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$58+ Cheap flights from John F Kennedy Intl, NY (JFK) 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 3/30. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Find cheap flights from John F Kennedy Intl to Chicago with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from New York John F Kennedy Intl to Chicago are usually found in January or November, booked 41 days in advance, depart on a Saturday or Wednesday and return on a Friday

Cheap flight deals from John F Kennedy Intl to Chicago

Cheapest flights from John F Kennedy Intl to Chicago
Explore the most affordable flight options available from John F Kennedy Intl to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Frontier deal was found by Cheapflights users on 12/21. 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 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Mon 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/21$105
This Kiwi.com deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Sat 1/36:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/22$116
This Priceline deal was found by Cheapflights users on 12/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mMultiple Airlines
Sun 1/257:45 amORD - JFK
1 stop6h 13mMultiple Airlines
Deal found 12/21$122
This CheapOair deal was found by Cheapflights users on 12/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:00 amJFK - ORD
Nonstop2h 57mFrontier
Sat 1/108:35 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/21$126
This Frontier deal was found by Cheapflights users on 12/21. 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 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Fri 1/26:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/21$136
This Frontier deal was found by Cheapflights users on 12/21. 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.
Sat 12/2711:00 amJFK - ORD
Nonstop2h 57mFrontier
Mon 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/21$140
This Trip.com deal was found by Cheapflights users on 12/22. 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.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mMultiple Airlines
Tue 1/69:35 amORD - JFK
Nonstop2h 16mMultiple Airlines
Deal found 12/22$151
This Frontier deal was found by Cheapflights users on 12/22. 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 12/316:20 amJFK - MDW
1 stop8h 01mFrontier
Mon 1/265:01 pmMDW - JFK
1 stop7h 02mFrontier
Deal found 12/22$282
This CheapOair deal was found by Cheapflights users on 12/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/294:29 pmJFK - MDW
1 stop28h 26mFrontier
Fri 1/94:31 pmMDW - JFK
1 stop16h 29mFrontier
Deal found 12/21$293
This Expedia deal was found by Cheapflights users on 12/22. 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.
Wed 12/316:20 amJFK - MDW
1 stop8h 01mFrontier
Sun 1/410:50 pmMDW - JFK
1 stop15h 30mFrontier
Deal found 12/22$297
This Priceline deal was found by Cheapflights users on 12/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:20 amJFK - MDW
1 stop8h 01mFrontier
Sun 1/255:01 pmMDW - JFK
1 stop7h 02mFrontier
Deal found 12/21$317
This CheapOair deal was found by Cheapflights users on 12/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:00 pmJFK - MDW
1 stop10h 12mFrontier
Sun 1/410:50 pmMDW - JFK
1 stop15h 30mFrontier
Deal found 12/21$318

Find flight deals from John F Kennedy Intl to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from John F Kennedy Intl (JFK) 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 December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$85
(Frontier)

One-way from

$58
(Trip.com)

Popular in

May

Cheapest in

January

Average price

$220

Good round-trip deal

$144 or less

Good one-way deal

$86 or less
Provider with most accurate pricing for New York John F Kennedy Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York John F Kennedy Intl-Chicago (CHI) flights.
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From New York John F Kennedy Intl to Chicago (CHI)
Search Deals
One-way flight from New York John F Kennedy Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from New York John F Kennedy Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from New York John F Kennedy Intl to Chicago (CHI).
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Cheapflights Fare Finder

 
Customize your flight search to find flights from John F Kennedy Intl 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 December 23, 2025.
Use the filters below to find and compare flights from New York John F Kennedy Intl Airport to Chicago that are best for you.

