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Cheap flights from Milan to Chicago from $376

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 6/10. 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
6:40 am - 5:54 pm
LIN
-
MDW
18h 14m
2 stops
Delta Logo
1:24 pm - 11:20 am
MDW
-
LIN
14h 56m
2 stops
$621Delta
Thu, Apr 9 - Wed, Apr 22
Delta Logo
6:40 am - 5:54 pm
LIN
-
MDW
18h 14m
2 stops
Delta Logo
1:24 pm - 11:20 am
MDW
-
LIN
14h 56m
2 stops
$623Delta
Thu, Apr 9 - Wed, Apr 22
Delta Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
Delta Logo
9:27 am - 12:05 pm
MDW
-
MXP
19h 38m
2 stops
$626Delta
Fri, Apr 10 - Sun, Apr 26
Delta Logo
6:40 am - 5:54 pm
LIN
-
MDW
18h 14m
2 stops
Delta Logo
6:38 pm - 3:55 pm
MDW
-
LIN
14h 17m
2 stops
$628Delta
Fri, Apr 10 - Sun, Apr 26
Multiple Airlines Logo
11:25 am - 10:28 pm
MXP
-
MDW
18h 03m
2 stops
Multiple Airlines Logo
5:21 pm - 9:25 am
MDW
-
MXP
33h 04m
1 stop
$629Multiple Airlines
Fri, Apr 17 - Sat, May 2
Delta Logo
6:40 am - 5:54 pm
LIN
-
MDW
18h 14m
2 stops
Delta Logo
1:24 pm - 11:20 am
MDW
-
LIN
14h 56m
2 stops
$633Delta
Thu, Apr 9 - Sat, Apr 25
Delta Logo
6:25 am - 4:26 pm
LIN
-
MDW
17h 01m
2 stops
Delta Logo
6:38 pm - 3:55 pm
MDW
-
LIN
14h 17m
2 stops
$634Delta
Fri, Apr 24 - Sun, Apr 26
Delta Logo
6:25 am - 4:26 pm
LIN
-
MDW
17h 01m
2 stops
Delta Logo
6:38 pm - 3:55 pm
MDW
-
LIN
14h 17m
2 stops
$635Delta
Fri, Apr 24 - Sun, Apr 26
KLM Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
KLM Logo
5:21 pm - 9:25 am
MDW
-
MXP
33h 04m
1 stop
$652KLM
Fri, Apr 10 - Sun, Apr 26
KLM Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
KLM Logo
10:41 am - 9:25 am
MDW
-
MXP
15h 44m
1 stop
$691KLM
Wed, Apr 15 - Tue, Apr 21

Delta flights from Milan to Chicago Midway Airport

Our best Delta deals on Milan to Chicago Midway Airport flight tickets
Delta
Apr 9
LIN6:40 amMilan Linate
18h 14m
2 stops
MDW5:54 pmChicago Midway
Apr 22
MDW1:24 pmChicago Midway
14h 56m
2 stops
LIN11:20 amMilan Linate
$621
Delta
Apr 9
LIN6:40 amMilan Linate
18h 14m
2 stops
MDW5:54 pmChicago Midway
Apr 22
MDW1:24 pmChicago Midway
14h 56m
2 stops
LIN11:20 amMilan Linate
$623
Delta
Apr 10
MXP11:40 amMilan Malpensa
17h 51m
1 stop
MDW10:31 pmChicago Midway
Apr 26
MDW9:27 amChicago Midway
19h 38m
2 stops
MXP12:05 pmMilan Malpensa
$626

KLM flights from Milan to Chicago Midway Airport

Our best KLM deals on Milan to Chicago Midway Airport flight tickets
KLM
Apr 10
MXP11:40 amMilan Malpensa
17h 51m
1 stop
MDW10:31 pmChicago Midway
Apr 26
MDW5:21 pmChicago Midway
33h 04m
1 stop
MXP9:25 amMilan Malpensa
$652
KLM
Apr 15
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
Apr 21
MDW10:41 amChicago Midway
15h 44m
1 stop
MXP9:25 amMilan Malpensa
$691
KLM
May 1
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
May 5
MDW10:41 amChicago Midway
15h 44m
1 stop
MXP9:25 amMilan Malpensa
$782

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 February 27, 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

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 4/9

6:40 am-5:54 pm

2 stops18h 14m

Chicago Midway

Wed 4/22

1:24 pm-11:20 am

2 stops14h 56m

$621

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 4/9

6:40 am-5:54 pm

2 stops18h 14m

Chicago Midway

Wed 4/22

1:24 pm-11:20 am

2 stops14h 56m

$623

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 4/10

11:40 am-10:31 pm

1 stop17h 51m

Chicago Midway

Sun 4/26

9:27 am-12:05 pm

2 stops19h 38m

$626

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 4/10

6:40 am-5:54 pm

2 stops18h 14m

Chicago Midway

Sun 4/26

6:38 pm-3:55 pm

2 stops14h 17m

$628

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 4/17

11:25 am-10:28 pm

2 stops18h 03m

Chicago Midway

Sat 5/2

5:21 pm-9:25 am

1 stop33h 04m

$629

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 4/9

6:40 am-5:54 pm

2 stops18h 14m

Chicago Midway

Sat 4/25

1:24 pm-11:20 am

2 stops14h 56m

$633

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 4/24

6:25 am-4:26 pm

2 stops17h 01m

Chicago Midway

Sun 4/26

6:38 pm-3:55 pm

2 stops14h 17m

$634

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 4/24

6:25 am-4:26 pm

2 stops17h 01m

Chicago Midway

Sun 4/26

6:38 pm-3:55 pm

2 stops14h 17m

$635

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 4/10

11:40 am-10:31 pm

1 stop17h 51m

Chicago Midway

Sun 4/26

5:21 pm-9:25 am

1 stop33h 04m

$652

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 4/15

11:40 am-10:28 pm

1 stop17h 48m

Chicago Midway

Tue 4/21

10:41 am-9:25 am

1 stop15h 44m

$691

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

16h 29m

Direct flights

None
The fastest flight from Milan to Chicago Midway Airport takes 16h 29m
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 29m.

  • 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
Schererville
Valparaiso
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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