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MDW - MIL

$259 Find cheap flights from Chicago Midway Airport to Milan

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 9/18. 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
Mon 6/10
Mon 6/17

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 42,369,914 times on KAYAK, and here is why:

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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
10:11 am - 9:05 amMDW-MXP
15h 54m1 stop
12:00 pm - 9:44 pmMXP-MDW
16h 44m2 stops
$711Delta
Find Deal
Mon, Nov 4 - Mon, Nov 11
6:15 pm - 5:05 pmMDW-MXP
15h 50m2 stops
12:00 pm - 9:44 pmMXP-MDW
16h 44m2 stops
$728Delta
Find Deal
Mon, Nov 4 - Mon, Nov 11
11:05 am - 1:15 pmMDW-MXP
19h 10m3 stops
7:20 am - 9:37 pmMXP-MDW
21h 17m3 stops
$998
Find Deal
Thu, Sep 19 - Tue, Sep 24
12:30 pm - 7:35 pmMDW-MXP
24h 05m3 stops
7:10 am - 9:37 pmMXP-MDW
21h 27m3 stops
$1,068
Find Deal
Sat, Jun 8 - Mon, Jun 17
8:00 am - 7:35 pmMDW-MXP
28h 35m3 stops
6:30 am - 9:37 pmMXP-MDW
22h 07m3 stops
$1,088
Find Deal
Sat, Jun 8 - Sun, Jun 16
11:25 am - 2:30 pmMDW-MXP
20h 05m3 stops
7:10 am - 9:37 pmMXP-MDW
21h 27m3 stops
$1,093
Find Deal
Mon, Jun 10 - Mon, Jun 17
11:01 am - 9:55 amMDW-MXP
15h 54m1 stop
11:30 am - 9:46 pmMXP-MDW
17h 16m1 stop
$1,155KLM
Find Deal
Sun, May 26 - Tue, Jun 11
12:45 pm - 9:55 amMDW-MXP
14h 10m1 stop
11:30 am - 9:46 pmMXP-MDW
17h 16m1 stop
$1,186KLM
Find Deal
Mon, Jun 10 - Tue, Jun 18
1:24 pm - 8:50 amMDW-LIN
12h 26m2 stops
6:50 am - 6:36 pmLIN-MDW
18h 46m2 stops
$1,274Air France
Find Deal
Tue, Jun 11 - Wed, Jun 19
1:21 pm - 9:30 amMDW-MXP
13h 09m2 stops
7:15 am - 6:36 pmMXP-MDW
18h 21m2 stops
$1,311Air France
Find Deal
Wed, May 29 - Sun, Jun 9

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 $533 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $1,267 and $1,201 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 7 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 ($1,567). The cheapest round-trip tickets were found on Delta ($711) and KLM ($1,155).

Good to know

Cheapest flight

$259
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 $259 for a one-way ticket and $711 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.
9/18Wed
2 stops
37h 07mMDW-MXP
$259
9/18Wed
2 stops
33h 17mMDW-LIN
$262
7/5Fri
2 stops
32h 37mMDW-MXP
$290
9/28Sat
2 stops
25h 17mMDW-MXP
$300
7/10Wed
2 stops
43h 57mMDW-MXP
$305
9/27Fri
2 stops
20h 47mMDW-MXP
$308
9/18Wed
1 stopDelta
13h 50mMDW-MXP
$1,215
9/30Mon
2 stopsDelta
13h 55mMDW-LIN
$1,245
7/5Fri
1 stopKLM
14h 10mMDW-MXP
$1,567
6/7Fri
1 stopAir France
16h 16mMDW-MXP
$1,772

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Last minute flights from Midway to Milan

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Milan that are departing in the next 10 days.
5/15Wed
multi-stopDelta
18h 10mMDW-MXP
5/28Tue
multi-stopDelta
17h 31mMXP-MDW
$2,241
5/15Wed
multi-stopDelta
17h 30mMDW-MXP
5/28Tue
multi-stopDelta
16h 51mMXP-MDW
$2,246
5/14Tue
multi-stopKLM
14h 13mMDW-MXP
5/28Tue
multi-stopKLM
17h 31mMXP-MDW
$2,257
5/16Thu
multi-stopDelta
17h 30mMDW-MXP
6/10Mon
multi-stopDelta
16h 36mMXP-MDW
$2,261
5/15Wed
multi-stopKLM
14h 13mMDW-MXP
6/11Tue
multi-stopKLM
17h 16mMXP-MDW
$2,262
5/14Tue
multi-stopDelta
18h 10mMDW-MXP
5/26Sun
multi-stopDelta
17h 31mMXP-MDW
$2,291
5/16Thu
multi-stopDelta
13h 09mMDW-MXP
5/28Tue
multi-stopDelta
17h 31mMXP-MDW
$2,296
5/14Tue
multi-stopKLM
14h 13mMDW-MXP
5/27Mon
multi-stopKLM
17h 31mMXP-MDW
$2,307
5/15Wed
multi-stopAir France
15h 45mMDW-LIN
5/28Tue
multi-stopAir France
22h 11mLIN-MDW
$2,349
5/16Thu
multi-stopAir France
14h 15mMDW-LIN
6/10Mon
multi-stopAir France
18h 46mLIN-MDW
$2,449

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Chicago Midway Airport - Milan Flights

Departure:

Chicago Midway Airport (undefined)United States

Return flight deals:

Milan - Chicago Midway Airport

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