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Cheap flights from Milan to Chicago from $357

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 9/21. 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.
Multiple Airlines Logo
6:55 am - 10:05 pm
MXP
-
MDW
22h 10m
2 stops
Multiple Airlines Logo
6:00 am - 11:00 am
MDW
-
MXP
22h 00m
2 stops
$745Multiple Airlines
Thu, Sep 3 - Sun, Sep 13
Multiple Airlines Logo
6:55 am - 8:20 pm
MXP
-
MDW
20h 25m
2 stops
Multiple Airlines Logo
6:00 am - 11:00 am
MDW
-
MXP
22h 00m
2 stops
$747Multiple Airlines
Fri, Aug 28 - Sun, Sep 13
Multiple Airlines Logo
7:00 am - 8:50 pm
MXP
-
MDW
20h 50m
2 stops
Multiple Airlines Logo
8:15 am - 11:00 am
MDW
-
MXP
19h 45m
2 stops
$801Multiple Airlines
Wed, Sep 2 - Mon, Sep 7
Delta Logo
6:40 am - 6:01 pm
LIN
-
MDW
18h 21m
2 stops
Delta Logo
11:35 am - 8:50 am
MDW
-
LIN
14h 15m
2 stops
$819Delta
Fri, Sep 4 - Fri, Sep 11
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
Delta Logo
5:45 pm - 2:45 pm
MDW
-
MXP
14h 00m
2 stops
$819Delta
Mon, Aug 24 - Mon, Aug 31
Delta Logo
6:30 am - 4:47 pm
LIN
-
MDW
16h 17m
2 stops
Delta Logo
1:27 pm - 11:15 am
MDW
-
LIN
14h 48m
2 stops
$820Delta
Tue, Oct 27 - Sat, Nov 7
Delta Logo
1:05 pm - 10:33 pm
MXP
-
MDW
15h 28m
1 stop
Delta Logo
1:27 pm - 11:45 am
MDW
-
MXP
15h 18m
2 stops
$820Delta
Tue, Oct 27 - Sat, Nov 7
Delta Logo
11:40 am - 10:44 pm
MXP
-
MDW
18h 04m
1 stop
Delta Logo
10:01 am - 10:25 am
MDW
-
MXP
17h 24m
2 stops
$821Delta
Mon, Sep 21 - Sun, Oct 11
Delta Logo
6:40 am - 5:59 pm
LIN
-
MDW
18h 19m
2 stops
Delta Logo
11:35 am - 8:50 am
MDW
-
LIN
14h 15m
2 stops
$822Delta
Sat, Sep 26 - Sat, Oct 3
Delta Logo
1:05 pm - 10:56 pm
MXP
-
MDW
16h 51m
1 stop
Delta Logo
10:22 am - 9:50 am
MDW
-
MXP
16h 28m
2 stops
$822Delta
Thu, Dec 10 - Mon, Dec 14

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KLM flights from Milan to Chicago Midway Airport

Our best KLM deals on Milan to Chicago Midway Airport flight tickets
KLM
Oct 29
MXP1:05 pmMilan Malpensa
15h 28m
1 stop
MDW10:33 pmChicago Midway
Nov 9
MDW1:00 pmChicago Midway
14h 55m
1 stop
MXP10:55 amMilan Malpensa
$823
KLM
Sep 21
MXP11:40 amMilan Malpensa
18h 04m
1 stop
MDW10:44 pmChicago Midway
Oct 11
MDW10:58 amChicago Midway
15h 27m
1 stop
MXP9:25 amMilan Malpensa
$833
KLM
Oct 1
MXP11:40 amMilan Malpensa
18h 04m
1 stop
MDW10:44 pmChicago Midway
Oct 6
MDW12:45 pmChicago Midway
13h 40m
1 stop
MXP9:25 amMilan Malpensa
$846

Delta flights from Milan to Chicago Midway Airport

Our best Delta deals on Milan to Chicago Midway Airport flight tickets
Delta
Aug 24
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
Aug 31
MDW5:45 pmChicago Midway
14h 00m
2 stops
MXP2:45 pmMilan Malpensa
$819
Delta
Oct 27
LIN6:30 amMilan Linate
16h 17m
2 stops
MDW4:47 pmChicago Midway
Nov 7
MDW1:27 pmChicago Midway
14h 48m
2 stops
LIN11:15 amMilan Linate
$820
Delta
Sep 21
MXP11:40 amMilan Malpensa
18h 04m
1 stop
MDW10:44 pmChicago Midway
Oct 11
MDW10:01 amChicago Midway
17h 24m
2 stops
MXP10:25 amMilan Malpensa
$821

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 August 1, 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

MXP - MDW

MXPMDW

Milan Malpensa

Thu 9/3

6:55 am-10:05 pm

2 stops22h 10m

Chicago Midway

Sun 9/13

6:00 am-11:00 am

2 stops22h 00m

$745

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 8/28

6:55 am-8:20 pm

2 stops20h 25m

Chicago Midway

Sun 9/13

6:00 am-11:00 am

2 stops22h 00m

$747

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 9/2

7:00 am-8:50 pm

2 stops20h 50m

Chicago Midway

Mon 9/7

8:15 am-11:00 am

2 stops19h 45m

$801

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 9/4

6:40 am-6:01 pm

2 stops18h 21m

Chicago Midway

Fri 9/11

11:35 am-8:50 am

2 stops14h 15m

$819

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Mon 8/24

11:40 am-10:36 pm

1 stop17h 56m

Chicago Midway

Mon 8/31

5:45 pm-2:45 pm

2 stops14h 00m

$819

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Tue 10/27

6:30 am-4:47 pm

2 stops16h 17m

Chicago Midway

Sat 11/7

1:27 pm-11:15 am

2 stops14h 48m

$820
Quickest round-trip

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 10/27

1:05 pm-10:33 pm

1 stop15h 28m

Chicago Midway

Sat 11/7

1:27 pm-11:45 am

2 stops15h 18m

$820

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Mon 9/21

11:40 am-10:44 pm

1 stop18h 04m

Chicago Midway

Sun 10/11

10:01 am-10:25 am

2 stops17h 24m

$821

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Sat 9/26

6:40 am-5:59 pm

2 stops18h 19m

Chicago Midway

Sat 10/3

11:35 am-8:50 am

2 stops14h 15m

$822

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 12/10

1:05 pm-10:56 pm

1 stop16h 51m

Chicago Midway

Mon 12/14

10:22 am-9:50 am

2 stops16h 28m

$822

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 13m

Direct flights

None
The fastest flight from Milan to Chicago Midway Airport takes 16h 13m
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 16h 13m.

  • 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
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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