How long is the flight from Chicago Midway Airport to Milan?

For as low as $1,199, KLM can have you in Milan from Chicago Midway Airport in 13h 34m. Chicago Midway Airport and Milan are separated by a distance of 4539 mi. This flight may include one or multiple stops.

In terms of precipitation, rainfall in Milan ranges from 2.2 - 5.2 inches per month. May is typically the wettest month, when rainfall can reach 5.2 in. December is typically the driest time to visit Milan when rainfall is around 2.2 in.

If weather is an important factor for your trip to Milan, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

What is the cheapest time of day to fly from MDW to MIL?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Milan as you normally would.

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.

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.

$258+ Flights from Chicago Midway Airport to Milan

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Cheap 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 December 28, 2025.

Tue 12/306:08 pmMDW - LIN

2 stops12h 47mDelta

Tue 1/66:30 amLIN - MDW

2 stops19h 02mDelta

Deal found 12/27

$2,018

Wed 12/319:50 amMDW - MXP

1 stop16h 15mKLM

Thu 1/2211:05 amMXP - MDW

1 stop18h 17mKLM

Deal found 12/26

$2,130

Wed 12/319:50 amMDW - MXP

2 stops17h 45mDelta

Thu 1/2211:05 amMXP - MDW

1 stop18h 17mDelta

Deal found 12/26

$2,134

Sun 12/289:50 amMDW - MXP

1 stop16h 15mDelta

Tue 1/136:55 amMXP - MDW

2 stops18h 37mDelta

Deal found 12/27

$2,141

Mon 12/2912:45 pmMDW - MXP

1 stop13h 20mKLM

Mon 1/1211:05 amMXP - MDW

1 stop18h 02mKLM

Deal found 12/25

$2,230

Mon 12/299:29 amMDW - MXP

2 stops16h 36mDelta

Mon 1/1211:05 amMXP - MDW

1 stop18h 02mDelta

Deal found 12/25

$2,234

Tue 12/309:50 amMDW - MXP

2 stops16h 55mDelta

Tue 1/136:55 amMXP - MDW

2 stops18h 37mDelta

Deal found 12/27

$2,455

Tue 12/309:29 amMDW - LIN

2 stops17h 31mDelta

Tue 1/136:30 amLIN - MDW

2 stops19h 02mDelta

Deal found 12/27

$2,459

Tue 12/309:29 amMDW - MXP

2 stops17h 16mDelta

Tue 1/66:55 amMXP - MDW

2 stops18h 37mDelta

Deal found 12/26

$2,812

Sat 12/2711:48 amMDW - LIN

2 stops16h 27mDelta

Sat 1/36:30 amLIN - MDW

2 stops17h 56mDelta

Deal found 12/25

$3,067

Sun 12/2812:45 pmMDW - MXP

2 stops14h 50mDelta

Fri 1/212:00 pmMXP - MDW

2 stops17h 22mDelta

Deal found 12/26

$3,816

Sun 12/2812:45 pmMDW - LIN

2 stops15h 30mDelta

Sat 1/36:30 amLIN - MDW

2 stops17h 49mDelta

Deal found 12/27

$3,891

Best flights from Midway to Milan
Discover carefully curated flight deals from Midway to Milan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 28, 2025.

