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Montego Bay

$114+ Cheap flights from Chicago (CHI) to Montego Bay (MBJ)

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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
dic. 3 — dic. 101
mié. 12/3
mié. 12/10
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Montego Bay Sangster Intl are usually found in September or February, booked 28 days in advance, depart on a Sunday or Monday and return on a Wednesday

Find flight deals from Chicago to Montego Bay

Cheapest flights from Chicago to Montego Bay
Explore the most affordable flight options available from Chicago to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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.
mar. 12/95:00 amORD - MBJ
1 stop6h 10mSpirit Airlines
mar. 12/161:05 pmMBJ - ORD
1 stop12h 04mSpirit Airlines
Deal found 11/1$353
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/1512:17 pmORD - MBJ
3 stops22h 45mSpirit Airlines
sáb. 11/221:07 pmMBJ - ORD
1 stop11h 22mSpirit Airlines
Deal found 11/1$355
This United Airlines deal was found by Cheapflights users on 11/3. 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.
mar. 12/28:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
dom. 12/72:48 pmMBJ - ORD
Nonstop4h 25mUnited Airlines
Deal found 11/3$356
This Priceline deal was found by Cheapflights users on 11/1. 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.
mar. 12/95:00 amORD - MBJ
1 stop6h 10mMultiple Airlines
mar. 12/162:40 pmMBJ - ORD
2 stops18h 21mMultiple Airlines
Deal found 11/1$357
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/115:10 amORD - MBJ
1 stop5h 52mSpirit Airlines
sáb. 11/221:07 pmMBJ - ORD
2 stops20h 54mSpirit Airlines
Deal found 11/1$358
This Delta deal was found by Cheapflights users on 11/3. 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.
lun. 11/175:23 amORD - MBJ
1 stop6h 29mDelta
lun. 11/245:59 pmMBJ - ORD
2 stops15h 07mDelta
Deal found 11/3$360
This American Airlines deal was found by Cheapflights users on 11/3. 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.
mar. 12/25:00 amORD - MBJ
1 stop8h 53mAmerican Airlines
lun. 12/83:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 11/3$361
This Southwest deal was found by Cheapflights users on 11/1. 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.
sáb. 11/156:40 amMDW - MBJ
1 stop6h 25mSouthwest
sáb. 11/221:55 pmMBJ - MDW
Nonstop4h 10mSouthwest
Deal found 11/1$361
This CheapOair deal was found by Cheapflights users on 11/3. 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.
sáb. 11/225:00 amORD - MBJ
1 stop6h 02mSpirit Airlines
jue. 11/271:07 pmMBJ - ORD
1 stop11h 06mSpirit Airlines
Deal found 11/3$363
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
jue. 11/205:00 amORD - MBJ
1 stop6h 02mSpirit Airlines
jue. 11/271:07 pmMBJ - ORD
1 stop8h 20mSpirit Airlines
Deal found 11/2$366
This United Airlines deal was found by Cheapflights users on 11/1. 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.
lun. 12/18:42 amORD - MBJ
Nonstop4h 04mUnited Airlines
lun. 12/83:36 pmMBJ - ORD
1 stop8h 56mUnited Airlines
Deal found 11/1$367
This Expedia deal was found by Cheapflights users on 11/2. 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.
mar. 12/165:00 amORD - MBJ
1 stop6h 10mSpirit Airlines
mar. 12/231:05 pmMBJ - ORD
1 stop12h 25mSpirit Airlines
Deal found 11/2$369

Cheap flight deals from Chicago to Montego Bay

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Montego Bay (MBJ). 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 noviembre 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$353
(Cheapflightsfares)

One-way from

$114
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$570

Good round-trip deal

$421 or less

Good one-way deal

$195 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
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From Chicago (CHI) to Montego Bay Sangster Intl
Search Deals
One-way flight from Chicago (CHI) to Montego Bay Sangster Intl
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Montego Bay Sangster Intl.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Montego Bay Sangster Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Montego Bay 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 noviembre 3, 2025.
Use the filters below to find and compare flights from Chicago to Montego Bay that are best for you.

