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Cheap flights from Milan to Chicago from $294

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 3/30. 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 round-trip flights

These are some of the best round-trip 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 layovers.

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 from Milan to Chicago

The cheapest plane tickets from Milan to Chicago found on KAYAK recently.
2:10 pm - 5:20 pmMXP-ORD
34h 10m1 stop
6:30 pm - 1:10 pmORD-MXP
11h 40m1 stop
$378Icelandair
Find Deal
Thu, Feb 13 - Wed, Feb 26
7:40 pm - 7:40 pmMXP-ORD
31h 00m1 stop
9:40 pm - 6:50 pmORD-MXP
14h 10m1 stop
$428LOT
Find Deal
Wed, Apr 23 - Sun, Apr 27
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
8:25 pm - 11:35 pmORD-MXP
20h 10m1 stop
$433TAP AIR PORTUGAL
Find Deal
Fri, Jan 31 - Sun, Feb 16
5:55 am - 4:10 pmMXP-ORD
17h 15m1 stop
6:00 pm - 12:35 amORD-MXP
23h 35m1 stop
$435TAP AIR PORTUGAL
Find Deal
Wed, Apr 30 - Sat, May 3
11:20 am - 7:00 pmLIN-ORD
14h 40m1 stop
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
$476Aer Lingus
Find Deal
Wed, Apr 30 - Tue, May 6
8:00 pm - 5:50 pmMXP-ORD
28h 50m1 stop
7:40 pm - 7:10 pmORD-MXP
16h 30m1 stop
$487Scandinavian Airlines
Find Deal
Fri, Feb 14 - Sun, Feb 23
11:45 am - 3:00 pmLIN-ORD
33h 15m1 stop
4:55 pm - 11:05 amORD-LIN
12h 10m1 stop
$501Aer Lingus
Find Deal
Mon, Mar 10 - Tue, Mar 25
11:20 am - 6:50 pmMXP-ORD
13h 30m1 stop
7:15 pm - 7:15 pmORD-MXP
17h 00m1 stop
$503Scandinavian Airlines
Find Deal
Sat, Mar 15 - Sun, Mar 30
6:20 am - 2:45 pmLIN-ORD
15h 25m2 stops
4:05 pm - 4:55 pmORD-LIN
18h 50m2 stops
$552United Airlines
Find Deal
Sun, Mar 2 - Sun, Mar 9
11:15 am - 9:01 amMXP-ORD
27h 46m2 stops
3:35 pm - 10:00 amORD-MXP
11h 25m1 stop
$552United Airlines
Find Deal
Fri, Mar 28 - Tue, Apr 1
10:20 pm - 7:44 amMXP-ORD
40h 24m3 stops
Sun, Mar 30
5:30 am - 10:31 amMXP-ORD
36h 01m2 stops
Fri, May 16
5:55 am - 4:10 pmMXP-ORD
17h 15m1 stop
$490TAP AIR PORTUGAL
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Wed, Apr 23
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
$498TAP AIR PORTUGAL
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Fri, Mar 7
11:20 am - 7:00 pmLIN-ORD
14h 40m1 stop
$512Aer Lingus
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Sun, May 4
11:20 am - 7:00 pmLIN-ORD
14h 40m1 stop
$516Aer Lingus
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Fri, May 23
6:30 am - 1:10 pmLIN-ORD
13h 40m1 stop
$541ITA Airways
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Sat, Jun 14
6:30 am - 1:10 pmLIN-ORD
13h 40m1 stop
$620ITA Airways
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Wed, May 21
8:45 pm - 4:10 pmMXP-ORD
26h 25m2 stops
$650Scandinavian Airlines
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Mon, Jun 2
8:40 pm - 4:10 pmMXP-ORD
26h 30m2 stops
$753Scandinavian Airlines
Find Deal
Sun, Jul 6
12:20 pm - 7:55 pmMXP-ORD
14h 35m1 stop
6:30 pm - 5:40 pmORD-MXP
16h 10m1 stop
Tue, Jan 21 - Tue, Jan 28
12:20 pm - 7:55 pmMXP-ORD
14h 35m1 stop
11:15 am - 7:30 amORD-MXP
13h 15m2 stops
$562United Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
8:35 pm - 5:38 pmMXP-ORD
28h 03m2 stops
5:20 pm - 2:40 pmORD-MXP
14h 20m2 stops
$579British Airways
Find Deal
Tue, Jan 21 - Tue, Jan 28
9:55 pm - 7:55 pmMXP-ORD
29h 00m3 stops
3:35 pm - 11:10 pmORD-MXP
24h 35m2 stops
Tue, Jan 21 - Tue, Jan 28
7:25 am - 2:45 pmLIN-ORD
14h 20m1 stop
9:45 pm - 5:50 pmORD-LIN
13h 05m1 stop
$657British Airways
Find Deal
Tue, Jan 21 - Tue, Jan 28
12:20 pm - 4:10 pmMXP-ORD
34h 50m3 stops
5:11 am - 12:35 pmORD-MXP
24h 24m3 stops
Tue, Jan 21 - Tue, Jan 28
11:45 am - 7:15 pmLIN-ORD
14h 30m1 stop
9:45 pm - 11:05 amORD-LIN
30h 20m2 stops
$792Aer Lingus
Find Deal
Tue, Jan 21 - Tue, Jan 28
7:00 am - 6:35 pmMXP-ORD
18h 35m1 stop
8:30 pm - 9:45 pmORD-MXP
18h 15m1 stop
$2,574Turkish Airlines
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Tue, Jan 21 - Tue, Jan 28
12:15 pm - 2:55 pmBGY-ORD
33h 40m1 stop
7:45 pm - 11:15 amORD-BGY
32h 30m1 stop
$3,016Emirates
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Tue, Jan 21 - Tue, Jan 28
12:15 pm - 2:55 pmBGY-ORD
33h 40m1 stop
7:45 pm - 11:15 amORD-BGY
32h 30m1 stop
$11,459Emirates
Find Deal
Tue, Jan 21 - Tue, Jan 28
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$564United Airlines
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Tue, Apr 8 - Mon, May 5
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$614United Airlines
Find Deal
Tue, Apr 29 - Mon, May 5
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$616United Airlines
Find Deal
Mon, May 5 - Tue, May 13
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$618United Airlines
Find Deal
Fri, Apr 11 - Mon, May 5
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$646United Airlines
Find Deal
Wed, Apr 9 - Wed, May 7
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$670United Airlines
Find Deal
Thu, May 8 - Mon, May 12
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$672United Airlines
Find Deal
Fri, Apr 11 - Wed, May 7
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$673United Airlines
Find Deal
Wed, May 7 - Sun, May 11
3:20 pm - 6:10 pmMXP-ORD
9h 50mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$719Lufthansa
Find Deal
Fri, May 23 - Wed, May 28
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$835Lufthansa
Find Deal
Wed, Apr 30 - Tue, May 6

