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$96+ Cheap flights from Orlando (MCO) 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Aug 6 — Aug 131
Thu 8/6
Thu 8/13
1 adult, Economy
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Find cheap flights from Orlando to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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3. Compare prices and book

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Cheapflights Tip: The best prices from Orlando to Chicago are usually found in February or September, booked 70 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap flight deals from Orlando to Chicago

Cheapest flights from Orlando to Chicago
Explore the most affordable flight options available from Orlando to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 7, 2026.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:58 am
MCO
-
ORD
Nonstop3h 18m
Frontier
Tue 10/274:44 pm
ORD
-
MCO
Nonstop2h 53m
Frontier
Deal found 7/3$199
This Frontier deal was found by Cheapflights users on 7/5. 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.
Tue 7/288:59 pm
MCO
-
ORD
Nonstop3h 11m
Frontier
Tue 8/45:13 pm
ORD
-
MCO
Nonstop3h 12m
Frontier
Deal found 7/5$200
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/39:00 pm
MCO
-
ORD
Nonstop3h 08m
Frontier
Mon 9/76:05 am
ORD
-
MCO
Nonstop2h 58m
Frontier
Deal found 7/2$201
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:05 am
MCO
-
MDW
1 stop4h 15m
Southwest
Wed 8/123:40 pm
MDW
-
MCO
Nonstop2h 35m
Southwest
Deal found 7/6$201
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:59 pm
MCO
-
ORD
Nonstop3h 11m
Frontier
Sun 8/165:13 pm
ORD
-
MCO
Nonstop3h 12m
Frontier
Deal found 7/2$202
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.
Tue 7/218:59 pm
MCO
-
ORD
Nonstop3h 11m
Frontier
Sat 7/255:13 pm
ORD
-
MCO
Nonstop3h 12m
Frontier
Deal found 7/2$203
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:00 am
MCO
-
ORD
Nonstop3h 11m
Frontier
Thu 8/65:13 pm
ORD
-
MCO
Nonstop3h 12m
Frontier
Deal found 7/3$204
This Super.com deal was found by Cheapflights users on 7/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:59 pm
MCO
-
ORD
Nonstop3h 11m
Frontier
Sat 8/225:59 pm
ORD
-
MCO
Nonstop3h 12m
Frontier
Deal found 7/6$205
This Cheapflightsfares deal was found by Cheapflights users on 7/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:00 pm
MCO
-
ORD
Nonstop3h 08m
Frontier
Sat 8/295:59 pm
ORD
-
MCO
Nonstop3h 12m
Frontier
Deal found 7/7$206
This Southwest deal was found by Cheapflights users on 7/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:00 am
MCO
-
MDW
1 stop4h 05m
Southwest
Wed 8/128:15 am
MDW
-
MCO
1 stop4h 50m
Southwest
Deal found 7/6$206
This Cheapflightsfares deal was found by Cheapflights users on 7/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:30 am
MCO
-
ORD
1 stop7h 30m
Frontier
Sat 9/57:44 pm
ORD
-
MCO
Nonstop2h 45m
Frontier
Deal found 7/7$207
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.
Tue 8/45:24 pm
MCO
-
MDW
1 stop5h 39m
Frontier
Wed 8/54:45 pm
MDW
-
MCO
1 stop6h 14m
Frontier
Deal found 7/2$207

Find flight deals from Orlando to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (MCO) 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 July 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(Frontier)

One-way from

$96
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$241

Good round-trip deal

$278 or less

Good one-way deal

$157 or less
Provider with most accurate pricing for Orlando-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando-Chicago (CHI) flights.
Search Deals
From Orlando to Chicago (CHI)
Search Deals
One-way flight from Orlando to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Orlando to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Orlando to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando 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 7, 2026.
Use the filters below to find and compare flights from Orlando Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 8/5

