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O'Hare Intl

$60+ Cheap flights from Boston (BOS) to O'Hare Intl (ORD)

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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
May 25 — Jun 11
Sun 5/25
Sun 6/1
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in September or August, booked 50 days in advance, depart on a Friday or Wednesday and return on a Wednesday

Cheap flight deals from Boston to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to O'Hare Intl (ORD). 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 May 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$118
(Booking.com)

One-way from

$60
(FlightHub)

Popular in

November

Cheapest in

September

Average price

$277

Good round-trip deal

$204 or less

Good one-way deal

$95 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago O'Hare Intl flights.
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From Boston Logan Intl to Chicago O'Hare Intl
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One-way flight from Boston Logan Intl to Chicago O'Hare Intl
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Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
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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 May 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Boston Logan Intl to Chicago O'Hare Intl.
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Find flight deals from Boston to O'Hare Intl

Cheapest flights from Boston to O'Hare Intl
Explore the most affordable flight options available from Boston to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 20, 2025.

This Booking.com deal was found by Cheapflights users on 5/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/55:42 pmBOS - ORD
1 stop6h 47mSpirit Airlines
Tue 6/105:05 amORD - BOS
1 stop8h 39mSpirit Airlines
Deal found 5/18$118
This JetBlue deal was found by Cheapflights users on 5/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/116:00 amBOS - ORD
Nonstop3h 00mJetBlue
Fri 6/134:51 pmORD - BOS
Nonstop2h 36mJetBlue
Deal found 5/19$137
This American Airlines deal was found by Cheapflights users on 5/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/35:00 amBOS - ORD
Nonstop2h 54mAmerican Airlines
Thu 7/107:25 amORD - BOS
Nonstop2h 28mAmerican Airlines
Deal found 5/19$138
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/108:30 amBOS - ORD
1 stop8h 55mSouthwest
Thu 6/124:00 pmORD - BOS
1 stop7h 05mSouthwest
Deal found 5/19$142
This United Airlines deal was found by Cheapflights users on 5/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/206:00 amBOS - ORD
Nonstop2h 58mUnited Airlines
Sun 6/229:30 pmORD - BOS
Nonstop2h 29mUnited Airlines
Deal found 5/20$151
This Delta deal was found by Cheapflights users on 5/18. 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.
Fri 6/138:05 pmBOS - ORD
Nonstop3h 00mDelta
Wed 6/187:00 amORD - BOS
Nonstop2h 31mDelta
Deal found 5/18$155
This CheapOair deal was found by Cheapflights users on 5/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/148:22 amBOS - ORD
1 stop9h 36mMultiple Airlines
Tue 9/163:29 pmORD - BOS
1 stop8h 10mMultiple Airlines
Deal found 5/19$158
This CheapOair deal was found by Cheapflights users on 5/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/136:00 amBOS - ORD
1 stop17h 29mFrontier
Sun 6/158:14 amORD - BOS
1 stop23h 26mFrontier
Deal found 5/19$184

Cheapflights Fare Finder

Customize your flight search to find flights from Boston to O'Hare Intl 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 May 20, 2025.
Use the filters below to find and compare flights from Boston to Chicago O'Hare Intl Airport that are best for you.

