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$222+ Cheap flights from O'Hare Intl (ORD) 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MIL
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Find cheap flights from O'Hare Intl to Milan with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Milan are usually found in February or October, booked 16 days in advance, depart on a Tuesday or Sunday and return on a Tuesday

Cheap flight deals from O'Hare Intl to Milan

Cheapest flights from O'Hare Intl to Milan
Explore the most affordable flight options available from O'Hare Intl to Milan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This lol.travel deal was found by Cheapflights users on 1/20. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/77:20 pm
ORD
-
MXP
1 stop18h 50m
Scandinavian Airlines
Fri 2/2011:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 1/20$425
This CrystalTravel deal was found by Cheapflights users on 1/19. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:10 pm
ORD
-
MXP
1 stop17h 00m
Scandinavian Airlines
Thu 2/2611:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 1/19$427
This oojo deal was found by Cheapflights users on 1/19. 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.
Wed 2/187:20 pm
ORD
-
MXP
1 stop16h 50m
Scandinavian Airlines
Wed 2/259:15 am
MXP
-
ORD
1 stop14h 30m
Scandinavian Airlines
Deal found 1/19$430
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/47:10 pm
ORD
-
MXP
1 stop21h 25m
TAP AIR PORTUGAL
Sat 2/1411:55 am
MXP
-
ORD
1 stop33h 50m
TAP AIR PORTUGAL
Deal found 1/20$435
This oojo deal was found by Cheapflights users on 1/19. 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 4/207:15 pm
ORD
-
MXP
2 stops33h 10m
Scandinavian Airlines
Sun 4/268:00 pm
MXP
-
ORD
1 stop27h 10m
Scandinavian Airlines
Deal found 1/19$436
This CrystalTravel deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/157:10 pm
ORD
-
MXP
1 stop17h 00m
Scandinavian Airlines
Fri 2/2011:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 1/21$437
This FlightHub deal was found by Cheapflights users on 1/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:15 pm
ORD
-
MXP
1 stop30h 15m
Scandinavian Airlines
Sat 4/188:40 pm
MXP
-
ORD
2 stops50h 30m
Scandinavian Airlines
Deal found 1/19$438
This oojo deal was found by Cheapflights users on 1/19. 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 2/87:10 pm
ORD
-
MXP
1 stop30h 15m
Scandinavian Airlines
Fri 2/208:00 pm
MXP
-
ORD
1 stop27h 45m
Scandinavian Airlines
Deal found 1/19$440
This oojo deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/47:15 pm
ORD
-
MXP
1 stop30h 15m
Scandinavian Airlines
Thu 4/3011:20 am
MXP
-
ORD
2 stops35h 50m
Scandinavian Airlines
Deal found 1/21$441
This oojo deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:20 pm
ORD
-
LIN
2 stops15h 55m
Scandinavian Airlines
Sat 11/712:55 pm
LIN
-
ORD
2 stops34h 50m
Scandinavian Airlines
Deal found 1/21$444
This oojo deal was found by Cheapflights users on 1/19. 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 2/237:20 pm
ORD
-
LIN
2 stops33h 45m
Scandinavian Airlines
Thu 2/2612:55 pm
LIN
-
ORD
2 stops34h 50m
Scandinavian Airlines
Deal found 1/19$474
This FlightHub deal was found by Cheapflights users on 1/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:15 pm
ORD
-
LIN
2 stops33h 55m
Scandinavian Airlines
Sun 4/2612:00 pm
LIN
-
ORD
1 stop35h 10m
Scandinavian Airlines
Deal found 1/19$482

Find flight deals from O'Hare Intl to Milan

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$425
(lol.travel)

One-way from

$222
(Trip.com)

Popular in

June

Cheapest in

February

Average price

$703

Good round-trip deal

$1,104 or less

Good one-way deal

$764 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Milan (MIL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Milan (MIL) flights.
Search Deals
From Chicago O'Hare Intl to Milan (MIL)
Search Deals
One-way flight from Chicago O'Hare Intl to Milan (MIL)
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($270 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Milan (MIL).
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Milan (MIL).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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 January 21, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Milan that are best for you.

Fly from

O'Hare Intl

Fly to

Milan

Route

Depart

Return

Price

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 2/18

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Wed 2/25

12:55 pm-4:45 pm

2 stops34h 50m

$465

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 2/7

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Tue 11/17

9:15 am-4:45 pm

1 stop14h 30m

$469

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 2/19

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Thu 2/26

12:20 pm-4:45 pm

2 stops35h 25m

$475

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 2/8

7:10 pm-7:10 pm

1 stop17h 00m

Milan Malpensa

Fri 11/20

9:15 am-4:45 pm

1 stop14h 30m

$479

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 2/2

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Thu 2/5

8:00 pm-4:45 pm

1 stop27h 45m

$499

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Thu 2/5

6:30 pm-8:05 pm

2 stops18h 35m

Bergamo Orio Al Serio

Tue 2/10

5:45 am-5:20 pm

2 stops18h 35m

$503

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Fri 2/6

6:30 pm-9:20 pm

2 stops19h 50m

Bergamo Orio Al Serio

Tue 2/10

5:45 am-5:20 pm

2 stops18h 35m

$503

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 2/11

7:20 pm-8:25 am

1 stop30h 05m

Milan Malpensa

Tue 2/17

8:00 pm-4:45 pm

1 stop27h 45m

$510

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 3/16

8:20 pm-9:55 am

2 stops31h 35m

Milan Malpensa

Tue 3/31

8:40 pm-4:20 pm

2 stops26h 40m

$511

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 2/20

8:20 pm-9:40 pm

1 stop18h 20m

Milan Malpensa

Sun 2/22

6:55 am-6:25 pm

1 stop18h 30m

$539

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 58 results
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Compare providers for flights from O'Hare Intl 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 O'Hare Intl to Milan in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
Justfly.comPrice 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 O'Hare Intl Airport-Milan flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Milan flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Milan flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Milan flights, Cheapflights users trust Expedia the most. Expedia 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 O'Hare Intl Airport-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 O'Hare Intl to Milan

Have a flexible travel schedule? Discover the best time to fly to Milan from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Milan

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

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Milan. Price data was last updated on January 16, 2026.

