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$398+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — MDW
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This Delta deal was found by Cheapflights users on 12/26. 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 12/3110:55 amLIN - MDW
2 stops28h 54mDelta
Wed 10/215:59 pmMDW - LIN
2 stops12h 56mDelta
Deal found 12/26$1,049
This Delta deal was found by Cheapflights users on 12/26. 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 12/296:30 amLIN - MDW
2 stops16h 50mDelta
Wed 1/71:28 pmMDW - LIN
2 stops14h 47mDelta
Deal found 12/26$1,114
This Delta deal was found by Cheapflights users on 12/26. 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 12/3110:55 amLIN - MDW
2 stops28h 54mDelta
Tue 6/235:59 pmMDW - LIN
2 stops18h 46mDelta
Deal found 12/26$1,126
This Delta deal was found by Cheapflights users on 12/26. 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 12/3110:55 amLIN - MDW
2 stops28h 54mDelta
Wed 6/245:25 pmMDW - LIN
2 stops15h 30mDelta
Deal found 12/26$1,131
This Delta deal was found by Cheapflights users on 12/26. 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.
Sun 12/2811:35 amMXP - MDW
2 stops17h 47mDelta
Sun 1/49:50 amMDW - MXP
1 stop16h 15mDelta
Deal found 12/26$1,257
This KLM deal was found by Cheapflights users on 12/27. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2911:05 amMXP - MDW
1 stop18h 17mKLM
Wed 1/711:21 amMDW - MXP
1 stop14h 44mKLM
Deal found 12/27$1,297
This KLM deal was found by Cheapflights users on 12/26. 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.
Tue 12/3011:05 amMXP - MDW
1 stop18h 17mKLM
Tue 10/201:05 pmMDW - MXP
1 stop13h 20mKLM
Deal found 12/26$1,348
This Air France deal was found by Cheapflights users on 12/26. 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.
Tue 12/3011:05 amMXP - MDW
1 stop18h 17mMultiple Airlines
Thu 10/221:05 pmMDW - MXP
1 stop13h 20mMultiple Airlines
Deal found 12/26$1,360
This Delta deal was found by Cheapflights users on 12/26. 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.
Tue 12/3011:05 amMXP - MDW
1 stop18h 17mDelta
Wed 6/245:59 pmMDW - MXP
2 stops13h 46mDelta
Deal found 12/26$1,534
This Delta deal was found by Cheapflights users on 12/26. 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.
Tue 12/3012:20 pmLIN - MDW
2 stops17h 02mDelta
Wed 6/241:00 pmMDW - LIN
2 stops16h 00mDelta
Deal found 12/26$1,535
This KLM deal was found by Cheapflights users on 12/26. 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.
Tue 12/3011:05 amMXP - MDW
1 stop18h 17mKLM
Fri 6/261:05 pmMDW - MXP
1 stop13h 20mKLM
Deal found 12/26$1,560
This KLM deal was found by Cheapflights users on 12/26. 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.
Tue 12/3011:05 amMXP - MDW
1 stop18h 17mKLM
Thu 6/251:05 pmMDW - MXP
1 stop13h 20mKLM
Deal found 12/26$1,651

Find 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$635
(Delta)

One-way from

$398
(Kiwi.com)

Popular in

July

Cheapest in

February

Average price

$783
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 ($128 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 28, 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

LIN - MDW

LINMDW

Milan Linate

Fri 4/24

6:40 am-4:36 pm

2 stops16h 56m

Chicago Midway

Sun 4/26

6:34 pm-1:55 pm

2 stops12h 21m

$635

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 1/15

11:05 am-10:07 pm

1 stop18h 02m

Chicago Midway

Wed 1/28

1:49 pm-11:40 am

2 stops14h 51m

$635

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 2/19

1:20 pm-10:31 pm

1 stop16h 11m

Chicago Midway

Sun 2/22

1:28 pm-10:35 am

2 stops14h 07m

$635

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 1/16

6:30 am-5:37 pm

2 stops18h 07m

Chicago Midway

Sun 2/1

6:35 pm-1:55 pm

2 stops12h 20m

$636

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Wed 1/28

6:30 am-5:29 pm

2 stops17h 59m

Chicago Midway

Mon 2/2

1:26 pm-11:15 am

2 stops14h 49m

$636

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 1/15

6:30 am-6:32 pm

2 stops19h 02m

Chicago Midway

Wed 1/28

1:49 pm-11:15 am

2 stops14h 26m

$636

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 1/23

6:30 am-5:29 pm

2 stops17h 59m

Chicago Midway

Sun 1/25

6:35 pm-1:55 pm

2 stops12h 20m

$636

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 4/24

11:40 am-10:29 pm

1 stop17h 49m

Chicago Midway

Sun 4/26

10:49 am-9:25 am

1 stop15h 36m

$638

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 2/19

11:05 am-10:31 pm

1 stop18h 26m

Chicago Midway

Sun 2/22

10:53 am-9:05 am

1 stop15h 12m

$638

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 4/24

6:45 am-5:54 pm

2 stops18h 09m

Chicago Midway

Sun 4/26

6:34 pm-2:45 pm

2 stops13h 11m

$638

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 32 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

How often are flights from Milan to Chicago delayed?

About 0% of weekly flights between Milan and Chicago have experienced delays in the past year, with the average delay time being 0 minutes.

What is the most punctual flight time for Milan to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the morning tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Monday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

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 56m. Fly via Delta to get the fastest option. The distance from Milan to Chicago Midway Airport is about 4539 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
Merrillville
Hammond
Porter
Benton Harbor

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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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