Which layover airport has the shortest travel time from Chicago to Milan?

Flights connecting via Dublin (DUB) have the shortest average one-way travel time: 11h 55m.

How many flights depart from Chicago to Milan on average per week?

As of November 2026, there are 35 flights per week flying from Chicago to Milan. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

Which layover airport has the shortest connection time from Chicago to Milan?

Rome (FCO) has the shortest average layover time for this route: 1h 25m.

How many flights depart from Chicago to Milan on average per day?

As of November 2026, there are 5 flights per day flying from Chicago to Milan. The most common time of day flights depart is 9:00PM, with 100% of flights taking off in the evening.

Which layover airport offers the lowest fares from Chicago to Milan?

Flights via Reykjavik (KEF) offer the lowest average round-trip price of $403.

Which airport is the most popular layover for flights between Chicago and Milan?

Copenhagen (CPH) was the most common stop: 47% of momondo users choosing 1-stop flights on this route connected there.

What airlines fly to Milan?

United Airlines, Scandinavian Airlines and Lufthansa are the top three most popular airlines that fly to Milan from Chicago according to our data. United Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Milan. Keep in mind that there are 7 different airlines that fly to Milan on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Chicago to Milan?

Iberia, Aer Lingus, and Scandinavian Airlines are the most popular carriers operating from Chicago to Milan

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?

The number of operators available for flights from Chicago to Milan is 7 as of November 2026.

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.

$290 Cheap Flights from Chicago to Milan in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Milan

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:10 pm - 7:55 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

17h 45m2 stops Kastrup Copenhagen Stockholm Arlanda

11:20 am - 5:45 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

12h 25m1 stop Kastrup Copenhagen

$761Scandinavian Airlines

Thu, Mar 11 - Sun, Mar 21

7:30 pm - 8:40 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

19h 10m2 stops Reykjavik Keflavik Intl Berlin Brandenburg

4:20 pm - 6:15 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

32h 55m1 stop Reykjavik Keflavik Intl

$761Multiple Airlines

Thu, Mar 25 - Wed, Mar 31

6:30 pm - 8:35 amORD Chicago O'Hare Intl-MXP Milan Malpensa

32h 05m1 stop Belgrade Nikola Tesla

9:20 am - 2:30 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

36h 10m1 stop Belgrade Nikola Tesla

$762Air Serbia

Sat, Mar 20 - Tue, Mar 30

7:10 pm - 7:15 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

17h 05m1 stop Kastrup Copenhagen

11:20 am - 5:45 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

12h 25m1 stop Kastrup Copenhagen

$762Scandinavian Airlines

Fri, Mar 12 - Sun, Mar 21

12:45 pm - 9:05 amORD Chicago O'Hare Intl-MXP Milan Malpensa

14h 20m1 stop Istanbul

10:50 am - 9:35 amMXP Milan Malpensa-ORD Chicago O'Hare Intl

29h 45m1 stop Istanbul

$763Turkish Airlines

Thu, Mar 25 - Sun, Apr 11

8:15 pm - 1:30 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

34h 15m1 stop Istanbul

3:10 pm - 10:00 amMXP Milan Malpensa-ORD Chicago O'Hare Intl

25h 50m1 stop Istanbul

$763Turkish Airlines

Wed, Dec 2 - Mon, Dec 14

9:50 pm - 4:30 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

11h 40m1 stop Munich Franz Josef Strauss

6:55 am - 1:10 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

13h 15m1 stop Frankfurt am Main

$791Lufthansa

Tue, Dec 29 - Thu, Jan 14

9:50 pm - 4:30 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

11h 40m1 stop Munich Franz Josef Strauss

6:55 am - 1:10 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

13h 15m1 stop Frankfurt am Main

$791Lufthansa

Tue, Dec 29 - Tue, Jan 12

3:45 pm - 10:05 amORD Chicago O'Hare Intl-MXP Milan Malpensa

11h 20m1 stop Montreal Pierre Elliott Trudeau Intl

12:55 pm - 1:09 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

31h 14m2 stops Montreal Pierre Elliott Trudeau Intl Newark

$800United Airlines

Tue, Dec 29 - Tue, Jan 12

3:43 pm - 7:30 amORD Chicago O'Hare Intl-MXP Milan Malpensa

32h 47m1 stop Newark

12:55 pm - 8:07 amMXP Milan Malpensa-ORD Chicago O'Hare Intl

26h 12m1 stop Montreal Pierre Elliott Trudeau Intl

$802United Airlines

Tue, Dec 29 - Fri, Jan 15

Cheap last minute flights

Enter your travel dates to find the best prices.

