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Cheap flights from Chicago Midway Airport to Milan from $200

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 12/9. 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

Enter your travel dates to find the best prices.
Delta Logo
1:28 pm - 9:45 amMDW-MXP
13h 17m2 stops
Delta Logo
9:25 am - 10:44 pmMXP-MDW
20h 19m2 stops
$834Delta
Find Deal
Tue, Feb 17 - Tue, Feb 24
Delta Logo
12:46 pm - 9:05 amMDW-MXP
13h 19m1 stop
Delta Logo
8:25 am - 9:46 pmMXP-MDW
19h 21m2 stops
$884Delta
Find Deal
Mon, Feb 16 - Mon, Mar 16
KLM Logo
12:46 pm - 9:05 amMDW-MXP
13h 19m1 stop
KLM Logo
11:05 am - 10:44 pmMXP-MDW
18h 39m1 stop
$929KLM
Find Deal
Fri, Feb 20 - Sun, Mar 1
Delta Logo
1:28 pm - 11:40 amMDW-MXP
15h 12m2 stops
Delta Logo
11:05 am - 10:26 pmMXP-MDW
18h 21m1 stop
$933Delta
Find Deal
Fri, Jan 23 - Mon, Feb 2
Delta Logo
9:34 am - 9:05 amMDW-MXP
16h 31m2 stops
Delta Logo
11:05 am - 10:44 pmMXP-MDW
18h 39m1 stop
$934Delta
Find Deal
Fri, Feb 20 - Mon, Mar 2
KLM Logo
12:46 pm - 9:05 amMDW-MXP
13h 19m1 stop
KLM Logo
11:05 am - 10:44 pmMXP-MDW
18h 39m1 stop
$954KLM
Find Deal
Tue, Feb 17 - Tue, Feb 24
Multiple Airlines Logo
7:44 am - 7:00 amMDW-MXP
16h 16m1 stop
Multiple Airlines Logo
6:20 am - 9:53 pmMXP-MDW
22h 33m2 stops
$966Multiple Airlines
Find Deal
Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
1:05 pm - 9:05 amMDW-MXP
13h 00m1 stop
Multiple Airlines Logo
11:05 am - 11:47 pmMXP-MDW
19h 42m1 stop
$1,068Multiple Airlines
Find Deal
Wed, Dec 3 - Thu, Dec 11
Air France Logo
5:31 pm - 9:05 amMDW-MXP
32h 34m1 stop
Air France Logo
11:40 am - 9:46 pmMXP-MDW
17h 06m1 stop
$1,143Air France
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Thu, Jan 15 - Wed, Sep 23
Air France Logo
11:21 am - 9:45 amMDW-MXP
15h 24m2 stops
Air France Logo
11:40 am - 9:46 pmMXP-MDW
17h 06m1 stop
$1,206Air France
Find Deal
Thu, Jan 15 - Wed, Sep 23

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 17
MDW1:28 pmChicago Midway
13h 17m
2 stops
MXP9:45 amMilan Malpensa
Feb 24
MXP9:25 amMilan Malpensa
20h 19m
2 stops
MDW10:44 pmChicago Midway
$834
Find similar
Delta
Feb 16
MDW12:46 pmChicago Midway
13h 19m
1 stop
MXP9:05 amMilan Malpensa
Mar 16
MXP8:25 amMilan Malpensa
19h 21m
2 stops
MDW9:46 pmChicago Midway
$884
Find similar
Delta
Jan 23
MDW1:28 pmChicago Midway
15h 12m
2 stops
MXP11:40 amMilan Malpensa
Feb 2
MXP11:05 amMilan Malpensa
18h 21m
1 stop
MDW10:26 pmChicago Midway
$933
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
Feb 20
MDW12:46 pmChicago Midway
13h 19m
1 stop
MXP9:05 amMilan Malpensa
Mar 1
MXP11:05 amMilan Malpensa
18h 39m
1 stop
MDW10:44 pmChicago Midway
$929
Find similar
KLM
Feb 17
MDW12:46 pmChicago Midway
13h 19m
1 stop
MXP9:05 amMilan Malpensa
Feb 24
MXP11:05 amMilan Malpensa
18h 39m
1 stop
MDW10:44 pmChicago Midway
$954
Find similar
KLM
Jan 31
MDW10:46 amChicago Midway
15h 19m
1 stop
MXP9:05 amMilan Malpensa
Feb 8
MXP11:05 amMilan Malpensa
18h 21m
1 stop
MDW10:26 pmChicago Midway
$1,054
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 November 6, 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

Tue 2/17

1:28 pm-9:45 am

2 stops13h 17m

Milan Malpensa

Tue 2/24

9:25 am-10:44 pm

2 stops20h 19m

$834

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 2/16

12:46 pm-9:05 am

1 stop13h 19m

Milan Malpensa

Mon 3/16

8:25 am-9:46 pm

2 stops19h 21m

$884

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 2/20

12:46 pm-9:05 am

1 stop13h 19m

Milan Malpensa

Sun 3/1

11:05 am-10:44 pm

1 stop18h 39m

$929

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 1/23

1:28 pm-11:40 am

2 stops15h 12m

Milan Malpensa

Mon 2/2

11:05 am-10:26 pm

1 stop18h 21m

$933

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 2/20

9:34 am-9:05 am

2 stops16h 31m

Milan Malpensa

Mon 3/2

11:05 am-10:44 pm

1 stop18h 39m

$934

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 2/17

12:46 pm-9:05 am

1 stop13h 19m

Milan Malpensa

Tue 2/24

11:05 am-10:44 pm

1 stop18h 39m

$954

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 12/4

7:44 am-7:00 am

1 stop16h 16m

Milan Malpensa

Thu 12/11

6:20 am-9:53 pm

2 stops22h 33m

$966

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 12/3

1:05 pm-9:05 am

1 stop13h 00m

Milan Malpensa

Thu 12/11

11:05 am-11:47 pm

1 stop19h 42m

$1,068

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 1/15

5:31 pm-9:05 am

1 stop32h 34m

Milan Malpensa

Wed 9/23

11:40 am-9:46 pm

1 stop17h 06m

$1,143

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 1/15

11:21 am-9:45 am

2 stops15h 24m

Milan Malpensa

Wed 9/23

11:40 am-9:46 pm

1 stop17h 06m

$1,206

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 $1,189. 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 $1,492.

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 $1,351.

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

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

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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