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$77+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Jul 22 — Jul 291
Wed 7/22
Wed 7/29
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 June 22, 2026.

This Frontier deal was found by Cheapflights users on 6/16. 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.
Thu 10/89:50 pm
DFW
-
ORD
Nonstop2h 34m
Frontier
Thu 10/156:05 am
ORD
-
DFW
Nonstop2h 39m
Frontier
Deal found 6/16$163
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/111:17 pm
DFW
-
ORD
Nonstop2h 43m
Frontier
Thu 8/209:34 pm
ORD
-
DFW
Nonstop2h 45m
Frontier
Deal found 6/16$165
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 8/121:17 pm
DFW
-
ORD
Nonstop2h 43m
Frontier
Wed 8/192:06 pm
ORD
-
DFW
1 stop8h 25m
Frontier
Deal found 6/17$166
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/151:17 pm
DFW
-
ORD
Nonstop2h 43m
Frontier
Thu 8/209:34 pm
ORD
-
DFW
Nonstop2h 45m
Frontier
Deal found 6/16$167
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Thu 8/201:17 pm
DFW
-
ORD
Nonstop2h 43m
Frontier
Wed 8/262:06 pm
ORD
-
DFW
1 stop8h 25m
Frontier
Deal found 6/19$168
This Frontier deal was found by Cheapflights users on 6/16. 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 10/287:00 am
DFW
-
ORD
1 stop6h 26m
Frontier
Tue 11/36:00 am
ORD
-
DFW
Nonstop2h 39m
Frontier
Deal found 6/16$169
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Sat 9/269:50 pm
DFW
-
ORD
Nonstop2h 34m
Frontier
Wed 9/301:22 pm
ORD
-
DFW
Nonstop2h 46m
Frontier
Deal found 6/18$170
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Thu 9/249:44 am
DFW
-
MDW
Nonstop2h 23m
Frontier
Sat 10/31:02 pm
MDW
-
DFW
Nonstop2h 33m
Frontier
Deal found 6/18$170
This Frontier deal was found by Cheapflights users on 6/17. 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.
Thu 8/201:17 pm
DFW
-
ORD
Nonstop2h 43m
Frontier
Mon 8/319:20 am
ORD
-
DFW
Nonstop2h 52m
Frontier
Deal found 6/17$171
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Sun 8/96:08 pm
DFW
-
MDW
Nonstop2h 24m
Frontier
Wed 8/124:45 pm
MDW
-
DFW
Nonstop2h 35m
Frontier
Deal found 6/17$171
This Frontier deal was found by Cheapflights users on 6/16. 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.
Sun 8/165:43 pm
DFW
-
ORD
Nonstop2h 44m
Frontier
Sun 8/239:34 pm
ORD
-
DFW
Nonstop2h 45m
Frontier
Deal found 6/16$172
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Mon 8/101:17 pm
DFW
-
ORD
Nonstop2h 43m
Frontier
Wed 8/199:33 am
ORD
-
DFW
Nonstop2h 41m
Frontier
Deal found 6/17$173

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 June 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$163
(Frontier)

One-way from

$77
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$436

Good round-trip deal

$375 or less

Good one-way deal

$229 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. 10% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 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
Quickest round-trip

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Tue 9/8

3:30 pm-5:10 pm

Nonstop1h 40m

Chicago Midway

Tue 9/15

8:45 pm-10:35 pm

Nonstop1h 50m

$217

TulsaChicago

TUL - ORD

TULORD

Tulsa

Tue 9/8

7:00 am-9:03 am

Nonstop2h 03m

Chicago O'Hare Intl

Tue 9/15

8:45 am-11:03 am

Nonstop2h 18m

$217

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 7/8

4:50 pm-12:10 am

1 stop7h 20m

Chicago Midway

Tue 7/14

10:00 am-2:35 pm

1 stop4h 35m

$237

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 8/8

5:05 am-6:45 am

Nonstop1h 40m

Chicago Midway

Mon 8/10

5:30 am-12:20 pm

1 stop6h 50m

$242

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Wed 7/15

6:37 pm-8:40 pm

Nonstop2h 03m

Chicago O'Hare Intl

Sat 7/18

9:30 pm-11:31 pm

Nonstop2h 01m

$269

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Sat 9/26

6:25 pm-8:35 pm

Nonstop2h 10m

Chicago O'Hare Intl

Sun 9/27

8:40 am-10:39 am

Nonstop1h 59m

$269

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Mon 8/10

5:00 pm-11:20 pm

2 stops6h 20m

Chicago Midway

Thu 8/13

5:55 am-12:20 pm

2 stops6h 25m

$278

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Tue 9/8

9:15 am-11:50 am

Nonstop2h 35m

Chicago O'Hare Intl

Thu 9/10

10:00 am-12:22 pm

Nonstop2h 22m

$282

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 8/26

7:35 am-1:30 pm

1 stop5h 55m

Chicago Midway

Sat 8/29

10:10 am-12:15 pm

Nonstop2h 05m

$285

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Wed 8/26

3:28 pm-10:36 pm

1 stop7h 08m

Chicago Midway

Sat 8/29

6:05 am-1:11 pm

1 stop7h 06m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/18

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, September is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $93). Flying from Oklahoma to Chicago in June is currently the most expensive (average of $209). 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 June 22, 2026.

It’s optimal to fly from Oklahoma to Chicago in the morning. By choosing this option you can save up to 20% 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 June 22, 2026.

The most flights from USOK to CHI are scheduled on a Friday (32 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (26 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 77 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 June 20, 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 40m. Fly via Southwest, United Airlines, or Delta 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 $104 on Frontier. Other airlines that offer cheap prices include American Airlines from $114 and United Airlines from $118 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 (96%), Emirates (94%), United Airlines (88%).

  • What are the cheapest flights from Oklahoma to Chicago?

    Looking for the cheapest flight from Oklahoma to Chicago? While on average our users pay $1,051, our data indicates the cheapest price to be $227. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $150.

  • 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, September is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $93). Flying from Oklahoma to Chicago in June is currently the most expensive (average of $209). 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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Minneapolis to O'Hare Intl flights
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Miami to Midway flights
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Portland to O'Hare Intl flights
LaGuardia to Midway flights
Newark to St. Louis flights
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Tampa to Midway flights
LaGuardia to St. Louis flights
George Bush Intcntl to Midway flights
San Francisco to Midway flights
Denver to Midway flights
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Philadelphia to Midway flights
San Jose 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 June 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$151Average$200FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$196Average$382FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$217Average$393FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$230Average$390FlexibilityNo cancel feeOn-time69%

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