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MDW - MIL

Find cheap flights from Chicago Midway Airport to Milan from $361

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Milan departing on 9/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 5/19
Sun 5/26

Search hundreds of travel sites at once for deals on flights to Milan

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Milan, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Milan, as well as popular online travel agencies
In the last 7 days travelers have searched 44,553,814 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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Cheap flight deals from Midway to Milan (MDW-MIL)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Milan that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:42 pm - 9:55 amMDW-MXP
14h 13m1 stop
11:30 am - 9:47 pmMXP-MDW
17h 17m1 stop
$826KLM
Find Deal
Sun, May 19 - Wed, Aug 28
3:45 pm - 11:40 amMDW-MXP
36h 55m2 stops
11:30 am - 9:44 pmMXP-MDW
17h 14m1 stop
$839Air France
Find Deal
Sun, Oct 6 - Wed, Oct 9
1:10 pm - 10:10 amMDW-MXP
14h 00m2 stops
11:30 am - 9:47 pmMXP-MDW
17h 17m1 stop
$842Delta
Find Deal
Wed, Aug 14 - Wed, Aug 21
3:45 pm - 11:40 amMDW-MXP
36h 55m2 stops
8:40 am - 9:44 pmMXP-MDW
20h 04m2 stops
$843Air France
Find Deal
Sun, Oct 6 - Wed, Oct 9
1:10 pm - 10:10 amMDW-MXP
14h 00m2 stops
7:15 am - 6:06 pmMXP-MDW
17h 51m2 stops
$866Delta
Find Deal
Wed, Aug 14 - Wed, Aug 21
12:42 pm - 9:55 amMDW-MXP
14h 13m1 stop
11:30 am - 9:47 pmMXP-MDW
17h 17m1 stop
$876KLM
Find Deal
Thu, May 16 - Wed, Aug 28
1:21 pm - 11:40 amMDW-MXP
15h 19m2 stops
11:30 am - 10:01 pmMXP-MDW
17h 31m1 stop
$892Delta
Find Deal
Thu, May 16 - Thu, May 23
1:21 pm - 11:40 amMDW-MXP
15h 19m2 stops
12:10 pm - 10:01 pmMXP-MDW
16h 51m2 stops
$897Delta
Find Deal
Thu, May 16 - Thu, May 23
12:45 pm - 9:55 amMDW-MXP
14h 10m1 stop
11:30 am - 10:01 pmMXP-MDW
17h 31m1 stop
$920KLM
Find Deal
Mon, May 6 - Tue, May 14
12:42 pm - 9:55 amMDW-MXP
14h 13m1 stop
11:30 am - 9:47 pmMXP-MDW
17h 17m1 stop
$926Delta
Find Deal
Tue, May 14 - Wed, Aug 28

Flights from Midway to Milan - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Milan to help you find the cheapest flights, the best time to fly and much more.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Milan, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Milan is February, where tickets cost $443 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $1,512 and $1,242 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Milan, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Milan, you should book around 2 days before departure. For the absolute cheapest price, our data suggests you should book 80 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Milan?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Delta ($1,215) and KLM ($1,532). The cheapest round-trip tickets were found on KLM ($826) and Air France ($839).

Good to know

Cheapest flight

$361
Flight from Chicago Midway Airport to Milan Malpensa Airport

When to book flights from Midway to Milan

Are your dates flexible? Find out the best times to travel from Midway to Milan based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Milan flights

  • What is the cheapest flight from Chicago Midway Airport to Milan?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Milan was $361 for a one-way ticket and $826 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Milan?

    Yes, you’ll need a passport to travel to Milan from Chicago Midway Airport.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Milan?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago Midway Airport to Milan?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Milan.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Milan?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Milan.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Milan?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Milan from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Milan?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Milan with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Milan?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Milan from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Book cheap flights from Chicago to Milan

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Milan found on KAYAK in the last 72 hours.
9/4Wed
2 stops
42h 22mMDW-MXP
$361
6/11Tue
2 stops
45h 03mMDW-MXP
$378
9/4Wed
2 stops
33h 17mMDW-LIN
$384
6/13Thu
2 stops
56h 22mMDW-MXP
$389
9/18Wed
2 stopsDelta
16h 19mMDW-MXP
$1,215
9/18Wed
2 stopsDelta
13h 25mMDW-LIN
$1,244
9/28Sat
1 stopDelta
13h 50mMDW-MXP
$1,265
6/11Tue
1 stopKLM
14h 10mMDW-MXP
$1,532
6/13Thu
1 stopKLM
14h 10mMDW-MXP
$1,582
5/6Mon
1 stopKLM
14h 10mMDW-MXP
$1,655

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Chicago Midway Airport - Milan Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Milan - Chicago Midway Airport

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