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 $1,050). 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.

How far in advance should I book a flight from Chicago Midway Airport to Milan?

Users have found that booking a flight from Chicago Midway Airport to Milan at least 48 days early can save you up to 18% on average compared to booking a flight this week. If booking 48 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to Milan for as little as $585 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $698 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago Midway Airport to Milan?

The best pricing can be found in the month of November. Prices to Milan from Chicago Midway Airport average $844. You can even find prices in November for less than $844, as users have found deals to Milan from as low as $432. The month of December appears to be one of the more expensive times to travel to Milan from Chicago Midway Airport. Flying in the targeted month can save you up to 47%.

Most accurate provider : When it comes to deals on Chicago Midway Airport-Milan flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-Milan flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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.

$369+ Flights from Chicago Midway Airport to Milan

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Cheap flight deals from Midway to Milan

Most accurate provider	AranGrant 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$994 (Mytrip)
One-way from	$452 (Kiwi.com)
Popular in	December
Cheapest in	November
Average price	$919

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

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

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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. 1% potential increase in price ($14 potential increase over avg. RT price).

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Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).

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Average for round-trip flights in May 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 mayo 1, 2025.

mié. 10/151:05 pmMDW - MXP

1 stop13h 20mKLM

lun. 11/311:05 amMXP - MDW

1 stop17h 39mKLM

Deal found 4/30

$913

mié. 10/151:05 pmMDW - MXP

2 stops16h 00mDelta

lun. 11/311:05 amMXP - MDW

1 stop17h 39mDelta

Deal found 4/30

$925

jue. 5/299:40 amMDW - MXP

3 stops30h 40mMultiple Airlines

mié. 6/47:10 amMXP - MDW

3 stops40h 14mMultiple Airlines

Deal found 4/30

$994

vie. 12/266:25 pmMDW - LIN

2 stops12h 35mDelta

jue. 2/56:30 amLIN - MDW

2 stops16h 55mDelta

Deal found 4/30

$1,034

vie. 5/169:40 amMDW - LIN

3 stops20h 05mMultiple Airlines

vie. 5/232:30 pmLIN - MDW

3 stops29h 45mMultiple Airlines

Deal found 4/30

$1,350

mié. 9/101:05 pmMDW - MXP

1 stop13h 20mAir France

dom. 9/1411:40 amMXP - MDW

1 stop17h 04mAir France

Deal found 4/30

$1,356

mar. 5/136:25 pmMDW - LIN

2 stops14h 30mKLM

vie. 5/166:40 amLIN - MDW

2 stops18h 03mKLM

Deal found 4/29

$2,114

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 mayo 1, 2025.

jue. 5/299:40 amMDW - MXP

3 stops30h 40mMultiple Airlines

mié. 6/47:10 amMXP - MDW

3 stops40h 14mMultiple Airlines

Deal found 4/30

$994

dom. 7/612:44 pmMDW - MXP

1 stop13h 41mDelta

mié. 7/1611:40 amMXP - MDW

1 stop17h 01mDelta

Deal found 4/30

$1,176

mié. 7/910:26 amMDW - MXP

1 stop15h 59mKLM

mar. 7/2211:40 amMXP - MDW

1 stop17h 01mKLM

Deal found 4/30

$1,181

vie. 7/1112:38 pmMDW - MXP

1 stop13h 47mAir France

dom. 7/2011:40 amMXP - MDW

1 stop17h 01mAir France

Deal found 4/30

$1,501

mié. 7/26:20 pmMDW - LIN

2 stops12h 35mDelta

dom. 7/136:40 amLIN - MDW

2 stops19h 00mDelta

Deal found 4/30

$1,304

vie. 5/169:40 amMDW - LIN

3 stops20h 05mMultiple Airlines

vie. 5/232:30 pmLIN - MDW

3 stops29h 45mMultiple Airlines

Deal found 4/30

$1,350

Last-minute flights from Midway to Milan
Discover last-minute flight deals from Midway to Milan. Data last updated mayo 1, 2025 and is based on user searches.

