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Cheap flights from Chicago to Milan from $212

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Milan departing on 10/14. 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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Cheap round-trip flights

Scandinavian Airlines Logo
7:15 pm - 7:55 pmORD-MXP
17h 40m2 stops
Scandinavian Airlines Logo
8:00 pm - 4:45 pmMXP-ORD
27h 45m1 stop
$511Scandinavian Airlines
Find Deal
Tue, Sep 30 - Tue, Nov 18
Scandinavian Airlines Logo
7:15 pm - 7:15 pmORD-MXP
17h 00m1 stop
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
$515Scandinavian Airlines
Find Deal
Tue, Sep 30 - Wed, Nov 19
Logo
10:40 am - 2:45 pmORD-MXP
21h 05m3 stops
Logo
10:15 pm - 8:17 pmMXP-ORD
29h 02m3 stops
$530
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Tue, Oct 14 - Tue, Oct 21
TAP AIR PORTUGAL Logo
6:00 pm - 4:25 pmORD-MXP
15h 25m1 stop
TAP AIR PORTUGAL Logo
5:30 pm - 12:35 pmMXP-ORD
26h 05m1 stop
$535TAP AIR PORTUGAL
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Sun, Oct 5 - Wed, Oct 15
Logo
10:40 am - 6:50 pmORD-MXP
25h 10m2 stops
Logo
10:50 pm - 2:48 pmMXP-ORD
22h 58m3 stops
$536
Find Deal
Tue, Sep 23 - Mon, Oct 6
Turkish Airlines Logo
7:50 pm - 8:45 amORD-MXP
29h 55m1 stop
Turkish Airlines Logo
2:30 pm - 11:05 amMXP-ORD
26h 35m1 stop
$540Turkish Airlines
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Wed, Oct 22 - Fri, Oct 31
Turkish Airlines Logo
7:50 pm - 8:45 amORD-MXP
29h 55m1 stop
Turkish Airlines Logo
11:05 am - 11:05 amMXP-ORD
30h 00m1 stop
$550Turkish Airlines
Find Deal
Wed, Oct 22 - Fri, Oct 31
TAP AIR PORTUGAL Logo
6:00 pm - 7:15 pmORD-MXP
18h 15m1 stop
TAP AIR PORTUGAL Logo
5:45 pm - 4:00 pmMXP-ORD
28h 15m1 stop
$580TAP AIR PORTUGAL
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Fri, Oct 24 - Sat, Nov 1
KLM Logo
10:40 am - 9:05 amMDW-MXP
15h 25m1 stop
KLM Logo
11:05 am - 11:32 pmMXP-MDW
19h 27m1 stop
$830KLM
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Sun, Nov 2 - Thu, Dec 11
KLM Logo
1:05 pm - 9:05 amMDW-MXP
13h 00m1 stop
KLM Logo
11:05 am - 11:32 pmMXP-MDW
19h 27m1 stop
$880KLM
Find Deal
Sun, Nov 9 - Mon, Nov 17

TAP AIR PORTUGAL flights from Chicago to Milan Malpensa Airport

Our best TAP AIR PORTUGAL deals on Chicago to Milan Malpensa Airport flight tickets
TAP AIR PORTUGAL
Oct 5
ORD6:00 pmChicago O'Hare Intl
15h 25m
1 stop
MXP4:25 pmMilan Malpensa
Oct 15
MXP5:30 pmMilan Malpensa
26h 05m
1 stop
ORD12:35 pmChicago O'Hare Intl
$535
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TAP AIR PORTUGAL
Oct 24
ORD6:00 pmChicago O'Hare Intl
18h 15m
1 stop
MXP7:15 pmMilan Malpensa
Nov 1
MXP5:45 pmMilan Malpensa
28h 15m
1 stop
ORD4:00 pmChicago O'Hare Intl
$580
Find similar
TAP AIR PORTUGAL
Sep 21
ORD6:00 pmChicago O'Hare Intl
23h 45m
1 stop
MXP12:45 amMilan Malpensa
Oct 7
MXP11:50 amMilan Malpensa
35h 20m
1 stop
ORD4:10 pmChicago O'Hare Intl
$799
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KLM flights from Chicago to Milan Malpensa Airport

Our best KLM deals on Chicago to Milan Malpensa Airport flight tickets
KLM
Nov 2
MDW10:40 amChicago Midway
15h 25m
1 stop
MXP9:05 amMilan Malpensa
Dec 11
MXP11:05 amMilan Malpensa
19h 27m
1 stop
MDW11:32 pmChicago Midway
$830
Find similar
KLM
Nov 9
MDW1:05 pmChicago Midway
13h 00m
1 stop
MXP9:05 amMilan Malpensa
Nov 17
MXP11:05 amMilan Malpensa
19h 27m
1 stop
MDW11:32 pmChicago Midway
$880
Find similar
KLM
Dec 28
MDW12:43 pmChicago Midway
13h 22m
1 stop
MXP9:05 amMilan Malpensa
Jan 8
MXP11:05 amMilan Malpensa
17h 41m
1 stop
MDW9:46 pmChicago Midway
$975
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momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Milan Malpensa Airport 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, momondo users made 832,500 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Chicago to Milan Malpensa Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 9/30