6:30 pm - 5:05 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

15h 35m1 stop Reykjavik Keflavik Intl

6:10 am - 5:20 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

18h 10m1 stop Reykjavik Keflavik Intl

$765Multiple Airlines

Mon, Nov 16 - Wed, Dec 2

8:10 pm - 11:35 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

20h 25m1 stop Lisbon Humberto Delgado

8:35 pm - 2:45 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

25h 10m1 stop Belgrade Nikola Tesla

$767Multiple Airlines

Fri, Nov 13 - Thu, Nov 26

7:00 pm - 11:05 amORD Chicago O'Hare Intl-MXP Milan Malpensa

33h 05m1 stop Lisbon Humberto Delgado

6:20 am - 3:30 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

16h 10m1 stop Lisbon Humberto Delgado

$785TAP AIR PORTUGAL

Wed, Nov 11 - Wed, Nov 18

7:00 pm - 11:05 amORD Chicago O'Hare Intl-MXP Milan Malpensa

33h 05m1 stop Lisbon Humberto Delgado

6:20 am - 3:30 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

16h 10m1 stop Lisbon Humberto Delgado

$795TAP AIR PORTUGAL

Wed, Nov 11 - Wed, Nov 18

7:10 pm - 7:15 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

17h 05m1 stop Kastrup Copenhagen

8:05 pm - 4:45 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

27h 40m1 stop Kastrup Copenhagen

$810Scandinavian Airlines

Sun, Nov 15 - Wed, Dec 2

7:10 pm - 7:15 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

17h 05m1 stop Kastrup Copenhagen

11:20 am - 4:45 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

12h 25m1 stop Kastrup Copenhagen

$813Scandinavian Airlines

Fri, Nov 13 - Sun, Nov 22

6:50 pm - 6:30 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

16h 40m1 stop Zurich

10:30 am - 4:15 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

12h 45m1 stop Zurich

$846SWISS

Sun, Nov 15 - Sun, Nov 22

5:54 pm - 10:05 amORD Chicago O'Hare Intl-MXP Milan Malpensa

33h 11m1 stop Montreal Pierre Elliott Trudeau Intl

3:15 pm - 6:15 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

10h 00mnonstop

$855United Airlines

Sat, Nov 14 - Fri, Nov 27

9:35 pm - 1:15 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 40mnonstop

3:15 pm - 6:15 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

10h 00mnonstop

$856United Airlines

Mon, Nov 16 - Thu, Nov 26

6:50 pm - 2:15 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

12h 25m1 stop Zurich

10:30 am - 4:15 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

12h 45m1 stop Zurich

$877SWISS

Fri, Nov 13 - Thu, Nov 26

Cheap direct flights

Enter your travel dates to find the best prices.

