OKC - CHI

$97 Find Cheap Flights from Oklahoma City to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$258
Typical prices: $319-$507
Frontier
Mon 11/5Thu 11/8
OKC - ORD • 1 stop
Cheapest non-stop
$276
Typical prices: $328-$522
Southwest
Wed 10/24Fri 10/26
OKC - MDW • Non-stop
Nonstop flights
You can fly direct with American Airlines, United Airlines and Southwest. Average duration is 2h 20m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 18 weeks in advance save around 58% 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 $201 (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

Thu, Nov 5 - Sun, Nov 8
Frontier Logo
8:19 pm - 12:21 amOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
28h 02m1 stop Denver Intl
Frontier Logo
6:30 am - 7:24 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
12h 54m1 stop Denver Intl
$258Frontier
Tue, Nov 3 - Fri, Nov 6
Frontier Logo
8:19 pm - 7:08 pmOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
22h 49m2 stops Denver Intl Dallas/Fort Worth
Frontier Logo
6:30 am - 7:24 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
12h 54m1 stop Denver Intl
$260Frontier
Tue, Oct 6 - Tue, Oct 13
American Airlines Logo
1:37 pm - 3:59 pmOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
2h 22mnonstop
American Airlines Logo
6:55 am - 11:46 amORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
4h 51m1 stop Dallas/Fort Worth
$267American Airlines
Tue, Oct 6 - Tue, Oct 13
Southwest Logo
4:00 pm - 9:05 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
5h 05m1 stop Houston Hobby
Southwest Logo
8:55 pm - 11:05 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
2h 10mnonstop
$267Southwest
Tue, Oct 20 - Tue, Oct 27
Southwest Logo
3:05 pm - 5:00 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
10:00 am - 3:20 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
5h 20m1 stop Austin Bergstrom
$268Southwest
Sat, Oct 24 - Mon, Oct 26
American Airlines Logo
7:20 pm - 9:48 pmOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
2h 28mnonstop
American Airlines Logo
6:10 pm - 8:47 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
2h 37mnonstop
$276American Airlines
Tue, Oct 6 - Tue, Oct 13
Delta Logo
5:23 pm - 10:33 pmOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
5h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:27 pm - 8:17 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
7h 50m1 stop Minneapolis St Paul
$277Delta
Tue, Oct 27 - Thu, Oct 29
United Airlines Logo
7:00 am - 9:18 amOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
2h 18mnonstop
United Airlines Logo
4:40 pm - 7:20 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
2h 40mnonstop
$288United Airlines
Sat, Oct 24 - Mon, Oct 26
United Airlines Logo
7:15 am - 9:40 amOKC  Oklahoma City Will Rogers World-ORD Chicago O'Hare Intl
2h 25mnonstop
United Airlines Logo
9:25 pm - 11:54 pmORD  Chicago O'Hare Intl-OKC Oklahoma City Will Rogers World
2h 29mnonstop
$288United Airlines
Wed, Oct 21 - Fri, Oct 23
Delta Logo
5:20 am - 10:03 amOKC  Oklahoma City Will Rogers World-MDW Chicago Midway
4h 43m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:27 pm - 8:17 pmMDW  Chicago Midway-OKC Oklahoma City Will Rogers World
7h 50m1 stop Minneapolis St Paul
$315Delta
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 from Oklahoma City to Chicago with more confidence.

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

Round-trip flights from Oklahoma City to Chicago start at $258. Prices are below average for this route right now, with typical round-trip fares ranging from $319 to $507. The lowest price found in the past 5 days was $258 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 $386 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?

Saturday is the cheapest day of the week to fly from Oklahoma City to Chicago, it is 8% cheaper than the average day. Sunday is the most expensive day with flight prices 22% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • September is the cheapest month to fly from Oklahoma City to Chicago at $323 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 42% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Oklahoma City to Chicago the cheapest?

Flights from Oklahoma City to Chicago are cheapest 18 weeks before departure. Booking in this window typically costs about 58% 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

$97
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 13% increase in price.
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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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.

  • What airlines are available 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

  • 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 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 travelers should check the fare details before booking.

  • 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 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 $201 round-trip via Denver Intl (DEN), compared to $391 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.

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

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

    • Denver Intl (DEN) - 52% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 35% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 9% of one-stop connections
    • Las Vegas Harry Reid Intl (LAS) - 4% of one-stop connections

    Denver Intl (DEN) handles the largest share of one-stop connections on this route.

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

    On the Oklahoma City to Chicago route, being flexible with your departure day can save you up to 25%. Saturday is the cheapest day at $357 round-trip on average, while Sunday is the most expensive at $472: a $115 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • 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 40% of flights leaving in that window. Afternoon departures account for 40%, evening flights for 20%, and night flights for 0%.

  • What popular places can I visit in Chicago?

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

  • 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 7:20 am
    • Latest: departs at 7:29 pm and lands at 9:49 pm.

    The flight takes about 2h 20m.

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

    Last-minute fares on this route - booked within 2 weeks of departure - run 58% above the route average of $384. Book 18 weeks before departure for the lowest fares.

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

    A nonstop flight from Oklahoma City to Chicago takes 2h 20m, 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.

  • Have flight prices from Oklahoma City to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $258 to $1,492. That means the highest observed fare was about 6x higher than the lowest one.

  • 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 $126, which is 53% below the typical average for this route.

  • 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 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 from around $17:

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

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

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

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

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

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

    Round-trip flights from Oklahoma City to Chicago range from $319 to $507, with an average of $384 over the past 12 months. Anything below $319 counts as a good deal.

  • 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.

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 can be flexible, aim for a Saturday departure instead of Sunday. On this route, Saturday flights average $357 - about $115 less than Sunday (24% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 18 weeks before you fly. On this route, that window historically saves about 58% 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 September. Fares historically average $323 round-trip in that month - typically $136 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 Denver Intl Airport (DEN) can be cheaper than flying direct. The cheapest layover option averages $201 round-trip on this route - about $191 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

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