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Cheap flights from Chicago to Milan from $218

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Milan departing on 3/3. 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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0 bags

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Find the cheapest flights from Chicago to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Scandinavian Airlines Logo
7:15 pm - 7:10 pm
ORD
-
MXP
16h 55m
1 stop
Scandinavian Airlines Logo
8:00 pm - 4:10 pm
MXP
-
ORD
27h 10m
1 stop
$435Scandinavian Airlines
Mon, Apr 20 - Sun, Apr 26
Aer Lingus Logo
3:50 pm - 11:05 am
ORD
-
LIN
12h 15m
1 stop
Aer Lingus Logo
11:45 am - 7:15 pm
LIN
-
ORD
14h 30m
1 stop
$437Aer Lingus
Sun, Mar 1 - Fri, Mar 6
Scandinavian Airlines Logo
7:15 pm - 11:25 am
ORD
-
MXP
33h 10m
2 stops
Scandinavian Airlines Logo
8:40 pm - 4:10 pm
MXP
-
ORD
50h 30m
2 stops
$441Scandinavian Airlines
Mon, Apr 20 - Sat, Apr 25
Scandinavian Airlines Logo
7:15 pm - 7:10 pm
ORD
-
MXP
16h 55m
1 stop
Scandinavian Airlines Logo
8:40 pm - 4:10 pm
MXP
-
ORD
50h 30m
2 stops
$442Scandinavian Airlines
Mon, Apr 20 - Sat, Apr 25
Aer Lingus Logo
3:50 pm - 11:05 am
ORD
-
LIN
12h 15m
1 stop
Aer Lingus Logo
11:45 am - 7:15 pm
LIN
-
ORD
14h 30m
1 stop
$559Aer Lingus
Sun, Mar 1 - Sat, Mar 7
ITA Airways Logo
11:00 am - 10:10 am
ORD
-
LIN
16h 10m
2 stops
ITA Airways Logo
7:00 pm - 1:10 pm
LIN
-
ORD
25h 10m
1 stop
$612ITA Airways
Tue, May 5 - Sun, May 10
Delta Logo
12:52 pm - 12:05 pm
MDW
-
MXP
16h 13m
2 stops
Delta Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$836Delta
Wed, Apr 15 - Wed, Apr 22
KLM Logo
12:53 pm - 9:25 am
MDW
-
MXP
13h 32m
1 stop
KLM Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$896KLM
Wed, Apr 15 - Wed, Apr 22
KLM Logo
1:05 pm - 9:25 am
MDW
-
MXP
13h 20m
1 stop
KLM Logo
11:40 am - 9:46 pm
MXP
-
MDW
17h 06m
1 stop
$932KLM
Fri, Aug 7 - Mon, Aug 24
Delta Logo
10:41 am - 9:25 am
MDW
-
MXP
15h 44m
1 stop
Delta Logo
11:40 am - 10:28 pm
MXP
-
MDW
17h 48m
1 stop
$976Delta
Mon, Apr 20 - Wed, Apr 29

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets
Scandinavian Airlines
Apr 20
ORD7:15 pmChicago O'Hare Intl
16h 55m
1 stop
MXP7:10 pmMilan Malpensa
Apr 26
MXP8:00 pmMilan Malpensa
27h 10m
1 stop
ORD4:10 pmChicago O'Hare Intl
$435
Scandinavian Airlines
Apr 20
ORD7:15 pmChicago O'Hare Intl
33h 10m
2 stops
MXP11:25 amMilan Malpensa
Apr 25
MXP8:40 pmMilan Malpensa
50h 30m
2 stops
ORD4:10 pmChicago O'Hare Intl
$441
Scandinavian Airlines
Apr 20
ORD7:15 pmChicago O'Hare Intl
16h 55m
1 stop
MXP7:10 pmMilan Malpensa
Apr 25
MXP8:40 pmMilan Malpensa
50h 30m
2 stops
ORD4:10 pmChicago O'Hare Intl
$442

KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets
KLM
Apr 15
MDW12:53 pmChicago Midway
13h 32m
1 stop
MXP9:25 amMilan Malpensa
Apr 22
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
$896
KLM
Aug 7
MDW1:05 pmChicago Midway
13h 20m
1 stop
MXP9:25 amMilan Malpensa
Aug 24
MXP11:40 amMilan Malpensa
17h 06m
1 stop
MDW9:46 pmChicago Midway
$932
KLM
Apr 20
MDW6:00 amChicago Midway
20h 25m
1 stop
MXP9:25 amMilan Malpensa
Apr 29
MXP11:40 amMilan Malpensa
17h 48m
1 stop
MDW10:28 pmChicago Midway
$976

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Milan 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 19, 2026.
Use the filters below to find and compare flights from Chicago to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/20

