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Midway

$559+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — MDW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$623
(Delta)

One-way from

$559
(Kiwi.com)

Popular in

July

Cheapest in

November

Average price

$937
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. 19% potential increase in price ($165 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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 8/299:00 amMXP - MDW
2 stops19h 44mDelta
Sun 9/146:00 amMDW - MXP
1 stop20h 25mDelta
Deal found 7/29$623
This flugladen.de deal was found by Cheapflights users on 7/29. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:40 amLIN - MDW
2 stops17h 55mKLM
Fri 10/36:15 pmMDW - LIN
2 stops14h 40mKLM
Deal found 7/29$625
This Delta deal was found by Cheapflights users on 7/28. 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 9/186:40 amLIN - MDW
2 stops17h 55mDelta
Thu 10/27:15 pmMDW - LIN
2 stops13h 40mDelta
Deal found 7/28$631
This KLM deal was found by Cheapflights users on 7/30. 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.
Thu 9/2511:40 amMXP - MDW
1 stop16h 56mKLM
Tue 9/3012:43 pmMDW - MXP
1 stop13h 42mKLM
Deal found 7/30$703
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/119:20 amMXP - MDW
2 stops43h 24mAir France
Wed 8/209:31 amMDW - MXP
2 stops17h 54mAir France
Deal found 7/30$946
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/118:45 pmLIN - MDW
2 stops52h 52mAir France
Wed 8/201:08 pmMDW - LIN
2 stops12h 42mAir France
Deal found 7/30$955
This Booking.com deal was found by Cheapflights users on 7/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/187:10 amMXP - MDW
3 stops40h 14mMultiple Airlines
Mon 9/221:08 pmMDW - MXP
2 stops17h 47mMultiple Airlines
Deal found 7/28$1,159
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/279:45 amLIN - MDW
3 stops30h 20mMultiple Airlines
Fri 11/74:15 pmMDW - LIN
3 stops34h 50mMultiple Airlines
Deal found 7/28$1,189

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 July 30, 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

Fri 8/29

9:00 am-9:44 pm

2 stops19h 44m

Chicago Midway

Sun 9/14

6:00 am-9:25 am

1 stop20h 25m

$623

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 9/18

6:40 am-5:35 pm

2 stops17h 55m

Chicago Midway

Fri 10/3

6:15 pm-3:55 pm

2 stops14h 40m

$625

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 9/18

6:40 am-5:35 pm

2 stops17h 55m

Chicago Midway

Thu 10/2

7:15 pm-3:55 pm

2 stops13h 40m

$631

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 9/25

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Tue 9/30

12:43 pm-9:25 am

1 stop13h 42m

$703

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Mon 8/11

9:20 am-9:44 pm

2 stops43h 24m

Chicago Midway

Wed 8/20

9:31 am-10:25 am

2 stops17h 54m

$946

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Mon 8/11

8:45 pm-6:37 pm

2 stops52h 52m

Chicago Midway

Wed 8/20

1:08 pm-8:50 am

2 stops12h 42m

$955

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 9/18

7:10 am-4:24 pm

3 stops40h 14m

Chicago Midway

Mon 9/22

1:08 pm-1:55 pm

2 stops17h 47m

$1,159

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Mon 10/27

9:45 am-10:05 am

3 stops30h 20m

Chicago Midway

Fri 11/7

4:15 pm-10:05 am

3 stops34h 50m

$1,189

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Sat 8/30

8:00 am-3:46 pm

3 stops38h 46m

$559

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Sat 8/30

8:25 am-3:46 pm

3 stops38h 21m

$571

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 13 results
1
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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.

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 July 30, 2025.
Get a feel of what it's like to fly with Delta, KLM, and Air France from Milan to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air France
7.5
Good
1,465 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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.

  • 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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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
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