Fly from

Boston

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/5

5:42 pm-11:29 pm

1 stop6h 47m

Chicago O'Hare Intl

Tue 6/10

5:05 am-2:44 pm

1 stop8h 39m

$118

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/11

4:05 pm-6:04 pm

Nonstop2h 59m

Chicago O'Hare Intl

Fri 6/13

6:59 pm-10:45 pm

Nonstop2h 46m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/3

5:00 am-6:54 am

Nonstop2h 54m

Chicago O'Hare Intl

Thu 7/10

7:25 am-10:53 am

Nonstop2h 28m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/10

8:30 am-4:25 pm

1 stop8h 55m

Chicago O'Hare Intl

Thu 6/12

4:00 pm-12:05 am

1 stop7h 05m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 6/20

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 6/22

9:30 pm-12:59 am

Nonstop2h 29m

$151

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 5/26

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Wed 5/28

10:50 am-2:18 pm

Nonstop2h 28m

$168

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/5

5:42 pm-11:29 pm

1 stop6h 47m

Chicago O'Hare Intl

Sun 6/8

5:08 pm-9:56 am

1 stop15h 48m

$169

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/19

6:00 am-1:50 pm

1 stop8h 50m

Chicago O'Hare Intl

Mon 6/23

8:17 pm-8:06 am

1 stop10h 49m

$174

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 7/2

4:44 pm-11:45 pm

1 stop8h 01m

$60

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/27

6:00 am-8:00 am

Nonstop3h 00m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

Showing 1-10 of 16 results
1
2

Compare providers for flights from Boston to O'Hare Intl

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 Boston to O'Hare Intl in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
FareScanPrice Accuracy-Trust Score*3 stars
FlightnetworkPrice Accuracy-Trust 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 Boston-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Chicago O'Hare Intl Airport flights, Cheapflights users trust eDreams the most. eDreams 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 Boston-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Boston to Chicago O'Hare Intl Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Boston to Chicago O'Hare Intl Airport trip
Airlines
United Airlines

United's Economy Plus offers extra legroom and priority boarding, enhancing comfort on domestic flights.


Prepay for checked bags on United to save money. Avoid fees by using MileagePlus Premier benefits.

Read more about United Airlinesby Harriet Baskas
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom, ideal for comfort on short flights.


Use Spirit's self-service bag drop for a faster airport experience. Print boarding pass beforehand to avoid fees.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
BOS

Use the FlyLogan App to pre-order meals and save time at BOS. Most restaurants participate in this convenient service.

Read more about BOSby Paul Rubio
ORD

Take the 'L' train from downtown Chicago to ORD to avoid traffic delays. It's a reliable public transport option.

Read more about ORDby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

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
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

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 BOS

Paul Rubio

Paul Rubio

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

Best time to book a flight from Boston to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Boston 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 Boston to Chicago O'Hare Intl Airport

How far ahead should I book a flight from Boston to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Boston to O'Hare Intl. Price data was last updated on May 16, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Chicago O'Hare Intl Airport, you should look to book at least 50 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Boston to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of $245). Flying from Boston to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 BOS to ORD?

Find hourly flight availability from Boston to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 20, 2025.

It’s optimal to fly from Boston to Chicago O'Hare Intl Airport in the evening. By choosing this option you can save up to 31% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Boston to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Boston to O'Hare Intl. Price data was last updated on May 18, 2025.

Travelers seeking maximum savings on their Boston to Chicago O'Hare Intl Airport flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Boston to Chicago O'Hare Intl Airport

Explore weekly flight availability from Boston to O'Hare Intl. 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 May 20, 2025.

The most flights from BOS to ORD are scheduled on a Monday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated May 20, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Boston to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,290 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,951 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,744 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,928 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Food

7.1

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Boston to O'Hare Intl. 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 Boston to Chicago O'Hare Intl?

    Most people fly from Boston Logan Intl (BOS) if they book a flight from Boston to Chicago O'Hare Intl. On average, Logan Intl has 44 outbound flights to Chicago O'Hare Intl per day from 7 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • What are the cheapest airlines flying from Boston to Chicago O'Hare Intl Airport round-trip?

    Flying on Spirit Airlines is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at $118. Additional round-trip tickets that might be worth considering are offered by JetBlue and American Airlines, with the lowest prices starting at $137 and $138, respectively. Spirit Airlines is priced at 51% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Boston to Chicago O'Hare Intl Airport one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $60. Users have also found prices from $69 and $70 on JetBlue and American Airlines, respectively.

  • What are the most reliable airlines from Boston to Chicago O'Hare Intl Airport?

    No one likes to see their flight delayed. When booking a flight from Boston to Chicago O'Hare Intl Airport consider choosing Japan Airlines (93%), Avianca (90%) or ANA (89%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Chicago O'Hare Intl Airport?

    The cheapest flight price from Boston to Chicago O'Hare Intl Airport is $58. On average you can expect to pay $687. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $105.

  • Can I find deals for flights from Boston to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Boston to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to O'Hare Intl.

  • Can I find deals for business class flights from Boston to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Boston to O'Hare Intl 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 Boston to Chicago O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of $245). Flying from Boston to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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

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Top 7 airlines flying from Boston to O'Hare Intl

Discover the top 7 airlines that operate flights from Boston to O'Hare Intl. 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 May 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$104FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$80Average$213FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$239FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$134FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$256FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$141Average$284FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$182Average$378FlexibilityNo cancel feeOn-time63%

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