Mon 3/2310:45 amMDW - MXP

1 stop15h 20mKLM

Wed 4/111:40 amMXP - MDW

1 stop17h 51mKLM

Deal found 12/27

$830

Wed 3/119:35 amMDW - MXP

2 stops16h 30mDelta

Wed 3/2510:05 amMXP - MDW

1 stop18h 26mDelta

Deal found 12/26

$834

Fri 3/66:00 amMDW - MXP

1 stop20h 05mMultiple Airlines

Mon 3/96:25 pmMXP - MDW

2 stops28h 30mMultiple Airlines

Deal found 12/27

$1,054

Wed 3/410:49 amMDW - MXP

1 stop15h 16mKLM

Wed 3/1810:05 amMXP - MDW

1 stop18h 26mKLM

Deal found 12/27

$830

Tue 3/109:35 amMDW - MXP

2 stops16h 30mDelta

Tue 3/2411:00 amMXP - MDW

2 stops17h 31mDelta

Deal found 12/27

$834

Mon 2/1612:45 pmMDW - MXP

1 stop13h 20mKLM

Wed 2/2511:05 amMXP - MDW

1 stop18h 26mKLM

Deal found 12/26

$830

Mon 3/232:05 pmMDW - MXP

2 stops14h 30mDelta

Wed 4/111:40 amMXP - MDW

1 stop17h 51mDelta

Deal found 12/27

$834

Wed 2/2512:45 pmMDW - MXP

1 stop13h 20mKLM

Wed 3/411:05 amMXP - MDW

1 stop18h 26mKLM

Deal found 12/26

$830

Thu 3/59:34 amMDW - MXP

2 stops16h 31mDelta

Tue 3/1711:00 amMXP - MDW

2 stops17h 31mDelta

Deal found 12/26

$884

Wed 3/1112:47 pmMDW - MXP

1 stop13h 18mKLM

Wed 3/2510:05 amMXP - MDW

1 stop18h 24mKLM

Deal found 12/26

$830

Thu 3/59:34 amMDW - MXP

2 stops17h 11mDelta

Tue 3/1011:00 amMXP - MDW

2 stops17h 31mDelta

Deal found 12/26

$1,034

Mon 2/212:46 pmMDW - MXP

1 stop13h 19mDelta

Fri 2/1311:05 amMXP - MDW

1 stop18h 26mDelta

Deal found 12/27

$1,080

Fri 2/61:26 pmMDW - LIN

2 stops13h 34mDelta

Sun 2/226:30 amLIN - MDW

2 stops19h 10mDelta

Deal found 12/27

$1,199

Wed 1/211:49 pmMDW - LIN

2 stops14h 26mDelta

Tue 1/271:00 pmLIN - MDW

2 stops35h 29mDelta

Deal found 12/26

$1,344

Mon 1/196:14 pmMDW - LIN

2 stops18h 21mDelta

Tue 1/276:30 amLIN - MDW

2 stops17h 59mDelta

Deal found 12/26

$1,344

Tue 1/206:35 pmMDW - LIN

2 stops12h 20mDelta

Mon 1/261:00 pmLIN - MDW

2 stops35h 29mDelta

Deal found 12/26

$1,344

Mon 1/196:14 pmMDW - LIN

2 stops18h 21mDelta

Mon 1/261:00 pmLIN - MDW

2 stops40h 22mDelta

Deal found 12/26

$1,344

Mon 1/191:26 pmMDW - LIN

2 stops13h 34mDelta

Sun 1/251:00 pmLIN - MDW

2 stops35h 55mDelta

Deal found 12/26

$1,400

Fri 1/231:26 pmMDW - LIN

2 stops13h 34mDelta

Mon 1/261:00 pmLIN - MDW

2 stops35h 55mDelta

Deal found 12/26

$1,450

Thu 2/51:26 pmMDW - LIN

2 stops13h 34mDelta

Thu 2/126:30 amLIN - MDW

2 stops18h 07mDelta

Deal found 12/27

$1,460

Sat 3/211:10 pmMDW - LIN

2 stops16h 05mDelta

Sat 3/286:30 amLIN - MDW

2 stops17h 24mDelta

Deal found 12/26

$1,488

Fri 1/2310:48 amMDW - LIN

2 stops14h 57mDelta

Sun 1/2512:20 pmLIN - MDW

2 stops17h 02mDelta

Deal found 12/26

$1,499

Mon 6/226:00 amMDW - LIN

2 stops22h 20mDelta

Thu 7/26:40 amLIN - MDW

2 stops18h 25mDelta

Deal found 12/27

$1,542

Mon 6/226:00 amMDW - LIN

2 stops22h 20mDelta

Wed 7/16:40 amLIN - MDW

2 stops18h 25mDelta

Deal found 12/27

$1,542

Last-minute flights from Midway to Milan
Discover last-minute flight deals from Midway to Milan. Data last updated December 28, 2025 and is based on user searches.

Sun 1/186:45 amMDW - MXP

1 stop19h 20mDelta

Sat 1/3111:05 amMXP - MDW

1 stop18h 17mDelta

Deal found 12/26

$1,380

Mon 1/1910:46 amMDW - MXP

2 stops15h 59mDelta

Tue 1/2712:00 pmMXP - MDW

2 stops27h 52mDelta

Deal found 12/26

$1,334

Mon 1/196:14 pmMDW - LIN

2 stops18h 21mDelta

Mon 1/261:00 pmLIN - MDW

2 stops40h 22mDelta

Deal found 12/26

$1,344

Mon 1/191:26 pmMDW - MXP

2 stops14h 09mDelta

Mon 1/2611:35 amMXP - MDW

2 stops36h 54mDelta

Deal found 12/26

$1,358

Mon 1/191:26 pmMDW - LIN

2 stops13h 34mDelta

Sun 1/251:00 pmLIN - MDW

2 stops35h 55mDelta

Deal found 12/26

$1,400

Mon 1/191:26 pmMDW - MXP

2 stops14h 09mDelta

Sun 1/2511:35 amMXP - MDW

2 stops37h 20mDelta

Deal found 12/26

$1,408

Wed 1/2112:48 pmMDW - MXP

1 stop13h 17mDelta

Tue 1/2711:35 amMXP - MDW

2 stops36h 54mDelta

Deal found 12/26

$1,354

Fri 1/2310:48 amMDW - LIN

2 stops14h 57mDelta

Tue 1/2712:20 pmLIN - MDW

2 stops17h 02mDelta

Deal found 12/26

$1,449

Fri 1/231:26 pmMDW - LIN

2 stops13h 34mDelta

Mon 1/261:00 pmLIN - MDW

2 stops35h 55mDelta

Deal found 12/26

$1,450

Sat 1/2410:46 amMDW - MXP

2 stops15h 59mDelta

Sat 1/3111:05 amMXP - MDW

1 stop18h 17mDelta

Deal found 12/26

$1,184

Sat 1/3110:46 amMDW - MXP

1 stop15h 19mDelta

Sun 2/86:55 amMXP - MDW

2 stops16h 21mDelta

Deal found 12/27

$1,191

Sat 1/314:30 pmMDW - MXP

1 stop33h 35mKLM

Sun 2/811:05 amMXP - MDW

1 stop18h 17mKLM

Deal found 12/27

$1,290

One-way flights from Midway to Milan
Search for one-way flight options from Midway to Milan. Find affordable one-way fares based on user searches. Data last updated December 28, 2025.

