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Cheap flights from Chicago Midway Airport to Milan from $219

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 Midway Airport to Milan departing on 1/18. 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 Midway Airport to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:30 am - 5:55 pm
MDW
-
MXP
28h 25m2 stops
Multiple Airlines Logo
11:55 am - 1:02 pm
MXP
-
MDW
31h 07m1 stop
$759Multiple Airlines
Sun, Mar 15 - Mon, Mar 23
KLM Logo
10:53 am - 9:05 am
MDW
-
MXP
15h 12m1 stop
KLM Logo
11:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
$880KLM
Wed, Feb 25 - Sat, Mar 7
Delta Logo
1:26 pm - 10:35 am
MDW
-
MXP
14h 09m2 stops
Delta Logo
11:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
$884Delta
Wed, Feb 25 - Sat, Mar 7
KLM Logo
10:53 am - 9:05 am
MDW
-
MXP
15h 12m1 stop
KLM Logo
10:05 am - 10:29 pm
MXP
-
MDW
18h 24m1 stop
$1,030KLM
Thu, Mar 5 - Tue, Mar 10
Delta Logo
9:34 am - 9:45 am
MDW
-
MXP
17h 11m2 stops
Delta Logo
11:00 am - 10:31 pm
MXP
-
MDW
17h 31m2 stops
$1,034Delta
Thu, Mar 5 - Tue, Mar 10
Delta Logo
10:45 am - 8:05 am
MDW
-
MXP
15h 20m1 stop
Delta Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m1 stop
$1,035Delta
Sun, Mar 22 - Sun, Apr 5
Delta Logo
5:40 pm - 2:55 pm
MDW
-
MXP
15h 15m2 stops
Delta Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m1 stop
$1,039Delta
Mon, Mar 23 - Sun, Apr 5
KLM Logo
12:48 pm - 9:05 am
MDW
-
MXP
13h 17m1 stop
KLM Logo
11:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
$1,080KLM
Wed, Feb 11 - Wed, Feb 18
Delta Logo
9:33 am - 9:05 am
MDW
-
MXP
16h 32m2 stops
Delta Logo
11:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
$1,084Delta
Wed, Feb 11 - Wed, Feb 18
Multiple Airlines Logo
10:49 am - 8:05 am
MDW
-
MXP
15h 16m1 stop
Multiple Airlines Logo
11:40 am - 10:29 pm
MXP
-
MDW
17h 49m1 stop
$1,085Multiple Airlines
Thu, Mar 19 - Sun, Apr 5

KLM flights from Chicago Midway Airport to Milan Malpensa Airport

Our best KLM deals on Chicago Midway Airport to Milan Malpensa Airport flight tickets
KLM
Feb 25
MDW10:53 amChicago Midway
15h 12m
1 stop
MXP9:05 amMilan Malpensa
Mar 7
MXP11:05 amMilan Malpensa
18h 26m
1 stop
MDW10:31 pmChicago Midway
$880
Find similar
KLM
Mar 5
MDW10:53 amChicago Midway
15h 12m
1 stop
MXP9:05 amMilan Malpensa
Mar 10
MXP10:05 amMilan Malpensa
18h 24m
1 stop
MDW10:29 pmChicago Midway
$1,030
Find similar
KLM
Feb 11
MDW12:48 pmChicago Midway
13h 17m
1 stop
MXP9:05 amMilan Malpensa
Feb 18
MXP11:05 amMilan Malpensa
18h 26m
1 stop
MDW10:31 pmChicago Midway
$1,080
Find similar

Delta flights from Chicago Midway Airport to Milan Malpensa Airport

Our best Delta deals on Chicago Midway Airport to Milan Malpensa Airport flight tickets
Delta
Feb 25
MDW1:26 pmChicago Midway
14h 09m
2 stops
MXP10:35 amMilan Malpensa
Mar 7
MXP11:05 amMilan Malpensa
18h 26m
1 stop
MDW10:31 pmChicago Midway
$884
Find similar
Delta
Mar 5
MDW1:29 pmChicago Midway
14h 06m
2 stops
MXP10:35 amMilan Malpensa
Mar 10
MXP10:05 amMilan Malpensa
18h 26m
1 stop
MDW10:31 pmChicago Midway
$1,034
Find similar
Delta
Mar 22
MDW10:45 amChicago Midway
15h 20m
1 stop
MXP8:05 amMilan Malpensa
Apr 5
MXP11:40 amMilan Malpensa
17h 51m
1 stop
MDW10:31 pmChicago Midway
$1,035
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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 December 26, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Milan Malpensa Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 3/15

7:30 am-5:55 pm

2 stops28h 25m

Milan Malpensa

Mon 3/23

11:55 am-1:02 pm

1 stop31h 07m

$759

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 2/25

10:53 am-9:05 am

1 stop15h 12m

Milan Malpensa

Sat 3/7

11:05 am-10:31 pm

1 stop18h 26m

$880

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 2/25

1:26 pm-10:35 am

2 stops14h 09m

Milan Malpensa

Sat 3/7

11:05 am-10:31 pm

1 stop18h 26m

$884

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/5

10:53 am-9:05 am

1 stop15h 12m

Milan Malpensa

Tue 3/10

10:05 am-10:29 pm

1 stop18h 24m

$1,030

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/5

9:34 am-9:45 am

2 stops17h 11m

Milan Malpensa

Tue 3/10

11:00 am-10:31 pm

2 stops17h 31m

$1,034

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 3/22

10:45 am-8:05 am

1 stop15h 20m

Milan Malpensa

Sun 4/5

11:40 am-10:31 pm

1 stop17h 51m

$1,035

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/23

5:40 pm-2:55 pm

2 stops15h 15m

Milan Malpensa

Sun 4/5

11:40 am-10:31 pm

1 stop17h 51m

$1,039

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 2/11

12:48 pm-9:05 am

1 stop13h 17m

Milan Malpensa

Wed 2/18

11:05 am-10:31 pm

1 stop18h 26m

$1,080

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 2/11

9:33 am-9:05 am

2 stops16h 32m

Milan Malpensa

Wed 2/18

11:05 am-10:31 pm

1 stop18h 26m

$1,084

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/19

10:49 am-8:05 am

1 stop15h 16m

Milan Malpensa

Sun 4/5

11:40 am-10:29 pm

1 stop17h 49m

$1,085

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 Midway Airport 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 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 Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,485.

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 Midway Airport 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 $1,349.

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

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Milan Malpensa Airport flight.

When to book flights from Chicago Midway Airport to Milan Malpensa Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport 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 Midway Airport to Milan Malpensa Airport (MDW to MXP) flight deals and tips

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

Fastest flight time

13h 18m

Direct flights

None
The fastest flight from Chicago Midway Airport to Milan Malpensa Airport takes 13h 18m
There are no direct flights from Chicago Midway Airport to Milan Malpensa Airport. There are no popular flight routes from Chicago Midway Airport to Milan Malpensa Airport.
Search flight deals

  • How far is Chicago Midway to Milan Malpensa by plane?

    Chicago Midway and Milan Malpensa are 4510.1 mi apart from one another. A reasonable flight in good conditions will take 13h 18m.

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

    Prices for flights from Chicago Midway Airport to Milan Malpensa Airport refresh daily.

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan Malpensa Airport.

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

    The travel and health documents required for your trip to Milan Malpensa Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Milan Malpensa Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Milan?

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

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Milan from Chicago.

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?

Price alerts on flights to Milan from Chicago 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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