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$59+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$134
(Kiwi.com)

One-way from

$59
(Priceline)

Popular in

March

Cheapest in

February

Average price

$364

Good round-trip deal

$286 or less

Good one-way deal

$199 or less
From Oklahoma to Chicago (CHI)
Search Deals
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 July 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 July 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/2. 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 7/232:56 pmDFW - ORD
Nonstop2h 14mMultiple Airlines
Wed 7/305:01 amORD - DFW
1 stop8h 32mMultiple Airlines
Deal found 7/2$134
This Priceline deal was found by Cheapflights users on 7/2. 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.
Wed 7/302:40 pmDFW - MDW
Nonstop2h 23mFrontier
Wed 8/62:48 pmMDW - DFW
1 stop7h 46mFrontier
Deal found 7/2$134
This Frontier deal was found by Cheapflights users on 7/2. 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 7/261:30 pmDFW - ORD
Nonstop2h 44mFrontier
Tue 7/299:55 amORD - DFW
Nonstop2h 42mFrontier
Deal found 7/2$137
This Cheapflightsfares deal was found by Cheapflights users on 7/3. 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 7/267:15 amDFW - ORD
1 stop9h 42mSpirit Airlines
Sat 8/210:00 amORD - DFW
1 stop12h 14mSpirit Airlines
Deal found 7/3$149
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Sat 8/27:00 amDFW - ORD
Nonstop2h 40mUnited Airlines
Mon 8/47:00 amORD - DFW
Nonstop2h 39mUnited Airlines
Deal found 7/3$167
This Southwest deal was found by Cheapflights users on 7/1. 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 9/49:50 amTUL - MDW
Nonstop1h 45mSouthwest
Tue 9/94:50 pmMDW - TUL
Nonstop1h 50mSouthwest
Deal found 7/1$197
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Wed 8/202:41 pmTUL - ORD
Nonstop2h 04mUnited Airlines
Thu 8/2112:45 pmORD - TUL
Nonstop2h 11mUnited Airlines
Deal found 7/2$197
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/77:00 amTUL - ORD
Nonstop2h 04mAmerican Airlines
Mon 8/1110:20 pmORD - TUL
Nonstop2h 01mAmerican Airlines
Deal found 7/2$199
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/87:05 amXNA - ORD
Nonstop1h 57mAmerican Airlines
Mon 8/117:01 amORD - XNA
Nonstop1h 58mAmerican Airlines
Deal found 7/2$209
This Booking.com deal was found by Cheapflights users on 7/2. 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.
Wed 8/136:05 amOKC - ORD
1 stop18h 27mFrontier
Sat 8/167:00 amORD - OKC
1 stop15h 38mFrontier
Deal found 7/2$211
This Southwest deal was found by Cheapflights users on 7/1. 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.
Wed 10/292:55 pmOKC - MDW
Nonstop1h 55mSouthwest
Mon 11/37:45 amMDW - OKC
2 stops7h 50mSouthwest
Deal found 7/1$212
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/132:02 pmOKC - ORD
Nonstop2h 16mAmerican Airlines
Sat 8/166:46 pmORD - OKC
Nonstop2h 31mAmerican Airlines
Deal found 7/2$213

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 3, 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 7/23

2:56 pm-5:10 pm

Nonstop2h 14m

Chicago O'Hare Intl

Wed 7/30

5:01 am-1:33 pm

1 stop8h 32m

$134

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 7/30

2:40 pm-5:03 pm

Nonstop2h 23m

Chicago Midway

Wed 8/6

2:48 pm-10:34 pm

1 stop7h 46m

$134

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Tue 7/15

1:30 pm-4:14 pm

Nonstop2h 44m

Chicago O'Hare Intl

Tue 7/29

9:55 am-12:37 pm

Nonstop2h 42m

$136

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Fri 9/19

9:57 am-9:58 pm

1 stop12h 01m

Chicago O'Hare Intl

Sun 10/19

8:00 am-12:11 am

1 stop16h 11m

$150

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Fri 8/8

8:05 pm-10:43 pm

Nonstop2h 38m

Chicago O'Hare Intl

Wed 8/13

7:50 pm-10:29 pm

Nonstop2h 39m

$178

TulsaChicago

TUL - MDW

TULMDW

Tulsa

Thu 9/4

9:50 am-11:35 am

Nonstop1h 45m

Chicago Midway

Tue 9/9

4:50 pm-6:40 pm

Nonstop1h 50m

$197

TulsaChicago

TUL - ORD

TULORD

Tulsa

Wed 8/20

2:41 pm-4:45 pm

Nonstop2h 04m

Chicago O'Hare Intl

Thu 8/21

12:45 pm-2:56 pm

Nonstop2h 11m

$197

TulsaChicago

TUL - ORD

TULORD

Tulsa

Thu 8/7

7:00 am-9:04 am

Nonstop2h 04m

Chicago O'Hare Intl

Mon 8/11

10:20 pm-12:21 am

Nonstop2h 01m

$199

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Fri 8/8

2:11 pm-4:10 pm

Nonstop1h 59m

Chicago O'Hare Intl

Mon 8/11

9:09 pm-11:10 pm

Nonstop2h 01m

$209

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Wed 8/13

6:05 am-12:32 am

1 stop18h 27m

Chicago O'Hare Intl

Sat 8/16

7:00 am-10:38 pm

1 stop15h 38m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 59 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 July 3, 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 July 3, 2025.

The most flights from USOK to CHI are scheduled on a Thursday (30 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip from Oklahoma to Chicago?

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 July 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Oklahoma to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,270 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,970 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,845 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.2
Good
709 reviews
Southwest
8.0
Very good
4,270 reviews

Comfort

8.0

Boarding

8.2

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $59 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $74 and United Airlines 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: Envoy Air (90%), Emirates (83%), Republic Airways (82%).

  • What are the cheapest flights from Oklahoma to Chicago?

    Looking for the cheapest flight from Oklahoma to Chicago? While on average our users pay $3,716, our data indicates the cheapest price to be $148. The most popular route (Dallas/Fort Worth - Chicago O'Hare Intl), is priced around $89.

  • 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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Miami to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
LaGuardia to Midway flights
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Hobby to Midway flights
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Philadelphia to Midway flights
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Oakland to O'Hare Intl flights
Newark to St. Louis flights
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Sacramento to O'Hare Intl flights
Love Field to O'Hare Intl flights
LaGuardia 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$118Average$193FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$167Average$363FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$192Average$356FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$268Average$411FlexibilityNo cancel feeOn-time69%

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