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O'Hare Intl

$68+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Find cheap flights from Boston to O'Hare Intl with Cheapflights

1. Tell us where you want to go

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2. Select your favorite providers

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Cheapflights Tip: The best prices from Boston Logan Intl to Chicago O'Hare Intl are usually found in January or September, booked 46 days in advance, depart on a Wednesday or Friday and return on a Wednesday

Cheap 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 February 21, 2026.

This Priceline deal was found by Cheapflights users on 2/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 pm
BOS
-
ORD
Nonstop3h 01m
Multiple Airlines
Tue 5/53:31 pm
ORD
-
BOS
1 stop6h 47m
Multiple Airlines
Deal found 2/20$129
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:00 am
BOS
-
ORD
Nonstop3h 00m
United Airlines
Mon 4/69:30 pm
ORD
-
BOS
Nonstop2h 29m
United Airlines
Deal found 2/19$130
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/115:31 pm
BOS
-
ORD
Nonstop3h 17m
American Airlines
Sun 4/126:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Deal found 2/19$131
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:16 am
BOS
-
ORD
Nonstop3h 06m
United Airlines
Thu 3/269:15 pm
ORD
-
BOS
Nonstop2h 20m
United Airlines
Deal found 2/19$136
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/27:15 am
BOS
-
ORD
Nonstop3h 10m
Delta
Sun 4/56:15 am
ORD
-
BOS
Nonstop2h 25m
Delta
Deal found 2/20$137
This Expedia deal was found by Cheapflights users on 2/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:52 am
BOS
-
ORD
Nonstop2h 59m
Multiple Airlines
Wed 4/296:08 pm
ORD
-
BOS
1 stop6h 23m
Multiple Airlines
Deal found 2/20$139
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
BOS
-
ORD
Nonstop3h 10m
JetBlue
Sat 2/2810:00 am
ORD
-
BOS
Nonstop2h 20m
JetBlue
Deal found 2/20$140
This United Airlines deal was found by Cheapflights users on 2/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:05 am
BOS
-
ORD
Nonstop3h 01m
United Airlines
Mon 5/186:00 am
ORD
-
BOS
Nonstop2h 25m
United Airlines
Deal found 2/17$141
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/26:52 am
BOS
-
ORD
Nonstop3h 11m
American Airlines
Sun 4/58:20 am
ORD
-
BOS
Nonstop2h 18m
American Airlines
Deal found 2/19$142
This Priceline deal was found by Cheapflights users on 2/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:55 pm
BOS
-
ORD
1 stop10h 44m
Multiple Airlines
Fri 5/86:00 am
ORD
-
BOS
Nonstop2h 15m
Multiple Airlines
Deal found 2/18$144

Find 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 February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$129
(Priceline)

One-way from

$68
(Cheapflightsfares)

Popular in

April

Cheapest in

January

Average price

$242

Good round-trip deal

$219 or less

Good one-way deal

$102 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago O'Hare Intl flight deals.
Search Deals
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
Search Deals
One-way flight from Boston Logan Intl to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Chicago O'Hare Intl.
Search Deals

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 February 21, 2026.
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

Sat 5/9

5:30 pm-7:33 pm

Nonstop3h 03m

Chicago O'Hare Intl

Mon 5/11

7:15 pm-10:49 pm

Nonstop2h 34m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/1

8:05 am-10:06 am

Nonstop3h 01m

Chicago O'Hare Intl

Fri 5/1

9:30 pm-12:59 am

Nonstop2h 29m

$139

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/14

8:05 am-10:06 am

Nonstop3h 01m

Chicago O'Hare Intl

Tue 5/19

6:23 pm-9:59 pm

Nonstop2h 36m

$141

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/14

8:05 am-10:06 am

Nonstop3h 01m

Chicago O'Hare Intl

Mon 5/18

6:00 am-9:25 am

Nonstop2h 25m

$141

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/9

7:00 am-9:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 4/12

6:00 am-9:25 am

Nonstop2h 25m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 4/11

6:19 pm-11:37 pm

1 stop6h 18m

Chicago O'Hare Intl

Tue 4/14

4:10 pm-7:41 pm

Nonstop2h 31m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/1

7:26 pm-11:37 pm

1 stop5h 11m

Chicago O'Hare Intl

Mon 5/4

6:00 am-9:25 am

Nonstop2h 25m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/29

11:00 am-12:59 pm

Nonstop2h 59m

Chicago O'Hare Intl

Sat 5/2

7:00 am-1:51 pm

1 stop5h 51m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/2

5:45 am-9:38 am

1 stop4h 53m

Chicago O'Hare Intl

Sun 4/5

6:00 am-9:25 am

Nonstop2h 25m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 3/20

6:30 pm-11:13 pm

1 stop5h 43m

Chicago O'Hare Intl

Tue 3/31

4:10 pm-7:41 pm

Nonstop2h 31m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 22 results
1
2
3

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 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 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 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 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.

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 February 20, 2026.

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 46 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, September is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of $91). Flying from Boston to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $134). 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 February 21, 2026.

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 28% on the cost of your flight, compared to a flight at noon.

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 February 21, 2026.

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.

The best insider tips for Boston to Chicago O'Hare Intl Airport 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 Boston to Chicago O'Hare Intl Airport trip
Our travel experts
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
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

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

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

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

Read more

Reviews of airlines servicing 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 February 21, 2026.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Boston to Chicago O'Hare Intl Airport. 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
8,228 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,228 reviews
Delta
7.9
Good
8,228 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,335 reviews
Delta
7.9
Good
8,228 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,334 reviews
Delta
7.9
Good
8,228 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,898 reviews
Delta
7.9
Good
8,228 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,482 reviews
Delta
7.9
Good
8,228 reviews

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 38 outbound flights to Chicago O'Hare Intl per day from 6 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • How long is the flight from Boston to Chicago O'Hare Intl Airport?

    There are many flights that can get you from Boston to Chicago O'Hare Intl Airport in 3h 01m. Fly via Delta or United Airlines to get the fastest option. There are 864 mi between Boston and Chicago O'Hare Intl Airport. Generally, flights for this route are nonstop.

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

    Flying on JetBlue is currently your cheapest option to Chicago O'Hare Intl Airport, with prices starting at $66. Additional round-trip tickets that might be worth considering are offered by Delta and Spirit Airlines, with the lowest prices starting at $82 and $85, respectively. JetBlue is priced at 73% 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 Frontier. According to our data, you can fly for as low as $47. Users have also found prices from $58 and $58 on American Airlines and JetBlue, 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 ANA (89%), Emirates (87%) or LATAM Airlines (84%) 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 $66. On average you can expect to pay $832. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $115.

  • 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, September is the cheapest month in which you can book a flight from Boston to Chicago O'Hare Intl Airport (average of $91). Flying from Boston to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $134). 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Gurnee
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Elgin
Downers Grove
Elk Grove Village
Skokie
Libertyville
Oakbrook Terrace
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville

Browse thousands of different options on Cheapflights for your next trip

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Top 6 airlines flying from Boston to O'Hare Intl

Discover the top 6 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 February 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$66Average$173FlexibilityNo cancel feeOn-time62%
DeltaCheapest$82Average$254FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$85Average$162FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$117Average$262FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$127Average$258FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$182FlexibilityNo cancel feeOn-time63%

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