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Cheap flights from Chicago to Milan from $264

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:10 pm - 12:45 amORD  Chicago O'Hare Intl-BGY Bergamo Orio Al Serio
22h 35m2 stops Kastrup Copenhagen Stockholm Arlanda
Multiple Airlines Logo
6:00 am - 4:45 pmBGY  Bergamo Orio Al Serio-ORD Chicago O'Hare Intl
17h 45m2 stops Stockholm Arlanda Kastrup Copenhagen
$636Multiple Airlines
Wed, Nov 25 - Wed, Dec 2
Multiple Airlines Logo
7:10 pm - 7:40 pmORD  Chicago O'Hare Intl-BGY Bergamo Orio Al Serio
17h 30m2 stops Kastrup Copenhagen Stockholm Arlanda
Multiple Airlines Logo
8:05 pm - 4:45 pmBGY  Bergamo Orio Al Serio-ORD Chicago O'Hare Intl
27h 40m2 stops Stockholm Arlanda Kastrup Copenhagen
$680Multiple Airlines
Mon, Nov 9 - Tue, Nov 17
Turkish Airlines Logo
11:45 am - 9:05 amORD  Chicago O'Hare Intl-MXP Milan Malpensa
14h 20m1 stop Istanbul
Turkish Airlines Logo
6:55 pm - 10:00 amMXP  Milan Malpensa-ORD Chicago O'Hare Intl
22h 05m1 stop Istanbul
$712Turkish Airlines
Sat, Nov 14 - Mon, Nov 16
Scandinavian Airlines Logo
7:15 pm - 8:30 amORD  Chicago O'Hare Intl-MXP Milan Malpensa
30h 15m1 stop Kastrup Copenhagen
Scandinavian Airlines Logo
9:20 am - 4:10 pmMXP  Milan Malpensa-ORD Chicago O'Hare Intl
13h 50m1 stop Kastrup Copenhagen
$713Scandinavian Airlines
Fri, Apr 9 - Sat, Apr 17
TAP AIR PORTUGAL Logo
8:10 pm - 11:35 pmORD  Chicago O'Hare Intl-MXP Milan Malpensa
20h 25m1 stop Lisbon Humberto Delgado
TAP AIR PORTUGAL Logo
5:45 pm - 3:30 pmMXP  Milan Malpensa-ORD Chicago O'Hare Intl
28h 45m1 stop Lisbon Humberto Delgado
$713TAP AIR PORTUGAL
Sun, Nov 29 - Thu, Dec 24
Scandinavian Airlines Logo
7:10 pm - 10:30 amORD  Chicago O'Hare Intl-MXP Milan Malpensa
32h 20m1 stop Kastrup Copenhagen
Scandinavian Airlines Logo
11:20 am - 4:45 pmMXP  Milan Malpensa-ORD Chicago O'Hare Intl
12h 25m1 stop Kastrup Copenhagen
$720Scandinavian Airlines
Fri, Jan 22 - Sun, Jan 31
TAP AIR PORTUGAL Logo
8:10 pm - 4:55 pmORD  Chicago O'Hare Intl-MXP Milan Malpensa
13h 45m1 stop Lisbon Humberto Delgado
TAP AIR PORTUGAL Logo
5:45 pm - 3:30 pmMXP  Milan Malpensa-ORD Chicago O'Hare Intl
28h 45m1 stop Lisbon Humberto Delgado
$720TAP AIR PORTUGAL
Fri, Nov 27 - Thu, Dec 24
Turkish Airlines Logo
8:15 pm - 4:50 pmORD  Chicago O'Hare Intl-MXP Milan Malpensa
37h 35m1 stop Istanbul
Turkish Airlines Logo
6:55 am - 6:20 pmMXP  Milan Malpensa-ORD Chicago O'Hare Intl
18h 25m1 stop Istanbul
$724Turkish Airlines
Sun, Nov 29 - Thu, Dec 3
Aer Lingus Logo
3:55 pm - 11:05 amORD  Chicago O'Hare Intl-LIN Milan Linate
12h 10m1 stop Dublin
Aer Lingus Logo
11:45 am - 7:15 pmLIN  Milan Linate-ORD Chicago O'Hare Intl
14h 30m1 stop Dublin
$777Aer Lingus
Wed, Dec 30 - Sun, Jan 10
Aer Lingus Logo
3:55 pm - 11:05 amORD  Chicago O'Hare Intl-LIN Milan Linate
12h 10m1 stop Dublin
Aer Lingus Logo
11:45 am - 7:15 pmLIN  Milan Linate-ORD Chicago O'Hare Intl
14h 30m1 stop Dublin
$779Aer Lingus
Wed, Dec 30 - Thu, Jan 14

