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Cheap flights from Milan to Chicago from $360

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milan to Chicago departing on 1/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
11:05 am - 10:07 pm
MXP
-
MDW
18h 02m1 stop
Delta Logo
1:49 pm - 11:40 am
MDW
-
MXP
14h 51m2 stops
$634Delta
Thu, Jan 15 - Wed, Jan 28
Delta Logo
6:40 am - 5:54 pm
LIN
-
MDW
18h 14m2 stops
Delta Logo
10:49 am - 8:50 am
MDW
-
LIN
15h 01m2 stops
$635Delta
Fri, Apr 24 - Sun, Apr 26
Delta Logo
11:05 am - 10:07 pm
MXP
-
MDW
18h 02m1 stop
Delta Logo
1:49 pm - 11:40 am
MDW
-
MXP
14h 51m2 stops
$635Delta
Thu, Jan 15 - Wed, Jan 28
Delta Logo
6:30 am - 6:32 pm
LIN
-
MDW
19h 02m2 stops
Delta Logo
1:49 pm - 11:15 am
MDW
-
LIN
14h 26m2 stops
$636Delta
Thu, Jan 15 - Wed, Jan 28
Delta Logo
6:55 am - 6:32 pm
MXP
-
MDW
18h 37m2 stops
Delta Logo
1:49 pm - 11:40 am
MDW
-
MXP
14h 51m2 stops
$637Delta
Thu, Jan 15 - Wed, Jan 28
Delta Logo
6:55 am - 6:32 pm
MXP
-
MDW
18h 37m2 stops
Delta Logo
1:49 pm - 11:40 am
MDW
-
MXP
14h 51m2 stops
$638Delta
Thu, Jan 15 - Wed, Jan 28
KLM Logo
11:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
KLM Logo
12:45 pm - 9:05 am
MDW
-
MXP
13h 20m1 stop
$639KLM
Thu, Feb 19 - Sun, Feb 22
KLM Logo
11:05 am - 10:22 pm
MXP
-
MDW
18h 17m1 stop
KLM Logo
12:45 pm - 9:05 am
MDW
-
MXP
13h 20m1 stop
$648KLM
Tue, Feb 10 - Tue, Feb 17
KLM Logo
11:05 am - 10:22 pm
MXP
-
MDW
18h 17m1 stop
KLM Logo
10:46 am - 9:05 am
MDW
-
MXP
15h 19m1 stop
$650KLM
Mon, Feb 2 - Mon, Feb 9
Air France Logo
11:35 am - 10:31 pm
MXP
-
MDW
17h 56m2 stops
Air France Logo
4:13 pm - 8:05 am
MDW
-
MXP
32h 52m1 stop
$653Air France
Sat, Feb 28 - Sat, Mar 7

KLM flights from Milan to Chicago Midway Airport

Our best KLM deals on Milan to Chicago Midway Airport flight tickets
KLM
Feb 11
MXP11:05 amMilan Malpensa
18h 17m
1 stop
MDW10:22 pmChicago Midway
Feb 18
MDW12:45 pmChicago Midway
13h 20m
1 stop
MXP9:05 amMilan Malpensa
$638
Find similar
KLM
Feb 19
MXP11:05 amMilan Malpensa
18h 26m
1 stop
MDW10:31 pmChicago Midway
Feb 22
MDW12:45 pmChicago Midway
13h 20m
1 stop
MXP9:05 amMilan Malpensa
$639
Find similar
KLM
Feb 10
MXP11:05 amMilan Malpensa
18h 17m
1 stop
MDW10:22 pmChicago Midway
Feb 17
MDW12:45 pmChicago Midway
13h 20m
1 stop
MXP9:05 amMilan Malpensa
$648
Find similar

Air France flights from Milan to Chicago Midway Airport

Our best Air France deals on Milan to Chicago Midway Airport flight tickets
Air France
Feb 28
MXP11:35 amMilan Malpensa
17h 56m
2 stops
MDW10:31 pmChicago Midway
Mar 7
MDW4:13 pmChicago Midway
32h 52m
1 stop
MXP8:05 amMilan Malpensa
$653
Find similar
Air France
Jan 15
MXP11:05 amMilan Malpensa
36h 24m
1 stop
MDW4:29 pmChicago Midway
Jan 28
MDW10:46 amChicago Midway
15h 19m
1 stop
MXP9:05 amMilan Malpensa
$660
Find similar
Air France
Jan 8
MXP11:05 amMilan Malpensa
18h 02m
1 stop
MDW10:07 pmChicago Midway
Jan 14
MDW11:21 amChicago Midway
14h 44m
1 stop
MXP9:05 amMilan Malpensa
$1,093
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Milan to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated December 29, 2025.
Use the filters below to find and compare flights from Milan to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 1/15

11:05 am-10:07 pm

1 stop18h 02m

Chicago Midway

Wed 1/28

1:49 pm-11:40 am

2 stops14h 51m

$634

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 4/24

6:40 am-5:54 pm

2 stops18h 14m

Chicago Midway

Sun 4/26

10:49 am-8:50 am

2 stops15h 01m

$635

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 1/15

11:05 am-10:07 pm

1 stop18h 02m

Chicago Midway

Wed 1/28

1:49 pm-11:40 am

2 stops14h 51m

$635

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 1/15

6:30 am-6:32 pm

2 stops19h 02m

Chicago Midway

Wed 1/28

1:49 pm-11:15 am

2 stops14h 26m

$636

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 1/15

6:55 am-6:32 pm

2 stops18h 37m

Chicago Midway

Wed 1/28

1:49 pm-11:40 am

2 stops14h 51m

$637

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 1/15

6:55 am-6:32 pm

2 stops18h 37m

Chicago Midway

Wed 1/28

1:49 pm-11:40 am

2 stops14h 51m

$638

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 2/19

11:05 am-10:31 pm

1 stop18h 26m

Chicago Midway

Sun 2/22

12:45 pm-9:05 am

1 stop13h 20m

$639

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 2/10

11:05 am-10:22 pm

1 stop18h 17m

Chicago Midway

Tue 2/17

12:45 pm-9:05 am

1 stop13h 20m

$648

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Mon 2/2

11:05 am-10:22 pm

1 stop18h 17m

Chicago Midway

Mon 2/9

10:46 am-9:05 am

1 stop15h 19m

$650

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Sat 2/28

11:35 am-10:31 pm

2 stops17h 56m

Chicago Midway

Sat 3/7

4:13 pm-8:05 am

1 stop32h 52m

$653

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Milan to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

How often are flights from Milan to Chicago delayed?

Historically, on average around 0% of flights between Milan and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 0 minutes.

What is the most punctual flight time for Milan to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

When to book flights from Milan to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Milan to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Milan to Chicago Midway Airport (MIL to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milan to Chicago Midway Airport

Fastest flight time

16h 11m

Direct flights

None
The fastest flight from Milan to Chicago Midway Airport takes 16h 11m
There are no direct flights from Milan to Chicago Midway Airport. There are no popular flight routes from Milan to Chicago Midway Airport.
Search flight deals

  • How far is Milan to Chicago Midway by plane?

    The straight-line distance from Milan to Chicago Midway is 4534.8 mi. By plane, this route typically takes 16h 11m.

  • When did momondo last update prices for flights from Milan to Chicago Midway Airport?

    Prices for flights from Milan to Chicago Midway Airport are updated daily.

  • How old do you have to be to fly from Milan to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milan to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Milan to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Milan to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Milan to Chicago with flexible booking policies on momondo?

Flights from Milan to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Milan to Chicago?

Once you have performed a search for Milan to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Milan to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Milan are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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