to Chicago O'Hare Intl 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

Your Oklahoma City to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Oklahoma City to Chicago?

    These are the earliest and latest flight times available from Oklahoma City to Chicago:

    • Earliest: departs at 5:00 am and lands at 7:19 am
    • Latest: departs at 7:36 pm and lands at 9:55 pm.

    The flight takes about 2h 19m.

  • What cabin classes can I book on flights from Oklahoma City to Chicago?

    Two cabin classes are available on flights from Oklahoma City to Chicago:

    • Economy Class
    • First Class

  • How long is a flight from Oklahoma City to Chicago?

    A nonstop flight from Oklahoma City to Chicago takes 2h 19m, covering 699 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Oklahoma City to Chicago flight?

    Round-trip flights from Oklahoma City to Chicago range from $331 to $518, with an average of $394 over the past 12 months. Anything below $331 counts as a good deal.

  • How expensive are last-minute Oklahoma City to Chicago flights?

    Last-minute fares on this route (booked within two weeks of departure) run 49% above the $394 route average. Book 16 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Oklahoma City to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $245 round-trip via Atlanta Hartsfield-Jackson (ATL), compared to $396 for nonstop.

  • What is the standard checked-bag allowance on flights from Oklahoma City to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Oklahoma City to Chicago spread across the day?

    Morning is the busiest departure period on Oklahoma City to Chicago flights, with 45% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 22%, and night flights for 0%.

  • Which airlines offer Wi-Fi on Oklahoma City to Chicago flights?

    Two airlines offer in-flight Wi-Fi on Oklahoma City to Chicago flights:

    • American Airlines
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from Oklahoma City to Chicago looking right now?

    One-way fares from Oklahoma City to Chicago are currently lower than usual. Average one-way flight prices are about $115, which is 57% below the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates averaging $84:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Oklahoma City to Chicago?

    Flights from Oklahoma City to Chicago usually depart from Oklahoma City Will Rogers World (OKC) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Oklahoma City to Chicago pass through?

    One-stop flights from Oklahoma City to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 53% of one-stop connections
    • Denver Intl (DEN) - 27% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 13% of one-stop connections
    • Las Vegas Harry Reid Intl (LAS) - 7% of one-stop connections

  • Can I save money by using flexible dates for flights from Oklahoma City to Chicago?

    Yes. Flexible dates can save you up to 26% on flights from Oklahoma City to Chicago. Saturday is the cheapest departure day at $359 round-trip on average, while Sunday is the most expensive at $483, a difference of $124.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Oklahoma City to Chicago?

    3 airlines operate flights between Oklahoma City and Chicago. The airlines offering nonstop flights on this route include:

    • American Airlines
    • United Airlines
    • Southwest

  • How much time can I save by choosing a different layover airport from Oklahoma City to Chicago?

    Flying via Chicago O'Hare Intl (ORD) gives the shortest average 1-stop total travel time at 5h 20m, compared with 7h 29m via Atlanta Hartsfield-Jackson (ATL) and 10h 41m via Las Vegas Harry Reid Intl (LAS).

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Oklahoma City to Chicago flights?

    Among airlines operating Oklahoma City to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Oklahoma City to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Oklahoma City to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Saturday departure and avoid flying on Sunday. On this route, Saturday flights average $359, about $124 less than Sunday fares (26% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 16 weeks before you fly. On this route, that window historically saves about 50% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Oklahoma City to Chicago trip for February. Fares historically average $333 round-trip in that month - typically $126 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Atlanta Hartsfield-Jackson Airport (ATL) can be cheaper than flying direct. The cheapest layover option averages $245 round-trip on this route - about $151 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

Prefer to fly direct from Oklahoma City 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

More options for your flight from Oklahoma City to Chicago

Complete your trip to Chicago with a hotel stay or car rental