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Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets
Turkish Airlines
Nov 4
ORD12:45 pmChicago O'Hare Intl
26h 05m
1 stop
MXP9:50 pmMilan Malpensa
Nov 18
MXP11:05 amMilan Malpensa
29h 55m
1 stop
ORD10:00 amChicago O'Hare Intl
$707
Turkish Airlines
Nov 14
ORD11:45 amChicago O'Hare Intl
14h 20m
1 stop
MXP9:05 amMilan Malpensa
Nov 16
MXP6:55 pmMilan Malpensa
22h 05m
1 stop
ORD10:00 amChicago O'Hare Intl
$712
Turkish Airlines
Nov 5
ORD12:45 pmChicago O'Hare Intl
17h 45m
1 stop
MXP1:30 pmMilan Malpensa
Nov 8
MXP6:55 amMilan Malpensa
34h 05m
1 stop
ORD10:00 amChicago O'Hare Intl
$714

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets
Scandinavian Airlines
Apr 9
ORD7:15 pmChicago O'Hare Intl
30h 15m
1 stop
MXP8:30 amMilan Malpensa
Apr 17
MXP9:20 amMilan Malpensa
13h 50m
1 stop
ORD4:10 pmChicago O'Hare Intl
$713
Scandinavian Airlines
Apr 7
ORD7:15 pmChicago O'Hare Intl
12h 50m
1 stop
MXP3:05 pmMilan Malpensa
Apr 13
MXP8:40 pmMilan Malpensa
26h 30m
2 stops
ORD4:10 pmChicago O'Hare Intl
$729
Scandinavian Airlines
Apr 22
ORD7:15 pmChicago O'Hare Intl
16h 45m
2 stops
MXP7:00 pmMilan Malpensa
Apr 30
MXP9:20 amMilan Malpensa
13h 50m
1 stop
ORD4:10 pmChicago O'Hare Intl
$730

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago to Milan that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

