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$345+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIL
dic. 13 — dic. 201
sáb. 12/13
sáb. 12/20
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 noviembre 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$813
(Kiwi.com)

One-way from

$345
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$674
Provider with most accurate pricing for Chicago Midway-Milan (MIL) flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Milan (MIL) flights.
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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. 8% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($52 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
jue. 12/47:44 amMDW - MXP
1 stop16h 16mMultiple Airlines
lun. 12/811:55 amMXP - MDW
2 stops32h 06mMultiple Airlines
Deal found 11/11$813
This Delta deal was found by Cheapflights users on 11/11. 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. 12/91:50 pmMDW - MXP
2 stops14h 50mDelta
mar. 12/1611:05 amMXP - MDW
1 stop19h 42mDelta
Deal found 11/11$1,083
This Delta deal was found by Cheapflights users on 11/11. 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. 12/1012:50 pmMDW - MXP
2 stops13h 55mDelta
mié. 12/1712:00 pmMXP - MDW
2 stops18h 47mDelta
Deal found 11/11$1,084
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
mar. 12/97:44 amMDW - MXP
2 stops27h 01mMultiple Airlines
mar. 1/63:40 pmMXP - MDW
1 stop15h 21mMultiple Airlines
Deal found 11/12$1,182
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
jue. 11/276:20 amMDW - MXP
1 stop17h 40mMultiple Airlines
dom. 11/307:55 amMXP - MDW
2 stops33h 10mMultiple Airlines
Deal found 11/12$1,185
This Delta deal was found by Cheapflights users on 11/11. 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. 12/319:50 amMDW - MXP
1 stop16h 15mDelta
jue. 1/811:05 amMXP - MDW
1 stop18h 04mDelta
Deal found 11/11$1,229
This KLM deal was found by Cheapflights users on 11/12. 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.
lun. 12/2912:45 pmMDW - MXP
1 stop13h 20mKLM
lun. 1/1211:05 amMXP - MDW
1 stop18h 04mKLM
Deal found 11/12$1,284
This Delta deal was found by Cheapflights users on 11/12. 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. 12/296:08 pmMDW - MXP
2 stops13h 47mDelta
lun. 1/1211:05 amMXP - MDW
1 stop18h 04mDelta
Deal found 11/12$1,288
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
dom. 12/77:44 amMDW - MXP
2 stops21h 06mMultiple Airlines
mar. 1/63:40 pmMXP - MDW
1 stop15h 21mMultiple Airlines
Deal found 11/12$1,304
This Air France deal was found by Cheapflights users on 11/11. 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.
lun. 12/110:47 amMDW - MXP
1 stop15h 18mAir France
mar. 12/1611:05 amMXP - MDW
1 stop19h 42mAir France
Deal found 11/11$1,321
This Delta deal was found by Cheapflights users on 11/11. 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. 12/110:47 amMDW - LIN
2 stops14h 58mDelta
mar. 12/161:00 pmLIN - MDW
2 stops17h 47mDelta
Deal found 11/11$1,342
This Delta deal was found by Cheapflights users on 11/11. 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. 12/246:08 pmMDW - LIN
2 stops18h 27mDelta
mié. 12/311:00 pmLIN - MDW
2 stops27h 05mDelta
Deal found 11/11$1,442

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 noviembre 13, 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

mié. 1/14

6:45 am-9:05 am

1 stop19h 20m

Milan Malpensa

mié. 1/21

11:35 am-10:26 pm

2 stops17h 51m

$839

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

mié. 2/4

1:28 pm-12:00 pm

2 stops15h 32m

Milan Linate

dom. 2/15

6:30 am-4:16 pm

2 stops16h 46m

$897

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

jue. 3/19

1:00 pm-10:00 am

2 stops15h 00m

Milan Linate

dom. 3/29

6:40 am-6:34 pm

2 stops18h 54m

$947

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

dom. 2/1

6:35 pm-1:55 pm

2 stops12h 20m

Milan Linate

dom. 2/22

12:20 pm-10:44 pm

2 stops17h 24m

$1,022

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

mié. 2/18

1:28 pm-11:15 am

2 stops14h 47m

Milan Linate

lun. 2/23

6:30 am-6:37 pm

2 stops19h 07m

$1,041

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

jue. 1/15

6:14 pm-1:55 pm

2 stops12h 41m

Milan Linate

mié. 1/21

6:30 am-6:36 pm

2 stops19h 06m

$1,041

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

sáb. 1/31

6:00 am-9:05 am

1 stop20h 05m

Milan Malpensa

dom. 2/8

11:05 am-10:26 pm

1 stop18h 21m

$1,054

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

mié. 12/10

12:50 pm-9:45 am

2 stops13h 55m

Milan Malpensa

mié. 12/17

12:00 pm-11:47 pm

2 stops18h 47m

$1,084

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

jue. 3/26

1:05 pm-11:15 am

2 stops16h 10m

Milan Linate

jue. 4/2

6:40 am-6:08 pm

2 stops18h 28m

$1,146

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

vie. 1/9

1:28 pm-10:35 am

2 stops14h 07m

Milan Malpensa

jue. 4/23

6:45 am-6:31 pm

2 stops18h 46m

$1,193

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 34 results
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Compare providers for flights from Midway to Milan

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Milan in November.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Milan flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Milan flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Milan flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Milan flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Milan flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $839, Delta can have you in Milan from Chicago Midway Airport in 19h 20m. 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.

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
Assago
Bellagio
Stresa
Domodossola

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