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$115+ Cheap flights from Jacksonville (JAX) 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Apr 21 — Apr 281
Tue 4/21
Tue 4/28
1 adult, Economy
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Find cheap flights from Jacksonville to Chicago with Cheapflights

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Cheapflights Tip: The best prices from Jacksonville to Chicago are usually found in September or August, booked 71 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap flight deals from Jacksonville to Chicago

Cheapest flights from Jacksonville to Chicago
Explore the most affordable flight options available from Jacksonville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 22, 2026.

This Southwest deal was found by Cheapflights users on 3/17. 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.
Tue 4/216:30 am
JAX
-
ORD
1 stop7h 20m
Southwest
Wed 5/611:55 am
ORD
-
JAX
2 stops9h 20m
Southwest
Deal found 3/17$258
This American Airlines deal was found by Cheapflights users on 3/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:45 am
JAX
-
ORD
Nonstop3h 04m
American Airlines
Mon 5/49:10 am
ORD
-
JAX
Nonstop2h 37m
American Airlines
Deal found 3/17$260
This Southwest deal was found by Cheapflights users on 3/17. 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.
Tue 4/217:20 am
JAX
-
MDW
Nonstop2h 30m
Southwest
Thu 5/76:50 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Deal found 3/17$260
This United Airlines deal was found by Cheapflights users on 3/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:00 am
JAX
-
ORD
Nonstop2h 50m
United Airlines
Tue 4/281:00 pm
ORD
-
JAX
1 stop6h 02m
United Airlines
Deal found 3/18$261
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:05 pm
JAX
-
MDW
Nonstop2h 30m
Southwest
Tue 4/284:50 pm
MDW
-
JAX
1 stop3h 40m
Southwest
Deal found 3/18$261
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Mon 4/206:49 pm
JAX
-
ORD
1 stop15h 51m
Multiple Airlines
Wed 4/227:15 pm
ORD
-
JAX
2 stops22h 20m
Multiple Airlines
Deal found 3/19$262
This Southwest deal was found by Cheapflights users on 3/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/141:15 pm
JAX
-
ORD
2 stops9h 40m
Southwest
Tue 4/2111:55 am
ORD
-
JAX
2 stops9h 20m
Southwest
Deal found 3/19$263
This Southwest deal was found by Cheapflights users on 3/17. 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.
Tue 4/1411:50 am
JAX
-
MDW
2 stops8h 35m
Southwest
Tue 4/2110:15 am
MDW
-
JAX
2 stops9h 30m
Southwest
Deal found 3/17$263
This American Airlines deal was found by Cheapflights users on 3/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:00 am
JAX
-
ORD
1 stop6h 49m
American Airlines
Wed 5/133:04 pm
ORD
-
JAX
Nonstop2h 36m
American Airlines
Deal found 3/17$265
This Southwest deal was found by Cheapflights users on 3/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:20 pm
JAX
-
MDW
1 stop6h 15m
Southwest
Sat 4/183:45 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Deal found 3/19$265
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Mon 4/278:00 am
JAX
-
ORD
Nonstop2h 50m
United Airlines
Wed 4/291:00 pm
ORD
-
JAX
1 stop6h 02m
United Airlines
Deal found 3/17$266
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Thu 4/166:25 pm
JAX
-
ORD
1 stop16h 58m
Multiple Airlines
Thu 4/231:12 pm
ORD
-
JAX
2 stops29h 54m
Multiple Airlines
Deal found 3/17$268

Find flight deals from Jacksonville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (JAX) 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 March 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$258
(Southwest)

One-way from

$115
(Frontier)

Popular in

March

Cheapest in

September

Average price

$384

Good round-trip deal

$352 or less

Good one-way deal

$189 or less
Provider with most accurate pricing for Jacksonville-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jacksonville-Chicago (CHI) flights.
Search Deals
From Jacksonville to Chicago (CHI)
Search Deals
One-way flight from Jacksonville to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Jacksonville to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Jacksonville to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jacksonville 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 March 22, 2026.
Use the filters below to find and compare flights from Jacksonville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 4/21

