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$68+ Cheap flights from Oklahoma to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Jun 21 — Jun 281
Sun 6/21
Sun 6/28
1 adult, Economy
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Cheap flight deals from Oklahoma to Chicago

Cheapest flights from Oklahoma to Chicago
Explore the most affordable flight options available from Oklahoma to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 22, 2026.

This Super.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:43 pm
DFW
-
ORD
Nonstop2h 44m
Frontier
Thu 7/309:28 am
ORD
-
DFW
Nonstop2h 52m
Frontier
Deal found 5/18$142
This Super.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:43 pm
DFW
-
ORD
Nonstop2h 44m
Frontier
Sat 8/159:28 am
ORD
-
DFW
Nonstop2h 52m
Frontier
Deal found 5/18$146
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:26 pm
DFW
-
ORD
Nonstop2h 40m
Frontier
Thu 7/99:28 am
ORD
-
DFW
Nonstop2h 52m
Frontier
Deal found 5/18$148
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:13 pm
DFW
-
ORD
Nonstop2h 42m
Frontier
Thu 9/101:22 pm
ORD
-
DFW
Nonstop2h 46m
Frontier
Deal found 5/20$149
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:43 pm
DFW
-
ORD
Nonstop2h 46m
Frontier
Sat 8/299:33 am
ORD
-
DFW
Nonstop2h 41m
Frontier
Deal found 5/20$151
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/151:25 pm
DFW
-
ORD
Nonstop2h 43m
Frontier
Sat 8/229:33 am
ORD
-
DFW
Nonstop2h 41m
Frontier
Deal found 5/20$152
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:13 pm
DFW
-
ORD
Nonstop2h 42m
Frontier
Sat 9/121:22 pm
ORD
-
DFW
Nonstop2h 46m
Frontier
Deal found 5/20$160
This Expedia deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2510:00 am
DFW
-
ORD
1 stop9h 53m
Frontier
Tue 7/289:34 pm
ORD
-
DFW
Nonstop2h 43m
Frontier
Deal found 5/18$163
This Priceline deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:16 pm
DFW
-
MDW
1 stop5h 55m
Frontier
Sat 6/134:10 pm
MDW
-
DFW
Nonstop2h 43m
Frontier
Deal found 5/18$163
This Kiwi.com deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/201:02 pm
DFW
-
ORD
Nonstop2h 51m
Frontier
Sat 6/279:10 am
ORD
-
DFW
Nonstop2h 47m
Frontier
Deal found 5/22$166
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:26 pm
DFW
-
ORD
Nonstop2h 40m
Frontier
Wed 7/87:05 am
ORD
-
DFW
1 stop9h 02m
Frontier
Deal found 5/18$168
This Super.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:55 am
DFW
-
MDW
Nonstop2h 17m
Frontier
Sat 6/134:10 pm
MDW
-
DFW
Nonstop2h 43m
Frontier
Deal found 5/20$168

Find flight deals from Oklahoma to Chicago

Keep the following information in mind while searching for Oklahoma to Chicago flight deals. Data was last updated May 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$142
(Super.com)

One-way from

$68
(Super.com)

Popular in

March

Cheapest in

September

Average price

$393

Good round-trip deal

$373 or less

Good one-way deal

$167 or less
Provider with most accurate pricing for Oklahoma City Will Rogers World-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oklahoma City Will Rogers World-Chicago (CHI) flights.
Search Deals
From Oklahoma to Chicago (CHI)
Search Deals
One-way flight from Oklahoma to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Oklahoma to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Oklahoma to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oklahoma to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 22, 2026.
Use the filters below to find and compare flights from Oklahoma to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Fri 7/10

