Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Milan to Chicago from $390

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 6/8. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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 - 5:56 pm
LIN
-
MDW
18h 16m
2 stops
Delta Logo
1:22 pm - 11:20 am
MDW
-
LIN
14h 58m
2 stops
$685Delta
Thu, May 7 - Mon, May 11
Multiple Airlines Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
Multiple Airlines Logo
12:53 pm - 9:25 am
MDW
-
MXP
13h 32m
1 stop
$687Multiple Airlines
Wed, May 6 - Sun, May 10
Delta Logo
6:40 am - 5:58 pm
LIN
-
MDW
18h 18m
2 stops
Delta Logo
6:36 pm - 3:55 pm
MDW
-
LIN
14h 19m
2 stops
$689Delta
Wed, May 6 - Sun, May 10
Delta Logo
6:45 am - 5:58 pm
MXP
-
MDW
18h 13m
2 stops
Delta Logo
12:53 pm - 9:25 am
MDW
-
MXP
13h 32m
1 stop
$690Delta
Wed, May 6 - Sun, May 10
Delta Logo
6:40 am - 5:58 pm
LIN
-
MDW
18h 18m
2 stops
Delta Logo
1:22 pm - 12:00 pm
MDW
-
LIN
15h 38m
2 stops
$691Delta
Fri, May 1 - Fri, May 8
KLM Logo
11:40 am - 9:46 pm
MXP
-
MDW
17h 06m
1 stop
KLM Logo
10:35 am - 9:25 am
MDW
-
MXP
15h 50m
1 stop
$700KLM
Thu, Oct 1 - Wed, Oct 14
KLM Logo
11:40 am - 9:46 pm
MXP
-
MDW
17h 06m
1 stop
KLM Logo
1:05 pm - 9:25 am
MDW
-
MXP
13h 20m
1 stop
$701KLM
Tue, Sep 15 - Mon, Sep 28
Delta Logo
11:40 am - 9:45 pm
MXP
-
MDW
17h 05m
1 stop
Delta Logo
5:59 pm - 2:45 pm
MDW
-
MXP
13h 46m
2 stops
$707Delta
Thu, Oct 8 - Sat, Oct 17
Delta Logo
6:40 am - 6:33 pm
LIN
-
MDW
18h 53m
2 stops
Delta Logo
1:22 pm - 11:20 am
MDW
-
LIN
14h 58m
2 stops
$708Delta
Sat, May 16 - Tue, May 26
Delta Logo
11:40 am - 9:46 pm
MXP
-
MDW
17h 06m
1 stop
Delta Logo
5:59 pm - 2:45 pm
MDW
-
MXP
13h 46m
2 stops
$709Delta
Mon, Sep 14 - Mon, Sep 28

Delta flights from Milan to Chicago Midway Airport

Our best Delta deals on Milan to Chicago Midway Airport flight tickets
Delta
May 7
LIN6:40 amMilan Linate
18h 16m
2 stops
MDW5:56 pmChicago Midway
May 11
MDW1:22 pmChicago Midway
14h 58m
2 stops
LIN11:20 amMilan Linate
$685
Delta
May 6
LIN6:40 amMilan Linate
18h 18m
2 stops
MDW5:58 pmChicago Midway
May 10
MDW6:36 pmChicago Midway
14h 19m
2 stops
LIN3:55 pmMilan Linate
$689
Delta
May 6
MXP6:45 amMilan Malpensa
18h 13m
2 stops
MDW5:58 pmChicago Midway
May 10
MDW12:53 pmChicago Midway
13h 32m
1 stop
MXP9:25 amMilan Malpensa
$690

KLM flights from Milan to Chicago Midway Airport

Our best KLM deals on Milan to Chicago Midway Airport flight tickets
KLM
Sep 15
MXP11:40 amMilan Malpensa
17h 06m
1 stop
MDW9:46 pmChicago Midway
Sep 28
MDW1:05 pmChicago Midway
13h 20m
1 stop
MXP9:25 amMilan Malpensa
$701
KLM
Sep 13
MXP11:40 amMilan Malpensa
17h 06m
1 stop
MDW9:46 pmChicago Midway
Sep 28
MDW1:05 pmChicago Midway
13h 20m
1 stop
MXP9:25 amMilan Malpensa
$796
KLM
May 18
MXP11:40 amMilan Malpensa
16h 29m
1 stop
MDW9:09 pmChicago Midway
May 31
MDW12:53 pmChicago Midway
13h 32m
1 stop
MXP9:25 amMilan Malpensa
$839

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 April 22, 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 5/7

6:40 am-5:56 pm

2 stops18h 16m

Chicago Midway

Mon 5/11

1:22 pm-11:20 am

2 stops14h 58m

$685

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 5/6

11:40 am-10:28 pm

1 stop17h 48m

Chicago Midway

Sun 5/10

12:53 pm-9:25 am

1 stop13h 32m

$687

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Wed 5/6

6:40 am-5:58 pm

2 stops18h 18m

Chicago Midway

Sun 5/10

6:36 pm-3:55 pm

2 stops14h 19m

$689

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Wed 5/6

6:45 am-5:58 pm

2 stops18h 13m

Chicago Midway

Sun 5/10

12:53 pm-9:25 am

1 stop13h 32m

$690

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 5/1

6:40 am-5:58 pm

2 stops18h 18m

Chicago Midway

Fri 5/8

1:22 pm-12:00 pm

2 stops15h 38m

$691

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 10/1

11:40 am-9:46 pm

1 stop17h 06m

Chicago Midway

Wed 10/14

10:35 am-9:25 am

1 stop15h 50m

$700
Quickest round-trip

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 9/15

11:40 am-9:46 pm

1 stop17h 06m

Chicago Midway

Mon 9/28

1:05 pm-9:25 am

1 stop13h 20m

$701

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 10/8

11:40 am-9:45 pm

1 stop17h 05m

Chicago Midway

Sat 10/17

5:59 pm-2:45 pm

2 stops13h 46m

$707

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Sat 5/16

6:40 am-6:33 pm

2 stops18h 53m

Chicago Midway

Tue 5/26

1:22 pm-11:20 am

2 stops14h 58m

$708

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Mon 9/14

11:40 am-9:46 pm

1 stop17h 06m

Chicago Midway

Mon 9/28

5:59 pm-2:45 pm

2 stops13h 46m

$709

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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

How often are flights from Milan to Chicago delayed?

Historically, on average around 0% of flights between Milan and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 0 minutes.

What is the most punctual flight time for Milan to Chicago flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Monday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday has historically seen more delays on average compared to the rest of the week.

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

14h 33m

Direct flights

None
The fastest flight from Milan to Chicago Midway Airport takes 14h 33m
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 14h 33m.

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 5/22
Fri 5/29
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago