Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago Midway Airport to Milan from $374

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.
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.
Air France Logo
1:00 pm - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
14h 55m1 stop Atlanta Hartsfield-Jackson
Air France Logo
1:05 pm - 10:56 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 51m1 stop Atlanta Hartsfield-Jackson
$782Air France
Mon, Nov 9 - Tue, Nov 17
Air France Logo
1:05 pm - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
14h 50m1 stop Atlanta Hartsfield-Jackson
Air France Logo
1:05 pm - 10:10 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 05m1 stop Atlanta Hartsfield-Jackson
$782Air France
Mon, Feb 1 - Wed, Feb 24
Delta Logo
10:35 am - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
17h 20m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:10 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 05m1 stop Atlanta Hartsfield-Jackson
$782Delta
Mon, Feb 1 - Tue, Feb 23
Delta Logo
1:05 pm - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
14h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:10 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 05m1 stop Atlanta Hartsfield-Jackson
$782Delta
Mon, Feb 1 - Fri, Feb 26
Delta Logo
10:35 am - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
17h 20m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:10 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 05m1 stop Atlanta Hartsfield-Jackson
$782Delta
Wed, Feb 3 - Thu, Feb 25
Delta Logo
1:00 pm - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
14h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:56 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 51m1 stop Atlanta Hartsfield-Jackson
$782Delta
Mon, Nov 23 - Thu, Dec 3
Delta Logo
1:00 pm - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
14h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:56 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 51m1 stop Atlanta Hartsfield-Jackson
$782Delta
Wed, Nov 25 - Thu, Dec 3
Delta Logo
1:05 pm - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
14h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:10 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 05m1 stop Atlanta Hartsfield-Jackson
$782Delta
Wed, Feb 3 - Wed, Feb 24
Delta Logo
1:05 pm - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
14h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:10 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 05m1 stop Atlanta Hartsfield-Jackson
$782Delta
Wed, Feb 3 - Fri, Feb 26
Delta Logo
1:05 pm - 10:55 amMDW  Chicago Midway-MXP Milan Malpensa
14h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 10:10 pmMXP  Milan Malpensa-MDW Chicago Midway
16h 05m1 stop Atlanta Hartsfield-Jackson
$782Delta
Wed, Feb 3 - Tue, Feb 23

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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 1
MDW1:05 pmChicago Midway
14h 50m
1 stop
MXP10:55 amMilan Malpensa
Feb 25
MXP1:05 pmMilan Malpensa
16h 05m
1 stop
MDW10:10 pmChicago Midway
$782
Delta
Oct 21
MDW12:45 pmChicago Midway
13h 40m
1 stop
MXP9:25 amMilan Malpensa
Nov 5
MXP6:40 amMilan Malpensa
18h 20m
2 stops
MDW6:00 pmChicago Midway
$792
Delta
Aug 23
MDW1:25 pmChicago Midway
14h 00m
2 stops
MXP10:25 amMilan Malpensa
Aug 26
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$796

Air France flights from Chicago Midway Airport to Milan Malpensa Airport

Our best Air France deals on Chicago Midway Airport to Milan Malpensa Airport flight tickets
Air France
Nov 10
MDW1:22 pmChicago Midway
15h 23m
2 stops
MXP11:45 amMilan Malpensa
Nov 20
MXP6:40 amMilan Malpensa
18h 24m
2 stops
MDW6:04 pmChicago Midway
$796
Air France
Sep 29
MDW10:48 amChicago Midway
15h 37m
1 stop
MXP9:25 amMilan Malpensa
Oct 6
MXP11:40 amMilan Malpensa
17h 53m
1 stop
MDW10:33 pmChicago Midway
$835
Air France
Aug 19
MDW12:46 pmChicago Midway
14h 39m
2 stops
MXP10:25 amMilan Malpensa
Aug 22
MXP6:45 amMilan Malpensa
15h 53m
2 stops
MDW3:38 pmChicago Midway
$856

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 August 17, 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 Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Mon 11/9

1:00 pm-10:55 am

1 stop14h 55m

Milan Malpensa

Tue 11/17

1:05 pm-10:56 pm

1 stop16h 51m

$782
Quickest round-trip

ChicagoMilan

MDW Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Mon 2/1

1:05 pm-10:55 am

1 stop14h 50m

Milan Malpensa

Wed 2/24

1:05 pm-10:10 pm

1 stop16h 05m

$782

ChicagoMilan

MDW Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Mon 2/1

10:35 am-10:55 am

1 stop17h 20m

Milan Malpensa

Tue 2/23

1:05 pm-10:10 pm

1 stop16h 05m

$782

ChicagoMilan

MDW Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Mon 2/1

1:05 pm-10:55 am

1 stop14h 50m

Milan Malpensa

Fri 2/26

1:05 pm-10:10 pm

1 stop16h 05m

$782

ChicagoMilan

MDW Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Wed 2/3

10:35 am-10:55 am

1 stop17h 20m

Milan Malpensa

Thu 2/25

1:05 pm-10:10 pm

1 stop16h 05m

$782

ChicagoMilan

MDW Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Mon 11/23

1:00 pm-10:55 am

1 stop14h 55m

Milan Malpensa

Thu 12/3

1:05 pm-10:56 pm

1 stop16h 51m

$782

ChicagoMilan

MDW Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Wed 11/25

1:00 pm-10:55 am

1 stop14h 55m

Milan Malpensa

Thu 12/3

1:05 pm-10:56 pm

1 stop16h 51m

$782

ChicagoMilan

MDW Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Wed 2/3

1:05 pm-10:55 am

1 stop14h 50m

Milan Malpensa

Wed 2/24

1:05 pm-10:10 pm

1 stop16h 05m

$782

ChicagoMilan

MDW Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Wed 2/3

1:05 pm-10:55 am

1 stop14h 50m

Milan Malpensa

Fri 2/26

1:05 pm-10:10 pm

1 stop16h 05m

$782

ChicagoMilan

MDW Chicago Midway - MXP Milan Malpensa

MDWMXP

Chicago Midway

Wed 2/3

1:05 pm-10:55 am

1 stop14h 50m

Milan Malpensa

Tue 2/23

1:05 pm-10:10 pm

1 stop16h 05m

$782

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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 Tuesday is the least expensive day to fly to Milan Malpensa Airport. Tickets to fly out on this day can be as low as $1,289. 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 $1,585.

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 25m

Direct flights

None
The fastest flight from Chicago Midway Airport to Milan Malpensa Airport takes 13h 25m
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 25m.

  • 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
Varenna
Bellagio
Stresa
Breuil-Cervinia
Livigno
Brescia
Lecco
Monza
Menaggio
Crema
Bellano
Cernobbio
Domodossola
Levanto
Rho
Iseo
Novara
Baveno
Saint Vincent
Assago

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.

An easier way to manage your Milan Malpensa Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 9/16
Wed 9/23
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Milan

Popular cities in Italy

Popular flights according to clicks in the last 7 days on momondo
Flights to Rome Fiumicino Airportfrom $455
Flights to Venice Marco Polo Airportfrom $551
Flights to Milan Linate Airportfrom $572
Flights to Rome Ciampino Airportfrom $586
Flights to Venice Treviso A. Canova Airportfrom $567