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$90+ Cheap flights from Denver (DEN) 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
DEN — CHI
Apr 25 — May 21
Sat 4/25
Sat 5/2
1 adult, Economy
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Find cheap flights from Denver 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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Cheapflights Tip: The best prices from Denver Intl to Chicago are usually found in August or September, booked 79 days in advance, depart on a Thursday or Friday and return on a Saturday

Cheap flight deals from Denver to Chicago

Cheapest flights from Denver to Chicago
Explore the most affordable flight options available from Denver to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2026.

This Southwest deal was found by Cheapflights users on 3/24. 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 5/1211:25 am
DEN
-
ORD
Nonstop2h 35m
Southwest
Wed 5/1311:55 am
ORD
-
DEN
2 stops8h 30m
Southwest
Deal found 3/24$174
This United Airlines deal was found by Cheapflights users on 3/24. 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.
Tue 5/58:20 pm
DEN
-
ORD
Nonstop2h 37m
United Airlines
Sat 5/98:20 pm
ORD
-
DEN
Nonstop2h 59m
United Airlines
Deal found 3/24$175
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:20 pm
DEN
-
MDW
Nonstop2h 20m
Southwest
Tue 4/288:50 pm
MDW
-
DEN
Nonstop2h 45m
Southwest
Deal found 3/24$175
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sat 4/49:00 pm
DEN
-
ORD
Nonstop2h 38m
Frontier
Thu 4/95:15 am
ORD
-
DEN
1 stop7h 54m
Frontier
Deal found 3/24$176
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:35 am
DEN
-
MDW
Nonstop2h 20m
Southwest
Tue 5/126:30 am
MDW
-
DEN
Nonstop2h 40m
Southwest
Deal found 3/23$176
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 5/75:05 am
DEN
-
ORD
2 stops8h 00m
Multiple Airlines
Mon 5/119:42 pm
ORD
-
DEN
Nonstop3h 10m
Multiple Airlines
Deal found 3/25$177
This Cheapflightsfares deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/119:00 pm
DEN
-
ORD
Nonstop2h 38m
Frontier
Sun 4/127:40 am
ORD
-
DEN
1 stop17h 56m
Frontier
Deal found 3/25$178
This Trip.com deal was found by Cheapflights users on 3/24. 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.
Fri 4/2411:59 pm
DEN
-
MDW
1 stop15h 14m
Frontier
Sun 4/262:00 pm
MDW
-
DEN
1 stop19h 11m
Frontier
Deal found 3/24$178
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 4/91:31 pm
DEN
-
ORD
1 stop7h 16m
Frontier
Sun 4/125:25 am
ORD
-
DEN
1 stop27h 45m
Frontier
Deal found 3/25$179
This Frontier deal was found by Cheapflights users on 3/21. 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.
Wed 5/65:05 am
DEN
-
MDW
1 stop8h 07m
Frontier
Wed 5/1312:04 pm
MDW
-
DEN
1 stop11h 20m
Frontier
Deal found 3/21$179
This Frontier deal was found by Cheapflights users on 3/24. 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 5/2911:54 pm
DEN
-
ORD
1 stop7h 01m
Frontier
Sat 5/304:05 pm
ORD
-
DEN
1 stop9h 13m
Frontier
Deal found 3/24$180
This Frontier deal was found by Cheapflights users on 3/24. 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 5/295:05 am
DEN
-
MDW
1 stop8h 07m
Frontier
Sat 5/303:07 pm
MDW
-
DEN
1 stop9h 41m
Frontier
Deal found 3/24$180

Find flight deals from Denver to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Denver (DEN) 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 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$174
(Southwest)

One-way from

$90
(Cheapflightsfares)

Popular in

March

Cheapest in

August

Average price

$275

Good round-trip deal

$268 or less

Good one-way deal

$149 or less
Provider with most accurate pricing for Denver Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Denver Intl-Chicago (CHI) flights.
Search Deals
From Denver Intl to Chicago (CHI)
Search Deals
One-way flight from Denver Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($20 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 Denver Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Denver Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Denver 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 26, 2026.
Use the filters below to find and compare flights from Denver to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 4/15

