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$244+ Cheap flights from Chicago (CHI) to Milan (MIL)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIL
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to Milan are usually found in November or February, booked 47 days in advance, depart on a Tuesday or Thursday and return on a Thursday

Cheap flight deals from Chicago to Milan

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Milan (MIL). 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 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$502
(Kiwi.com)

One-way from

$318
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$631

Good round-trip deal

$1,353 or less

Good one-way deal

$848 or less
Provider with most accurate pricing for Chicago (CHI)-Milan (MIL) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Milan (MIL) flights.
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From Chicago (CHI) to Milan (MIL)
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One-way flight from Chicago (CHI) to Milan (MIL)
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Highest demand for flights based on searches. 1% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Milan (MIL).
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Price to beat on a one-way flight from Chicago (CHI) to Milan (MIL).
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Find flight deals from Chicago to Milan

Cheapest flights from Chicago to Milan
Explore the most affordable flight options available from Chicago to Milan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/27:40 pmORD - MXP
2 stops16h 10mScandinavian Airlines
Thu 3/2011:20 amMXP - ORD
1 stop13h 30mScandinavian Airlines
Deal found 2/18$502
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/136:00 pmORD - MXP
1 stop34h 00mTAP AIR PORTUGAL
Tue 4/2911:50 amMXP - ORD
1 stop35h 20mTAP AIR PORTUGAL
Deal found 2/19$516
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/157:50 pmORD - MXP
1 stop29h 55mTurkish Airlines
Thu 9/2510:45 amMXP - ORD
1 stop29h 55mTurkish Airlines
Deal found 2/19$518
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/13:45 pmORD - LIN
1 stop11h 55mAer Lingus
Tue 4/1511:20 amLIN - ORD
1 stop14h 40mAer Lingus
Deal found 2/20$521
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/15:22 pmORD - MXP
2 stops16h 03mMultiple Airlines
Tue 4/85:55 amMXP - ORD
2 stops32h 08mMultiple Airlines
Deal found 2/19$574
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/3011:35 amORD - BGY
2 stops20h 40mMultiple Airlines
Tue 4/88:20 amBGY - ORD
2 stops18h 40mMultiple Airlines
Deal found 2/20$618
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/268:30 pmORD - LIN
2 stops33h 35mScandinavian Airlines
Thu 11/612:55 pmLIN - ORD
2 stops34h 50mScandinavian Airlines
Deal found 2/19$620
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/12:53 pmORD - LIN
2 stops20h 47mMultiple Airlines
Tue 4/89:00 amLIN - ORD
2 stops27h 46mMultiple Airlines
Deal found 2/19$653
This Air Serbia 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 Air Serbia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/156:30 pmORD - MXP
1 stop32h 15mAir Serbia
Tue 4/89:25 amMXP - ORD
1 stop36h 00mAir Serbia
Deal found 2/19$655
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/93:00 pmORD - LIN
1 stop23h 10mITA Airways
Wed 5/146:30 amLIN - ORD
1 stop13h 40mITA Airways
Deal found 2/19$750
This Lufthansa 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 Lufthansa is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:25 pmORD - LIN
1 stop13h 35mLufthansa
Tue 11/259:45 amLIN - ORD
1 stop15h 40mLufthansa
Deal found 2/19$891
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 11/1310:10 amMDW - MXP
2 stops14h 15mDelta
Tue 11/1811:05 amMXP - MDW
1 stop17h 42mDelta
Deal found 2/20$1,073

Find flights from Chicago to Milan within your budget

Customize your flight search to find flights from Chicago to Milan 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 20, 2025.

Fly from

Chicago

Fly to

Milan

Route

Depart

Return

Price

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 3/2

7:40 pm-6:50 pm

2 stops16h 10m

Milan Malpensa

Thu 3/20

11:20 am-6:50 pm

1 stop13h 30m

$502

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 4/13

6:00 pm-11:00 am

1 stop34h 00m

Milan Malpensa

Tue 4/29

11:50 am-4:10 pm

1 stop35h 20m

$516

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 4/1

3:45 pm-10:40 am

1 stop11h 55m

Milan Linate

Tue 4/15

11:20 am-7:00 pm

1 stop14h 40m

$521

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 3/11

9:30 pm-1:35 pm

1 stop34h 05m

Milan Malpensa

Wed 3/19

6:35 pm-11:10 am

1 stop22h 35m

$533

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 4/1

5:22 pm-4:25 pm

2 stops16h 03m

Milan Malpensa

Tue 4/8

5:55 am-7:03 am

2 stops32h 08m

$574

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 3/30

11:35 am-3:15 pm

2 stops20h 40m

Bergamo Orio Al Serio

Tue 4/8

8:20 am-8:00 pm

2 stops18h 40m

$618

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 4/1

2:53 pm-6:40 pm

2 stops20h 47m

Milan Linate

Tue 4/8

9:00 am-5:46 am

2 stops27h 46m

$653

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 3/15

6:30 pm-8:45 am

1 stop32h 15m

Milan Malpensa

Tue 4/8

9:25 am-2:25 pm

1 stop36h 00m

$655

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 4/27

7:15 pm-12:10 pm

2 stops33h 55m

Milan Linate

Sat 5/3

2:50 pm-4:10 pm

1 stop32h 20m

$675

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Fri 5/9

3:00 pm-9:10 pm

1 stop23h 10m

Milan Linate

Wed 5/14

6:30 am-1:10 pm

1 stop13h 40m

$750

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 44 results
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Compare providers for flights from Chicago to Milan

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 Milan in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
FlightHubPrice Accuracy3 starsTrust 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 Chicago-Milan flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Milan flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Milan flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Milan 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 Chicago-Milan 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 Milan

Have a flexible travel schedule? Discover the best time to fly to Milan 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.

