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Cheap flights from Milan to Chicago from £303

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milan to Chicago departing on 20/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Milan to Chicago

Cheap return flights

These are some of the best return flight deals from Milan to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Milan to Chicago.

Cheap last-minute flights

Planning a quick getaway from Milan to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without stopovers.

Cheap bus & train deals from Milan to Chicago

Find recent round-trip train or bus tickets from Milan to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
06:20 - 15:30MXP-ORD
16h 10m1 stop
19:15 - 23:35ORD-MXP
21h 20m1 stop
£368TAP AIR PORTUGAL
Find Deal
dim., 23 févr. - mer., 5 mars
11:55 - 15:30MXP-ORD
34h 35m1 stop
19:15 - 23:35ORD-MXP
21h 20m1 stop
£372TAP AIR PORTUGAL
Find Deal
jeu., 27 févr. - mer., 5 mars
11:20 - 17:50MXP-ORD
13h 30m1 stop
19:40 - 19:10ORD-MXP
16h 30m1 stop
£383Scandinavian Airlines
Find Deal
lun., 24 févr. - dim., 2 mars
11:20 - 17:50MXP-ORD
13h 30m1 stop
19:40 - 18:50ORD-MXP
16h 10m2 stops
£388Scandinavian Airlines
Find Deal
lun., 24 févr. - jeu., 6 mars
11:20 - 17:50MXP-ORD
13h 30m1 stop
19:40 - 19:10ORD-MXP
16h 30m1 stop
£400Scandinavian Airlines
Find Deal
sam., 8 févr. - sam., 1 mars
08:00 - 19:45LIN-ORD
18h 45m2 stops
11:45 - 10:10ORD-LIN
15h 25m2 stops
lun., 14 avr. - dim., 27 avr.
11:05 - 17:25MXP-ORD
13h 20m1 stop
22:55 - 18:00ORD-MXP
12h 05m1 stop
jeu., 10 avr. - mar., 6 mai
11:20 - 08:57MXP-ORD
28h 37m2 stops
10:50 - 07:30ORD-MXP
13h 40m1 stop
£481United Airlines
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mar., 14 janv. - mar., 21 janv.
06:25 - 14:45LIN-ORD
15h 20m2 stops
18:30 - 16:55ORD-LIN
15h 25m1 stop
£483United Airlines
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ven., 24 janv. - mer., 29 janv.
11:05 - 17:25MXP-ORD
13h 20m1 stop
21:30 - 18:15ORD-MXP
13h 45m1 stop
£483Finnair
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jeu., 10 avr. - jeu., 24 avr.
09:25 - 14:25MXP-ORD
36h 00m1 stop
£303Air Serbia
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mar., 20 mai
20:55 - 21:00MXP-ORD
31h 05m1 stop
£313Air Serbia
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ven., 13 juin
09:25 - 16:40MXP-ORD
14h 15m1 stop
£338Air Serbia
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lun., 2 juin
15:10 - 21:15MXP-ORD
13h 05m1 stop
£412Icelandair
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lun., 19 mai
11:10 - 11:10MXP-ORD
30h 00m1 stop
£413Turkish Airlines
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mer., 26 mars
14:35 - 18:35MXP-ORD
35h 00m1 stop
£414Turkish Airlines
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lun., 3 mars
06:30 - 15:30LIN-ORD
15h 00m1 stop
£539KLM
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mer., 26 mars
14:05 - 23:57LIN-ORD
15h 52m2 stops
£544Delta
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mer., 26 mars
15:55 - 14:10LIN-ORD
29h 15m1 stop
£545KLM
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lun., 19 mai
06:55 - 20:34MXP-ORD
19h 39m2 stops
£546Delta
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mer., 26 mars
06:20 - 08:07MXP-ORD
32h 47m2 stops
18:20 - 23:35ORD-MXP
22h 15m3 stops
£2,143TAP AIR PORTUGAL
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ven., 20 déc. - mar., 7 janv.
06:20 - 09:26MXP-ORD
34h 06m2 stops
10:11 - 16:55ORD-MXP
23h 44m2 stops
£2,721TAP AIR PORTUGAL
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lun., 23 déc. - lun., 30 déc.
11:30 - 23:10MXP-ORD
42h 40m3 stops
06:30 - 07:40ORD-MXP
42h 10m2 stops
£10,625
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jeu., 19 déc. - mer., 8 janv.
12:15 - 23:10MXP-ORD
41h 55m3 stops
14:40 - 18:25ORD-MXP
44h 45m2 stops
£10,640
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dim., 22 déc. - ven., 3 janv.
18:55 - 05:46LIN-ORD
41h 51m3 stops
14:40 - 14:00ORD-LIN
40h 20m2 stops
£10,641
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dim., 22 déc. - ven., 3 janv.
17:45 - 05:12MXP-ORD
42h 27m3 stops
14:40 - 11:55ORD-MXP
38h 15m2 stops
£10,659
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dim., 22 déc. - sam., 28 déc.
14:15 - 23:10LIN-ORD
39h 55m3 stops
14:40 - 10:15ORD-LIN
36h 35m2 stops
£10,660
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dim., 22 déc. - sam., 28 déc.
18:55 - 05:12LIN-ORD
41h 17m3 stops
14:40 - 13:20ORD-LIN
39h 40m2 stops
£10,661
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ven., 20 déc. - mar., 7 janv.
11:45 - 23:59MXP-ORD
43h 14m2 stops
13:55 - 19:45ORD-MXP
46h 50m3 stops
£24,526
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lun., 23 déc. - lun., 30 déc.
15:30 - 05:46MXP-ORD
45h 16m3 stops
13:55 - 19:45ORD-MXP
46h 50m3 stops
£24,577
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lun., 23 déc. - lun., 30 déc.
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£492United Airlines
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jeu., 10 avr. - mar., 6 mai
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£493United Airlines
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mar., 15 avr. - lun., 21 avr.
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£538United Airlines
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jeu., 10 avr. - jeu., 24 avr.
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£539United Airlines
Find Deal
jeu., 10 avr. - jeu., 24 avr.
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£588United Airlines
Find Deal
mar., 6 mai - mer., 14 mai
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£895United Airlines
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jeu., 10 avr. - sam., 10 mai
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£939United Airlines
Find Deal
sam., 19 avr. - dim., 4 mai
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£1,089United Airlines
Find Deal
ven., 18 avr. - ven., 25 avr.
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£1,225United Airlines
Find Deal
sam., 19 avr. - sam., 3 mai
15:20 - 18:00MXP-ORD
9h 40mdirect
21:35 - 13:20ORD-MXP
8h 45mdirect
£2,800United Airlines
Find Deal
mar., 15 avr. - lun., 21 avr.