Mon 2/91:00 pmMDW - MXP

2 stops21h 50mMultiple Airlines

Deal found 12/25

$258

Sun 3/19:04 pmMDW - MXP

3 stops37h 01mMultiple Airlines

Deal found 12/26

$273

Sun 3/19:04 pmMDW - LIN

3 stops41h 51mMultiple Airlines

Deal found 12/27

$284

Wed 1/211:20 pmMDW - MXP

3 stops51h 35mMultiple Airlines

Deal found 12/27

$297

Mon 2/97:00 pmMDW - LIN

3 stops43h 55mMultiple Airlines

Deal found 12/25

$336

Thu 1/156:30 pmMDW - MXP

2 stops15h 25mMultiple Airlines

Deal found 12/26

$397

Thu 1/156:30 pmMDW - LIN

2 stops16h 30mMultiple Airlines

Deal found 12/26

$425

Sat 3/146:00 amMDW - MXP

3 stops23h 45mMultiple Airlines

Deal found 12/27

$503

Sun 3/16:00 amMDW - MXP

1 stop20h 05mDelta

Deal found 12/26

$585

Sun 3/110:49 amMDW - MXP

1 stop15h 16mKLM

Deal found 12/27

$588

Sun 3/11:49 pmMDW - LIN

2 stops14h 26mDelta

Deal found 12/26

$592

Sat 3/146:15 amMDW - LIN

3 stops22h 35mMultiple Airlines

Deal found 12/27

$616

Find flight deals from Midway to Milan

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$830 (KLM)
One-way from	$258 (Kiwi.com)
Popular in	December
Cheapest in	January
Average price	$1,393

Provider with most accurate pricing for Chicago Midway-Milan (MIL) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Chicago Midway-Milan (MIL) flights.

Search Deals

From Chicago Midway to Milan (MIL)

Search Deals

One-way flight from Chicago Midway to Milan (MIL)

Search Deals

Highest demand for flights based on searches. 4% potential increase in price ($41 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 6% potential price decrease ($52 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/23

10:45 am-8:05 am

1 stop15h 20m

Milan Malpensa

Wed 4/1

11:40 am-10:31 pm

1 stop17h 51m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 3/4

10:49 am-9:05 am

1 stop15h 16m

Milan Malpensa

Wed 3/18

10:05 am-10:31 pm

1 stop18h 26m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 2/16

12:45 pm-9:05 am

1 stop13h 20m

Milan Malpensa

Wed 2/25

11:05 am-10:31 pm

1 stop18h 26m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 2/25

12:45 pm-9:05 am

1 stop13h 20m

Milan Malpensa

Wed 3/4

11:05 am-10:31 pm

1 stop18h 26m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 3/11

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Wed 3/25

10:05 am-10:29 pm

1 stop18h 24m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 3/11

9:35 am-8:05 am

2 stops16h 30m

Milan Malpensa

Wed 3/25

10:05 am-10:31 pm

1 stop18h 26m

$834

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 3/10

9:35 am-8:05 am

2 stops16h 30m

Milan Malpensa

Tue 3/24

11:00 am-10:31 pm

2 stops17h 31m

$834

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/23

2:05 pm-10:35 am

2 stops14h 30m

Milan Malpensa

Wed 4/1

11:40 am-10:31 pm

1 stop17h 51m

$834

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/5

9:34 am-9:05 am

2 stops16h 31m

Milan Malpensa

Tue 3/17

11:00 am-10:31 pm

2 stops17h 31m

$884

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/5

9:34 am-9:45 am

2 stops17h 11m

Milan Malpensa

Tue 3/10

11:00 am-10:31 pm

2 stops17h 31m

$1,034

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 40 results

Compare providers for flights from Midway to Milan

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Milan in December.

Provider	Price Accuracy	Trust Score*
eDreams	Price Accuracy3 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust 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

How long is the flight from Chicago Midway Airport to Milan?
For as low as $1,199, KLM can have you in Milan from Chicago Midway Airport in 13h 34m. Chicago Midway Airport and Milan are separated by a distance of 4539 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.

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$258+ 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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Milan with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to Milan

Cheapest flights from Midway to MilanExplore 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 December 28, 2025.

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 December 28, 2025.

Find flight deals from Midway to Milan

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

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 December.

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Milan

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?

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

How can I find direct flights from Midway to Milan?

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

Traveling to a place near Milan?

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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 December 28, 2025.