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$99+ Cheap flights from Tampa (TPA) 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — CHI
jul. 21 — jul. 281
di 7/21
di 7/28
1 adult, Economy
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Find cheap flights from Tampa to Chicago with Cheapflights

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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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Cheapflights Tip: The best prices from Tampa to Chicago are usually found in October or January, booked 83 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from Tampa to Chicago

Cheapest flights from Tampa to Chicago
Explore the most affordable flight options available from Tampa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on juni 21, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
di 8/1110:27 am
TPA
-
ORD
1 stop6h 33m
Frontier
wo 8/121:50 pm
ORD
-
TPA
1 stop7h 25m
Frontier
Deal found 6/16$208
This Expedia deal was found by Cheapflights users on 6/16. 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.
wo 8/52:10 pm
TPA
-
MDW
1 stop8h 53m
Frontier
wo 8/126:05 am
MDW
-
TPA
1 stop11h 30m
Frontier
Deal found 6/16$210
This Frontier deal was found by Cheapflights users on 6/16. 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.
wo 7/222:25 pm
TPA
-
MDW
1 stop8h 38m
Frontier
wo 8/56:05 am
MDW
-
TPA
1 stop11h 30m
Frontier
Deal found 6/16$220
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 7/142:25 pm
TPA
-
ORD
1 stop6h 28m
Frontier
di 7/281:50 pm
ORD
-
TPA
1 stop6h 26m
Frontier
Deal found 6/18$224
This Southwest deal was found by Cheapflights users on 6/20. 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.
do 8/69:30 am
TPA
-
MDW
2 stops7h 15m
Southwest
za 8/87:40 am
MDW
-
TPA
1 stop6h 10m
Southwest
Deal found 6/20$225
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
di 7/142:25 pm
TPA
-
ORD
1 stop6h 28m
Frontier
di 7/211:50 pm
ORD
-
TPA
1 stop6h 26m
Frontier
Deal found 6/16$225
This Trip.com deal was found by Cheapflights users on 6/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
di 6/304:46 pm
TPA
-
MDW
1 stop6h 25m
Frontier
za 7/411:59 am
MDW
-
TPA
1 stop6h 53m
Frontier
Deal found 6/18$226
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
za 7/41:18 pm
TPA
-
ORD
1 stop7h 32m
Frontier
wo 7/81:50 pm
ORD
-
TPA
1 stop6h 26m
Frontier
Deal found 6/19$226
This Frontier deal was found by Cheapflights users on 6/20. 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.
za 8/222:25 pm
TPA
-
MDW
1 stop9h 22m
Frontier
di 8/256:05 am
MDW
-
TPA
1 stop11h 44m
Frontier
Deal found 6/20$227
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
wo 7/158:57 pm
TPA
-
RFD
1 stop14h 40m
Multiple Airlines
zo 7/1911:27 am
RFD
-
TPA
1 stop18h 56m
Multiple Airlines
Deal found 6/17$227
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
za 8/84:32 pm
TPA
-
ORD
1 stop5h 23m
Delta
ma 8/105:30 am
ORD
-
TPA
1 stop5h 59m
Delta
Deal found 6/18$227
This Southwest deal was found by Cheapflights users on 6/19. 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.
do 8/209:40 am
TPA
-
MDW
2 stops7h 20m
Southwest
ma 8/2412:20 pm
MDW
-
TPA
1 stop3h 50m
Southwest
Deal found 6/19$228

Find flight deals from Tampa to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Tampa (TPA) 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 juni 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Kiwi.com)

One-way from

$99
(Kiwi.com)

Popular in

June

Cheapest in

October

Average price

$328

Good round-trip deal

$238 or less

Good one-way deal

$144 or less
Provider with most accurate pricing for Tampa-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tampa-Chicago (CHI) flights.
Search Deals
From Tampa to Chicago (CHI)
Search Deals
One-way flight from Tampa to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Tampa to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Tampa to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tampa 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 juni 21, 2026.
Use the filters below to find and compare flights from Tampa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