Fly from

Chicago

Fly to

Montego Bay

Route

Depart

Return

Price

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 12/13

8:42 am-1:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

jue. 12/18

2:48 pm-6:13 pm

Nonstop4h 25m

$356

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 1/6

6:05 am-2:37 pm

1 stop7h 32m

Montego Bay Sangster Intl

mar. 1/13

2:48 pm-6:13 pm

Nonstop4h 25m

$361

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

dom. 1/4

9:50 am-8:41 pm

1 stop9h 51m

Montego Bay Sangster Intl

vie. 1/9

12:38 pm-10:09 pm

1 stop10h 31m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 12/2

6:00 am-4:33 pm

1 stop9h 33m

Montego Bay Sangster Intl

sáb. 12/6

5:58 pm-11:47 pm

1 stop6h 49m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

mar. 1/27

6:00 am-3:20 pm

1 stop8h 20m

Montego Bay Sangster Intl

sáb. 1/31

4:45 pm-10:26 pm

1 stop6h 41m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 11/17

6:00 am-2:11 pm

1 stop7h 11m

Montego Bay Sangster Intl

lun. 11/24

2:17 pm-11:40 pm

1 stop10h 23m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 1/24

10:46 am-8:36 pm

1 stop8h 50m

Montego Bay Sangster Intl

sáb. 1/31

4:45 pm-10:26 pm

1 stop6h 41m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 1/24

6:00 am-8:36 pm

1 stop13h 36m

Montego Bay Sangster Intl

jue. 1/29

4:45 pm-10:26 pm

1 stop6h 41m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

lun. 1/5

6:45 am-8:36 pm

1 stop12h 51m

Montego Bay Sangster Intl

vie. 1/9

12:38 pm-10:09 pm

1 stop10h 31m

$371

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

sáb. 11/22

6:00 am-2:06 pm

1 stop7h 06m

Montego Bay Sangster Intl

mar. 12/2

3:38 pm-11:47 pm

1 stop9h 09m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 33 results
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Compare providers for flights from Chicago to Montego Bay

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 Chicago to Montego Bay in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 Chicago-Montego Bay flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago-Montego Bay flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Chicago-Montego Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Montego Bay 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 Chicago-Montego Bay 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 Chicago to Montego Bay

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Montego Bay. Price data was last updated on October 31, 2025.

The best time to book flights from Chicago to Montego Bay is 28 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Montego Bay (average of $260). Flying from Chicago to Montego Bay in March is currently the most expensive (average of $419). 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 CHI to MBJ?

Find hourly flight availability from Chicago to Montego Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 3, 2025.

It’s optimal to fly from Chicago to Montego Bay in the evening. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Chicago to Montego Bay?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Montego Bay. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Chicago to Montego Bay flight should consider departing on Sunday at noon when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Montego Bay

Explore weekly flight availability from Chicago to Montego Bay. 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 noviembre 3, 2025.

The most flights from CHI to MBJ are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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

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

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

Fort Lauderdale (FLL) – chosen by Cheapflights users on 88% of 1-stop itineraries from Chicago to Montego Bay on Cheapflights.

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

Average round-trip fare for 1-stop flights from Chicago to Montego Bay, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $370.

What’s the fastest layover option from Chicago to Montego Bay?

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

Flights via Fort Lauderdale (FLL) have the shortest average one-way travel time for 1-stop routes: 7h 16m.

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

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

Flights via Fort Lauderdale (FLL) offer the fastest connection on this route, with an average layover time of 2h 42m.

The best insider tips for Chicago to Montego Bay 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 Chicago to Montego Bay trip
Airports
ORD

For a smooth departure from ORD, consider taking the “L” train to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
MBJ

Fill out the immigration form online before arriving at MBJ to save time and avoid long lines.

Read more about MBJby Mark Chesnut
Our travel experts
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
Mark Chesnut

Mark Chesnut

Expert on MBJ

Mark Chesnut

Mark Chesnut

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more

Reviews of airlines servicing Montego Bay

Get insights into the airlines that provide service to Montego Bay. 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 Montego Bay. Reviews last updated noviembre 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to Montego Bay. 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.
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,115 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Montego Bay. 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 into for flights to Montego Bay from Chicago?

    If you book a flight to Montego Bay from Chicago, you will be flying to Sangster Intl, which is the city’s only airport. Montego Bay Sangster Intl (MBJ) is located 2.3 mi from the center of Montego Bay. There are 2 flights from Chicago to Sangster Intl per day from 6 different airlines.

  • How long is the flight from Chicago to Montego Bay?

    A quick flight from Chicago to Montego Bay can take about 4h 04m. United Airlines provides one of the quickest options available for as low as $356. The distance between Chicago and Montego Bay is about 1724 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Our cheapest airline available from Chicago to Montego Bay is Delta. Our recent data shows that you can find tickets from as low as $186 on this airline. Additional options worth looking into are Spirit Airlines and Frontier, starting at $194 and $333 round-trip. Delta is 68% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest flights from Chicago to Montego Bay?

    Looking for the cheapest flight from Chicago to Montego Bay? While on average our users pay $786, our data indicates the cheapest price to be $157. The most popular route (Chicago O'Hare Intl - Montego Bay Sangster Intl), is priced around $292.

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

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

  • How can I find direct flights from Chicago to Montego Bay?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Montego Bay 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 Chicago to Montego Bay?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Montego Bay (average of $260). Flying from Chicago to Montego Bay in March is currently the most expensive (average of $419). 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 Montego Bay?

Book flights to Montego Bay if you plan to visit one of these locations
Whitehouse
Lucea

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Top 6 airlines flying from Chicago to Montego Bay

Discover the top 6 airlines that operate flights from Chicago to Montego Bay. 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 noviembre 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$186Average$711FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$194Average$438FlexibilityNo cancel feeOn-time65%
FrontierCheapest$333Average$662FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$373Average$626FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$441Average$597FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$549Average$724FlexibilityNo cancel feeOn-time63%

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