Best time to go: what is the RIGHT price for a round-trip flight to Milan (from: Chicago)

The average price to go to Milan from Chicago airport is $ 935 (round trip). However, there are variations depending on the departure month. Thus, it is possible to pay for your plane ticket on average between $ 518 (in february) and $ 1431 (in june), which is a saving of $ 417 or a surplus of $ 497 (compared to the average price) depending on the period you leave.

The analysis of all prices reveals that the most frequent price is between $424 to $477 and it is generally more economical to leave on a wednesday and return on a tuesday on a flight with 1 or more layovers.

Be careful, the cheapest months may correspond to unfavorable weather periods . Check out our page best time to go to Milan before booking your flight.

If you want to know when to book your flight at the best price, go straight to the second part of this page: When to buy your Chicago-Milan plane ticket.

How are these data calculated?

We have studied a sample of 60002 airfare prices from previous years for flights to Milan from Chicago and can thus establish precise and credible price variation trends based on different parameters. Of course, prices can vary from year to year, but the seasonal aspect of this data (recurrence of school holidays, events... from year to year) makes these statistics quite reliable.

Average price depending on the departure month

Data analysis:

By leaving in february, the price of the plane ticket will statistically be the cheapest ($ 518, saving $ 417 compared to the average price over the year which is $ 935). Conversely, june will be the most expensive ($ 1431).

Flight Chicago-Milan: when is the best time to go for the best price?

Month Good price* Average price Our opinion
January$ 484 $ 550 good price
February$ 448 $ 518 very good price
March$ 506 $ 607 good price
April$ 534 $ 801 good price
May$ 735 $ 1110 high price
June$ 1068 $ 1431 very high price
July$ 1099 $ 1404 high price
August$ 909 $ 1237 high price
September$ 754 $ 1129 high price
October$ 683 $ 983 fair price
November$ 564 $ 653 good price
December$ 635 $ 786 good price

*great price to buy your plane ticket: if you see this price or cheaper during your flight search, go for it and buy it!

Price breakdown to travel from Chicago to Milan

Data analysis:

The prices for flights from Chicago to Milan range from $371 to $1852. 3% of tickets were purchased at the minimum price (from $371 to $424), 1% at the maximum price (from $1799 to $1852). The majority of plane tickets were purchased in the range of $635 to $688 (8% of tickets).

Cheapest airlines for the Chicago->Milan flight

There are 13 companies that serve Chicago from Milan airport: United, SAS, TAP, Lufthansa, Icelandair, Spirit Airlines, Aer Lingus, Turkish Airlines, Frontier Airlines, British Airways, LOT, Austrian Airlines and Brussels Airlines.

Data analysis:

Of the 60002 flights analyzed in previous years, United was the airline that offered the best fare most often in the flight ticket search results (21% of the time) on the Chicago->Milan route.

Direct flight or flight with layover?

Data analysis:

To get the best price for the Chicago-Milan flight, you should take a flight with one or more layovers (you will save an average of $ 976 compared to a direct flight).

Which day of the week to leave?

Data analysis:

Statistically, Chicago-Milan flights departing on a wednesday are cheaper than on other days of the week. By choosing a wednesday as your departure date, you can save an average of $76. On the other hand, departing on a saturday may cost you an additional $68.

Which day of the week to come back?

Data analysis:

Statistically, return flights from Milan to Chicago departing on a tuesday are cheaper than on other days of the week. By choosing a tuesday for your return date, you will save an average of $47. Conversely, departing from Milan on a saturday may cost you an additional $79.


Top prices Chicago-Milan

Round tripDatesPrice
Chicago → Milan15-01 to 22-01-2025$ 522 
Chicago → Milan22-01 to 26-01-2025$ 527 
Chicago → Milan02-02 to 10-02-2025$ 527 
Chicago → Milan03-02 to 10-02-2025$ 527 
Chicago → Milan09-02 to 21-02-2025$ 510 
Chicago → Milan16-02 to 24-02-2025$ 526 
Chicago → Milan02-04 to 09-04-2025$ 529 
Chicago → Milan03-04 to 10-04-2025$ 509 
Chicago → Milan07-04 to 14-04-2025$ 425 
Chicago → Milan06-05 to 12-05-2025$ 526 


When to book your flight Chicago - Milan to get the cheapest price?

Statistically, you will make the biggest savings by buying your plane ticket between 11 to 12 months in advance. However, you may end up paying a high price if you book between 0 to 1 month in advance.

Did you know: the price of plane tickets not only varies depending on how far in advance you book, but also on the day of the week you book! So, to maximize your chances of getting the best price for a Chicago-Milan flight, it is recommended to book your ticket on a tuesday.

