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$70+ Cheap flights from Oklahoma City (OKC) 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
OKC — CHI
May 10 — May 171
Sun 5/10
Sun 5/17
1 adult, Economy
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Find cheap flights from Oklahoma City to Chicago with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Oklahoma City Will Rogers World to Chicago are usually found in September or January, booked 49 days in advance, depart on a Thursday or Saturday and return on a Wednesday

Cheap flight deals from Oklahoma City to Chicago

Cheapest flights from Oklahoma City to Chicago
Explore the most affordable flight options available from Oklahoma City to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 10, 2026.

This Frontier deal was found by Cheapflights users on 4/8. 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 4/305:05 pm
OKC
-
MDW
1 stop5h 14m
Frontier
Mon 5/46:00 am
MDW
-
OKC
1 stop8h 21m
Frontier
Deal found 4/8$140
This Priceline deal was found by Cheapflights users on 4/5. 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.
Thu 4/305:05 pm
OKC
-
ORD
1 stop5h 34m
Frontier
Sun 5/35:50 am
ORD
-
OKC
1 stop10h 29m
Frontier
Deal found 4/5$140
This Frontier deal was found by Cheapflights users on 4/6. 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 4/305:05 pm
OKC
-
ORD
1 stop5h 34m
Frontier
Mon 5/45:50 am
ORD
-
OKC
1 stop8h 31m
Frontier
Deal found 4/6$141
This Expedia deal was found by Cheapflights users on 4/5. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:05 pm
OKC
-
ORD
1 stop5h 34m
Frontier
Sun 4/265:50 am
ORD
-
OKC
1 stop10h 29m
Frontier
Deal found 4/5$160
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/512:41 pm
OKC
-
ORD
2 stops19h 14m
Frontier
Tue 5/129:37 pm
ORD
-
OKC
1 stop15h 33m
Frontier
Deal found 4/5$163
This Frontier deal was found by Cheapflights users on 4/8. 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 4/235:05 pm
OKC
-
MDW
1 stop5h 14m
Frontier
Mon 4/276:00 am
MDW
-
OKC
1 stop8h 21m
Frontier
Deal found 4/8$180
This Priceline deal was found by Cheapflights users on 4/7. 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.
Mon 4/273:06 pm
OKC
-
ORD
1 stop7h 33m
Frontier
Thu 4/305:50 am
ORD
-
OKC
1 stop10h 30m
Frontier
Deal found 4/7$181
This Frontier deal was found by Cheapflights users on 4/5. 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.
Fri 4/176:07 pm
OKC
-
ORD
1 stop12h 01m
Frontier
Sun 4/195:59 am
ORD
-
OKC
1 stop10h 20m
Frontier
Deal found 4/5$201
This Priceline deal was found by Cheapflights users on 4/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Thu 5/146:00 am
MDW
-
OKC
1 stop7h 01m
Frontier
Deal found 4/9$205
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/61:55 pm
OKC
-
ORD
2 stops33h 06m
Frontier
Sat 5/99:37 pm
ORD
-
OKC
1 stop14h 19m
Frontier
Deal found 4/7$205
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Fri 5/18:29 pm
OKC
-
ORD
2 stops24h 43m
Multiple Airlines
Fri 5/89:37 pm
ORD
-
OKC
1 stop16h 19m
Multiple Airlines
Deal found 4/9$206
This Frontier deal was found by Cheapflights users on 4/6. 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 6/41:56 pm
OKC
-
MDW
1 stop8h 06m
Frontier
Tue 6/96:00 am
MDW
-
OKC
1 stop6h 53m
Frontier
Deal found 4/6$246

Find flight deals from Oklahoma City to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Oklahoma City (OKC) 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 April 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(Priceline)

One-way from

$70
(Frontier)

Popular in

March

Cheapest in

September

Average price

$357

Good round-trip deal

$392 or less

Good one-way deal

$223 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 City Will Rogers World to Chicago (CHI)
Search Deals
One-way flight from Oklahoma City Will Rogers World to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Oklahoma City Will Rogers World to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Oklahoma City Will Rogers World to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oklahoma City 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 April 10, 2026.
Use the filters below to find and compare flights from Oklahoma City to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 5/5

