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$74+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheap 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 12, 2025.

Round-trip from

$136
(Kiwi.com)

One-way from

$74
(Kiwi.com)

Popular in

March

Cheapest in

February

Average price

$363

Good round-trip deal

$286 or less

Good one-way deal

$181 or less
From Oklahoma to Chicago (CHI)
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One-way flight from Oklahoma to Chicago (CHI)
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Oklahoma to Chicago (CHI).
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Price to beat on a one-way flight from Oklahoma to Chicago (CHI).
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Find 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 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/97:30 pmDFW - ORD
1 stop13h 25mSpirit Airlines
Mon 7/145:49 pmORD - DFW
1 stop5h 06mSpirit Airlines
Deal found 6/9$136
This Frontier deal was found by Cheapflights users on 6/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/121:30 pmDFW - ORD
Nonstop2h 44mFrontier
Wed 8/205:27 pmORD - DFW
Nonstop2h 49mFrontier
Deal found 6/10$139
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/209:30 amDFW - MDW
Nonstop2h 23mFrontier
Mon 9/226:50 pmMDW - DFW
Nonstop2h 35mFrontier
Deal found 6/11$141
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/102:56 pmDFW - ORD
Nonstop2h 14mMultiple Airlines
Sat 7/199:55 amORD - DFW
Nonstop2h 42mMultiple Airlines
Deal found 6/11$142
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/219:50 amTUL - MDW
Nonstop1h 45mSouthwest
Mon 8/252:55 pmMDW - TUL
Nonstop1h 45mSouthwest
Deal found 6/11$157
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/277:00 amTUL - ORD
Nonstop2h 04mAmerican Airlines
Thu 9/44:42 pmORD - TUL
Nonstop1h 58mAmerican Airlines
Deal found 6/11$157
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/216:30 amTUL - ORD
1 stop4h 15mSouthwest
Mon 8/257:00 amORD - TUL
1 stop5h 40mSouthwest
Deal found 6/11$177
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/132:30 pmSWO - ORD
1 stop6h 54mAmerican Airlines
Tue 9/168:25 amORD - SWO
1 stop5h 34mAmerican Airlines
Deal found 6/11$189
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/266:45 amDFW - ORD
1 stop5h 17mDelta
Sat 7/265:35 pmORD - DFW
1 stop4h 57mDelta
Deal found 6/11$197
This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/127:00 amDFW - MDW
1 stop4h 48mDelta
Thu 8/146:04 amMDW - DFW
1 stop6h 14mDelta
Deal found 6/9$197
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/16:15 amDFW - ORD
Nonstop2h 26mAmerican Airlines
Tue 8/510:05 pmORD - DFW
Nonstop2h 33mAmerican Airlines
Deal found 6/11$198
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/44:18 pmDFW - ORD
Nonstop2h 37mUnited Airlines
Wed 7/94:20 pmORD - DFW
Nonstop2h 38mUnited Airlines
Deal found 6/10$199

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 12, 2025.
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 - ORD

DFWORD

Dallas/Fort Worth

Wed 7/9

7:30 pm-8:55 am

1 stop13h 25m

Chicago O'Hare Intl

Mon 7/14

5:49 pm-10:55 pm

1 stop5h 06m

$136

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Tue 8/12

1:30 pm-4:14 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sat 8/16

9:55 am-12:37 pm

Nonstop2h 42m

$139

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 7/23

2:40 pm-5:03 pm

Nonstop2h 23m

Chicago Midway

Wed 8/13

6:02 pm-8:39 pm

Nonstop2h 37m

$141

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 7/10

2:56 pm-5:10 pm

Nonstop2h 14m

Chicago O'Hare Intl

Sat 7/19

9:55 am-12:37 pm

Nonstop2h 42m

$142

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 8/21

9:50 am-11:35 am

Nonstop1h 45m

Chicago Midway

Mon 8/25

2:55 pm-4:40 pm

Nonstop1h 45m

$157

TulsaChicago

TUL - ORD

TULORD

Tulsa

Wed 8/27

7:00 am-9:04 am

Nonstop2h 04m

Chicago O'Hare Intl

Thu 9/4

4:42 pm-6:40 pm

Nonstop1h 58m

$157

TulsaChicago

TUL - ORD

TULORD

Tulsa

Thu 8/21

6:30 am-10:45 am

1 stop4h 15m

Chicago O'Hare Intl

Mon 8/25

7:00 am-12:40 pm

1 stop5h 40m

$177

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Sat 9/13

2:30 pm-9:24 pm

1 stop6h 54m

Chicago O'Hare Intl

Tue 9/16

8:25 am-1:59 pm

1 stop5h 34m

$189

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 7/26

6:45 am-12:02 pm

1 stop5h 17m

Chicago O'Hare Intl

Sat 7/26

5:35 pm-10:32 pm

1 stop4h 57m

$197

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 8/12

4:05 pm-9:49 pm

1 stop5h 44m

Chicago Midway

Wed 8/20

10:11 am-2:58 pm

1 stop4h 47m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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, August is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $245). Flying from Oklahoma to Chicago in March is currently the most expensive (average of $321). 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 12, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oklahoma to Chicago as you normally would.

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 12, 2025.

The most flights from USOK to CHI are scheduled on a Thursday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 12, 2025.
Read through reviews of airlines operating flights from Oklahoma to Chicago, such as Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
725 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • 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 $74 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $79 and Southwest from $79 one-way.

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

    While some choose either Dallas/Fort Worth - Chicago Midway or Oklahoma City Will Rogers World - 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 (92%), Republic Airways (91%), Japan 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 $3,368, our data indicates the cheapest price to be $131. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $88.

  • 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, August is the cheapest month in which you can book a flight from Oklahoma to Chicago (average of $245). Flying from Oklahoma to Chicago in March is currently the most expensive (average of $321). 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 Oklahoma?

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

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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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LaGuardia to Midway flights
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Los Angeles to Midway flights
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Boston to Midway flights
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Dulles Intl to St. Louis 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$193FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$201Average$359FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$259Average$417FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$278Average$367FlexibilityNo cancel feeOn-time63%

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