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Cheap flights from Chicago to Milan from $548

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 7/21. 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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0 bags

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Find the cheapest flights from Chicago to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Scandinavian Airlines Logo
10:30 am - 10:35 am
ORD
-
MXP
17h 05m
2 stops
Scandinavian Airlines Logo
11:15 am - 5:45 pm
MXP
-
ORD
12h 30m
1 stop
$732Scandinavian Airlines
Tue, Oct 20 - Fri, Oct 30
Air Serbia Logo
4:40 pm - 8:30 am
ORD
-
MXP
32h 50m
1 stop
Air Serbia Logo
8:50 pm - 9:15 pm
MXP
-
ORD
31h 25m
1 stop
$734Air Serbia
Mon, Sep 14 - Fri, Oct 2
Turkish Airlines Logo
11:25 am - 8:40 am
ORD
-
MXP
14h 15m
1 stop
Turkish Airlines Logo
2:30 pm - 7:25 pm
MXP
-
ORD
34h 55m
1 stop
$735Turkish Airlines
Tue, Oct 20 - Fri, Oct 30
Scandinavian Airlines Logo
7:15 pm - 11:25 am
ORD
-
MXP
57h 10m
2 stops
Scandinavian Airlines Logo
8:00 pm - 10:06 pm
MXP
-
ORD
33h 06m
2 stops
$736Scandinavian Airlines
Sat, Sep 5 - Fri, Sep 18
Scandinavian Airlines Logo
7:15 pm - 3:05 pm
ORD
-
MXP
12h 50m
1 stop
Scandinavian Airlines Logo
3:55 pm - 10:06 pm
MXP
-
ORD
37h 11m
2 stops
$738Scandinavian Airlines
Mon, Sep 7 - Mon, Sep 14
SWISS Logo
7:05 pm - 9:50 am
ORD
-
MXP
31h 45m
1 stop
SWISS Logo
7:25 pm - 12:35 pm
MXP
-
ORD
24h 10m
1 stop
$743SWISS
Tue, Aug 11 - Tue, Aug 18
KLM Logo
1:05 pm - 11:10 am
MDW
-
MXP
16h 05m
1 stop
KLM Logo
1:05 pm - 9:45 pm
MXP
-
MDW
15h 40m
1 stop
$842KLM
Sun, Oct 25 - Sun, Nov 8
Delta Logo
5:25 pm - 2:55 pm
MDW
-
MXP
15h 30m
2 stops
Delta Logo
1:05 pm - 9:45 pm
MXP
-
MDW
15h 40m
1 stop
$846Delta
Sun, Oct 25 - Sun, Nov 8
KLM Logo
1:05 pm - 9:25 am
MDW
-
MXP
13h 20m
1 stop
KLM Logo
1:05 pm - 9:45 pm
MXP
-
MDW
15h 40m
1 stop
$857KLM
Tue, Oct 20 - Tue, Nov 3
Delta Logo
12:30 pm - 10:25 am
MDW
-
MXP
14h 55m
2 stops
Delta Logo
1:05 pm - 9:45 pm
MXP
-
MDW
15h 40m
1 stop
$861Delta
Tue, Oct 20 - Tue, Nov 3

SWISS flights from Chicago to Milan Malpensa Airport

Our best SWISS deals on Chicago to Milan Malpensa Airport flight tickets
SWISS
Aug 11
ORD7:05 pmChicago O'Hare Intl
31h 45m
1 stop
MXP9:50 amMilan Malpensa
Aug 18
MXP7:25 pmMilan Malpensa
24h 10m
1 stop
ORD12:35 pmChicago O'Hare Intl
$743
SWISS
Aug 13
ORD2:20 pmChicago O'Hare Intl
12h 30m
1 stop
MXP9:50 amMilan Malpensa
Aug 23
MXP5:50 amMilan Malpensa
13h 45m
1 stop
ORD12:35 pmChicago O'Hare Intl
$751
SWISS
Aug 11
ORD7:05 pmChicago O'Hare Intl
31h 45m
1 stop
MXP9:50 amMilan Malpensa
Aug 18
MXP7:25 pmMilan Malpensa
24h 10m
1 stop
ORD12:35 pmChicago O'Hare Intl
$770

Air France flights from Chicago to Milan Malpensa Airport

Our best Air France deals on Chicago to Milan Malpensa Airport flight tickets
Air France
Aug 8
MDW10:55 amChicago Midway
15h 30m
1 stop
MXP9:25 amMilan Malpensa
Aug 22
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$892
Air France
Nov 1
MDW5:59 pmChicago Midway
13h 56m
2 stops
MXP2:55 pmMilan Malpensa
Nov 8
MXP12:00 pmMilan Malpensa
16h 45m
2 stops
MDW9:45 pmChicago Midway
$1,126

