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Cheap flights from Milan to Chicago from $419

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 8/30. 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

Delta Logo
9:00 am - 9:36 pmMXP-MDW
19h 36m2 stops
Delta Logo
9:35 am - 10:30 amMDW-MXP
17h 55m2 stops
$612Delta
Find Deal
Thu, Sep 18 - Fri, Oct 3
Delta Logo
6:40 am - 5:35 pmLIN-MDW
17h 55m2 stops
Delta Logo
1:08 pm - 11:20 amMDW-LIN
15h 12m2 stops
$613Delta
Find Deal
Thu, Sep 18 - Fri, Oct 3
Delta Logo
11:40 am - 9:36 pmMXP-MDW
16h 56m1 stop
Delta Logo
9:35 am - 11:00 amMDW-MXP
18h 25m2 stops
$614Delta
Find Deal
Thu, Sep 11 - Sat, Sep 27
Delta Logo
6:40 am - 5:35 pmLIN-MDW
17h 55m2 stops
Delta Logo
6:15 pm - 1:55 pmMDW-LIN
12h 40m2 stops
$616Delta
Find Deal
Thu, Sep 25 - Sat, Oct 4
Delta Logo
9:00 am - 9:44 pmMXP-MDW
19h 44m2 stops
Delta Logo
6:00 am - 6:45 amMDW-MXP
17h 45m2 stops
$616Delta
Find Deal
Fri, Aug 29 - Sun, Sep 14
KLM Logo
11:40 am - 9:36 pmMXP-MDW
16h 56m1 stop
KLM Logo
11:00 am - 9:25 amMDW-MXP
15h 25m1 stop
$618KLM
Find Deal
Thu, Sep 11 - Sat, Sep 27
KLM Logo
11:40 am - 9:36 pmMXP-MDW
16h 56m1 stop
KLM Logo
12:43 pm - 9:25 amMDW-MXP
13h 42m1 stop
$624KLM
Find Deal
Wed, Sep 17 - Mon, Sep 29
Air France Logo
6:50 am - 9:44 pmMXP-MDW
21h 54m2 stops
Air France Logo
1:43 pm - 11:00 pmMDW-MXP
26h 17m2 stops
$945Air France
Find Deal
Tue, Aug 12 - Sat, Aug 23
Air France Logo
9:20 am - 9:44 pmMXP-MDW
43h 24m2 stops
Air France Logo
9:31 am - 10:25 amMDW-MXP
17h 54m2 stops
$946Air France
Find Deal
Mon, Aug 11 - Wed, Aug 20
Logo
7:00 am - 8:45 amLIN-MDW
32h 45m3 stops
Logo
1:43 pm - 6:55 pmMDW-LIN
22h 12m2 stops
$1,759
Find Deal
Mon, Aug 11 - Wed, Aug 20

Delta flights from Milan to Chicago Midway Airport

Our best Delta deals on Milan to Chicago Midway Airport flight tickets
Delta
Sep 18
MXP9:00 amMilan Malpensa
19h 36m
2 stops
MDW9:36 pmChicago Midway
Oct 3
MDW9:35 amChicago Midway
17h 55m
2 stops
MXP10:30 amMilan Malpensa
$612
Find similar
Delta
Sep 18
LIN6:40 amMilan Linate
17h 55m
2 stops
MDW5:35 pmChicago Midway
Oct 3
MDW1:08 pmChicago Midway
15h 12m
2 stops
LIN11:20 amMilan Linate
$613
Find similar
Delta
Sep 11
MXP11:40 amMilan Malpensa
16h 56m
1 stop
MDW9:36 pmChicago Midway
Sep 27
MDW9:35 amChicago Midway
18h 25m
2 stops
MXP11:00 amMilan Malpensa
$614
Find similar

KLM flights from Milan to Chicago Midway Airport

Our best KLM deals on Milan to Chicago Midway Airport flight tickets
KLM
Sep 11
MXP11:40 amMilan Malpensa
16h 56m
1 stop
MDW9:36 pmChicago Midway
Sep 27
MDW11:00 amChicago Midway
15h 25m
1 stop
MXP9:25 amMilan Malpensa
$618
Find similar
KLM
Sep 17
MXP11:40 amMilan Malpensa
16h 56m
1 stop
MDW9:36 pmChicago Midway
Sep 29
MDW12:43 pmChicago Midway
13h 42m
1 stop
MXP9:25 amMilan Malpensa
$624
Find similar
KLM
Sep 18
LIN6:40 amMilan Linate
17h 55m
2 stops
MDW5:35 pmChicago Midway
Oct 3
MDW6:15 pmChicago Midway
14h 40m
2 stops
LIN3:55 pmMilan Linate
$625
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 July 31, 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 9/18

9:00 am-9:36 pm

2 stops19h 36m

Chicago Midway

Fri 10/3

9:35 am-10:30 am

2 stops17h 55m

$612

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 9/18

6:40 am-5:35 pm

2 stops17h 55m

Chicago Midway

Fri 10/3

1:08 pm-11:20 am

2 stops15h 12m

$613

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 9/11

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Sat 9/27

9:35 am-11:00 am

2 stops18h 25m

$614

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Thu 9/25

6:40 am-5:35 pm

2 stops17h 55m

Chicago Midway

Sat 10/4

6:15 pm-1:55 pm

2 stops12h 40m

$616

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 8/29

9:00 am-9:44 pm

2 stops19h 44m

Chicago Midway

Sun 9/14

6:00 am-6:45 am

2 stops17h 45m

$616

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 9/11

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Sat 9/27

11:00 am-9:25 am

1 stop15h 25m

$618

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 9/17

11:40 am-9:36 pm

1 stop16h 56m

Chicago Midway

Mon 9/29

12:43 pm-9:25 am

1 stop13h 42m

$624

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 8/12

6:50 am-9:44 pm

2 stops21h 54m

Chicago Midway

Sat 8/23

1:43 pm-11:00 pm

2 stops26h 17m

$945

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Mon 8/11

9:20 am-9:44 pm

2 stops43h 24m

Chicago Midway

Wed 8/20

9:31 am-10:25 am

2 stops17h 54m

$946

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Mon 8/11

7:00 am-8:45 am

3 stops32h 45m

Chicago Midway

Wed 8/20

1:43 pm-6:55 pm

2 stops22h 12m

$1,759

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

Best Price Found

$419

Fastest flight time

16h 53m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Milan in the past 72 hours is $419. The best round-trip flight deal from Milan to Chicago Midway Airport found on momondo in the last 72 hours is $612.
The fastest flight from Milan to Chicago Midway Airport takes 16h 53m
There are no direct flights from Milan to Chicago Midway Airport. Popular non-direct routes for this connection are Milan Linate Airport - Chicago Midway Airport and Milan Malpensa Airport - 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 16h 53m.

  • 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
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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