TAP AIR PORTUGAL flights from Milan to Chicago

Our best TAP AIR PORTUGAL deals on Milan to Chicago flight tickets
TAP AIR PORTUGAL
Jan 31
MXP6:20 amMilan Malpensa
16h 10m
1 stop
ORD3:30 pmChicago O'Hare Intl
Feb 16
ORD8:25 pmChicago O'Hare Intl
20h 10m
1 stop
MXP11:35 pmMilan Malpensa
TAP AIR PORTUGAL
Apr 30
MXP5:55 amMilan Malpensa
17h 15m
1 stop
ORD4:10 pmChicago O'Hare Intl
May 3
ORD6:00 pmChicago O'Hare Intl
23h 35m
1 stop
MXP12:35 amMilan Malpensa
TAP AIR PORTUGAL
Feb 27
MXP11:55 amMilan Malpensa
34h 35m
1 stop
ORD3:30 pmChicago O'Hare Intl
Mar 12
ORD8:15 pmChicago O'Hare Intl
14h 40m
1 stop
MXP4:55 pmMilan Malpensa

United Airlines flights from Milan to Chicago

Our best United Airlines deals on Milan to Chicago flight tickets
United Airlines
Mar 2
LIN6:20 amMilan Linate
15h 25m
2 stops
ORD2:45 pmChicago O'Hare Intl
Mar 9
ORD4:05 pmChicago O'Hare Intl
18h 50m
2 stops
LIN4:55 pmMilan Linate
United Airlines
Jan 21
MXP12:20 pmMilan Malpensa
14h 35m
1 stop
ORD7:55 pmChicago O'Hare Intl
Jan 28
ORD11:15 amChicago O'Hare Intl
13h 15m
2 stops
MXP7:30 amMilan Malpensa
United Airlines
Jan 28
MXP9:45 amMilan Malpensa
16h 38m
2 stops
ORD7:23 pmChicago O'Hare Intl
Feb 4
ORD11:51 amChicago O'Hare Intl
12h 39m
1 stop
MXP7:30 amMilan 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 cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $439. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Milan to Chicago during February average around $486.

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 Friday when prices can be found for as low as $594. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Milan to Chicago for around $749.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Milan to Chicago during this time can be as low as $561. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $800.

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?

You are more likely to see cheaper flights to Chicago from Milan when booking 2 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $678 when searching 2 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Milan for as low as $563 on momondo.

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

There are 3 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.

How have Milan to Chicago flight prices changed over time?

As of January 2025, prices for Milan to Chicago flights are approximately 11% 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 round-trip 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

$294

Fastest flight time

9h 40m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Milan in the past 72 hours is $294. The best round-trip flight deal from Milan to Chicago found on momondo in the last 72 hours is $378.
The fastest flight from Milan to Chicago takes 9h 40m
Direct flights go from Milan to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • How far is Milan to Chicago by plane?

    The straight-line distance from Milan to Chicago is 4526.2 mi. In terms of flight time, this usually takes a little over 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 many operators does momondo search for flights from Milan to Chicago?

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milan to Chicago.

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

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

  • What is the most popular airline from Milan to Chicago?


Best airlines flying from Milan to Chicago

Compare and see reviews for airlines that fly from Milan to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Scandinavian AirlinesPriceFrom $350Free CancellationRating
7.3
1,308 reviews
Search Scandinavian Airlines flights
TAP AIR PORTUGALPriceFrom $560Free CancellationRating
7.1
1,862 reviews
Search TAP AIR PORTUGAL flights
United AirlinesPriceFrom $624Free CancellationRating
7.4
8,965 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Milan to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Milan with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Milan.

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

Price alerts on flights to Chicago from Milan are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


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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