za 10/17

12:18 pm-4:25 pm

1 stop5h 07m

Chicago Midway

za 10/24

9:30 am-4:41 pm

1 stop6h 11m

$227

TampaChicago

TPA - MDW

TPAMDW

Tampa

di 9/8

5:15 am-10:37 am

1 stop6h 22m

Chicago Midway

za 9/12

11:35 am-4:43 pm

1 stop4h 08m

$227

TampaChicago

TPA - ORD

TPAORD

Tampa

do 8/6

7:59 pm-11:57 pm

1 stop4h 58m

Chicago O'Hare Intl

do 8/20

8:48 am-4:48 pm

1 stop7h 00m

$227

TampaChicago

TPA - ORD

TPAORD

Tampa

do 9/10

8:05 am-12:59 pm

1 stop5h 54m

Chicago O'Hare Intl

ma 9/21

8:55 am-4:51 pm

1 stop6h 56m

$227

TampaChicago

TPA - RFD

TPARFD

Tampa

wo 7/8

8:57 pm-10:37 am

1 stop14h 40m

Chicago Greater Rockford

zo 7/12

11:27 am-7:23 am

1 stop18h 56m

$230

TampaChicago

TPA - ORD

TPAORD

Tampa

di 7/14

7:42 pm-9:53 pm

Nonstop3h 11m

Chicago O'Hare Intl

di 7/21

8:40 am-3:25 pm

1 stop5h 45m

$237

TampaChicago

TPA - RFD

TPARFD

Tampa

za 8/8

8:57 pm-10:47 am

1 stop14h 50m

Chicago Greater Rockford

ma 8/10

6:26 pm-11:40 am

2 stops16h 14m

$255
Quickest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

di 8/4

5:35 pm-7:10 pm

Nonstop2h 35m

Chicago Midway

di 8/11

7:30 am-11:00 am

Nonstop2h 30m

$271

TampaChicago

TPA - RFD

TPARFD

Tampa

wo 7/8

8:57 pm-10:37 am

1 stop14h 40m

Chicago Greater Rockford

ma 7/13

7:50 pm-11:40 am

2 stops14h 50m

$278

TampaChicago

TPA - ORD

TPAORD

Tampa

zo 7/26

7:42 pm-9:53 pm

Nonstop3h 11m

Chicago O'Hare Intl

za 8/1

2:30 pm-6:24 pm

Nonstop2h 54m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/20

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Compare providers for flights from Tampa 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 Tampa to Chicago in June.
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
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Super.comPrice Accuracy-Trust Score*3 stars
GotogatePrice Accuracy2 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 Tampa-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tampa-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tampa-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Tampa-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 Tampa-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 Tampa to Chicago

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

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

Currently, April is the cheapest month in which you can book a flight from Tampa to Chicago (average of $42). Flying from Tampa to Chicago in February is currently the most expensive (average of $683). 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 TPA to CHI?

Find hourly flight availability from Tampa 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 juni 21, 2026.

One of the essential ways to save on airfare from Tampa to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 23% on airfare.

Weekly flight availability from Tampa to Chicago

Explore weekly flight availability from Tampa 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 juni 21, 2026.

The most flights from TPA to CHI are scheduled on a Sunday (53 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (28 on average).

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

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

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

Atlanta (ATL) – chosen by Cheapflights users on 71% of 1-stop itineraries from Tampa to Chicago on Cheapflights.

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

Average round-trip fare for 1-stop flights from Tampa 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 $263.

What’s the fastest layover option from Tampa to Chicago?

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

Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 5h 01m.

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

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

Flights via Atlanta (ATL) offer the fastest connection on this route, with an average layover time of 2h 47m.

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

Booking 63 days in advance of your planned departure date is, on average, the best time to get cheap flights from Tampa to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Use this chart to determine the cheapest time to fly round-trip from Tampa to Chicago. Price data was last updated on June 20, 2026.

Travelers seeking maximum savings on their Tampa to Chicago flight should consider departing on Friday afternoons 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.

The best insider tips for Tampa 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 Tampa to Chicago trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier

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, MDW and TPA

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

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 juni 21, 2026.
Read through reviews of airlines operating flights from Tampa to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,243 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Food

7.0

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
4,243 reviews
Southwest
7.9
Good
4,243 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Food

7.0

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
9,866 reviews
Southwest
7.9
Good
4,243 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Food

7.0

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
11,724 reviews
Southwest
7.9
Good
4,243 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Food

7.0

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
2,990 reviews
Southwest
7.9
Good
4,243 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Food

7.0

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
2,877 reviews
Southwest
7.9
Good
4,243 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

Food

7.0

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 Tampa 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 Tampa to Chicago?

    Located just 4.9 mi from the city center, Tampa is the airport most travelers will use when flying to Chicago from Tampa. Booking flights from Tampa (TPA) to Chicago should be relatively easy as there are 41 daily outbound flights to Chicago from 6 different airlines.

  • How long is the flight from Tampa to Chicago?

    Departing from Tampa to Chicago will take you 2h 35m. The distance between Tampa and Chicago is about 998 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 Tampa to Chicago round-trip?

    Cheapflights users have booked flights from Tampa to Chicago round-trip from $46. Other airlines that can offer you cheap pricing are JetBlue, from $146, and American Airlines, from $156. These flights start at 80% lower than the current average price 3 months from now.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $49. Users have also found prices from $78 and $79 on Southwest and American Airlines, respectively.

  • What are the most popular routes from Tampa to Chicago?

    When deciding which route to take from Tampa to Chicago consider Tampa - Chicago O'Hare Intl, Tampa - Chicago Midway or Tampa - Chicago Greater Rockford as they are the most popular.

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

    Consider ANA (89%), Austrian Airlines (85%) or SWISS (84%) when booking your flight. These represent the most reliable airlines when flying from Tampa to Chicago.

  • What are the cheapest flights from Tampa to Chicago?

    Looking at all options, your cheapest flight can be booked for $144. While the most popular route (Tampa - Chicago O'Hare Intl) can be booked for $193 on average, our data indicates $1,102 when flying from Tampa to Chicago.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Tampa to Chicago (average of $42). Flying from Tampa to Chicago in February is currently the most expensive (average of $683). 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
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Tampa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Tampa to Chicago

Discover the top 6 airlines that operate flights from Tampa 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 juni 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$170FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$146Average$324FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$156Average$300FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$307FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$159Average$349FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$802FlexibilityNo cancel feeOn-timeN/A

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