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Cheap flights from Milan to Chicago from $430

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 9/14. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Milan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:40 am - 4:50 pm
LIN
-
MDW
17h 10m
2 stops
Delta Logo
1:00 pm - 11:20 am
MDW
-
LIN
15h 20m
2 stops
$702Delta
Thu, Oct 8 - Mon, Oct 12
Delta Logo
6:40 am - 4:50 pm
LIN
-
MDW
17h 10m
2 stops
Delta Logo
1:00 pm - 11:20 am
MDW
-
LIN
15h 20m
2 stops
$703Delta
Fri, Oct 9 - Mon, Oct 12
Delta Logo
11:40 am - 9:46 pm
MXP
-
MDW
17h 06m
1 stop
Delta Logo
1:00 pm - 12:05 pm
MDW
-
MXP
16h 05m
2 stops
$705Delta
Wed, Sep 9 - Tue, Sep 15
Delta Logo
6:40 am - 4:50 pm
LIN
-
MDW
17h 10m
2 stops
Delta Logo
12:30 pm - 10:05 am
MDW
-
LIN
14h 35m
2 stops
$708Delta
Thu, Oct 8 - Tue, Oct 13
Delta Logo
6:40 am - 6:37 pm
LIN
-
MDW
18h 57m
2 stops
Delta Logo
5:25 pm - 1:55 pm
MDW
-
LIN
14h 30m
2 stops
$713Delta
Sun, Oct 18 - Mon, Oct 26
Delta Logo
1:05 pm - 10:10 pm
MXP
-
MDW
15h 05m
1 stop
Delta Logo
1:00 pm - 11:40 am
MDW
-
MXP
15h 40m
2 stops
$713Delta
Sat, Oct 31 - Sun, Nov 8
Delta Logo
6:30 am - 4:25 pm
LIN
-
MDW
16h 55m
2 stops
Delta Logo
1:00 pm - 11:15 am
MDW
-
LIN
15h 15m
2 stops
$714Delta
Fri, Nov 27 - Thu, Dec 3
Delta Logo
1:05 pm - 10:10 pm
MXP
-
MDW
15h 05m
1 stop
Delta Logo
1:00 pm - 11:40 am
MDW
-
MXP
15h 40m
2 stops
$714Delta
Sat, Oct 31 - Sun, Nov 8
Multiple Airlines Logo
1:05 pm - 10:10 pm
MXP
-
MDW
16h 05m
1 stop
Multiple Airlines Logo
5:25 pm - 10:55 am
MDW
-
MXP
34h 30m
1 stop
$756Multiple Airlines
Fri, Nov 27 - Thu, Dec 3
Multiple Airlines Logo
7:00 am - 8:50 pm
MXP
-
MDW
20h 50m
2 stops
Multiple Airlines Logo
8:45 am - 9:20 pm
MDW
-
MXP
29h 35m
2 stops
$760Multiple Airlines
Wed, Sep 9 - Tue, Sep 15

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Air France flights from Milan to Chicago Midway Airport

Our best Air France deals on Milan to Chicago Midway Airport flight tickets
Air France
Aug 24
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
Sep 13
MDW10:35 amChicago Midway
15h 50m
1 stop
MXP9:25 amMilan Malpensa
$791
Air France
Sep 24
MXP11:40 amMilan Malpensa
17h 45m
1 stop
MDW10:25 pmChicago Midway
Sep 28
MDW10:48 amChicago Midway
15h 37m
2 stops
MXP9:25 amMilan Malpensa
$858
Air France
Jul 7
MXP11:40 amMilan Malpensa
17h 35m
1 stop
MDW10:15 pmChicago Midway
Oct 30
MDW5:25 pmChicago Midway
11h 45m
1 stop
MXP11:10 amMilan Malpensa
$937

KLM flights from Milan to Chicago Midway Airport

Our best KLM deals on Milan to Chicago Midway Airport flight tickets
KLM
Sep 23
MXP11:40 amMilan Malpensa
17h 45m
1 stop
MDW10:25 pmChicago Midway
Sep 27
MDW1:00 pmChicago Midway
13h 25m
1 stop
MXP9:25 amMilan Malpensa
$814
KLM
Sep 24
MXP11:40 amMilan Malpensa
17h 45m
1 stop
MDW10:25 pmChicago Midway
Sep 29
MDW1:00 pmChicago Midway
13h 25m
1 stop
MXP9:25 amMilan Malpensa
$859
KLM
Oct 1
MXP11:40 amMilan Malpensa
17h 45m
1 stop
MDW10:25 pmChicago Midway
Oct 14
MDW10:35 amChicago Midway
15h 50m
1 stop
MXP9:25 amMilan Malpensa
$860

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 June 12, 2026.
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

Cheapest round-trip

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 10/8

6:40 am-4:50 pm

2 stops17h 10m

Chicago Midway

Mon 10/12

1:00 pm-11:20 am

2 stops15h 20m

$702

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 10/9

6:40 am-4:50 pm

2 stops17h 10m

Chicago Midway

Mon 10/12

1:00 pm-11:20 am

2 stops15h 20m

$703

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 9/9

11:40 am-9:46 pm

1 stop17h 06m

Chicago Midway

Tue 9/15

1:00 pm-12:05 pm

2 stops16h 05m

$705

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 10/8

6:40 am-4:50 pm

2 stops17h 10m

Chicago Midway

Tue 10/13

12:30 pm-10:05 am

2 stops14h 35m

$708

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Sun 10/18

6:40 am-6:37 pm

2 stops18h 57m

Chicago Midway

Mon 10/26

5:25 pm-1:55 pm

2 stops14h 30m

$713
Quickest round-trip

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Sat 10/31

1:05 pm-10:10 pm

1 stop15h 05m

Chicago Midway

Sun 11/8

1:00 pm-11:40 am

2 stops15h 40m

$713

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 11/27

6:30 am-4:25 pm

2 stops16h 55m

Chicago Midway

Thu 12/3

1:00 pm-11:15 am

2 stops15h 15m

$714

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Sat 10/31

1:05 pm-10:10 pm

1 stop15h 05m

Chicago Midway

Sun 11/8

1:00 pm-11:40 am

2 stops15h 40m

$714

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 11/27

1:05 pm-10:10 pm

1 stop16h 05m

Chicago Midway

Thu 12/3

5:25 pm-10:55 am

1 stop34h 30m

$756

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 9/9

7:00 am-8:50 pm

2 stops20h 50m

Chicago Midway

Tue 9/15

8:45 am-9:20 pm

2 stops29h 35m

$760

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

What is the cheapest airline that flies from Milan to Chicago Midway?

Delta is the most popular carrier operating from Milan to Chicago Midway

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

15h 05m

Direct flights

None
The fastest flight from Milan to Chicago Midway Airport takes 15h 05m
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

Frequently asked questions about flying from Milan to Chicago Midway Airport

  • 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 15h 05m.

  • 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
Portage
Benton Harbor
Saint Joseph
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.

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