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$54+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
mar. 13 — mar. 201
vie. 3/13
vie. 3/20
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 febrero 11, 2026.

This Super.com deal was found by Cheapflights users on 2/11. 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.
jue. 4/3010:17 pm
DFW
-
ORD
Nonstop2h 35m
Frontier
dom. 5/35:11 am
ORD
-
DFW
Nonstop2h 49m
Frontier
Deal found 2/11$79
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
jue. 4/236:45 am
DFW
-
ORD
Nonstop2h 25m
Multiple Airlines
dom. 4/265:11 am
ORD
-
DFW
Nonstop2h 49m
Multiple Airlines
Deal found 2/11$80
This Frontier deal was found by Cheapflights users on 2/9. 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.
mar. 3/1012:37 pm
DFW
-
ORD
Nonstop2h 38m
Frontier
vie. 3/135:11 am
ORD
-
DFW
Nonstop2h 52m
Frontier
Deal found 2/9$81
This Priceline deal was found by Cheapflights users on 2/7. 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.
mar. 4/286:45 am
DFW
-
ORD
Nonstop2h 27m
Multiple Airlines
sáb. 5/94:55 pm
ORD
-
DFW
Nonstop3h 02m
Multiple Airlines
Deal found 2/7$82
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
mié. 3/118:00 am
DFW
-
MDW
Nonstop2h 25m
Frontier
jue. 3/124:55 pm
MDW
-
DFW
Nonstop2h 43m
Frontier
Deal found 2/10$82
This Frontier deal was found by Cheapflights users on 2/11. 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.
sáb. 3/79:48 pm
DFW
-
ORD
Nonstop2h 33m
Frontier
jue. 3/125:11 am
ORD
-
DFW
Nonstop2h 52m
Frontier
Deal found 2/11$83
This Priceline deal was found by Cheapflights users on 2/10. 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.
sáb. 3/76:05 pm
DFW
-
MDW
Nonstop2h 16m
Frontier
lun. 3/95:13 pm
MDW
-
DFW
Nonstop2h 47m
Frontier
Deal found 2/10$83
This Frontier deal was found by Cheapflights users on 2/11. 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.
jue. 5/710:17 pm
DFW
-
ORD
Nonstop2h 35m
Frontier
lun. 5/115:11 am
ORD
-
DFW
Nonstop2h 49m
Frontier
Deal found 2/11$84
This Frontier deal was found by Cheapflights users on 2/11. 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.
jue. 5/78:03 pm
DFW
-
MDW
Nonstop2h 18m
Frontier
lun. 5/114:09 pm
MDW
-
DFW
Nonstop2h 54m
Frontier
Deal found 2/11$84
This Priceline deal was found by Cheapflights users on 2/10. 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.
mar. 3/1011:06 am
DFW
-
ORD
1 stop8h 41m
Multiple Airlines
mié. 3/114:28 pm
ORD
-
DFW
Nonstop3h 01m
Multiple Airlines
Deal found 2/10$85
This Super.com deal was found by Cheapflights users on 2/9. 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.
vie. 4/178:03 pm
DFW
-
MDW
Nonstop2h 18m
Frontier
lun. 4/204:09 pm
MDW
-
DFW
Nonstop2h 54m
Frontier
Deal found 2/9$85
This Expedia deal was found by Cheapflights users on 2/9. 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.
vie. 4/248:03 pm
DFW
-
MDW
Nonstop2h 18m
Frontier
lun. 4/274:09 pm
MDW
-
DFW
Nonstop2h 54m
Frontier
Deal found 2/9$86

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 febrero 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$78
(Priceline)

One-way from

$54
(Super.com)

Popular in

March

Cheapest in

September

Average price

$347

Good round-trip deal

$343 or less

Good one-way deal

$185 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. 5% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 febrero 11, 2026.
Use the filters below to find and compare flights from Oklahoma to Chicago that are best for you.

Fly from

Oklahoma

Fly to

Chicago

Route

Depart

Return

Price

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

jue. 4/30

8:03 pm-10:21 pm

Nonstop2h 18m

Chicago Midway

dom. 5/3

4:09 pm-7:03 pm

Nonstop2h 54m

$110

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

sáb. 3/21

7:24 pm-9:59 pm

Nonstop2h 35m

Chicago O'Hare Intl

sáb. 3/28

8:10 pm-10:56 pm

Nonstop2h 46m

$137

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

mié. 3/11

7:00 am-9:31 am

Nonstop2h 31m

Chicago O'Hare Intl

sáb. 3/14

8:20 pm-11:06 pm

Nonstop2h 46m

$139

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

vie. 2/27

4:52 pm-10:39 pm

1 stop5h 47m

Chicago O'Hare Intl

lun. 3/2

5:05 am-3:56 pm

1 stop10h 51m

$154

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

vie. 2/27

4:52 pm-10:37 pm

1 stop5h 45m

Chicago Midway

lun. 3/2

6:00 am-3:56 pm

1 stop9h 56m

$160

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

dom. 4/5

8:55 pm-11:13 pm

Nonstop2h 18m

Chicago Midway

dom. 4/12

4:46 pm-7:40 pm

Nonstop2h 54m

$167

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

sáb. 6/6

10:00 am-12:40 pm

Nonstop2h 40m

Chicago O'Hare Intl

jue. 6/11

8:45 am-11:28 am

Nonstop2h 43m

$173

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

sáb. 5/16

5:15 am-10:05 am

1 stop4h 50m

Chicago O'Hare Intl

sáb. 5/23

12:40 pm-5:45 pm

1 stop5h 05m

$173

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

mar. 5/5

5:45 am-12:45 pm

1 stop7h 00m

Chicago O'Hare Intl

mar. 5/5

5:04 pm-11:24 pm

1 stop6h 20m

$177

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

mar. 5/5

5:45 am-12:45 pm

1 stop7h 00m

Chicago O'Hare Intl

mié. 5/6

8:15 am-3:14 pm

1 stop6h 59m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 60 results
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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, June is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $121). Flying from Oklahoma to Chicago in March is currently the most expensive (average of $303). 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 febrero 11, 2026.

It’s optimal to fly from Oklahoma to Chicago in the morning. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the evening.

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 February 7, 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. Wednesday 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 2h 18m. Fly via Frontier, United Airlines, or Delta to get the fastest option. There are 797 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 $115 on American Airlines. Other airlines that offer cheap prices include Southwest from $123 and United Airlines from $125 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: Republic Airways (90%), Envoy Air (85%), Iberia (80%).

  • What are the cheapest flights from Oklahoma to Chicago?

    Looking for the cheapest flight from Oklahoma to Chicago? While on average our users pay $1,066, our data indicates the cheapest price to be $193. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $78.

  • 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, June is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $121). Flying from Oklahoma to Chicago in March is currently the most expensive (average of $303). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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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Los Angeles to Midway flights
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Dulles Intl to Midway flights
Minneapolis to O'Hare Intl flights
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Atlanta to Midway flights
Newark to Midway flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Philadelphia to Midway flights
Hobby to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
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Hartford to O'Hare Intl flights
Seattle to Midway 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 febrero 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$138Average$249FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$182Average$394FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$189Average$353FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$371FlexibilityNo cancel feeOn-time63%

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