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Cheap flights from Chicago Midway Airport to Milan from $252

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 10/10. 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 Chicago Midway Airport to Milan

Cheap round-trip flights

Multiple Airlines Logo
11:49 am - 11:10 pmMDW-MXP
28h 21m2 stops
Multiple Airlines Logo
12:10 pm - 11:25 pmMXP-MDW
18h 15m1 stop
$798Multiple Airlines
Find Deal
jue., oct. 16 - jue., oct. 23
Multiple Airlines Logo
1:05 pm - 9:05 amMDW-MXP
13h 00m1 stop
Multiple Airlines Logo
11:05 am - 11:32 pmMXP-MDW
19h 27m1 stop
$822Multiple Airlines
Find Deal
dom., nov. 9 - mar., nov. 25
Multiple Airlines Logo
1:05 pm - 9:05 amMDW-MXP
13h 00m1 stop
Multiple Airlines Logo
11:05 am - 11:32 pmMXP-MDW
19h 27m1 stop
$823Multiple Airlines
Find Deal
dom., nov. 9 - mar., nov. 25
KLM Logo
1:05 pm - 9:05 amMDW-MXP
13h 00m1 stop
KLM Logo
11:05 am - 11:32 pmMXP-MDW
19h 27m1 stop
$826KLM
Find Deal
dom., nov. 9 - mar., nov. 25
Delta Logo
1:14 pm - 11:40 amMDW-MXP
15h 26m2 stops
Delta Logo
11:05 am - 11:32 pmMXP-MDW
19h 27m1 stop
$834Delta
Find Deal
dom., nov. 9 - mar., nov. 25
Delta Logo
9:32 am - 9:45 amMDW-MXP
17h 13m2 stops
Delta Logo
6:55 am - 6:08 pmMXP-MDW
18h 13m2 stops
$859Delta
Find Deal
mar., nov. 18 - mié., nov. 26
KLM Logo
10:35 am - 9:05 amMDW-MXP
15h 30m1 stop
KLM Logo
11:05 am - 9:46 pmMXP-MDW
17h 41m1 stop
$905KLM
Find Deal
dom., feb. 8 - mié., feb. 18
Air France Logo
1:47 pm - 10:35 amMDW-MXP
13h 48m2 stops
Air France Logo
6:55 am - 6:18 pmMXP-MDW
18h 23m2 stops
$912Air France
Find Deal
dom., nov. 9 - mar., nov. 25
Delta Logo
10:40 am - 9:05 amMDW-MXP
15h 25m1 stop
Delta Logo
12:00 pm - 11:32 pmMXP-MDW
18h 32m2 stops
$934Delta
Find Deal
vie., nov. 7 - sáb., nov. 15
Delta Logo
6:23 pm - 5:25 pmMDW-MXP
16h 02m2 stops
Delta Logo
12:00 pm - 11:32 pmMXP-MDW
18h 32m2 stops
$939Delta
Find Deal
vie., nov. 7 - sáb., nov. 15

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
Nov 9
MDW1:14 pmChicago Midway
15h 26m
2 stops
MXP11:40 amMilan Malpensa
Nov 25
MXP11:05 amMilan Malpensa
19h 27m
1 stop
MDW11:32 pmChicago Midway
$834
Find similar
Delta
Nov 18
MDW9:32 amChicago Midway
17h 13m
2 stops
MXP9:45 amMilan Malpensa
Nov 26
MXP6:55 amMilan Malpensa
18h 13m
2 stops
MDW6:08 pmChicago Midway
$859
Find similar
Delta
Nov 7
MDW10:40 amChicago Midway
15h 25m
1 stop
MXP9:05 amMilan Malpensa
Nov 15
MXP12:00 pmMilan Malpensa
18h 32m
2 stops
MDW11:32 pmChicago Midway
$934
Find similar

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
Nov 9
MDW1:05 pmChicago Midway
13h 00m
1 stop
MXP9:05 amMilan Malpensa
Nov 25
MXP11:05 amMilan Malpensa
19h 27m
1 stop
MDW11:32 pmChicago Midway
$826
Find similar
KLM
Feb 8
MDW10:35 amChicago Midway
15h 30m
1 stop
MXP9:05 amMilan Malpensa
Feb 18
MXP11:05 amMilan Malpensa
17h 41m
1 stop
MDW9:46 pmChicago Midway
$905
Find similar
KLM
Dec 29
MDW12:43 pmChicago Midway
13h 22m
1 stop
MXP9:05 amMilan Malpensa
Jan 12
MXP11:05 amMilan Malpensa
17h 41m
1 stop
MDW9:46 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 septiembre 18, 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

jue. 10/16

11:49 am-11:10 pm

2 stops28h 21m

Milan Malpensa

jue. 10/23

12:10 pm-11:25 pm

1 stop18h 15m

$798

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

dom. 11/9

1:05 pm-9:05 am

1 stop13h 00m

Milan Malpensa

mar. 11/25

11:05 am-11:32 pm

1 stop19h 27m

$822

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

dom. 11/9

1:05 pm-9:05 am

1 stop13h 00m

Milan Malpensa

mar. 11/25

11:05 am-11:32 pm

1 stop19h 27m

$823

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

dom. 11/9

1:05 pm-9:05 am

1 stop13h 00m

Milan Malpensa

mar. 11/25

11:05 am-11:32 pm

1 stop19h 27m

$826

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

dom. 11/9

1:14 pm-11:40 am

2 stops15h 26m

Milan Malpensa

mar. 11/25

11:05 am-11:32 pm

1 stop19h 27m

$834

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

mar. 11/18

9:32 am-9:45 am

2 stops17h 13m

Milan Malpensa

mié. 11/26

6:55 am-6:08 pm

2 stops18h 13m

$859

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

dom. 2/8

10:35 am-9:05 am

1 stop15h 30m

Milan Malpensa

mié. 2/18

11:05 am-9:46 pm

1 stop17h 41m

$905

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

dom. 11/9

1:47 pm-10:35 am

2 stops13h 48m

Milan Malpensa

mar. 11/25

6:55 am-6:18 pm

2 stops18h 23m

$912

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

vie. 11/7

10:40 am-9:05 am

1 stop15h 25m

Milan Malpensa

sáb. 11/15

12:00 pm-11:32 pm

2 stops18h 32m

$934

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

vie. 11/7

6:23 pm-5:25 pm

2 stops16h 02m

Milan Malpensa

sáb. 11/15

12:00 pm-11:32 pm

2 stops18h 32m

$939

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 $1,179. 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 $1,498.

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 $1,346.

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

Direct flights

None
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 00m.

  • 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
Livigno
Menaggio
Brescia
Stresa
Assago
Monza
Breuil-Cervinia
Levanto
Rho
Domodossola
Bellano
Bormio
Lecco
Crema
Novara
Cernobbio
Moltrasio
Saronno

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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