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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 10/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

KLM Logo
11:05 am - 11:32 pmMXP-MDW
19h 27m1 stop
KLM Logo
1:05 pm - 9:05 amMDW-MXP
13h 00m1 stop
$592KLM
Find Deal
Tue, Nov 25 - Mon, Dec 1
Delta Logo
6:55 am - 6:25 pmMXP-MDW
18h 30m2 stops
Delta Logo
12:47 pm - 9:05 amMDW-MXP
13h 18m1 stop
$594Delta
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Fri, Nov 7 - Sun, Nov 23
Delta Logo
11:40 am - 9:36 pmMXP-MDW
16h 56m1 stop
Delta Logo
12:48 pm - 10:25 amMDW-MXP
14h 37m2 stops
$600Delta
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Thu, Oct 2 - Tue, Oct 7
Delta Logo
6:40 am - 5:43 pmLIN-MDW
18h 03m2 stops
Delta Logo
6:23 pm - 1:55 pmMDW-LIN
12h 32m2 stops
$601Delta
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Thu, Oct 9 - Sun, Oct 12
Air France Logo
12:20 pm - 11:32 pmLIN-MDW
18h 12m2 stops
Air France Logo
1:14 pm - 11:15 amMDW-LIN
15h 01m2 stops
$603Air France
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Tue, Nov 25 - Mon, Dec 1
Delta Logo
11:40 am - 10:14 pmMXP-MDW
17h 34m1 stop
Delta Logo
10:35 am - 9:25 amMDW-MXP
15h 50m1 stop
$603Delta
Find Deal
Tue, Oct 7 - Mon, Oct 13
Delta Logo
11:40 am - 9:36 pmMXP-MDW
16h 56m1 stop
Delta Logo
12:48 pm - 12:05 pmMDW-MXP
16h 17m2 stops
$604Delta
Find Deal
Thu, Oct 2 - Wed, Oct 15
Air France Logo
11:05 am - 11:32 pmMXP-MDW
19h 27m1 stop
Air France Logo
1:14 pm - 11:40 amMDW-MXP
15h 26m2 stops
$613Air France
Find Deal
Tue, Nov 25 - Mon, Dec 1
KLM Logo
11:40 am - 9:36 pmMXP-MDW
16h 56m1 stop
KLM Logo
10:35 am - 9:25 amMDW-MXP
15h 50m1 stop
$616KLM
Find Deal
Fri, Oct 3 - Sat, Oct 18
Air France Logo
11:40 am - 10:14 pmMXP-MDW
17h 34m1 stop
Air France Logo
10:35 am - 10:35 amMDW-MXP
17h 00m2 stops
$630Air France
Find Deal
Thu, Oct 23 - Sat, Nov 8

Delta flights from Milan to Chicago Midway Airport

Our best Delta deals on Milan to Chicago Midway Airport flight tickets
Delta
Nov 7
MXP6:55 amMilan Malpensa
18h 30m
2 stops
MDW6:25 pmChicago Midway
Nov 23
MDW12:47 pmChicago Midway
13h 18m
1 stop
MXP9:05 amMilan Malpensa
$594
Find similar
Delta
Oct 2
MXP11:40 amMilan Malpensa
16h 56m
1 stop
MDW9:36 pmChicago Midway
Oct 7
MDW12:48 pmChicago Midway
14h 37m
2 stops
MXP10:25 amMilan Malpensa
$600
Find similar
Delta
Oct 9
LIN6:40 amMilan Linate
18h 03m
2 stops
MDW5:43 pmChicago Midway
Oct 12
MDW6:23 pmChicago Midway
12h 32m
2 stops
LIN1:55 pmMilan Linate
$601
Find similar

KLM flights from Milan to Chicago Midway Airport

Our best KLM deals on Milan to Chicago Midway Airport flight tickets
KLM
Nov 25
MXP11:05 amMilan Malpensa
19h 27m
1 stop
MDW11:32 pmChicago Midway
Dec 1
MDW1:05 pmChicago Midway
13h 00m
1 stop
MXP9:05 amMilan Malpensa
$592
Find similar
KLM
Oct 3
MXP11:40 amMilan Malpensa
16h 56m
1 stop
MDW9:36 pmChicago Midway
Oct 18
MDW10:35 amChicago Midway
15h 50m
1 stop
MXP9:25 amMilan Malpensa
$616
Find similar
KLM
Nov 25
LIN6:30 amMilan Linate
17h 08m
2 stops
MDW4:38 pmChicago Midway
Dec 1
MDW5:34 pmChicago Midway
15h 21m
2 stops
LIN3:55 pmMilan Linate
$620
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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 September 15, 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

Tue 11/25

11:05 am-11:32 pm

1 stop19h 27m

Chicago Midway

Mon 12/1

1:05 pm-9:05 am

1 stop13h 00m

$592

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 11/7

6:55 am-6:25 pm

2 stops18h 30m

Chicago Midway

Sun 11/23

12:47 pm-9:05 am

1 stop13h 18m

$594

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 10/2

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Tue 10/7

12:48 pm-10:25 am

2 stops14h 37m

$600

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 10/9

6:40 am-5:43 pm

2 stops18h 03m

Chicago Midway

Sun 10/12

6:23 pm-1:55 pm

2 stops12h 32m

$601

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Tue 11/25

12:20 pm-11:32 pm

2 stops18h 12m

Chicago Midway

Mon 12/1

1:14 pm-11:15 am

2 stops15h 01m

$603

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 10/7

11:40 am-10:14 pm

1 stop17h 34m

Chicago Midway

Mon 10/13

10:35 am-9:25 am

1 stop15h 50m

$603

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 10/2

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Wed 10/15

12:48 pm-12:05 pm

2 stops16h 17m

$604

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 11/25

11:05 am-11:32 pm

1 stop19h 27m

Chicago Midway

Mon 12/1

1:14 pm-11:40 am

2 stops15h 26m

$613

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 10/3

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Sat 10/18

10:35 am-9:25 am

1 stop15h 50m

$616

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 10/23

11:40 am-10:14 pm

1 stop17h 34m

Chicago Midway

Sat 11/8

10:35 am-10:35 am

2 stops17h 00m

$630

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 and KLM are the most popular carriers 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

Direct flights

None
There are no direct flights from Milan to Chicago Midway Airport. There are no popular flight routes from Milan to Chicago Midway Airport.
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  • 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 14h 54m.

  • 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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