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Cheap flights from Chicago Midway Airport to Milan from $311

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 7/7. 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
1 adult, Economy, 0 bags

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
10:54 am - 9:25 am
MDW
-
MXP
15h 31m
1 stop
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$777Delta
Mon, Aug 3 - Wed, Aug 19
Air France Logo
10:54 am - 9:25 am
MDW
-
MXP
15h 31m
1 stop
Air France Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$781Air France
Mon, Aug 3 - Wed, Aug 19
Delta Logo
10:54 am - 9:25 am
MDW
-
MXP
15h 31m
1 stop
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$782Delta
Mon, Aug 3 - Wed, Aug 19
Delta Logo
10:54 am - 9:25 am
MDW
-
MXP
15h 31m
1 stop
Delta Logo
11:40 am - 11:51 am
MXP
-
MDW
31h 11m
1 stop
$783Delta
Mon, Aug 3 - Wed, Aug 19
Delta Logo
10:54 am - 9:25 am
MDW
-
MXP
15h 31m
1 stop
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$792Delta
Sun, Aug 9 - Fri, Aug 21
Delta Logo
9:24 am - 9:25 am
MDW
-
MXP
17h 01m
2 stops
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$796Delta
Mon, Aug 3 - Wed, Aug 19
Delta Logo
1:25 pm - 12:05 pm
MDW
-
MXP
15h 40m
2 stops
Delta Logo
11:25 am - 10:36 pm
MXP
-
MDW
18h 11m
2 stops
$807Delta
Mon, Aug 3 - Wed, Aug 19
Delta Logo
1:27 pm - 12:05 pm
MDW
-
MXP
15h 38m
2 stops
Delta Logo
6:45 am - 4:15 pm
MXP
-
MDW
16h 30m
2 stops
$808Delta
Mon, Aug 3 - Wed, Aug 19
Multiple Airlines Logo
6:05 am - 9:25 am
MDW
-
MXP
20h 20m
1 stop
Multiple Airlines Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$818Multiple Airlines
Mon, Aug 3 - Wed, Aug 19
KLM Logo
5:10 pm - 9:25 am
MDW
-
MXP
33h 15m
1 stop
KLM Logo
11:40 am - 4:15 pm
MXP
-
MDW
35h 35m
1 stop
$823KLM
Tue, Aug 18 - Tue, Aug 25

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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 18
MDW5:10 pmChicago Midway
33h 15m
1 stop
MXP9:25 amMilan Malpensa
Aug 25
MXP11:40 amMilan Malpensa
35h 35m
1 stop
MDW4:15 pmChicago Midway
$823
KLM
Aug 19
MDW10:54 amChicago Midway
15h 31m
1 stop
MXP9:25 amMilan Malpensa
Aug 23
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$842
KLM
Aug 24
MDW6:05 amChicago Midway
20h 20m
1 stop
MXP9:25 amMilan Malpensa
Aug 31
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$950

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
Aug 3
MDW10:54 amChicago Midway
15h 31m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$777
Delta
Aug 3
MDW5:10 pmChicago Midway
33h 15m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$782
Delta
Aug 3
MDW10:54 amChicago Midway
15h 31m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$783

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 June 22, 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

Cheapest round-trip

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$777

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$781

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$782

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-11:51 am

1 stop31h 11m

$783

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 8/9

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Fri 8/21

11:40 am-10:36 pm

1 stop17h 56m

$792

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

9:24 am-9:25 am

2 stops17h 01m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$796

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

1:25 pm-12:05 pm

2 stops15h 40m

Milan Malpensa

Wed 8/19

11:25 am-10:36 pm

2 stops18h 11m

$807
Quickest round-trip

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

1:27 pm-12:05 pm

2 stops15h 38m

Milan Malpensa

Wed 8/19

6:45 am-4:15 pm

2 stops16h 30m

$808

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

6:05 am-9:25 am

1 stop20h 20m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$818

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 8/18

5:10 pm-9:25 am

1 stop33h 15m

Milan Malpensa

Tue 8/25

11:40 am-4:15 pm

1 stop35h 35m

$823

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

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 Monday is the least expensive day to fly to Milan Malpensa Airport. Tickets to fly out on this day can be as low as $1,339. On the other hand, Sunday 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 $1,574.

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 20m

Direct flights

None
The fastest flight from Chicago Midway Airport to Milan Malpensa Airport takes 13h 20m
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

Frequently asked questions about flying from Chicago Midway Airport to Milan Malpensa Airport

  • 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 20m.

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