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$347+ Cheap flights from Milan (MIL) to Midway (MDW)

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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Milan to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Milan (MIL) to Midway (MDW). 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 September 17, 2025.

Round-trip from

$593
(KLM)

One-way from

$347
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$715
From Milan (MIL) to Chicago Midway
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One-way flight from Milan (MIL) to Chicago Midway
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Highest demand for flights based on searches. 15% potential increase in price ($129 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 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 Milan to Midway

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

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.
Thu 10/211:40 amMXP - MDW
1 stop16h 56mDelta
Tue 10/712:48 pmMDW - MXP
2 stops14h 37mDelta
Deal found 9/15$600
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.
Fri 11/216:30 amLIN - MDW
2 stops17h 08mDelta
Sat 11/291:14 pmMDW - LIN
2 stops15h 01mDelta
Deal found 9/16$602
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.
Thu 10/211:40 amMXP - MDW
1 stop16h 56mDelta
Wed 10/1510:35 amMDW - MXP
1 stop15h 50mDelta
Deal found 9/15$604
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.
Thu 10/2311:40 amMXP - MDW
1 stop17h 34mDelta
Fri 11/76:23 pmMDW - MXP
2 stops13h 32mDelta
Deal found 9/16$606
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.
Fri 11/711:35 amMXP - MDW
2 stops17h 39mDelta
Fri 11/1412:47 pmMDW - MXP
1 stop13h 18mDelta
Deal found 9/16$607
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.
Mon 10/69:00 amMXP - MDW
2 stops20h 14mDelta
Sun 10/196:23 pmMDW - MXP
2 stops12h 32mDelta
Deal found 9/16$612
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.
Mon 10/136:40 amLIN - MDW
2 stops18h 45mDelta
Sun 10/196:23 pmMDW - LIN
2 stops12h 32mDelta
Deal found 9/15$613
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.
Mon 10/66:40 amLIN - MDW
2 stops16h 29mDelta
Sun 10/196:23 pmMDW - LIN
2 stops12h 32mDelta
Deal found 9/16$614
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:40 amLIN - MDW
2 stops21h 56mKLM
Wed 10/151:08 pmMDW - LIN
2 stops13h 57mKLM
Deal found 9/15$632
This flugladen.de 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:50 amMXP - MDW
2 stops18h 35mMultiple Airlines
Sun 10/196:00 amMDW - MXP
1 stop20h 25mMultiple Airlines
Deal found 9/17$645
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.
Fri 10/39:00 amMXP - MDW
2 stops19h 36mDelta
Tue 10/712:48 pmMDW - MXP
1 stop13h 37mDelta
Deal found 9/16$651
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:40 amLIN - MDW
2 stops18h 45mKLM
Sun 10/196:23 pmMDW - LIN
2 stops14h 32mKLM
Deal found 9/17$652

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milan to Midway 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 September 17, 2025.
Use the filters below to find and compare flights from Milan to Chicago Midway Airport that are best for you.

Fly from

Milan

Fly to

Midway

Route

Depart

Return

Price

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 2/5

11:05 am-9:46 pm

1 stop17h 41m

Chicago Midway

Wed 4/8

5:59 pm-1:55 pm

2 stops12h 56m

$595

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 12/5

6:55 am-6:18 pm

2 stops18h 23m

Chicago Midway

Mon 12/15

12:50 pm-9:05 am

1 stop13h 15m

$600

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 10/3

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Tue 10/7

12:48 pm-10:25 am

2 stops14h 37m

$600

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 10/2

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Wed 10/15

10:35 am-9:25 am

1 stop15h 50m

$604

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 10/23

11:40 am-10:14 pm

1 stop17h 34m

Chicago Midway

Fri 11/7

6:23 pm-2:55 pm

2 stops13h 32m

$606

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 11/7

11:35 am-10:14 pm

2 stops17h 39m

Chicago Midway

Fri 11/14

12:47 pm-9:05 am

1 stop13h 18m

$606

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 10/2

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Wed 10/15

12:48 pm-9:25 am

1 stop13h 37m

$608

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Sat 2/14

6:30 am-6:08 pm

2 stops18h 38m

Chicago Midway

Sun 2/22

9:30 am-10:00 am

2 stops17h 30m

$608

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 10/30

6:55 am-6:25 pm

2 stops17h 30m

Chicago Midway

Thu 11/6

6:23 pm-5:25 pm

2 stops16h 02m

$608

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 10/30

6:30 am-6:25 pm

2 stops17h 55m

Chicago Midway

Thu 11/6

1:08 pm-10:00 am

2 stops13h 52m

$613

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 36 results
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Best time to book a flight from Milan to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Milan 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 Milan to Chicago Midway Airport
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 Milan to Midway. 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 Milan to Chicago Midway Airport?

    There are many flights that can get you from Milan to Chicago Midway Airport in 16h 55m. Fly via Delta or KLM to get the fastest option. The distance from Milan to Chicago Midway Airport is about 4539 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milan to Midway 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 Milan to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Milan to Chicago Midway Airport (average of $160). Flying from Milan to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Milan to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Malpensa to O'Hare Intl flights
Linate to O'Hare Intl flights
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