How far in advance should I buy my flight?

Data analysis:

To get the cheapest flight ticket from Chicago to Milan, it is recommended to buy it 11 to 12 months before departure (it is then on average 832 $, which is a saving of 103 $ compared to the overall average price). On the other hand, if you buy your ticket 0 to 1 month in advance, you will pay the full price (146 $ more than the average price).

Depending on the departure month

The best time to buy your Chicago to Milan flight ticket may vary depending on your departure month. Therefore, we offer you statistics on when to book your flight month by month.

Departure on... How far in advance should I book?
January

Best time: 1 to 2 months before departure (average price: 514 $)

Other interesting period(s): 0 to 1 month ($ 548), 2 to 3 months ($ 522), 4 to 5 months ($ 545)

February

Best time: 1 to 2 months before departure (average price: 455 $)

Other interesting period(s): 2 to 3 months ($ 465), 3 to 4 months ($ 492)

March

Best time: 3 to 4 months before departure (average price: 492 $)

Other interesting period(s): 1 to 2 months ($ 583), 2 to 3 months ($ 528), 4 to 5 months ($ 591)

April

Best time: 4 to 5 months before departure (average price: 706 $)

Other interesting period(s): 1 to 2 months ($ 795), 2 to 3 months ($ 715), 5 to 6 months ($ 753)

May

Best time: 11 to 12 months before departure (average price: 790 $)

Other interesting period(s): 2 to 3 months ($ 1060), 4 to 5 months ($ 1023), 5 to 6 months ($ 880)

June

Best time: 11 to 12 months before departure (average price: 975 $)

Other interesting period(s): 5 to 6 months ($ 1334), 6 to 7 months ($ 1184), 7 to 8 months ($ 1217)

July

Best time: 11 to 12 months before departure (average price: 1023 $)

Other interesting period(s): 5 to 6 months ($ 1384), 6 to 7 months ($ 1328), 7 to 8 months ($ 1286), 8 to 9 months ($ 1240), 9 to 10 months ($ 1393)

August

Best time: 11 to 12 months before departure (average price: 760 $)

Other interesting period(s): 1 to 2 months ($ 1070), 6 to 7 months ($ 1199), 7 to 8 months ($ 1212), 8 to 9 months ($ 1144), 9 to 10 months ($ 1062)

September

Best time: 11 to 12 months before departure (average price: 788 $)

Other interesting period(s): 2 to 3 months ($ 1078), 7 to 8 months ($ 1057), 8 to 9 months ($ 1023), 9 to 10 months ($ 799), 10 to 11 months ($ 830)

October

Best time: 10 to 11 months before departure (average price: 788 $)

Other interesting period(s): 3 to 4 months ($ 973), 4 to 5 months ($ 978), 5 to 6 months ($ 901), 6 to 7 months ($ 963), 7 to 8 months ($ 965), 8 to 9 months ($ 855), 9 to 10 months ($ 871)

November

Best time: 10 to 11 months before departure (average price: 548 $)

Other interesting period(s): 4 to 5 months ($ 637), 5 to 6 months ($ 608), 6 to 7 months ($ 623), 7 to 8 months ($ 649), 8 to 9 months ($ 561), 9 to 10 months ($ 563)

December

Best time: 4 to 5 months before departure (average price: 719 $)

Other interesting period(s): 1 to 2 months ($ 740), 2 to 3 months ($ 744), 3 to 4 months ($ 743), 5 to 6 months ($ 771), 6 to 7 months ($ 776), 9 to 10 months ($ 720)

What day of the week should I book my flight ticket?

Data analysis:

Statistically, tuesday is the day when plane tickets for Chicago->Milan are the cheapest. So, by buying your plane ticket on a tuesday, you will save $27. Conversely, by buying it on a thursday, you may end up paying $23 more.



Chicago to Milan: flight price when booking today

Information: this data is not statistics but comes from real prices collected less than 7 days ago. Some months may not be available as we do not have enough data for them.

Month Current price
November 2024$ 2514
$1100 to $3734
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December 2024$ 1099
$555 to $2083
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January 2025$ 663
$466 to $900
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February 2025$ 601
$470 to $911
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March 2025$ 623
$444 to $921
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April 2025$ 1076
$425 to $2792
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May 2025$ 1457
$526 to $3965
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June 2025$ 1366
$837 to $1941
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July 2025$ 1348
$800 to $1840
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August 2025$ 1185
$615 to $1596
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September 2025$ 1240
$620 to $1617
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October 2025$ 1039
$558 to $1678
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Data analysis:

Compared to the average price, june, july and august are cheaper to travel to Milan. So it may be interesting to book now to leave during these months!



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