4:25 pm-11:55 pm

1 stop6h 30m

Chicago O'Hare Intl

Tue 4/21

11:55 am-7:25 pm

2 stops8h 30m

$184
Quickest round-trip

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 4/14

6:35 am-9:55 am

Nonstop2h 20m

Chicago Midway

Tue 4/21

5:30 pm-7:10 pm

Nonstop2h 40m

$187

DenverChicago

DEN - ORD

DENORD

Denver Intl

Mon 6/8

7:10 pm-10:49 pm

Nonstop2h 39m

Chicago O'Hare Intl

Thu 6/11

10:55 pm-12:53 am

Nonstop2h 58m

$191

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 4/17

7:50 pm-11:28 pm

Nonstop2h 38m

Chicago O'Hare Intl

Tue 4/21

2:05 pm-4:00 pm

Nonstop2h 55m

$191

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 4/14

6:15 am-12:50 pm

1 stop5h 35m

Chicago O'Hare Intl

Tue 4/21

10:30 am-12:15 pm

Nonstop2h 45m

$197

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 5/20

6:15 am-1:15 pm

1 stop6h 00m

Chicago O'Hare Intl

Mon 6/1

2:40 pm-11:45 pm

2 stops10h 05m

$200

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 5/5

2:50 pm-11:55 pm

1 stop8h 05m

Chicago O'Hare Intl

Thu 5/7

3:45 pm-11:45 pm

2 stops9h 00m

$201

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 5/30

8:35 am-2:20 pm

1 stop4h 45m

Chicago Midway

Mon 6/1

6:00 am-7:40 am

Nonstop2h 40m

$201

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 4/23

11:25 am-3:00 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 4/28

10:30 am-12:15 pm

Nonstop2h 45m

$202

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 4/21

6:35 am-9:55 am

Nonstop2h 20m

Chicago Midway

Sun 4/26

6:00 am-7:40 am

Nonstop2h 40m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from Denver 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 Denver to Chicago in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust 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 Denver-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Denver-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Denver-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Denver-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 Denver-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 Denver to Chicago

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

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

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

The price you pay for your flight from Denver to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 79 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 Denver to Chicago?

Currently, April is the cheapest month in which you can book a flight from Denver to Chicago (average of $81). Flying from Denver to Chicago in June is currently the most expensive (average of $140). 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 DEN to CHI?

Find hourly flight availability from Denver 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 26, 2026.

It’s optimal to fly from Denver to Chicago in the evening. By choosing this option you can save up to 54% on the cost of your flight, compared to a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Denver to Chicago. Price data was last updated on March 23, 2026.

Travelers seeking maximum savings on their Denver to Chicago flight should consider departing on Saturday 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.

Weekly flight availability from Denver to Chicago

Explore weekly flight availability from Denver 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 26, 2026.

The most flights from DEN to CHI are scheduled on a Wednesday (64 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (14 on average).

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

The best insider tips for Denver 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 Denver to Chicago trip
Our travel experts
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
Emily Zemler

Emily Zemler

Expert on DEN

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

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 26, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Denver 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
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

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
4,333 reviews
Southwest
8.0
Very good
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

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
9,486 reviews
Southwest
8.0
Very good
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

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
11,496 reviews
Southwest
8.0
Very good
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

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
3,015 reviews
Southwest
8.0
Very good
4,333 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

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 Denver 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 Denver to Chicago?

    Most people fly from Denver Intl (DEN) if they book a flight from Denver to Chicago. On average, Denver Intl has 45 outbound flights to Chicago per day from 5 airlines. Denver Intl is conveniently located just 18.5 mi from Denver’s city center.

  • How long is the flight from Denver to Chicago?

    Departing from Denver to Chicago will take you 2h 39m. There are 886 mi between Denver and Chicago. This flight may include one or multiple stops.

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

    Flying on Frontier is currently your cheapest option to Chicago, with prices starting at $75. Additional round-trip tickets that might be worth considering are offered by JetBlue and Southwest, with the lowest prices starting at $126 and $155, respectively. You may be able to fly from Denver to Chicago for 66% less than the average price by searching for these airlines.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $41. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Denver to Chicago for a low price.

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

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

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

    The top 3 most reliable airlines when flying from Denver to Chicago are Copa Airlines (82%), Cathay Pacific (80%) and British Airways (80%).

  • What are the cheapest flights from Denver to Chicago?

    Looking at all options, your cheapest flight can be booked for $89. While the most popular route (Denver Intl - Chicago O'Hare Intl) can be booked for $85 on average, our data indicates $740 when flying from Denver to Chicago.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Denver to Chicago (average of $81). Flying from Denver to Chicago in June is currently the most expensive (average of $140). 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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Top 5 airlines flying from Denver to Chicago

Discover the top 5 airlines that operate flights from Denver 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 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$75Average$186FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$126Average$191FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$155Average$266FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$157Average$254FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$162Average$307FlexibilityNo cancel feeOn-time69%

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