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$342+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — MDW
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$614
(Delta)

One-way from

$342
(Kiwi.com)

Popular in

July

Cheapest in

November

Average price

$622
Provider with most accurate pricing for Milan (MIL)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Milan (MIL)-Chicago (CHI) flights.
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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. 18% potential increase in price ($151 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 1, 2025.

This Delta deal was found by Cheapflights users on 3/31. 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 4/106:40 amLIN - MDW
2 stops18h 22mDelta
Wed 4/235:59 pmMDW - LIN
2 stops12h 56mDelta
Deal found 3/31$614
This Delta deal was found by Cheapflights users on 3/31. 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 4/2511:40 amMXP - MDW
1 stop17h 42mDelta
Mon 5/55:59 pmMDW - MXP
2 stops12h 56mDelta
Deal found 3/31$616
This KLM deal was found by Cheapflights users on 3/31. 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.
Wed 9/1711:40 amMXP - MDW
1 stop17h 07mKLM
Sun 9/2110:35 amMDW - MXP
1 stop15h 50mKLM
Deal found 3/31$642
This Aeromexico deal was found by Cheapflights users on 3/31. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/811:40 amMXP - MDW
1 stop16h 48mAir France
Mon 5/124:15 pmMDW - MXP
2 stops14h 40mAir France
Deal found 3/31$735
This Aeromexico deal was found by Cheapflights users on 3/31. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:30 amLIN - MDW
2 stops22h 14mAir France
Sun 9/211:00 pmMDW - LIN
2 stops17h 55mAir France
Deal found 3/31$787
This KLM deal was found by Cheapflights users on 3/31. 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 3/3111:25 amMXP - MDW
2 stops17h 58mMultiple Airlines
Mon 4/76:00 amMDW - MXP
1 stop20h 25mMultiple Airlines
Deal found 3/31$952

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 April 1, 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

Thu 4/10

6:40 am-6:02 pm

2 stops18h 22m

Chicago Midway

Wed 4/23

5:59 pm-1:55 pm

2 stops12h 56m

$614

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 4/25

11:40 am-10:22 pm

1 stop17h 42m

Chicago Midway

Mon 5/5

5:59 pm-1:55 pm

2 stops12h 56m

$616

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 9/17

11:40 am-9:47 pm

1 stop17h 07m

Chicago Midway

Sun 9/21

10:35 am-9:25 am

1 stop15h 50m

$642

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 5/8

11:40 am-9:28 pm

1 stop16h 48m

Chicago Midway

Mon 5/12

4:15 pm-1:55 pm

2 stops14h 40m

$735

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Wed 9/17

6:30 am-9:44 pm

2 stops22h 14m

Chicago Midway

Sun 9/21

1:00 pm-1:55 pm

2 stops17h 55m

$787

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 4/29

6:35 pm-12:24 pm

2 stops48h 49m

$342

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Tue 4/29

7:15 pm-12:24 pm

2 stops48h 09m

$355

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Sat 6/7

6:40 am-4:21 pm

2 stops16h 41m

$711

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 6/5

11:40 am-9:27 pm

1 stop16h 47m

$713

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 6/24

11:40 am-9:38 pm

1 stop16h 58m

$933

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 11 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

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated April 1, 2025.
Peruse reviews from past customers who have flown with Delta, KLM and Air France from Milan to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
KLM
7.8
Good
1,321 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air France
7.4
Good
1,425 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines to fly from Milan to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $711 on Delta. Other airlines that offer cheap prices include KLM from $933 and Air France from $1,378 one-way.

  • 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 Milan?

Book flights to Milan if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Milan to Midway

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