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Cheap flights from Chicago Midway Airport to Milan from $267

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 5/8. 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 Midway Airport to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
KLM Logo
1:05 pm - 9:25 am
MDW
-
MXP
13h 20m
1 stop
KLM Logo
11:40 am - 9:46 pm
MXP
-
MDW
17h 06m
1 stop
$901KLM
Sun, Aug 16 - Mon, Aug 31
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
9:45 am - 7:46 am
MXP
-
MDW
29h 01m
2 stops
$941Multiple Airlines
Thu, Apr 16 - Sun, May 3
Multiple Airlines Logo
7:30 am - 11:50 am
MDW
-
MXP
22h 20m
2 stops
Multiple Airlines Logo
11:55 am - 1:02 pm
MXP
-
MDW
31h 07m
1 stop
$973Multiple Airlines
Sun, Mar 15 - Mon, Mar 23
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
12:55 pm - 9:40 am
MXP
-
MDW
27h 45m
2 stops
$987Multiple Airlines
Thu, May 14 - Wed, May 20
Multiple Airlines Logo
9:25 am - 3:50 pm
MDW
-
MXP
23h 25m
2 stops
Multiple Airlines Logo
6:55 am - 8:45 pm
MXP
-
MDW
20h 50m
2 stops
$993Multiple Airlines
Mon, May 18 - Thu, May 28
Multiple Airlines Logo
9:22 am - 8:35 pm
MDW
-
MXP
28h 13m
3 stops
Multiple Airlines Logo
12:00 pm - 9:40 am
MXP
-
MDW
28h 40m
3 stops
$1,010Multiple Airlines
Thu, May 21 - Tue, Jun 2
Delta Logo
1:24 pm - 2:45 pm
MDW
-
MXP
18h 21m
2 stops
Delta Logo
6:45 am - 6:36 pm
MXP
-
MDW
18h 51m
2 stops
$1,012Delta
Mon, Apr 20 - Thu, Apr 30
Delta Logo
10:41 am - 12:05 pm
MDW
-
MXP
18h 24m
2 stops
Delta Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$1,051Delta
Sat, Apr 18 - Wed, Apr 29
Multiple Airlines Logo
6:10 am - 9:25 am
MDW
-
MXP
20h 15m
1 stop
Multiple Airlines Logo
11:25 am - 10:14 pm
MXP
-
MDW
17h 49m
2 stops
$1,061Multiple Airlines
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
8:45 am - 11:00 am
MDW
-
MXP
19h 15m
2 stops
Multiple Airlines Logo
7:00 am - 8:50 pm
MXP
-
MDW
20h 50m
2 stops
$1,065Multiple Airlines
Wed, Aug 26 - Wed, Sep 9

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
Apr 20
MDW1:24 pmChicago Midway
18h 21m
2 stops
MXP2:45 pmMilan Malpensa
Apr 30
MXP6:45 amMilan Malpensa
18h 51m
2 stops
MDW6:36 pmChicago Midway
$1,012
Delta
Apr 18
MDW10:41 amChicago Midway
18h 24m
2 stops
MXP12:05 pmMilan Malpensa
Apr 29
MXP9:00 amMilan Malpensa
20h 28m
2 stops
MDW10:28 pmChicago Midway
$1,051
Delta
Apr 15
MDW12:52 pmChicago Midway
13h 33m
1 stop
MXP9:25 amMilan Malpensa
Apr 22
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
$1,101

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
Aug 16
MDW1:05 pmChicago Midway
13h 20m
1 stop
MXP9:25 amMilan Malpensa
Aug 31
MXP11:40 amMilan Malpensa
17h 06m
1 stop
MDW9:46 pmChicago Midway
$901
KLM
Apr 15
MDW10:41 amChicago Midway
15h 44m
1 stop
MXP9:25 amMilan Malpensa
Apr 22
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
$1,094
KLM
Aug 25
MDW10:35 amChicago Midway
15h 50m
1 stop
MXP9:25 amMilan Malpensa
Sep 8
MXP11:40 amMilan Malpensa
17h 06m
1 stop
MDW9:46 pmChicago Midway
$1,134

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 March 1, 2026.
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 8/16

1:05 pm-9:25 am

1 stop13h 20m

Milan Malpensa

Mon 8/31

11:40 am-9:46 pm

1 stop17h 06m

$901

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 4/16

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Sun 5/3

9:45 am-7:46 am

2 stops29h 01m

$941

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 3/15

7:30 am-11:50 am

2 stops22h 20m

Milan Malpensa

Mon 3/23

11:55 am-1:02 pm

1 stop31h 07m

$973

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 5/14

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Wed 5/20

12:55 pm-9:40 am

2 stops27h 45m

$987

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 5/18

9:25 am-3:50 pm

2 stops23h 25m

Milan Malpensa

Thu 5/28

6:55 am-8:45 pm

2 stops20h 50m

$993

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 5/21

9:22 am-8:35 pm

3 stops28h 13m

Milan Malpensa

Tue 6/2

12:00 pm-9:40 am

3 stops28h 40m

$1,010

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 4/20

1:24 pm-2:45 pm

2 stops18h 21m

Milan Malpensa

Thu 4/30

6:45 am-6:36 pm

2 stops18h 51m

$1,012

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 4/18

10:41 am-12:05 pm

2 stops18h 24m

Milan Malpensa

Wed 4/29

11:40 am-10:28 pm

1 stop17h 48m

$1,051

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 4/14

6:10 am-9:25 am

1 stop20h 15m

Milan Malpensa

Tue 4/21

11:25 am-10:14 pm

2 stops17h 49m

$1,061

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 8/26

8:45 am-11:00 am

2 stops19h 15m

Milan Malpensa

Wed 9/9

7:00 am-8:50 pm

2 stops20h 50m

$1,065

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 $1,184. On the other hand, Thursday 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 $1,366.

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
Livigno
Levanto
Monza
Assago
Bellano
Lecco
Crema
Domodossola
Rho
Cernobbio
Moltrasio
Saronno
Bormio
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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