Fly from

John F Kennedy Intl

Fly to

Chicago

Route

Depart

Return

Price

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 2/18

9:15 pm-11:10 pm

Nonstop2h 55m

Chicago O'Hare Intl

Tue 2/24

6:04 am-9:20 am

Nonstop2h 16m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 2/2

3:52 pm-5:45 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sat 2/7

10:29 am-1:54 pm

Nonstop2h 25m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 2/18

9:15 pm-11:10 pm

Nonstop2h 55m

Chicago O'Hare Intl

Mon 2/23

6:04 am-9:20 am

Nonstop2h 16m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 1/18

7:50 am-9:49 am

Nonstop2h 59m

Chicago O'Hare Intl

Tue 1/20

10:29 am-1:54 pm

Nonstop2h 25m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 2/23

9:15 pm-11:10 pm

Nonstop2h 55m

Chicago O'Hare Intl

Wed 2/25

12:41 pm-4:02 pm

Nonstop2h 21m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 2/2

3:52 pm-5:45 pm

Nonstop2h 53m

Chicago O'Hare Intl

Tue 2/10

10:29 am-1:54 pm

Nonstop2h 25m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 2/7

5:30 pm-7:45 pm

Nonstop3h 15m

Chicago O'Hare Intl

Thu 2/12

6:04 am-9:20 am

Nonstop2h 16m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 1/17

3:55 pm-5:48 pm

Nonstop2h 53m

Chicago O'Hare Intl

Tue 2/3

1:57 pm-5:30 pm

Nonstop2h 33m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/5

5:25 pm-7:31 pm

Nonstop3h 06m

Chicago O'Hare Intl

Thu 2/12

6:04 am-9:20 am

Nonstop2h 16m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/19

9:15 pm-11:10 pm

Nonstop2h 55m

Chicago O'Hare Intl

Tue 2/24

12:41 pm-4:02 pm

Nonstop2h 21m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 39 results
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Compare providers for flights from John F Kennedy Intl 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 John F Kennedy Intl to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
GotogatePrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice 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 New York John F Kennedy Intl Airport-Chicago flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on New York John F Kennedy Intl Airport-Chicago flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from New York John F Kennedy Intl Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New York John F Kennedy Intl Airport-Chicago flights, Cheapflights users trust CheapOair the most. CheapOair 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 New York John F Kennedy Intl 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 John F Kennedy Intl to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from John F Kennedy Intl 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 New York John F Kennedy Intl Airport to Chicago

How far ahead should I book a flight from New York John F Kennedy Intl Airport to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from John F Kennedy Intl to Chicago. Price data was last updated on December 19, 2025.

Booking 41 days in advance of your planned departure date is, on average, the best time to get cheap flights from New York John F Kennedy Intl Airport 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 month to book a flight from New York John F Kennedy Intl Airport to Chicago?

Currently, May is the cheapest month in which you can book a flight from New York John F Kennedy Intl Airport to Chicago (average of $55). Flying from New York John F Kennedy Intl Airport to Chicago in July is currently the most expensive (average of $126). 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 JFK to CHI?

Find hourly flight availability from John F Kennedy Intl 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 December 23, 2025.

One of the essential ways to save on airfare from New York John F Kennedy Intl Airport 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 55% on airfare.

What is the cheapest day to fly from New York John F Kennedy Intl Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from John F Kennedy Intl to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their New York John F Kennedy Intl Airport to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from New York John F Kennedy Intl Airport to Chicago

Explore weekly flight availability from John F Kennedy Intl 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 December 23, 2025.

The most flights from JFK to CHI are scheduled on a Tuesday (39 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (11 on average).

How much does it cost to fly round-trip from New York John F Kennedy Intl Airport to Chicago?

How often are flights from New York to Chicago delayed?

About 21% of weekly flights between New York and Chicago have experienced delays in the past year, with the average delay time being 154 minutes.

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

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

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

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

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

Over the last year, Delta have had the lowest number of delays on this route, with just 12% of flights being delayed.

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 December 23, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and JetBlue from New York John F Kennedy Intl Airport to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,014 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
7.9
Good
8,014 reviews
Delta
7.9
Good
8,014 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,014 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
JetBlue
7.2
Good
2,898 reviews
Delta
7.9
Good
8,014 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Spirit Airlines
6.3
Okay
8,196 reviews
Delta
7.9
Good
8,014 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Frontier
5.8
Fair
3,075 reviews
Delta
7.9
Good
8,014 reviews

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from John F Kennedy Intl 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 New York John F Kennedy Intl Airport to Chicago?

    Departing from New York John F Kennedy Intl Airport to Chicago will take you 2h 53m. New York John F Kennedy Intl Airport and Chicago are separated by a distance of 738 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 New York John F Kennedy Intl Airport to Chicago round-trip?

    According to our current data, Frontier ($54), JetBlue ($75), and Delta ($87) offers the cheapest pricing from New York John F Kennedy Intl Airport to Chicago. These flights start at 76% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from New York John F Kennedy Intl Airport to Chicago one-way?

    The cheapest airlines for a one-way flight from New York John F Kennedy Intl Airport to Chicago are Frontier ($29), JetBlue ($69), and American Airlines ($74).

  • What are the most reliable airlines from New York John F Kennedy Intl Airport to Chicago?

    Before booking your flight to Chicago from New York John F Kennedy Intl Airport, check out the most reliable airlines to get you to your destination on time: China Airlines (85%), LATAM Airlines (81%), Delta( 76%).

  • What are the cheapest flights from New York John F Kennedy Intl Airport to Chicago?

    On average you can expect to pay $489 for a flight from New York John F Kennedy Intl Airport to Chicago. The cheapest flight overall is $66 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $59.

  • Can I find deals for flights from John F Kennedy Intl to Chicago that include hotel bookings?

    Yes. In addition to deals on John F Kennedy Intl to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from John F Kennedy Intl to Chicago?

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

  • Can I find deals for business class flights from John F Kennedy Intl to Chicago?

    Yes. Cheapflights offers flight deals from John F Kennedy Intl 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 New York John F Kennedy Intl Airport to Chicago?

    Currently, May is the cheapest month in which you can book a flight from New York John F Kennedy Intl Airport to Chicago (average of $55). Flying from New York John F Kennedy Intl Airport to Chicago in July is currently the most expensive (average of $126). 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?

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Alternative routes for John F Kennedy Intl to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
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Top 6 airlines flying from John F Kennedy Intl to Chicago

Discover the top 6 airlines that operate flights from John F Kennedy Intl 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$128FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$86Average$227FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$96Average$177FlexibilityNo cancel feeOn-time65%
DeltaCheapest$113Average$332FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$152Average$285FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$295FlexibilityNo cancel feeOn-time69%

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