mar. 5/69:52 amMDW - MXP

1 stop16h 33mAir France

sáb. 5/1711:40 amMXP - MDW

1 stop16h 34mAir France

Deal found 4/30

$12,581

jue. 5/812:48 pmMDW - MXP

1 stop13h 37mDelta

mar. 5/1311:40 amMXP - MDW

1 stop16h 48mDelta

Deal found 4/30

$2,061

jue. 5/81:08 pmMDW - LIN

2 stops15h 12mDelta

mar. 5/139:05 amLIN - MDW

2 stops16h 40mDelta

Deal found 4/29

$2,829

sáb. 5/1010:25 amMDW - MXP

1 stop16h 00mKLM

sáb. 5/1711:40 amMXP - MDW

1 stop16h 34mKLM

Deal found 4/30

$2,171

mar. 5/136:25 pmMDW - LIN

2 stops14h 30mKLM

vie. 5/166:40 amLIN - MDW

2 stops18h 03mKLM

Deal found 4/29

$2,114

vie. 5/169:40 amMDW - LIN

3 stops20h 05mMultiple Airlines

vie. 5/232:30 pmLIN - MDW

3 stops29h 45mMultiple Airlines

Deal found 4/30

$1,350

vie. 5/1612:48 pmMDW - MXP

1 stop13h 37mAir France

vie. 5/2311:40 amMXP - MDW

1 stop16h 48mAir France

Deal found 4/30

$2,066

jue. 5/221:08 pmMDW - LIN

2 stops15h 52mDelta

mié. 6/46:40 amLIN - MDW

2 stops18h 05mDelta

Deal found 4/29

$1,534

mar. 5/271:08 pmMDW - MXP

2 stops15h 57mDelta

mar. 6/311:40 amMXP - MDW

1 stop16h 47mDelta

Deal found 4/30

$1,235

jue. 5/299:40 amMDW - MXP

3 stops30h 40mMultiple Airlines

mié. 6/47:10 amMXP - MDW

3 stops40h 14mMultiple Airlines

Deal found 4/30

$994

jue. 5/2910:25 amMDW - MXP

1 stop16h 00mKLM

mié. 6/411:40 amMXP - MDW

1 stop16h 47mKLM

Deal found 4/30

$1,301

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 mayo 1, 2025.

jue. 5/299:40 amMDW - MXP

3 stops30h 40mMultiple Airlines

Deal found 4/30

$452

jue. 5/299:40 amMDW - LIN

3 stops26h 00mMultiple Airlines

Deal found 4/30

$510

lun. 6/301:09 pmMDW - MXP

2 stops15h 56mDelta

Deal found 4/30

$768

lun. 6/3012:44 pmMDW - MXP

1 stop13h 41mKLM

Deal found 4/30

$769

lun. 6/301:09 pmMDW - LIN

2 stops15h 11mDelta

Deal found 4/30

$786

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

mié. 10/15

1:05 pm-9:25 am

1 stop13h 20m

Milan Malpensa

lun. 11/3

11:05 am-9:44 pm

1 stop17h 39m

$913

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

mié. 10/15

1:05 pm-12:05 pm

2 stops16h 00m

Milan Malpensa

lun. 11/3

11:05 am-9:44 pm

1 stop17h 39m

$925

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

jue. 5/29

9:40 am-11:20 pm

3 stops30h 40m

Milan Malpensa

mié. 6/4

7:10 am-4:24 pm

3 stops40h 14m

$994

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

jue. 10/2

1:00 pm-11:20 am

2 stops15h 20m

Milan Linate

lun. 10/13

10:55 pm-6:36 pm

2 stops26h 41m

$1,269

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

vie. 5/16

9:40 am-12:45 pm

3 stops20h 05m

Milan Linate

vie. 5/23

2:30 pm-1:15 pm

3 stops29h 45m

$1,350

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

mié. 9/10

1:05 pm-9:25 am

1 stop13h 20m

Milan Malpensa

dom. 9/14

11:40 am-9:44 pm

1 stop17h 04m

$1,356

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

mar. 5/13

6:25 pm-3:55 pm

2 stops14h 30m

Milan Linate

vie. 5/16

6:40 am-5:43 pm

2 stops18h 03m

$2,114

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

mié. 6/18

9:40 am-5:35 pm

2 stops24h 55m

$369

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

jue. 5/29

9:40 am-11:20 pm

3 stops30h 40m

$452

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

lun. 6/30

1:09 pm-12:05 pm

2 stops15h 56m

$768

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 12 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 May.

Provider	Price Accuracy	Trust Score*
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
AranGrant	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars

*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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago Midway Airport-Milan flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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

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.

Rainfall in Milan by month

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.

Temperature in Milan by month

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).

Reviews of airlines servicing Milan

Peruse reviews from past customers who have flown with Delta, KLM and Air France from Chicago to Milan to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

7,934 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

KLM

7.8

Good

1,334 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air France

7.4

Good

1,446 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

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 $1,050). 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

Monza

Menaggio

Rho

Lainate

Porlezza

Novara

Lecco

Brescia

Assago

Bellagio

Saronno

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$369+ 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 6/18. 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

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find 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 mayo 1, 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 mayo 1, 2025.

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 May.

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

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

Find hourly flight availability from Midway to Milan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated mayo 1, 2025.

Rainfall in Milan by month

Plan your trip to Milan by taking into account the average rainfall totals by month.

Temperature in Milan by month

Plan your trip to Milan by taking into account the average temperature totals by month.

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 mayo 1, 2025.

Peruse reviews from past customers who have flown with Delta, KLM and Air France from Chicago to Milan to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

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.

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?

What is the cheapest month to book a flight from Chicago Midway Airport to Milan?

Traveling to a place near Chicago Midway Airport?

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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 mayo 1, 2025.