6:37 pm-8:40 pm

Nonstop2h 03m

Chicago O'Hare Intl

Sun 7/12

9:30 pm-11:31 pm

Nonstop2h 01m

$269

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Wed 7/15

3:25 pm-10:15 pm

1 stop6h 50m

Chicago Midway

Tue 7/21

11:05 am-6:05 pm

1 stop7h 00m

$289

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Tue 8/18

9:45 am-4:15 pm

1 stop6h 30m

Chicago Midway

Wed 8/26

10:54 am-4:46 pm

1 stop5h 52m

$289

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Sat 6/20

11:52 am-5:54 pm

1 stop6h 02m

Chicago Midway

Tue 6/23

6:00 am-11:17 am

1 stop5h 17m

$289

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Tue 6/16

11:52 am-6:18 pm

1 stop6h 26m

Chicago Midway

Tue 6/23

9:54 am-4:31 pm

1 stop6h 37m

$289

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Sat 10/17

11:45 am-4:37 pm

1 stop4h 52m

Chicago O'Hare Intl

Fri 10/23

1:15 pm-6:13 pm

1 stop4h 58m

$289

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Thu 8/20

11:45 am-5:04 pm

1 stop5h 19m

Chicago O'Hare Intl

Sun 8/23

5:28 am-11:11 am

1 stop5h 43m

$289

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Wed 6/24

11:52 am-7:31 pm

1 stop7h 39m

Chicago O'Hare Intl

Sun 6/28

6:30 am-11:09 am

1 stop4h 39m

$289

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Thu 7/16

5:11 pm-9:52 pm

1 stop4h 41m

Chicago O'Hare Intl

Mon 7/20

11:30 am-5:16 pm

1 stop5h 46m

$289

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Fri 9/18

5:10 pm-9:34 pm

1 stop4h 24m

Chicago O'Hare Intl

Sun 9/20

6:00 am-10:47 am

1 stop4h 47m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/19

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Oklahoma to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oklahoma with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oklahoma to Chicago

What is the cheapest month to book a flight from Oklahoma to Chicago?

Currently, July is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $84). Flying from Oklahoma to Chicago in May is currently the most expensive (average of $177). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OK to CHI?

Find hourly flight availability from Oklahoma to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 22, 2026.

It’s optimal to fly from Oklahoma to Chicago in the morning. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight in the evening.

Weekly flight availability from Oklahoma to Chicago

Explore weekly flight availability from Oklahoma to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 22, 2026.

The most flights from USOK to CHI are scheduled on a Monday (26 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (18 on average).

How much does it cost to fly round-trip from Oklahoma to Chicago?

How far ahead should I book a flight from Oklahoma to Chicago?

The price you pay for your flight from Oklahoma to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 79 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from Oklahoma to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Oklahoma to Chicago. Price data was last updated on May 16, 2026.

Travelers seeking maximum savings on their Oklahoma to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Oklahoma to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Oklahoma to Chicago?

    There are many flights that can get you from Oklahoma to Chicago in 1h 45m. Fly via United Airlines, Delta, or Southwest to get the fastest option. There are 582 mi between Oklahoma and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Oklahoma to Chicago one-way?

    One-way options have recently been found by users for as low as $114 on American Airlines. Other airlines that offer cheap prices include United Airlines from $121 and Southwest from $123 one-way.

  • What are the most popular routes from Oklahoma to Chicago?

    While some choose either Dallas/Fort Worth - Chicago Midway or Fayetteville Northwest Arkansas - Chicago O'Hare Intl, Dallas/Fort Worth - Chicago O'Hare Intl is the most popular route from Oklahoma to Chicago.

  • What are the most reliable airlines from Oklahoma to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Oklahoma to Chicago on time: United Airlines (86%), Emirates (84%), Republic Airways (84%).

  • What are the cheapest flights from Oklahoma to Chicago?

    Looking for the cheapest flight from Oklahoma to Chicago? While on average our users pay $1,035, our data indicates the cheapest price to be $186. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $201.

  • Can I find deals for flights from Oklahoma to Chicago that include hotel bookings?

    Yes. In addition to deals on Oklahoma to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oklahoma to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oklahoma to Chicago.

  • Can I find deals for business class flights from Oklahoma to Chicago?

    Yes. Cheapflights offers flight deals from Oklahoma to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oklahoma to Chicago?

    Currently, July is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $84). Flying from Oklahoma to Chicago in May is currently the most expensive (average of $177). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Oklahoma to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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George Bush Intcntl to O'Hare Intl flights
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Hobby to Midway flights
Boston to O'Hare Intl flights
Los Angeles to Midway flights
Dallas/Fort Worth to Midway flights
John F Kennedy Intl to Midway flights
Dulles Intl to Midway flights
Orlando to O'Hare Intl flights
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Sky Harbor Intl to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Austin to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
Atlanta to Midway flights
Miami to O'Hare Intl flights
LaGuardia to Midway flights
San Francisco to Midway flights
Raleigh to O'Hare Intl flights
Baltimore to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Minneapolis to Midway flights
Reagan-National to Midway flights
Minneapolis to O'Hare Intl flights
George Bush Intcntl to Midway flights
Hartford to O'Hare Intl flights
Seattle to Midway flights
Newark to St. Louis flights
San Jose to O'Hare Intl flights
LaGuardia to St. Louis flights
Sacramento to O'Hare Intl flights
Boston to Midway flights
Salt Lake City to O'Hare Intl flights

Top 4 airlines flying from Oklahoma to Chicago

Discover the top 4 airlines that operate flights from Oklahoma to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$138Average$210FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$196Average$373FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$380FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$230Average$387FlexibilityNo cancel feeOn-time69%

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