6:30 am-12:50 pm

1 stop7h 20m

Chicago O'Hare Intl

Wed 5/6

11:55 am-10:15 pm

2 stops9h 20m

$258

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 4/27

8:00 am-9:50 am

Nonstop2h 50m

Chicago O'Hare Intl

Wed 4/29

4:00 pm-7:34 pm

Nonstop2h 34m

$260

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 4/21

11:50 am-7:45 pm

2 stops8h 55m

Chicago Midway

Wed 5/6

10:10 am-5:20 pm

2 stops6h 10m

$263

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 4/20

6:59 pm-10:28 pm

1 stop4h 29m

Chicago Midway

Tue 4/21

5:21 pm-10:50 pm

1 stop4h 29m

$280

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 4/25

3:05 pm-4:35 pm

Nonstop2h 30m

Chicago Midway

Mon 4/27

6:50 pm-10:05 pm

Nonstop2h 15m

$282

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 4/20

7:59 pm-11:59 pm

1 stop5h 00m

Chicago O'Hare Intl

Thu 4/23

5:15 am-12:09 pm

1 stop5h 54m

$307

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 5/1

7:03 pm-11:44 pm

1 stop5h 41m

Chicago O'Hare Intl

Tue 5/5

11:00 am-2:38 pm

Nonstop2h 38m

$308

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 5/1

7:50 am-9:20 am

Nonstop2h 30m

Chicago Midway

Tue 5/5

6:00 pm-9:15 pm

Nonstop2h 15m

$315

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 5/1

7:50 am-9:20 am

Nonstop2h 30m

Chicago Midway

Wed 5/6

6:00 pm-9:15 pm

Nonstop2h 15m

$315

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 5/27

1:15 pm-9:55 pm

2 stops9h 40m

Chicago O'Hare Intl

Fri 5/29

2:40 pm-10:55 pm

1 stop7h 15m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

Showing 1-10 of 41 resultsSorted by cheapest first
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2
3
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5

Compare providers for flights from Jacksonville 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 Jacksonville to Chicago in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
MytripPrice Accuracy3 starsTrust Score*3 stars

*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 Jacksonville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jacksonville-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jacksonville-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 Jacksonville-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 Jacksonville to Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from Jacksonville to Chicago. Price data was last updated on March 13, 2026.

The price you pay for your flight from Jacksonville to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 71 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, May is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $98). Flying from Jacksonville to Chicago in April is currently the most expensive (average of $271). 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 JAX to CHI?

Find hourly flight availability from Jacksonville 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 March 22, 2026.

One of the essential ways to save on airfare from Jacksonville to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 22% on airfare.

What is the cheapest day to fly from Jacksonville to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Jacksonville to Chicago. Price data was last updated on March 14, 2026.

Travelers seeking maximum savings on their Jacksonville to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Jacksonville to Chicago

Explore weekly flight availability from Jacksonville 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 March 22, 2026.

The most flights from JAX to CHI are scheduled on a Monday (26 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (16 on average).

The best insider tips for Jacksonville to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Jacksonville to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Matt Meltzer

Matt Meltzer

Expert on JAX

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

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 March 22, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andJetBlue from Jacksonville to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,324 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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
9,459 reviews
Southwest
8.0
Very good
4,324 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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.
JetBlue
7.2
Good
2,911 reviews
Southwest
8.0
Very good
4,324 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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
11,486 reviews
Southwest
8.0
Very good
4,324 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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
3,020 reviews
Southwest
8.0
Very good
4,324 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Comfort

8.0

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 Jacksonville 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 Jacksonville to Chicago?

    Located just 11.2 mi from the city center, Jacksonville is the airport most travelers will use when flying to Chicago from Jacksonville. Booking flights from Jacksonville (JAX) to Chicago should be relatively easy as there are 23 daily outbound flights to Chicago from 5 different airlines.

  • How long is the flight from Jacksonville to Chicago?

    Airlines like Southwest, United Airlines, and Delta fly from Jacksonville to Chicago in about 2h 50m. The time it takes to get you to your destination can typically vary by up to 4h 30m. Jacksonville and Chicago are separated by a distance of 865 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Flying on Delta is currently your cheapest option to Chicago, with prices starting at $121. Additional round-trip tickets that might be worth considering are offered by Frontier and American Airlines, with the lowest prices starting at $136 and $179, respectively. Delta is priced at 64% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airlines for a one-way flight from Jacksonville to Chicago are Frontier ($71), American Airlines ($99), and Southwest ($123).

  • What are the most reliable airlines from Jacksonville to Chicago?

    Consider SkyWest Airlines (100%), Republic Airways (83%) or ANA (82%) when booking your flight. These represent the most reliable airlines when flying from Jacksonville to Chicago.

  • What are the cheapest flights from Jacksonville to Chicago?

    Looking for the cheapest flight from Jacksonville to Chicago? While on average our users pay $929, our data indicates the cheapest price to be $138. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $221.

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

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

  • How can I find direct flights from Jacksonville to Chicago?

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

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

    Yes. Cheapflights offers flight deals from Jacksonville 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 Jacksonville to Chicago?

    Currently, May is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $98). Flying from Jacksonville to Chicago in April is currently the most expensive (average of $271). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Jacksonville to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Jacksonville to Chicago

Discover the top 5 airlines that operate flights from Jacksonville 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 March 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$121Average$294FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$136Average$247FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$179Average$338FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$203Average$371FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$375FlexibilityNo cancel feeOn-time69%

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