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$284+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MIL
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$870
(KLM)

One-way from

$284
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$1,071
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. 4% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This KLM deal was found by Cheapflights users on 7/29. 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.
Wed 11/191:05 pmMDW - MXP
1 stop13h 00mKLM
Tue 12/211:05 amMXP - MDW
1 stop17h 39mKLM
Deal found 7/29$830
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 11/199:30 amMDW - MXP
2 stops16h 35mDelta
Tue 12/211:05 amMXP - MDW
1 stop17h 39mDelta
Deal found 7/29$834
This Air France deal was found by Cheapflights users on 7/27. 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.
Mon 10/1312:48 pmMDW - MXP
1 stop13h 37mAir France
Tue 10/2111:40 amMXP - MDW
1 stop17h 34mAir France
Deal found 7/27$975
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 10/11:08 pmMDW - LIN
2 stops15h 12mDelta
Wed 10/296:30 amLIN - MDW
2 stops17h 55mDelta
Deal found 7/29$1,169
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Sat 8/29:40 amMDW - LIN
3 stops25h 10mMultiple Airlines
Mon 8/42:30 pmLIN - MDW
3 stops32h 54mMultiple Airlines
Deal found 7/29$2,708

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 July 30, 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

Wed 10/15

12:48 pm-9:25 am

1 stop13h 37m

Milan Malpensa

Mon 11/3

11:05 am-10:14 pm

1 stop18h 09m

$870

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 10/26

1:08 pm-8:45 am

2 stops13h 37m

Milan Malpensa

Sat 11/8

12:00 pm-10:14 pm

2 stops17h 14m

$884

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 10/13

12:48 pm-9:25 am

1 stop13h 37m

Milan Malpensa

Tue 10/21

11:40 am-10:14 pm

1 stop17h 34m

$975

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Wed 10/1

1:08 pm-11:20 am

2 stops15h 12m

Milan Linate

Wed 10/29

6:30 am-6:25 pm

2 stops17h 55m

$1,169

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sat 8/2

9:40 am-5:50 pm

3 stops25h 10m

Milan Linate

Mon 8/4

2:30 pm-4:24 pm

3 stops32h 54m

$2,708

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 9/21

10:13 am-11:20 pm

2 stops30h 07m

$284

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sun 10/12

8:39 am-6:40 pm

2 stops27h 01m

$359

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 9/21

12:43 pm-9:25 am

1 stop13h 42m

$574

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 9/21

10:35 am-9:25 am

1 stop15h 50m

$583

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 9/21

1:08 pm-1:55 pm

2 stops17h 47m

$597

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 12 results
1
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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.

Reviews of airlines servicing Milan

Get insights into the airlines that provide service to Milan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milan. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Milan, such as Delta, KLM, and Air France. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,465 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Milan one-way?

    $574 is the cheapest one-way deal found within the past few days, from KLM. You may also be able to find cheap deals on Delta and Air France, with prices starting from $583 and $597, respectively.

  • 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 $977). 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
Brescia
Assago
Bellagio
Stresa
Saronno

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