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 May 8, 2026.
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

Cheapest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 10/20

10:30 am-10:35 am

2 stops17h 05m

Milan Malpensa

Fri 10/30

11:15 am-5:45 pm

1 stop12h 30m

$732

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 9/14

4:40 pm-8:30 am

1 stop32h 50m

Milan Malpensa

Fri 10/2

8:50 pm-9:15 pm

1 stop31h 25m

$734

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 10/20

11:25 am-8:40 am

1 stop14h 15m

Milan Malpensa

Fri 10/30

2:30 pm-7:25 pm

1 stop34h 55m

$735

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 9/5

7:15 pm-11:25 am

2 stops57h 10m

Milan Malpensa

Fri 9/18

8:00 pm-10:06 pm

2 stops33h 06m

$736

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 9/7

7:15 pm-3:05 pm

1 stop12h 50m

Milan Malpensa

Mon 9/14

3:55 pm-10:06 pm

2 stops37h 11m

$738

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 8/11

7:05 pm-9:50 am

1 stop31h 45m

Milan Malpensa

Tue 8/18

7:25 pm-12:35 pm

1 stop24h 10m

$743

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 10/25

1:05 pm-11:10 am

1 stop16h 05m

Milan Malpensa

Sun 11/8

1:05 pm-9:45 pm

1 stop15h 40m

$842

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 10/25

5:25 pm-2:55 pm

2 stops15h 30m

Milan Malpensa

Sun 11/8

1:05 pm-9:45 pm

1 stop15h 40m

$846
Quickest round-trip

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 10/20

1:05 pm-9:25 am

1 stop13h 20m

Milan Malpensa

Tue 11/3

1:05 pm-9:45 pm

1 stop15h 40m

$857

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 10/20

12:30 pm-10:25 am

2 stops14h 55m

Milan Malpensa

Tue 11/3

1:05 pm-9:45 pm

1 stop15h 40m

$861

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 typical price of a round-trip flight between Chicago and Milan Malpensa Airport?

What is the cheapest month to fly to Milan Malpensa Airport?

In general, September 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 $338. If you don’t want to visit Milan Malpensa Airport in September, then you should wait until November to fly from Chicago, when ticket prices are also cheap, with an average price of $373.

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 $1,226. On the other hand, Wednesday 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 $1,473.

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 from Chicago 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 $864 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 $560 on momondo.

Can stopping save me money on Chicago to Milan Malpensa Airport flights?

You could potentially save up to 33% on your flight if you consider stops on a Chicago to Milan Malpensa Airport flight.

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

$898

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 $898. The best round-trip flight deal from Chicago to Milan Malpensa Airport found on momondo in the last 72 hours is $1,273.
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

Frequently asked questions about flying from Chicago to Milan Malpensa Airport

  • 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 8h 30m.

  • 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
TAP AIR PORTUGALPriceFrom $401Free CancellationRating
7.2
2,242 reviews
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesPriceFrom $410Free CancellationRating
7.4
1,770 reviews
Search Scandinavian Airlines flights
British AirwaysPriceFrom $493Free CancellationRating
6.7
7,951 reviews
Search British Airways flights
Turkish AirlinesPriceFrom $534Free CancellationRating
7.4
4,355 reviews
Search Turkish Airlines flights
American AirlinesPriceFrom $624Free CancellationRating
7.1
11,668 reviews
Search American Airlines flights
SWISSPriceFrom $759Free CancellationRating
7.6
1,937 reviews
Search SWISS flights
United AirlinesPriceFrom $764Free CancellationRating
7.4
9,692 reviews
Search United Airlines flights
LufthansaPriceFrom $840Free CancellationRating
6.8
7,979 reviews
Search Lufthansa flights

  • SWISS Flights From Chicago to Milan Malpensa Airport

    SWISS flies from Chicago to Milan Malpensa Airport around 7 times per week, with 1,937 momondo users rating the airline 7.6/10. The cheapest SWISS deal from Chicago to Milan Malpensa Airport in the last 72 hours was $759 (round-trip), much lower than the average airfare cost of $1,131 for SWISS flights on this route.

  • United Airlines Flights From Chicago to Milan Malpensa Airport

    The best United Airlines deal for Chicago to Milan Malpensa Airport flight tickets found on momondo in the last 72 hours was $764, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $1,234 round-trip. United Airlines operates 7 flights out of Chicago into Milan Malpensa Airport in an average week, so prices vary by time and availability. 9,692 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Traveling to a place near Milan?

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

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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