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Cheap flights from Chicago to Milan from $239

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 3/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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
7:20 pm - 7:10 pm
ORD
-
MXP
16h 50m
1 stop
Scandinavian Airlines Logo
11:15 am - 4:45 pm
MXP
-
ORD
12h 30m
1 stop
$427Scandinavian Airlines
Wed, Feb 25 - Mon, Mar 2
Scandinavian Airlines Logo
7:10 pm - 7:10 pm
ORD
-
MXP
17h 00m
1 stop
Scandinavian Airlines Logo
8:00 pm - 4:45 pm
MXP
-
ORD
27h 45m
1 stop
$428Scandinavian Airlines
Sun, Feb 22 - Sun, Mar 1
Scandinavian Airlines Logo
7:15 pm - 7:10 pm
ORD
-
MXP
16h 55m
1 stop
Scandinavian Airlines Logo
11:45 am - 4:10 pm
MXP
-
ORD
35h 25m
2 stops
$430Scandinavian Airlines
Wed, Apr 15 - Fri, Apr 24
Scandinavian Airlines Logo
8:20 pm - 7:10 pm
ORD
-
MXP
16h 50m
1 stop
Scandinavian Airlines Logo
9:20 am - 4:10 pm
MXP
-
ORD
13h 50m
1 stop
$435Scandinavian Airlines
Sun, Mar 15 - Wed, Apr 15
Delta Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m
1 stop
Delta Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$831Delta
Wed, Mar 18 - Tue, Mar 31
Delta Logo
9:35 am - 8:05 am
MDW
-
MXP
16h 30m
2 stops
Delta Logo
6:55 am - 5:54 pm
MXP
-
MDW
16h 59m
2 stops
$896Delta
Thu, Mar 19 - Thu, Mar 26
KLM Logo
10:45 am - 8:05 am
MDW
-
MXP
15h 20m
1 stop
KLM Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$941KLM
Thu, Mar 19 - Tue, Mar 31
Multiple Airlines Logo
7:45 am - 9:20 pm
MDW
-
MXP
30h 35m
2 stops
Multiple Airlines Logo
7:00 am - 7:20 pm
MXP
-
MDW
19h 20m
2 stops
$958Multiple Airlines
Wed, Jun 3 - Wed, Jun 10
KLM Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m
1 stop
KLM Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$1,063KLM
Thu, Mar 19 - Wed, Apr 1
Multiple Airlines Logo
10:45 am - 8:05 am
MDW
-
MXP
15h 20m
1 stop
Multiple Airlines Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$1,077Multiple Airlines
Mon, Mar 16 - Tue, Mar 31

Delta flights from Chicago to Milan Malpensa Airport

Our best Delta deals on Chicago to Milan Malpensa Airport flight tickets
Delta
Mar 18
MDW12:47 pmChicago Midway
13h 18m
1 stop
MXP8:05 amMilan Malpensa
Mar 31
MXP11:40 amMilan Malpensa
17h 51m
1 stop
MDW10:31 pmChicago Midway
$831
Delta
Mar 19
MDW9:35 amChicago Midway
16h 30m
2 stops
MXP8:05 amMilan Malpensa
Mar 26
MXP6:55 amMilan Malpensa
16h 59m
2 stops
MDW5:54 pmChicago Midway
$896
Delta
Mar 19
MDW9:35 amChicago Midway
16h 30m
2 stops
MXP8:05 amMilan Malpensa
Apr 1
MXP6:45 amMilan Malpensa
18h 55m
2 stops
MDW6:40 pmChicago Midway
$897

KLM flights from Chicago to Milan Malpensa Airport

Our best KLM deals on Chicago to Milan Malpensa Airport flight tickets
KLM
Mar 19
MDW10:45 amChicago Midway
15h 20m
1 stop
MXP8:05 amMilan Malpensa
Mar 31
MXP11:40 amMilan Malpensa
17h 51m
1 stop
MDW10:31 pmChicago Midway
$941
KLM
Mar 19
MDW12:47 pmChicago Midway
13h 18m
1 stop
MXP8:05 amMilan Malpensa
Apr 1
MXP11:40 amMilan Malpensa
17h 51m
1 stop
MDW10:31 pmChicago Midway
$1,063
KLM
Mar 15
MDW6:07 pmChicago Midway
31h 58m
1 stop
MXP8:05 amMilan Malpensa
Apr 15
MXP11:40 amMilan Malpensa
17h 49m
1 stop
MDW10:29 pmChicago Midway
$1,079

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 January 29, 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

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 2/25

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Mon 3/2

11:15 am-4:45 pm

1 stop12h 30m

$427

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 2/22

7:10 pm-7:10 pm

1 stop17h 00m

Milan Malpensa

Sun 3/1

8:00 pm-4:45 pm

1 stop27h 45m

$428

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 4/15

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Fri 4/24

11:45 am-4:10 pm

2 stops35h 25m

$430

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 3/15

8:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Wed 4/15

9:20 am-4:10 pm

1 stop13h 50m

$435

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 3/18

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Tue 3/31

11:40 am-10:31 pm

1 stop17h 51m

$831

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/19

9:35 am-8:05 am

2 stops16h 30m

Milan Malpensa

Thu 3/26

6:55 am-5:54 pm

2 stops16h 59m

$896

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/19

10:45 am-8:05 am

1 stop15h 20m

Milan Malpensa

Tue 3/31

11:40 am-10:31 pm

1 stop17h 51m

$941

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 6/3

7:45 am-9:20 pm

2 stops30h 35m

Milan Malpensa

Wed 6/10

7:00 am-7:20 pm

2 stops19h 20m

$958

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/19

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Wed 4/1

11:40 am-10:31 pm

1 stop17h 51m

$1,063

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/16

10:45 am-8:05 am

1 stop15h 20m

Milan Malpensa

Tue 3/31

11:40 am-10:31 pm

1 stop17h 51m

$1,077

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, 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 March to fly from Chicago, when ticket prices are also cheap, with an average price of $542.

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 $1,189. 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 $1,478.

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 $918 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 $711 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.

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

You could potentially save up to 5% 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

$764

Fastest flight time

8h 40m

Direct flights

Every day
The best one-way flight to Milan Malpensa Airport from Chicago in the past 72 hours is $764. The best round-trip flight deal from Chicago to Milan Malpensa Airport found on momondo in the last 72 hours is $1,070.
The fastest flight from Chicago to Milan Malpensa Airport takes 8h 40m
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 8h 40m.

  • 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 $398Free CancellationRating
7.1
2,130 reviews
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesPriceFrom $410Free CancellationRating
7.3
1,674 reviews
Search Scandinavian Airlines flights
British AirwaysPriceFrom $496Free CancellationRating
6.7
7,705 reviews
Search British Airways flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
4,208 reviews
Search Turkish Airlines flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
11,206 reviews
Search American Airlines flights
IberiaPriceFrom $639Free CancellationRating
7.0
3,099 reviews
Search Iberia flights
United AirlinesPriceFrom $793Free CancellationRating
7.4
9,214 reviews
Search United Airlines flights

Traveling to a place near Milan?

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

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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