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Sun 4/26

8:00 pm-4:10 pm

1 stop27h 10m

$435

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 3/1

3:50 pm-11:05 am

1 stop12h 15m

Milan Linate

Fri 3/6

11:45 am-7:15 pm

1 stop14h 30m

$437

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/20

7:15 pm-11:25 am

2 stops33h 10m

Milan Malpensa

Sat 4/25

8:40 pm-4:10 pm

2 stops50h 30m

$441

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/20

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Sat 4/25

8:40 pm-4:10 pm

2 stops50h 30m

$442

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 3/1

3:50 pm-11:05 am

1 stop12h 15m

Milan Linate

Sat 3/7

11:45 am-7:15 pm

1 stop14h 30m

$559

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 5/5

11:00 am-10:10 am

2 stops16h 10m

Milan Linate

Sun 5/10

7:00 pm-1:10 pm

1 stop25h 10m

$612

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 4/15

12:52 pm-12:05 pm

2 stops16h 13m

Milan Malpensa

Wed 4/22

11:40 am-10:28 pm

1 stop17h 48m

$836

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 4/15

12:53 pm-9:25 am

1 stop13h 32m

Milan Malpensa

Wed 4/22

11:40 am-10:28 pm

1 stop17h 48m

$896

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 8/7

1:05 pm-9:25 am

1 stop13h 20m

Milan Malpensa

Mon 8/24

11:40 am-9:46 pm

1 stop17h 06m

$932

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 4/20

10:41 am-9:25 am

1 stop15h 44m

Milan Malpensa

Wed 4/29

11:40 am-10:28 pm

1 stop17h 48m

$976

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 Milan from

How to get the cheapest flight ticket from Chicago to Milan

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 month to fly to Milan?

The month of January is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $543. The month of February is another great option to travel to Milan, with average flight prices from Chicago averaging around $600.

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,188. The most expensive day to fly to Milan is Thursday, with ticket prices averaging around $1,363.

What is the cheapest Chicago to Milan flight route?

Fly from Chicago O'Hare Intl to Milan Malpensa for the best Chicago - Milan flight prices

How far in advance should I book a flight to Milan?

You are more likely to see cheaper flights to Milan from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Milan for around $899 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan from Chicago for as low as $560 on momondo.

What cabin class options are available on Chicago to Milan flights?

There are 3 cabin classes available to choose from on Chicago to Milan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Chicago to Milan flight prices changed over time?

As of February 2026, prices for Chicago to Milan flights are approximately 8% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Milan according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Milan (CHI to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Milan

Best Price Found

$764

Fastest flight time

8h 40m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Milan

2 airports
The best one-way flight to Milan from Chicago in the past 72 hours is $764. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,315.
The fastest flight from Chicago to Milan takes 8h 40m
Direct flights go from Chicago to Milan on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 2 airports in Milan. From Chicago there are direct flights to Milan Malpensa (MXP).
Search flight deals

  • How far is Chicago to Milan by plane?

    There are 4526.2 mi between Chicago and Milan. By plane, this route typically takes 8h 40m.

  • When did momondo last update prices for flights from Chicago to Milan?

    Prices for flights from Chicago to Milan are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago to Milan?

  • How old do you have to be to fly from Chicago to Milan?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Milan.

  • What documentation or ID do you need to fly to Milan?

    The required travel and health documents for your Milan trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Milan. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago to Milan?

  • What is the most popular airline from Chicago to Milan?

Best airlines flying from Chicago to Milan

Compare and see reviews for airlines that fly from Chicago to Milan with momondo
Airline
Rating
Free Cancellation
Price
TAP AIR PORTUGALPriceFrom $398Free CancellationRating
7.1
2,144 reviews
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesPriceFrom $410Free CancellationRating
7.3
1,691 reviews
Search Scandinavian Airlines flights
British AirwaysPriceFrom $496Free CancellationRating
6.7
7,752 reviews
Search British Airways flights
Turkish AirlinesPriceFrom $534Free CancellationRating
7.3
4,222 reviews
Search Turkish Airlines flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,149 reviews
Search ITA Airways flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
11,313 reviews
Search American Airlines flights
IberiaPriceFrom $639Free CancellationRating
7.0
3,117 reviews
Search Iberia flights
Aer LingusPriceFrom $699Free CancellationRating
7.2
1,455 reviews
Search Aer Lingus flights
United AirlinesPriceFrom $789Free CancellationRating
7.4
9,322 reviews
Search United Airlines flights

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Bellagio
Varenna
Menaggio
Brescia
Stresa
Levanto
Livigno
Monza
Assago
Bellano
Lecco
Domodossola
Crema
Rho
Cernobbio
Moltrasio
Saronno
Bormio
Baveno
Novara

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Milan from Chicago.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Milan.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Milan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan
Milan Linate Airport
Milan Malpensa Airport