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$89+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Aug 20 — Aug 271
Thu 8/20
Thu 8/27
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 July 21, 2026.

This Southwest deal was found by Cheapflights users on 7/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:35 am
TUL
-
MDW
Nonstop1h 40m
Southwest
Mon 8/108:55 pm
MDW
-
TUL
Nonstop1h 50m
Southwest
Deal found 7/16$177
This American Airlines deal was found by Cheapflights users on 7/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:49 pm
TUL
-
ORD
Nonstop2h 16m
American Airlines
Sun 9/69:25 pm
ORD
-
TUL
Nonstop2h 01m
American Airlines
Deal found 7/18$177
This American Airlines deal was found by Cheapflights users on 7/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:49 pm
TUL
-
ORD
Nonstop2h 16m
American Airlines
Mon 8/105:00 pm
ORD
-
TUL
Nonstop2h 05m
American Airlines
Deal found 7/16$178
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Mon 8/3110:00 am
DFW
-
ORD
1 stop9h 59m
Frontier
Sat 9/191:22 pm
ORD
-
DFW
Nonstop2h 46m
Frontier
Deal found 7/20$187
This Southwest deal was found by Cheapflights users on 7/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:05 am
TUL
-
MDW
Nonstop1h 40m
Southwest
Sat 8/226:50 am
MDW
-
TUL
1 stop6h 55m
Southwest
Deal found 7/20$187
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sat 9/129:50 pm
DFW
-
ORD
Nonstop2h 34m
Frontier
Fri 10/26:30 am
ORD
-
DFW
1 stop8h 20m
Frontier
Deal found 7/20$188
This Southwest deal was found by Cheapflights users on 7/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:35 am
TUL
-
MDW
Nonstop1h 40m
Southwest
Sat 9/56:05 pm
MDW
-
TUL
Nonstop1h 50m
Southwest
Deal found 7/17$190
This United Airlines deal was found by Cheapflights users on 7/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:40 am
TUL
-
ORD
Nonstop2h 02m
United Airlines
Mon 11/28:20 pm
ORD
-
TUL
Nonstop2h 11m
United Airlines
Deal found 7/17$190
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 10/229:50 pm
DFW
-
ORD
Nonstop2h 34m
Frontier
Sun 10/251:52 pm
ORD
-
DFW
Nonstop2h 46m
Frontier
Deal found 7/19$192
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Sat 11/73:59 pm
DFW
-
MDW
1 stop5h 54m
Frontier
Wed 11/1112:03 pm
MDW
-
DFW
1 stop7h 47m
Frontier
Deal found 7/17$192
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Mon 9/145:13 pm
DFW
-
ORD
Nonstop2h 42m
Frontier
Thu 10/16:30 am
ORD
-
DFW
1 stop8h 20m
Frontier
Deal found 7/20$193
This Super.com deal was found by Cheapflights users on 7/18. 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 7/211:25 pm
DFW
-
ORD
Nonstop2h 43m
Frontier
Wed 7/229:28 am
ORD
-
DFW
Nonstop2h 52m
Frontier
Deal found 7/18$195

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 July 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Southwest)

One-way from

$89
(Southwest)

Popular in

June

Cheapest in

September

Average price

$425

Good round-trip deal

$341 or less

Good one-way deal

$190 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. 13% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 21, 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

Sat 8/15

5:05 am-6:45 am

Nonstop1h 40m

Chicago Midway

Sat 8/22

6:05 pm-7:55 pm

Nonstop1h 50m

$177

TulsaChicago

TUL - ORD

TULORD

Tulsa

Tue 9/8

10:21 am-12:29 pm

Nonstop2h 08m

Chicago O'Hare Intl

Fri 9/11

9:20 pm-11:22 pm

Nonstop2h 02m

$177

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Mon 9/21

4:40 pm-9:55 pm

2 stops5h 15m

Chicago Midway

Wed 9/23

8:45 pm-10:35 pm

Nonstop1h 50m

$192

TulsaChicago

TUL - ORD

TULORD

Tulsa

Sat 8/8

2:17 pm-4:28 pm

Nonstop2h 11m

Chicago O'Hare Intl

Sat 8/8

9:20 pm-11:25 pm

Nonstop2h 05m

$203

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Sat 8/15

6:00 am-11:50 am

1 stop5h 50m

Chicago Midway

Sat 8/15

6:05 pm-7:55 pm

Nonstop1h 50m

$213

TulsaChicago

TUL - ORD

TULORD

Tulsa

Wed 8/19

12:41 pm-6:49 pm

1 stop6h 08m

Chicago O'Hare Intl

Thu 8/20

5:30 am-11:56 am

1 stop6h 26m

$223

TulsaChicago

TUL - ORD

TULORD

Tulsa

Mon 10/26

6:57 pm-11:51 pm

1 stop4h 54m

Chicago O'Hare Intl

Wed 10/28

5:30 am-12:04 pm

1 stop6h 34m

$223

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Wed 10/14

10:25 am-5:00 pm

1 stop6h 35m

Chicago Midway

Sat 10/17

6:35 am-1:10 pm

2 stops6h 35m

$228

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Fri 8/7

7:20 am-9:30 am

Nonstop2h 10m

Chicago O'Hare Intl

Sun 8/9

9:30 pm-11:31 pm

Nonstop2h 01m

$281

TulsaChicago

TUL - ORD

TULORD

Tulsa

Sat 8/8

2:17 pm-4:28 pm

Nonstop2h 11m

Chicago O'Hare Intl

Wed 8/12

9:25 pm-11:27 pm

Nonstop2h 02m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/20

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 $324). Flying from Oklahoma to Chicago in July is currently the most expensive (average of $441). 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 July 21, 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 at noon.

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 July 21, 2026.

The most flights from USOK to CHI are scheduled on a Saturday (32 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (28 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 July 18, 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 $106 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: Emirates (100%), Republic Airways (95%), United Airlines (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 $2,134, our data indicates the cheapest price to be $179. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $220.

  • 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 $324). Flying from Oklahoma to Chicago in July is currently the most expensive (average of $441). 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
Valparaiso
Hammond
Saint Joseph
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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Dallas/Fort Worth to Midway flights
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Atlanta to Midway flights
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LaGuardia to St. Louis flights
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Seattle to Midway flights
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Hartford to O'Hare Intl flights
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Jacksonville 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 July 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$151Average$182FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$196Average$386FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$233Average$389FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$237Average$391FlexibilityNo cancel feeOn-time63%

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