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$260+ Cheap flights from Midway (MDW) to Milan (MIL)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIL
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheap flight deals from Midway to Milan

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Milan (MIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septiembre 17, 2025.

Round-trip from

$822
(Air France)

One-way from

$260
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$778
From Chicago Midway to Milan (MIL)
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One-way flight from Chicago Midway to Milan (MIL)
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Highest demand for flights based on searches. 3% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($39 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Milan

Cheapest flights from Midway to Milan
Explore the most affordable flight options available from Midway to Milan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.

This Air France deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/91:05 pmMDW - MXP
1 stop13h 00mMultiple Airlines
mar. 11/2511:05 amMXP - MDW
1 stop19h 27mMultiple Airlines
Deal found 9/16$822
This KLM deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/91:05 pmMDW - MXP
1 stop13h 00mKLM
mar. 11/2511:05 amMXP - MDW
1 stop19h 27mKLM
Deal found 9/17$826
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/912:47 pmMDW - MXP
1 stop13h 18mDelta
mar. 11/2511:05 amMXP - MDW
1 stop19h 27mDelta
Deal found 9/15$830
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/189:32 amMDW - MXP
2 stops17h 13mDelta
mié. 11/266:55 amMXP - MDW
2 stops18h 13mDelta
Deal found 9/16$859
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/1010:47 amMDW - MXP
1 stop15h 18mDelta
lun. 11/1711:05 amMXP - MDW
1 stop19h 27mDelta
Deal found 9/15$880
This Vliegwinkel deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/91:14 pmMDW - LIN
2 stops13h 46mKLM
mar. 11/256:30 amLIN - MDW
2 stops17h 08mKLM
Deal found 9/15$930
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/221:49 pmMDW - MXP
2 stops22h 26mMultiple Airlines
mar. 10/712:10 pmMXP - MDW
1 stop18h 15mMultiple Airlines
Deal found 9/15$933
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/51:14 pmMDW - MXP
2 stops13h 31mDelta
dom. 12/1412:00 pmMXP - MDW
2 stops18h 32mDelta
Deal found 9/17$934
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/76:23 pmMDW - MXP
2 stops16h 02mDelta
sáb. 11/1512:00 pmMXP - MDW
2 stops18h 32mDelta
Deal found 9/16$953
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/510:40 amMDW - MXP
1 stop15h 25mDelta
mar. 11/1111:05 amMXP - MDW
1 stop19h 27mDelta
Deal found 9/15$980
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/236:00 pmMDW - LIN
2 stops12h 55mDelta
mié. 12/316:30 amLIN - MDW
2 stops22h 46mDelta
Deal found 9/16$1,188
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/199:35 amMDW - LIN
3 stops19h 45mMultiple Airlines
vie. 10/247:00 amLIN - MDW
3 stops16h 24mMultiple Airlines
Deal found 9/16$1,208

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Milan 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, Cheapflights users made 2,558,603 searches. Data last updated septiembre 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Midway

Fly to

Milan

Route

Depart

Return

Price

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

12:47 pm-9:05 am

1 stop13h 18m

Milan Malpensa

mar. 11/25

11:05 am-11:32 pm

1 stop19h 27m

$830

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

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

mié. 11/5

10:40 am-9:05 am

1 stop15h 25m

Milan Malpensa

mar. 11/11

12:00 pm-11:32 pm

2 stops18h 32m

$984

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

mar. 12/23

6:00 pm-1:55 pm

2 stops12h 55m

Milan Linate

mié. 12/31

6:30 am-10:16 pm

2 stops22h 46m

$1,188

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

dom. 10/19

9:35 am-12:20 pm

3 stops19h 45m

Milan Linate

vie. 10/24

7:00 am-4:24 pm

3 stops16h 24m

$1,208

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

jue. 10/30

1:08 pm-10:00 am

2 stops14h 52m

Milan Linate

jue. 11/6

6:30 am-4:14 pm

2 stops16h 44m

$1,312

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

vie. 10/17

1:08 pm-11:20 am

2 stops15h 12m

Milan Linate

mar. 10/21

6:30 am-10:14 pm

2 stops22h 44m

$1,589

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

dom. 9/28

9:35 am-6:20 pm

3 stops25h 45m

Milan Linate

mié. 10/1

2:30 pm-1:03 pm

3 stops29h 33m

$1,595

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 32 results
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Best time to book a flight from Midway to Milan

Have a flexible travel schedule? Discover the best time to fly to Milan from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Milan
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Midway to Milan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Milan?

    For as low as $826, KLM can have you in Milan from Chicago Midway Airport in 13h. Chicago Midway Airport and Milan are separated by a distance of 4510 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Midway to Milan that include hotel bookings?

    Yes. In addition to deals on Midway to Milan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Milan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Milan.

  • Can I find deals for business class flights from Midway to Milan?

    Yes. Cheapflights offers flight deals from Midway to Milan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Milan?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Milan (average of $594). Flying from Chicago Midway Airport to Milan in June is currently the most expensive (average of $970). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Monza
Menaggio
Rho
Lainate
Porlezza
Novara
Lecco
Assago
Brescia
Bellagio
Stresa

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