ChicagoBergamo

ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio

ORDBGY

Chicago O'Hare Intl

Wed 11/25

7:10 pm-12:45 am

2 stops22h 35m

Bergamo Orio Al Serio

Wed 12/2

6:00 am-4:45 pm

2 stops17h 45m

$636

ChicagoBergamo

ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio

ORDBGY

Chicago O'Hare Intl

Mon 11/9

7:10 pm-7:40 pm

2 stops17h 30m

Bergamo Orio Al Serio

Tue 11/17

8:05 pm-4:45 pm

2 stops27h 40m

$680

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Sat 11/14

11:45 am-9:05 am

1 stop14h 20m

Milan Malpensa

Mon 11/16

6:55 pm-10:00 am

1 stop22h 05m

$712

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Fri 4/9

7:15 pm-8:30 am

1 stop30h 15m

Milan Malpensa

Sat 4/17

9:20 am-4:10 pm

1 stop13h 50m

$713

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Sun 11/29

8:10 pm-11:35 pm

1 stop20h 25m

Milan Malpensa

Thu 12/24

5:45 pm-3:30 pm

1 stop28h 45m

$713

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Fri 1/22

7:10 pm-10:30 am

1 stop32h 20m

Milan Malpensa

Sun 1/31

11:20 am-4:45 pm

1 stop12h 25m

$720

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Fri 11/27

8:10 pm-4:55 pm

1 stop13h 45m

Milan Malpensa

Thu 12/24

5:45 pm-3:30 pm

1 stop28h 45m

$720

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Sun 11/29

8:15 pm-4:50 pm

1 stop37h 35m

Milan Malpensa

Thu 12/3

6:55 am-6:20 pm

1 stop18h 25m

$724
Quickest round-trip

ChicagoMilan

ORD Chicago O'Hare Intl - LIN Milan Linate

ORDLIN

Chicago O'Hare Intl

Wed 12/30

3:55 pm-11:05 am

1 stop12h 10m

Milan Linate

Sun 1/10

11:45 am-7:15 pm

1 stop14h 30m

$777

ChicagoMilan

ORD Chicago O'Hare Intl - LIN Milan Linate

ORDLIN

Chicago O'Hare Intl

Wed 12/30

3:55 pm-11:05 am

1 stop12h 10m

Milan Linate

Thu 1/14

11:45 am-7:15 pm

1 stop14h 30m

$779

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 typical price of a round-trip flight between Chicago and Milan?

Prices are currently low for flights on this route.

Typical prices usually range from $648 to $934.
The lowest price recently found on this route was $636.

What is the cheapest month to fly to Milan?

The month of February is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $587. The month of January is another great option to travel to Milan, with average flight prices from Chicago averaging around $602.

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 $1,289. The most expensive day to fly to Milan is Sunday, with ticket prices averaging around $1,585.

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 from Chicago 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 $916 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 $639 on momondo.

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

There are 4 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.

Can stopping save me money on Chicago to Milan flights?

You could potentially save up to 19% on your flight if you consider stops on a Chicago to Milan flight.

How have Chicago to Milan flight prices changed over time?

As of October 2026, prices for Chicago to Milan flights are approximately 23% 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

$264

Fastest flight time

8h 40m

Direct flights

Every day

Airports in Milan

2 airports
The best one-way flight to Milan from Chicago in the past 72 hours is $264. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $636.
The fastest flight from Chicago to Milan takes 8h 40m
Direct flights go from Chicago to Milan every day.
There are 2 airports in Milan. From Chicago there are direct flights to Milan Malpensa (MXP).
Search flight deals

Frequently asked questions about flying from Chicago to Milan

  • 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 $402Free CancellationRating
7.2
2,386 reviews
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesPriceFrom $453Free CancellationRating
7.4
2,028 reviews
Search Scandinavian Airlines flights
Turkish AirlinesPriceFrom $534Free CancellationRating
7.4
4,463 reviews
Search Turkish Airlines flights
Aer LingusPriceFrom $564Free CancellationRating
7.3
1,865 reviews
Search Aer Lingus flights
SWISSPriceFrom $779Free CancellationRating
7.5
2,114 reviews
Search SWISS flights
United AirlinesPriceFrom $780Free CancellationRating
7.3
10,444 reviews
Search United Airlines flights
LufthansaPriceFrom $823Free CancellationRating
6.8
8,295 reviews
Search Lufthansa flights

  • SWISS Flights From Chicago to Milan

    SWISS operates around 6 flights from Chicago to Milan every week. The average price of these flights found in the last 72 hours has been $1,131, but momondo users have found SWISS deals from Chicago to Milan from as low as $779 round-trip. SWISS has been scored 7.5/10 in 2,114 reviews.

  • United Airlines Flights From Chicago to Milan

    United Airlines is also a popular choice for this route. United Airlines flight deals for Chicago to Milan start from as low as $780 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $1,243. United Airlines operates 6 flights to Milan from Chicago in an average week. Users have rated it 7.3/10 across 10,444 reviews.

Traveling to a place near Milan?

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

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.

An easier way to manage your Milan trip

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Milan Linate Airport
Milan Malpensa Airport