7:15 pm-7:55 pm

2 stops17h 40m

Milan Malpensa

Tue 11/18

8:00 pm-4:45 pm

1 stop27h 45m

$511

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 9/30

7:15 pm-7:15 pm

1 stop17h 00m

Milan Malpensa

Wed 11/19

11:15 am-4:45 pm

1 stop12h 30m

$515

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 10/14

10:40 am-2:45 pm

3 stops21h 05m

Milan Malpensa

Tue 10/21

10:15 pm-8:17 pm

3 stops29h 02m

$530

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 10/5

6:00 pm-4:25 pm

1 stop15h 25m

Milan Malpensa

Wed 10/15

5:30 pm-12:35 pm

1 stop26h 05m

$535

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 9/23

10:40 am-6:50 pm

2 stops25h 10m

Milan Malpensa

Mon 10/6

10:50 pm-2:48 pm

3 stops22h 58m

$536

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 10/22

7:50 pm-8:45 am

1 stop29h 55m

Milan Malpensa

Fri 10/31

2:30 pm-11:05 am

1 stop26h 35m

$540

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 10/22

7:50 pm-8:45 am

1 stop29h 55m

Milan Malpensa

Fri 10/31

11:05 am-11:05 am

1 stop30h 00m

$550

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 10/24

6:00 pm-7:15 pm

1 stop18h 15m

Milan Malpensa

Sat 11/1

5:45 pm-4:00 pm

1 stop28h 15m

$580

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 11/2

10:40 am-9:05 am

1 stop15h 25m

Milan Malpensa

Thu 12/11

11:05 am-11:32 pm

1 stop19h 27m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 11/9

1:05 pm-9:05 am

1 stop13h 00m

Milan Malpensa

Mon 11/17

11:05 am-11:32 pm

1 stop19h 27m

$880

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Milan from

How to get the cheapest flight ticket from Chicago to Milan Malpensa Airport

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 Milan Malpensa Airport?

In general, November is the cheapest month to fly from Chicago to Milan Malpensa Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $513. If you don’t want to visit Milan Malpensa Airport in November, then you should wait until February to fly from Chicago, when ticket prices are also cheap, with an average price of $593.

What is the cheapest day to depart on your flight to Milan Malpensa Airport?

Our data shows that Tuesday is the least expensive day to fly to Milan Malpensa Airport. Tickets to fly out on this day can be as low as $1,183. On the other hand, Saturday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,496.

What is the cheapest time of day to depart on your flight to Milan Malpensa Airport?

According to our data, the cheapest time of day to fly to Milan Malpensa Airport is in the morning. momondo users have found flights departing from Chicago to Milan Malpensa Airport in the morning for as low as $796. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the evening are often more expensive with an average ticket price of $1,345.

What is the cheapest Chicago to Milan Malpensa flight route?

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

How far in advance should I book a flight to Milan Malpensa Airport?

You are more likely to see cheaper flights to Milan Malpensa Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Milan Malpensa Airport for around $945 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan Malpensa Airport from Chicago for as low as $693 on momondo.

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

There are 3 cabin classes available to choose from on Chicago to Milan Malpensa flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Chicago to Milan Malpensa Airport

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

Cheap Chicago to Milan Malpensa Airport (CHI to MXP) flight deals and tips

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

Best Price Found

$663

Fastest flight time

8h 30m

Direct flights

Every day
The best one-way flight to Milan Malpensa Airport from Chicago in the past 72 hours is $663. The best round-trip flight deal from Chicago to Milan Malpensa Airport found on momondo in the last 72 hours is $844.
The fastest flight from Chicago to Milan Malpensa Airport takes 8h 30m
Direct flights go from Chicago to Milan Malpensa Airport every day.
Search flight deals

  • How far is Chicago to Milan Malpensa by plane?

    There are 4501.5 mi between Chicago and Milan Malpensa. By plane, this route typically takes 13h 00m.

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

    Prices for flights from Chicago to Milan Malpensa Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Milan Malpensa Airport?

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Milan Malpensa Airport.

  • What documentation or ID do you need to fly to Milan Malpensa Airport?

    The required travel and health documents for your Milan Malpensa Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Milan Malpensa Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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

Best airlines flying from Chicago to Milan Malpensa Airport

Compare and see reviews for airlines that fly from Chicago to Milan Malpensa Airport with momondo
Airline
Rating
Free Cancellation
Price
IcelandairPriceFrom $382Free CancellationRating
7.0
546 reviews
Search Icelandair flights
DeltaPriceFrom $419Free CancellationRating
7.9
7,960 reviews
Search Delta flights
Scandinavian AirlinesPriceFrom $420Free CancellationRating
7.4
1,484 reviews
Search Scandinavian Airlines flights
TAP AIR PORTUGALPriceFrom $470Free CancellationRating
7.1
1,977 reviews
Search TAP AIR PORTUGAL flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
3,968 reviews
Search Turkish Airlines flights
British AirwaysPriceFrom $536Free CancellationRating
6.6
7,361 reviews
Search British Airways flights
American AirlinesPriceFrom $550Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Air FrancePriceFrom $575Free CancellationRating
7.4
1,469 reviews
Search Air France flights
IberiaPriceFrom $639Free CancellationRating
7.0
2,929 reviews
Search Iberia flights
United AirlinesPriceFrom $759Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights

  • United Airlines Flights From Chicago to Milan Malpensa Airport

    United Airlines flies from Chicago to Milan Malpensa Airport around 7 times per week, with 8,937 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Milan Malpensa Airport in the last 72 hours was $759 (round-trip), much lower than the average airfare cost of $1,275 for United Airlines flights on this route.

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Bellagio
Varenna
Menaggio
Livigno
Brescia
Stresa
Assago
Monza
Breuil-Cervinia
Rho
Levanto
Domodossola
Bormio
Crema
Bellano
Lecco
Cernobbio
Novara
Moltrasio
Saronno

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Milan for you.

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

Yes. momondo allows you to filter the results for Chicago to Milan flights to just show those with flexible booking policies.

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

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 Milan from Chicago.

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

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

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