9:05 am-12:20 pm

1 stop4h 15m

Chicago Midway

Wed 8/12

7:40 am-2:35 pm

2 stops5h 55m

$216

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 8/5

9:00 am-12:05 pm

1 stop4h 05m

Chicago Midway

Tue 8/11

12:20 pm-4:00 pm

Nonstop2h 40m

$223

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 8/20

8:15 am-10:00 am

Nonstop2h 45m

Chicago Midway

Tue 8/25

9:40 am-1:15 pm

Nonstop2h 35m

$232
Quickest round-trip

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 8/26

10:20 am-12:05 pm

Nonstop2h 45m

Chicago Midway

Mon 8/31

5:00 am-8:30 am

Nonstop2h 30m

$232

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 8/1

3:40 pm-8:33 pm

1 stop5h 53m

Chicago O'Hare Intl

Tue 8/4

5:30 am-10:57 am

1 stop4h 27m

$237

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 8/26

7:40 am-9:25 am

Nonstop2h 45m

Chicago Midway

Fri 8/28

1:00 pm-7:15 pm

1 stop5h 15m

$240

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Thu 8/20

9:05 am-3:09 pm

1 stop7h 04m

Chicago Greater Rockford

Sun 8/23

3:59 pm-2:25 pm

1 stop21h 26m

$243

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Thu 8/27

9:05 am-3:09 pm

1 stop7h 04m

Chicago Greater Rockford

Sun 8/30

3:59 pm-8:19 pm

1 stop27h 20m

$246

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 8/4

4:00 pm-8:10 pm

1 stop5h 10m

Chicago Midway

Tue 8/11

7:40 am-2:35 pm

2 stops5h 55m

$249

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 8/24

6:55 pm-11:57 pm

1 stop6h 02m

Chicago O'Hare Intl

Sat 8/29

8:05 am-4:40 pm

1 stop7h 35m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/7

Showing 1-10 of 59 resultsSorted by cheapest first
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Compare providers for flights from Orlando 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 Orlando to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Super.comPrice Accuracy-Trust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
WAYAPrice 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 Orlando Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando Airport-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 Orlando Airport-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 Orlando to Chicago

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

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

Currently, February is the cheapest month in which you can book a flight from Orlando Airport to Chicago (average of $40). Flying from Orlando Airport to Chicago in March is currently the most expensive (average of $897). 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 MCO to CHI?

Find hourly flight availability from Orlando 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 7, 2026.

It’s typically best to fly out from Orlando Airport to Chicago in the evening. Doing so could potentially save you 53% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from Orlando Airport to Chicago

Explore weekly flight availability from Orlando 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 7, 2026.

The most flights from MCO to CHI are scheduled on a Friday (82 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (59 on average).

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

How often are flights from Orlando to Chicago delayed?

About 18% of weekly flights between Orlando and Chicago have experienced delays in the past year, with the average delay time being 150 minutes.

What is the most punctual flight time for Orlando to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Orlando to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.

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

The best time to book flights from Orlando Airport to Chicago is 81 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest day to fly from Orlando Airport to Chicago?

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

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

The best insider tips for Orlando Airport 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 Orlando Airport to Chicago trip
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on British Airways

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

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
Paul Rubio

Paul Rubio

Expert on MCO

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

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 July 7, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Orlando Airport 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
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,945 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,783 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
JetBlue
7.1
Good
3,009 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,841 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

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

  • How long is the flight from Orlando Airport to Chicago?

    For as low as $318, Southwest can have you in Chicago from Orlando Airport in 3h 05m. There are 1006 mi between Orlando Airport and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $68, Frontier will fly you from Orlando Airport to Chicago and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and United Airlines - these airlines can fly you to your destination from $157 and $157, respectively. Users have found that Frontier is 66% cheaper than the other options available to this destination.

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

    The cheapest airlines for a one-way flight from Orlando Airport to Chicago are Frontier ($41), Southwest ($78), and American Airlines ($78).

  • What are the most popular routes from Orlando Airport to Chicago?

    The most popular route from Orlando Airport to Chicago is Orlando - Chicago O'Hare Intl. You may also consider Orlando - Chicago Midway or Orlando - Chicago Greater Rockford.

  • What are the most reliable airlines from Orlando Airport to Chicago?

    No one likes to see their flight delayed. When booking a flight from Orlando Airport to Chicago consider choosing ITA Airways (95%), Cathay Pacific (90%) or Japan Airlines (89%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Orlando Airport to Chicago?

    Looking at all options, your cheapest flight can be booked for $94. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $168 on average, our data indicates $1,554 when flying from Orlando Airport to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Orlando 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 Orlando Airport to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Orlando Airport to Chicago (average of $40). Flying from Orlando Airport to Chicago in March is currently the most expensive (average of $897). 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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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Top 4 airlines flying from Orlando to Chicago

Discover the top 4 airlines that operate flights from Orlando 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 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$184FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$272FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$326FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$292FlexibilityNo cancel feeOn-time71%

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