9:30 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 50mnonstop

3:20 pm - 6:00 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

9h 40mnonstop

$1,271United Airlines

Sun, Apr 11 - Thu, Apr 22

9:30 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 50mnonstop

3:20 pm - 6:00 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

9h 40mnonstop

$1,271United Airlines

Sun, Apr 18 - Wed, Apr 28

9:30 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 50mnonstop

3:20 pm - 6:00 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

9h 40mnonstop

$1,271United Airlines

Mon, Apr 5 - Fri, Apr 16

9:30 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 50mnonstop

3:20 pm - 6:00 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

9h 40mnonstop

$1,305Multiple Airlines

Mon, Apr 5 - Fri, Apr 16

9:30 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 50mnonstop

3:20 pm - 6:00 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

9h 40mnonstop

$1,310Multiple Airlines

Sun, Apr 11 - Wed, Apr 21

9:30 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 50mnonstop

3:20 pm - 6:00 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

9h 40mnonstop

$1,365Multiple Airlines

Fri, Apr 9 - Thu, Apr 22

9:30 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 50mnonstop

3:20 pm - 6:00 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

9h 40mnonstop

$1,475SWISS

Sun, Apr 11 - Sun, Apr 25

9:30 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 50mnonstop

3:20 pm - 6:00 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

9h 40mnonstop

$1,576Lufthansa

Sat, Apr 10 - Fri, Apr 23

9:30 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 50mnonstop

3:20 pm - 6:00 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

9h 40mnonstop

$1,610Lufthansa

Tue, Apr 6 - Sun, Apr 11

9:35 pm - 1:15 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 40mnonstop

3:15 pm - 6:15 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

10h 00mnonstop

$1,802Lufthansa

Fri, Nov 20 - Fri, Nov 27

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Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets

Turkish Airlines

Mar 18

ORD12:45 pmChicago O'Hare Intl

18h 45m

1 stop

MXP1:30 pmMilan Malpensa

Mar 23

MXP6:50 pmMilan Malpensa

22h 10m

1 stop

ORD11:00 amChicago O'Hare Intl

$764

Turkish Airlines

Nov 29

ORD11:45 amChicago O'Hare Intl

14h 20m

1 stop

MXP9:05 amMilan Malpensa

Dec 7

MXP6:55 amMilan Malpensa

18h 25m

1 stop

ORD6:20 pmChicago O'Hare Intl

$788

Turkish Airlines

Feb 5

ORD8:15 pmChicago O'Hare Intl

18h 35m

1 stop

MXP9:50 pmMilan Malpensa

Mar 17

MXP6:50 pmMilan Malpensa

30h 30m

1 stop

ORD7:20 pmChicago O'Hare Intl

$789

United Airlines flights from Chicago to Milan

Our best United Airlines deals on Chicago to Milan flight tickets

United Airlines

Dec 29

ORD5:45 pmChicago O'Hare Intl

30h 45m

1 stop

MXP7:30 amMilan Malpensa

Jan 12

MXP1:05 pmMilan Malpensa

26h 02m

1 stop

ORD8:07 amChicago O'Hare Intl

$802

United Airlines

Jan 12

ORD2:26 pmChicago O'Hare Intl

14h 54m

2 stops

LIN12:20 pmMilan Linate

Jan 26

LIN6:25 amMilan Linate

11h 40m

1 stop

ORD11:05 amChicago O'Hare Intl

$828

United Airlines

Dec 27

ORD4:20 pmChicago O'Hare Intl

14h 45m

1 stop

LIN2:05 pmMilan Linate

Jan 12

LIN6:25 amMilan Linate

16h 13m

2 stops

ORD3:38 pmChicago O'Hare Intl

$838

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Thu 3/11

7:10 pm-7:55 pm

2 stops17h 45m

Milan Malpensa

Sun 3/21

11:20 am-5:45 pm

1 stop12h 25m

$761

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Thu 3/25

7:30 pm-8:40 pm

2 stops19h 10m

Milan Malpensa

Wed 3/31

4:20 pm-6:15 pm

1 stop32h 55m

$761

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Sat 3/20

6:30 pm-8:35 am

1 stop32h 05m

Milan Malpensa

Tue 3/30

9:20 am-2:30 pm

1 stop36h 10m

$762

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Fri 3/12

7:10 pm-7:15 pm

1 stop17h 05m

Milan Malpensa

Sun 3/21

11:20 am-5:45 pm

1 stop12h 25m

$762

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Thu 3/25

12:45 pm-9:05 am

1 stop14h 20m

Milan Malpensa

Sun 4/11

10:50 am-9:35 am

1 stop29h 45m

$763

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Wed 12/2

8:15 pm-1:30 pm

1 stop34h 15m

Milan Malpensa

Mon 12/14

3:10 pm-10:00 am

1 stop25h 50m

$763

Quickest round-trip

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Tue 12/29

9:50 pm-4:30 pm

1 stop11h 40m

Milan Malpensa

Thu 1/14

6:55 am-1:10 pm

1 stop13h 15m

$791

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Tue 12/29

9:50 pm-4:30 pm

1 stop11h 40m

Milan Malpensa

Tue 1/12

6:55 am-1:10 pm

1 stop13h 15m

$791

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Tue 12/29

3:45 pm-10:05 am

1 stop11h 20m

Milan Malpensa

Tue 1/12

12:55 pm-1:09 pm

2 stops31h 14m

$800

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Tue 12/29

3:43 pm-7:30 am

1 stop32h 47m

Milan Malpensa

Fri 1/15

12:55 pm-8:07 am

1 stop26h 12m

$802

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Layovers

Other information

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

Prices are currently typical for flights on this route.