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Milan, you should look to book at least 16 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 Chicago O'Hare Intl Airport to Milan?

Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Milan (average of $398). Flying from Chicago O'Hare Intl Airport to Milan in July is currently the most expensive (average of $783). 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.

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Milan?

What’s the top layover airport for flights from Chicago O'Hare Intl Airport to Milan?

Share of 1-stop round-trip flights from Chicago O'Hare Intl Airport to Milan chosen by Cheapflights users in the past 12 months, using the same layover each way.

Montreal (YUL) – chosen by Cheapflights users on 29% of 1-stop itineraries from Chicago O'Hare Intl Airport to Milan on Cheapflights.

What’s the cheapest layover airport for flights from Chicago O'Hare Intl Airport to Milan?

Average round-trip fare for 1-stop flights from Chicago O'Hare Intl Airport to Milan, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Copenhagen (CPH) is the most affordable 1-stop option, with an average round-trip price of $566.

What’s the fastest layover option from Chicago O'Hare Intl Airport to Milan?

Shortest average travel time for 1-stop one-way flights from Chicago O'Hare Intl Airport to Milan, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Montreal (YUL) have the shortest average one-way travel time for 1-stop routes: 11h 20m.

Which airport typically offers the quickest layover for flights from Chicago O'Hare Intl Airport to Milan?

Average layover duration for 1-stop one-way flights from Chicago O'Hare Intl Airport to Milan, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Montreal (YUL) offer the fastest connection on this route, with an average layover time of 1h 48m.

The best insider tips for Chicago O'Hare Intl Airport to Milan 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 Chicago O'Hare Intl Airport to Milan trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MXP

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

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 January 21, 2026.
See what other customers who have flown with United Airlines, Scandinavian Airlines, and Aer Lingus from Chicago O'Hare Intl Airport to Milan have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,189 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,189 reviews
United Airlines
7.4
Good
9,189 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Scandinavian Airlines
7.3
Good
1,660 reviews
United Airlines
7.4
Good
9,189 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Aer Lingus
7.2
Good
1,437 reviews
United Airlines
7.4
Good
9,189 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
TAP AIR PORTUGAL
7.1
Good
2,123 reviews
United Airlines
7.4
Good
9,189 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
British Airways
6.7
Okay
7,690 reviews
United Airlines
7.4
Good
9,189 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

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

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

    Airlines like Scandinavian Airlines and British Airways fly from Chicago O'Hare Intl Airport to Milan in about 11h 20m. The time it takes to get you to your destination can typically vary by up to 5h 30m. Chicago O'Hare Intl Airport and Milan are separated by a distance of 4536 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    According to our current data, TAP AIR PORTUGAL ($398), Scandinavian Airlines ($421), and British Airways ($496) offers the cheapest pricing from Chicago O'Hare Intl Airport to Milan. TAP AIR PORTUGAL is currently priced 50% below the average price you’ll pay for this route.

  • What are the most popular routes from Chicago O'Hare Intl Airport to Milan?

    The most popular route from Chicago O'Hare Intl Airport to Milan is Chicago O'Hare Intl - Milan Malpensa. You may also consider Chicago O'Hare Intl - Milan Linate or Chicago O'Hare Intl - Bergamo Orio Al Serio.

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

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Milan are Air Canada (100%), Austrian Airlines (69%) and United Airlines (69%).

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

    Looking at all options, your cheapest flight can be booked for $647. While the most popular route (Chicago O'Hare Intl - Milan Malpensa) can be booked for $372 on average, our data indicates $1,081 when flying from Chicago O'Hare Intl Airport to Milan.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Milan (average of $398). Flying from Chicago O'Hare Intl Airport to Milan in July is currently the most expensive (average of $783). 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 Milan?

Book flights to Milan if you plan to visit one of these locations
Monza
Menaggio
Rho
Porlezza
Brescia
Novara
Assago
Bellagio
Stresa
Domodossola

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Alternative routes for O'Hare Intl to Milan

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Malpensa flights
O'Hare Intl to Linate flights
Midway to Malpensa flights
O'Hare Intl to Bergamo flights
Midway to Linate flights
O'Hare Intl to Verona flights

Top 10 airlines flying from O'Hare Intl to Milan

Discover the top 10 airlines that operate flights from O'Hare Intl 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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$398Average$520FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$421Average$562FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$496Average$884FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$518Average$689FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$584Average$913FlexibilityNo cancel feeOn-time81%
American AirlinesCheapest$624Average$1,443FlexibilityNo cancel feeOn-time71%
Aer LingusCheapest$626Average$853FlexibilityNo cancel feeOn-timeN/A
IberiaCheapest$639Average$1,029FlexibilityNo cancel feeOn-time77%
LOTCheapest$732Average$1,044FlexibilityNo cancel feeOn-time81%
United AirlinesCheapest$793Average$1,274FlexibilityNo cancel feeOn-time69%

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