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$358+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — MDW
Dec 16 — Dec 231
Tue 12/16
Tue 12/23
1 adult, Economy
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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 November 16, 2025.

This Delta deal was found by Cheapflights users on 11/13. 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 12/56:30 amLIN - MDW
2 stops18h 48mDelta
Tue 12/91:50 pmMDW - LIN
2 stops14h 25mDelta
Deal found 11/13$641
This Delta deal was found by Cheapflights users on 11/13. 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 12/56:55 amMXP - MDW
2 stops18h 05mDelta
Tue 12/91:14 pmMDW - MXP
2 stops14h 21mDelta
Deal found 11/13$642
This Delta deal was found by Cheapflights users on 11/14. 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 12/56:30 amLIN - MDW
2 stops18h 30mDelta
Mon 12/81:14 pmMDW - LIN
2 stops15h 01mDelta
Deal found 11/14$643
This Delta deal was found by Cheapflights users on 11/14. 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 12/56:55 amMXP - MDW
2 stops18h 05mDelta
Mon 12/81:14 pmMDW - MXP
2 stops15h 26mDelta
Deal found 11/14$644
This Delta deal was found by Cheapflights users on 11/13. 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 11/276:30 amLIN - MDW
2 stops24h 10mDelta
Sun 12/71:14 pmMDW - LIN
2 stops13h 46mDelta
Deal found 11/13$705
This Delta deal was found by Cheapflights users on 11/13. 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 11/276:30 amLIN - MDW
2 stops24h 10mDelta
Thu 12/41:14 pmMDW - LIN
2 stops13h 46mDelta
Deal found 11/13$716
This Delta deal was found by Cheapflights users on 11/14. 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 12/36:30 amLIN - MDW
2 stops18h 48mDelta
Sun 12/71:14 pmMDW - LIN
2 stops15h 46mDelta
Deal found 11/14$723
This Delta deal was found by Cheapflights users on 11/15. 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 11/276:55 amMXP - MDW
2 stops23h 45mDelta
Sun 12/79:34 amMDW - MXP
2 stops17h 11mDelta
Deal found 11/15$796
This Delta deal was found by Cheapflights users on 11/13. 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.
Sat 11/2211:05 amMXP - MDW
1 stop19h 35mDelta
Sat 12/61:50 pmMDW - MXP
2 stops14h 50mDelta
Deal found 11/13$810
This Delta deal was found by Cheapflights users on 11/13. 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.
Sat 11/226:30 amLIN - MDW
2 stops18h 38mDelta
Sat 12/61:50 pmMDW - LIN
2 stops14h 25mDelta
Deal found 11/13$811
This Delta deal was found by Cheapflights users on 11/13. 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 12/171:00 pmLIN - MDW
2 stops17h 47mDelta
Wed 12/316:08 pmMDW - LIN
2 stops12h 47mDelta
Deal found 11/13$842
This Delta deal was found by Cheapflights users on 11/15. 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.
Fri 12/266:30 amLIN - MDW
2 stops17h 56mDelta
Fri 1/91:49 pmMDW - LIN
2 stops14h 26mDelta
Deal found 11/15$846

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 November 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$642
(Delta)

One-way from

$358
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$646
Provider with most accurate pricing for Milan (MIL)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milan (MIL)-Chicago (CHI) flights.
Search Deals
From Milan (MIL) to Chicago Midway
Search Deals
One-way flight from Milan (MIL) to Chicago Midway
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($130 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 16, 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 1/8

11:05 am-10:09 pm

1 stop18h 04m

Chicago Midway

Sun 1/11

1:28 pm-10:35 am

2 stops14h 07m

$639

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 1/23

6:30 am-5:32 pm

2 stops18h 02m

Chicago Midway

Sun 1/25

6:35 pm-1:55 pm

2 stops12h 20m

$640

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 12/5

6:30 am-6:00 pm

2 stops18h 30m

Chicago Midway

Mon 12/8

1:14 pm-11:15 am

2 stops15h 01m

$641

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Wed 1/21

6:30 am-5:32 pm

2 stops18h 02m

Chicago Midway

Wed 1/28

1:28 pm-11:15 am

2 stops14h 47m

$642

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 12/5

6:55 am-6:00 pm

2 stops18h 05m

Chicago Midway

Mon 12/8

1:14 pm-10:35 am

2 stops14h 21m

$642

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 12/5

6:55 am-6:00 pm

2 stops18h 05m

Chicago Midway

Tue 12/9

1:14 pm-10:35 am

2 stops14h 21m

$642

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 1/8

11:05 am-10:09 pm

1 stop18h 04m

Chicago Midway

Sun 1/11

11:21 am-9:05 am

1 stop14h 44m

$643

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 4/24

6:40 am-6:31 pm

2 stops18h 51m

Chicago Midway

Sun 4/26

1:00 pm-12:00 pm

2 stops16h 00m

$643

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 3/13

6:30 am-6:34 pm

2 stops18h 04m

Chicago Midway

Wed 3/18

1:00 pm-11:15 am

2 stops16h 15m

$648

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 2/18

11:05 am-10:44 pm

1 stop18h 39m

Chicago Midway

Mon 2/23

1:49 pm-11:40 am

2 stops14h 51m

$671

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 30 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 18h 04m. Fly via Delta or KLM to get the fastest option. The distance from Milan to Chicago Midway Airport is about 4510 mi.

  • 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.

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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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
Bergamo to O'Hare Intl flights
Linate to O'Hare Intl flights
Verona to O'Hare Intl flights

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