Travel insights for flights from Chicago to Milan

Get recent, data-driven insights about flights from Chicago to Milan including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Milan. Price data was last updated on February 14, 2025.

The price you pay for your flight from Chicago to Milan may vary depending on when you book. For the best chance of a lower fare, look to book 47 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Milan (average of $594). Flying from Chicago to Milan in June is currently the most expensive (average of $1,063). 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 MIL?

Find hourly flight availability from Chicago to Milan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Milan in the morning. If you’re flexible enough to do this you can expect to save up to 50% on your trip compared to booking a flight in the evening.

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

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

Travelers seeking maximum savings on their Chicago to Milan flight should consider departing on Monday mornings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Milan by month

Plan your trip to Milan by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Milan ranges from 2.2 - 5.2 inches per month. May is typically the wettest month, when rainfall can reach 5.2 in. December is typically the driest time to visit Milan when rainfall is around 2.2 in.

Temperature in Milan by month

Plan your trip to Milan by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Milan, 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 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

Reviews of airlines servicing Milan

Get insights into the airlines that provide service to Milan. 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 Milan. Reviews last updated February 20, 2025.
To help decide which airline to fly from Chicago to Milan, see what other customers have to say about Singapore Airlines, Delta and KLM. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Singapore Airlines
8.1
Very good
1,301 reviews

Food

7.7

Boarding

8.2

Overall

8.1

Entertainment

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

Singapore Airlines
8.1
Very good
1,301 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Food

7.7

Boarding

8.2

Overall

8.1

Entertainment

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

Delta
8.0
Very good
8,219 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Food

7.7

Boarding

8.2

Overall

8.1

Entertainment

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

KLM
7.8
Good
1,333 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Food

7.7

Boarding

8.2

Overall

8.1

Entertainment

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

SWISS
7.5
Good
1,568 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Food

7.7

Boarding

8.2

Overall

8.1

Entertainment

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

Air France
7.4
Good
1,449 reviews
Singapore Airlines
8.1
Very good
1,301 reviews

Food

7.7

Boarding

8.2

Overall

8.1

Entertainment

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20

6.0
Good

Gina,Dec 2024

BLR - SIN

Overall the experience was good. First flight of 17 hours had no entertainment since Singapore airline has technical issues. Was informed that passengers would get a $350 voucher for future flight. Uncertain how that is being distributed but would like to understand if an email is required from my end or if it is an automatic email sent to me by Singapore Airlines. -Gina Robles

Related info for your journey

Find useful and relevant information for your journey from Chicago to Milan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Currently priced at $502, Scandinavian Airlines will fly you from Chicago to Milan and back. In addition to Scandinavian Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from TAP AIR PORTUGAL and Aer Lingus - these airlines can fly you to your destination from $516 and $521, respectively. Users have found that Scandinavian Airlines is 40% cheaper than the other options available to this destination.

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

    For one-way options, check prices for Scandinavian Airlines. According to our data, you can fly for as low as $386. Users have also found prices from $411 and $412 on Air Serbia and TAP AIR PORTUGAL, respectively.

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

    Most travelers choose Chicago O'Hare Intl - Milan Malpensa, Chicago O'Hare Intl - Milan Linate or Chicago Midway - Milan Malpensa when deciding on the best route from Chicago to Milan.

  • What are the cheapest flights from Chicago to Milan?

    The cheapest flight price from Chicago to Milan is $784. On average you can expect to pay $1,238. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $444.

  • Where are the most common layover locations when flying from Chicago to Milan?

    Chicago to Milan flights have a layover in Dublin most often. Stockholm sees the second most layovers for non-direct flights flying from Chicago to Milan.

  • What are some popular things to do or see while on a layover in Dublin?

    Most Dublin visitors opt to spend their time experiencing Molly Malone Statue, St. Patrick's Cathedral, and Parnell Square. Molly Malone Statue, St. Patrick's Cathedral, and Parnell Square are located about 5.8 mi, 6.1 mi, and 5.0 mi, respectively from Dublin. Those on a layover in Dublin in need of a rental car can book one at Dublin for about $20.

  • What are some popular points of interest to see during a layover in Stockholm?

    If you're on a layover in Stockholm and looking for things to do, consider visiting Stockholms Centralstation, Sergels Torg, or Stureplan. Stockholms Centralstation, Sergels Torg, and Stureplan are located about 22.7 mi, 22.5 mi, and 22.4 mi, respectively from Stockholm Arlanda. Those landing in Stockholm looking to spend some time exploring during their layover can rent a car for about $39 per day.

  • Where are the least popular layover locations for Chicago to Milan flights?

    Chicago to Milan flights that have layovers will least frequently stop in Stockholm.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Milan (average of $594). Flying from Chicago to Milan in June is currently the most expensive (average of $1,063). 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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Top 10 airlines flying from Chicago to Milan

Discover the top 10 airlines that operate flights from Chicago to Milan. 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$447Average$599FlexibilityNo cancel feeOn-time77%
Turkish AirlinesCheapest$518Average$587FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$519Average$810FlexibilityNo cancel feeOn-timeN/A
LufthansaCheapest$536Average$903FlexibilityNo cancel feeOn-time76%
American AirlinesCheapest$550Average$796FlexibilityNo cancel feeOn-time71%
TAP AIR PORTUGALCheapest$550Average$694FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$555Average$948FlexibilityNo cancel feeOn-timeN/A
IcelandairCheapest$597Average$751FlexibilityNo cancel feeOn-time76%
Air FranceCheapest$625Average$961FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$661Average$986FlexibilityNo cancel feeOn-time70%
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