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$52+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Oklahoma to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Oklahoma (USOK) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$104
(Frontier)

One-way from

$52
(Frontier)

Popular in

October

Cheapest in

April

Average price

$349

Good round-trip deal

$391 or less

Good one-way deal

$200 or less
Provider with most accurate pricing for Oklahoma City Will Rogers World-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Oklahoma City Will Rogers World-Chicago (CHI) flights.
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From Oklahoma to Chicago (CHI)
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One-way flight from Oklahoma to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($19 potential increase over avg. RT price).
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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 January 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 January 30, 2025.

This FlightHub deal was found by Cheapflights users on 1/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1912:49 pmDFW - ORD
1 stop8h 44mMultiple Airlines
Fri 2/216:50 amORD - DFW
1 stop17h 26mMultiple Airlines
Deal found 1/29$106
This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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.
Sun 3/169:00 amDFW - MDW
Nonstop2h 21mFrontier
Tue 3/187:50 amMDW - DFW
Nonstop2h 49mFrontier
Deal found 1/29$106
This Frontier deal was found by Cheapflights users on 1/29. 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 2/127:10 amDFW - ORD
1 stop7h 15mFrontier
Thu 2/202:25 pmORD - DFW
Nonstop2h 47mFrontier
Deal found 1/29$107
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/56:00 amDFW - ORD
Nonstop2h 21mSpirit Airlines
Fri 3/74:45 pmORD - DFW
1 stop20h 21mSpirit Airlines
Deal found 1/29$108
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/85:16 pmOKC - ORD
1 stop10h 53mFrontier
Mon 3/106:30 amORD - OKC
1 stop12h 57mFrontier
Deal found 1/29$114
This Booking.com deal was found by Cheapflights users on 1/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/38:14 pmOKC - MDW
1 stop9h 17mFrontier
Thu 3/66:40 amMDW - OKC
1 stop12h 47mFrontier
Deal found 1/29$120
This Frontier deal was found by Cheapflights users on 1/29. 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 3/82:49 pmXNA - MDW
1 stop9h 28mFrontier
Sat 3/156:40 amMDW - XNA
1 stop7h 19mFrontier
Deal found 1/29$128
This Mytrip deal was found by Cheapflights users on 1/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/610:25 amDFW - ORD
1 stop3h 50mContour
Wed 2/1211:45 amORD - DFW
1 stop3h 55mContour
Deal found 1/30$174
This United Airlines deal was found by Cheapflights users on 1/29. 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.
Thu 3/137:00 amDFW - ORD
Nonstop2h 25mUnited Airlines
Wed 4/307:00 amORD - DFW
Nonstop2h 42mUnited Airlines
Deal found 1/29$177
This Frontier deal was found by Cheapflights users on 1/29. 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.
Mon 3/312:49 pmXNA - ORD
1 stop9h 55mFrontier
Sat 4/56:45 amORD - XNA
1 stop7h 01mFrontier
Deal found 1/29$188
This Delta deal was found by Cheapflights users on 1/29. 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 3/181:29 pmDFW - ORD
1 stop7h 15mDelta
Tue 3/2510:25 amORD - DFW
1 stop7h 33mDelta
Deal found 1/29$197
This Delta deal was found by Cheapflights users on 1/28. 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 3/189:50 amDFW - MDW
1 stop6h 24mDelta
Wed 4/29:25 amMDW - DFW
1 stop5h 11mDelta
Deal found 1/28$197

Find flights from Oklahoma to Chicago within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Wed 2/19

12:49 pm-9:33 pm

1 stop8h 44m

Chicago O'Hare Intl

Fri 2/21

6:50 am-12:16 am

1 stop17h 26m

$106

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sat 2/15

9:07 am-11:28 am

Nonstop2h 21m

Chicago Midway

Wed 2/19

6:00 am-8:47 am

Nonstop2h 47m

$106

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Wed 2/12

7:10 am-2:25 pm

1 stop7h 15m

Chicago O'Hare Intl

Thu 2/20

2:25 pm-5:12 pm

Nonstop2h 47m

$107

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Wed 3/5

6:00 am-8:21 am

Nonstop2h 21m

Chicago O'Hare Intl

Fri 3/7

4:45 pm-1:06 pm

1 stop20h 21m

$108

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Sat 3/8

5:16 pm-4:09 am

1 stop10h 53m

Chicago O'Hare Intl

Mon 3/10

6:30 am-7:27 pm

1 stop12h 57m

$114

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Mon 3/3

8:14 pm-5:31 am

1 stop9h 17m

Chicago Midway

Thu 3/6

6:40 am-7:27 pm

1 stop12h 47m

$120

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Sat 3/8

2:49 pm-12:17 am

1 stop9h 28m

Chicago Midway

Sat 3/15

6:40 am-1:59 pm

1 stop7h 19m

$128

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 2/6

10:25 am-2:15 pm

1 stop3h 50m

Chicago O'Hare Intl

Wed 2/12

11:45 am-3:40 pm

1 stop3h 55m

$174

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 3/13

7:00 am-9:25 am

Nonstop2h 25m

Chicago O'Hare Intl

Wed 4/30

7:00 am-9:42 am

Nonstop2h 42m

$177

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Mon 3/31

2:49 pm-12:44 am

1 stop9h 55m

Chicago O'Hare Intl

Sat 4/5

6:45 am-1:46 pm

1 stop7h 01m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

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.

Travel insights for flights from Oklahoma to Chicago

Get recent, data-driven insights about flights from Oklahoma to Chicago including ideal travel times, pricing trends, and more.

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 $325). 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 January 30, 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 January 30, 2025.

The most flights from USOK to CHI are scheduled on a Monday (21 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (18 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 January 30, 2025.
Read through reviews of airlines operating flights from Oklahoma to Chicago, such as Southwest, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,913 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.3
Good
790 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,585 reviews

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $52 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $66 and Contour from $83 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 (93%), Republic Airways (93%), SkyWest Airlines (86%).

  • What are the cheapest flights from Oklahoma to Chicago?

    Looking for the cheapest flight from Oklahoma to Chicago? While on average our users pay $1,108, our data indicates the cheapest price to be $148. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $44.

  • 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 $325). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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.
John F Kennedy Intl to O'Hare Intl flights
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Top 5 airlines flying from Oklahoma to Chicago

Discover the top 5 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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$175FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$193Average$356FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$194Average$411FlexibilityNo cancel feeOn-time69%
DeltaCheapest$206Average$655FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$293Average$372FlexibilityNo cancel feeOn-time63%
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