5:05 am-6:55 am

Nonstop1h 50m

Chicago Midway

Tue 5/12

10:20 am-12:30 pm

Nonstop2h 10m

$319

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 4/30

4:00 pm-5:50 pm

Nonstop1h 50m

Chicago Midway

Mon 5/4

10:05 pm-12:15 am

Nonstop2h 10m

$335

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 5/6

3:05 pm-4:55 pm

Nonstop1h 50m

Chicago Midway

Sat 5/9

6:00 am-1:45 pm

1 stop7h 45m

$337

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Tue 5/5

2:45 pm-10:21 pm

1 stop7h 36m

Chicago O'Hare Intl

Tue 5/12

11:26 am-4:33 pm

1 stop5h 07m

$339

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Wed 5/6

8:35 am-4:20 pm

1 stop7h 45m

Chicago Midway

Wed 5/13

9:40 am-4:10 pm

2 stops6h 30m

$344

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Thu 5/14

6:10 pm-11:55 pm

1 stop5h 45m

Chicago Midway

Mon 5/18

10:05 pm-12:15 am

Nonstop2h 10m

$345

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Tue 5/19

7:25 pm-9:50 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 5/24

12:09 pm-2:30 pm

Nonstop2h 21m

$356

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Fri 6/5

5:45 pm-8:14 pm

Nonstop2h 29m

Chicago O'Hare Intl

Mon 6/8

12:45 pm-3:17 pm

Nonstop2h 32m

$364

Oklahoma CityChicago

OKC - MDW

OKCMDW

Oklahoma City Will Rogers World

Tue 5/19

5:05 am-6:55 am

Nonstop1h 50m

Chicago Midway

Sun 5/24

8:45 pm-10:55 pm

Nonstop2h 10m

$364

Oklahoma CityChicago

OKC - ORD

OKCORD

Oklahoma City Will Rogers World

Thu 5/7

1:40 pm-11:55 pm

2 stops10h 15m

Chicago O'Hare Intl

Sat 5/9

2:05 pm-9:45 pm

2 stops7h 40m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/6

Showing 1-10 of 37 resultsSorted by cheapest first
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Compare providers for flights from Oklahoma City to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oklahoma City to Chicago in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oklahoma City-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oklahoma City-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oklahoma City-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oklahoma City-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oklahoma City-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Oklahoma City to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oklahoma City 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 City to Chicago

How far ahead should I book a flight from Oklahoma City to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Oklahoma City to Chicago. Price data was last updated on April 3, 2026.

To ensure you get the cheapest price possible for a flight from Oklahoma City to Chicago, you should look to book at least 48 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Oklahoma City to Chicago?

Currently, January is the cheapest month in which you can book a flight from Oklahoma City to Chicago (average of $133). Flying from Oklahoma City to Chicago in November is currently the most expensive (average of $298). 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 OKC to CHI?

Find hourly flight availability from Oklahoma City 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 April 10, 2026.

One of the essential ways to save on airfare from Oklahoma City to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 27% on airfare.

What is the cheapest day to fly from Oklahoma City to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Oklahoma City to Chicago. Price data was last updated on April 4, 2026.

Travelers seeking maximum savings on their Oklahoma City to Chicago flight should consider departing on Saturday mornings when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Oklahoma City to Chicago

Explore weekly flight availability from Oklahoma City 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 April 10, 2026.

The most flights from OKC to CHI are scheduled on a Wednesday (34 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 on average).

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

What’s the top layover airport for flights from Oklahoma City to Chicago?

Share of 1-stop round-trip flights from Oklahoma City to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Atlanta (ATL) – chosen by Cheapflights users on 50% of 1-stop itineraries from Oklahoma City to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Oklahoma City to Chicago?

Average round-trip fare for 1-stop flights from Oklahoma City to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $313.

What’s the fastest layover option from Oklahoma City to Chicago?

Shortest average travel time for 1-stop one-way flights from Oklahoma City to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 14m.

Which airport typically offers the quickest layover for flights from Oklahoma City to Chicago?

Average layover duration for 1-stop one-way flights from Oklahoma City to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 3h 04m.

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 April 10, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Oklahoma City to Chicago have to say. 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
4,334 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,334 reviews
Southwest
8.0
Very good
4,334 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,561 reviews
Southwest
8.0
Very good
4,334 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,564 reviews
Southwest
8.0
Very good
4,334 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,997 reviews
Southwest
8.0
Very good
4,334 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Oklahoma City to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Oklahoma City to Chicago?

    Oklahoma City Will Rogers World (OKC) is the airport you will fly out of if you book a flight from Oklahoma City to Chicago. You should not have trouble finding flights to Chicago from Will Rogers World; the airport handles an average of 26 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 4 airlines have flights from the Oklahoma City airport to Chicago. It is only a 7.0 mi journey to Will Rogers World (OKC) from Oklahoma City’s city center.

  • How long is the flight from Oklahoma City to Chicago?

    Southwest, Delta, and American Airlines can get you from Oklahoma City to Chicago in just under 1h 50m. Your travel time can differ by up to 5h 46m. The distance between Oklahoma City and Chicago is about 690 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Oklahoma City to Chicago round-trip?

    Cheapflights users have booked flights from Oklahoma City to Chicago round-trip from $138. Other airlines that can offer you cheap pricing are Southwest, from $240, and United Airlines, from $243. Users have found that Frontier is 60% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Oklahoma City to Chicago one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $123. American Airlines flights start at $128 while deals on United Airlines start at $143 one-way.

  • What are the most reliable airlines from Oklahoma City to Chicago?

    Before booking your flight to Chicago from Oklahoma City, check out the most reliable airlines to get you to your destination on time: Envoy Air (100%), Emirates (89%), Air Canada( 85%).

  • What are the cheapest flights from Oklahoma City to Chicago?

    Looking for the cheapest flight from Oklahoma City to Chicago? While on average our users pay $1,016, our data indicates the cheapest price to be $185. The most popular route (Oklahoma City Will Rogers World - Chicago O'Hare Intl), is priced around $206.

  • Can I find deals for flights from Oklahoma City to Chicago that include hotel bookings?

    Yes. In addition to deals on Oklahoma City to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oklahoma City to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oklahoma City to Chicago.

  • Can I find deals for business class flights from Oklahoma City to Chicago?

    Yes. Cheapflights offers flight deals from Oklahoma City 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 City to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Oklahoma City to Chicago (average of $133). Flying from Oklahoma City to Chicago in November is currently the most expensive (average of $298). 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
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Top 4 airlines flying from Oklahoma City to Chicago

Discover the top 4 airlines that operate flights from Oklahoma City 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 April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$138Average$188FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$240Average$393FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$243Average$401FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$248Average$368FlexibilityNo cancel feeOn-time71%

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