Typical prices usually range from $648 to $934.
The lowest price recently found on this route was $761.

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 $577. 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 $1,290. The most expensive day to fly to Milan is Sunday, with ticket prices averaging around $1,574.

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 $918 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 38% 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 November 2026, prices for Chicago to Milan flights are approximately 18% 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	$290
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 $290. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $761.

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?
The number of operators available for flights from Chicago to Milan is 7 as of November 2026.
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?
Based on momondo bookings for flights between Chicago and Milan, the leading plane model is Boeing 787-8 Dreamliner, making up 62.46% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 22.92%, Boeing 787 Dreamliner with 10.89%, and Boeing 787-9 Dreamliner with 1.15%.
What is the most popular airline from Chicago to Milan?
momondo data reveals that the most frequently booked airline on the route from Chicago to Milan is Scandinavian Airlines, representing 32% of all bookings. The subsequent popular airlines are United Airlines at 31%, Lufthansa at 13%, and Aer Lingus at 8%.

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 PORTUGAL	PriceFrom $402	Free Cancellation	Rating 7.2 2,396 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $453	Free Cancellation	Rating 7.5 2,029 reviews	Search Scandinavian Airlines flights
Aer Lingus	PriceFrom $564	Free Cancellation	Rating 7.3 1,882 reviews	Search Aer Lingus flights
Turkish Airlines	PriceFrom $630	Free Cancellation	Rating 7.4 4,465 reviews	Search Turkish Airlines flights
SWISS	PriceFrom $779	Free Cancellation	Rating 7.5 2,120 reviews	Search SWISS flights
United Airlines	PriceFrom $780	Free Cancellation	Rating 7.3 10,474 reviews	Search United Airlines flights
Lufthansa	PriceFrom $823	Free Cancellation	Rating 6.8 8,294 reviews	Search Lufthansa flights

SWISS Flights From Chicago to Milan
SWISS operates around 7 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 2,120 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 $1,240. United Airlines operates 7 flights to Milan from Chicago in an average week. Users have rated it 7.3/10 across 10,474 reviews.

Varenna

Bellagio

Stresa

Brescia

Livigno

Monza

Lecco

Menaggio

Cernobbio

Crema

Novara

Bormio

Iseo

Domodossola

Baveno

Levanto

Bellano

Assago

Rho

Asti

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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Fly into one of these airports located in Milan

Milan Linate Airport

Milan Malpensa Airport

Cheap flights from Chicago to Milan from $290

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 11/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Chicago to Milan

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Cheap last minute flights

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Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets

United Airlines flights from Chicago to Milan

Our best United Airlines deals on Chicago to Milan flight tickets

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

See travel insights to Milan from

How to get the cheapest flight ticket from Chicago to Milan

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

What is the cheapest month to fly to Milan?

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

What is the cheapest Chicago to Milan flight route?

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

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

Can stopping save me money on Chicago to Milan flights?

How have Chicago to Milan flight prices changed over time?

What is the cheapest airline that flies from Chicago to Milan?

What airlines fly to Milan?

Which airport is the most popular layover for flights between Chicago and Milan?

Which layover airport offers the lowest fares from Chicago to Milan?

Which layover airport has the shortest travel time from Chicago to Milan?

Which layover airport has the shortest connection time from Chicago to Milan?

How many flights depart from Chicago to Milan on average per day?

How many flights depart from Chicago to Milan on average per week?

When to book flights from Chicago to Milan

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

Best Price Found

Fastest flight time

Direct flights

Airports in Milan

Frequently asked questions about flying 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

Traveling to a place near Milan?

Why use momondo?

An easier way to manage your Milan 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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

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