TAP AIR PORTUGAL flights from Milan to Chicago

Our best TAP AIR PORTUGAL deals on Milan to Chicago flight tickets
TAP AIR PORTUGAL
23 Feb
MXP06:20Milan Malpensa
16h 10m
1 stop
ORD15:30Chicago O'Hare Intl
5 Mar
ORD19:15Chicago O'Hare Intl
21h 20m
1 stop
MXP23:35Milan Malpensa
TAP AIR PORTUGAL
27 Feb
MXP11:55Milan Malpensa
34h 35m
1 stop
ORD15:30Chicago O'Hare Intl
5 Mar
ORD19:15Chicago O'Hare Intl
21h 20m
1 stop
MXP23:35Milan Malpensa
TAP AIR PORTUGAL
1 Mar
MXP17:45Milan Malpensa
28h 45m
1 stop
ORD15:30Chicago O'Hare Intl
5 Mar
ORD19:15Chicago O'Hare Intl
14h 40m
1 stop
MXP16:55Milan Malpensa

Scandinavian Airlines flights from Milan to Chicago

Our best Scandinavian Airlines deals on Milan to Chicago flight tickets
Scandinavian Airlines
24 Feb
MXP11:20Milan Malpensa
13h 30m
1 stop
ORD17:50Chicago O'Hare Intl
2 Mar
ORD19:40Chicago O'Hare Intl
16h 30m
1 stop
MXP19:10Milan Malpensa
Scandinavian Airlines
24 Feb
MXP11:20Milan Malpensa
13h 30m
1 stop
ORD17:50Chicago O'Hare Intl
6 Mar
ORD19:40Chicago O'Hare Intl
16h 10m
2 stops
MXP18:50Milan Malpensa
Scandinavian Airlines
8 Feb
MXP11:20Milan Malpensa
13h 30m
1 stop
ORD17:50Chicago O'Hare Intl
1 Mar
ORD19:40Chicago O'Hare Intl
16h 30m
1 stop
MXP19:10Milan Malpensa

See travel insights to Chicago from

How to get the cheapest flight ticket from Milan to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Milan and Chicago?

What is the cheapest month to fly to Chicago?

The cheapest month to fly to Chicago from Milan is in November. Flight prices, which tend to average around £346, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Chicago from Milan during February instead. Flights to Chicago in February, while not as cheap as those in November, still average around £376.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as £0. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Monday, with ticket prices averaging around £659.

What is the cheapest time of day to depart on your flight to Chicago?

Flying to Chicago from Milan at midday is the least expensive time of day to depart. momondo users have found prices as low as £0 when looking at flights departing at midday. Flights in the morning are often more expensive, with an average ticket price of £632.

What is the cheapest Milan to Chicago flight route?

Fly from Milan Malpensa to Chicago O'Hare Intl for the best Milan - Chicago flight prices

How far in advance should I book a flight to Chicago?

The ideal time to book your flight to Chicago is 60 days in advance, when prices tend to average £532. However, in the past 72 hours, people saw flights from Milan for as low as £217.

What cabin class options are available on Milan to Chicago flights?

There are 1 cabin classes available to choose from on Milan to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Milan to Chicago flights?

You could potentially save up to 44% on your flight if you consider stops on a Milan to Chicago flight.

How have Milan to Chicago flight prices changed over time?

As of December 2024, prices for Milan to Chicago flights are approximately 50% more expensive when compared to flights at the same time last year.

When to book flights from Milan to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Milan to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Milan to Chicago (MIL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milan to Chicago

Best price found

£303

Fastest flight time

9h 40m

Direct flights

Tue, Wed, Fri, Sat and Sun

Airports in Chicago

1 airport
The best one-way flight to Chicago from Milan in the past 72 hours is £303. The best return flight deal from Milan to Chicago found on momondo in the last 72 hours is £368.
The fastest flight from Milan to Chicago takes 9h 40m
Direct flights go from Milan to Chicago on Tuesday, Wednesday, Friday, Saturday and Sunday. Airline offering direct flights is United Airlines..
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • How far is Milan to Chicago by plane?

    There are 4526.2 mi between Milan and Chicago. By plane, this route typically takes 9h 40m.

  • When did momondo last update prices for flights from Milan to Chicago?

    Prices for flights from Milan to Chicago are updated daily.

  • How old do you have to be to fly from Milan to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milan to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Milan to Chicago?


Why use momondo?

Why should I use momondo to find a flight deal from Milan to Chicago?

Finding the right flight to Chicago from Milan is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Milan to Chicago with flexible booking policies on momondo?

Flights from Milan to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Milan to Chicago?

Once you have performed a search for Milan to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Milan to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Milan to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago