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

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

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

Copenhagen (CPH) was the most common stop: 43% of momondo users choosing 1-stop flights on this route connected there.

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

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

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 10:00PM, with 100% of flights taking off in the evening.

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.

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.

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.

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.

$216 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.

7:15 pm - 10:35 amORD Chicago O'Hare Intl-MXP Milan Malpensa

32h 20m1 stop Kastrup Copenhagen

11:25 am - 4:10 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

11h 45m1 stop Kastrup Copenhagen

$714Scandinavian Airlines

Fri, Apr 9 - Sat, Apr 17

7:15 pm - 8:30 amORD Chicago O'Hare Intl-MXP Milan Malpensa

30h 15m1 stop Kastrup Copenhagen

9:20 am - 4:10 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

13h 50m1 stop Kastrup Copenhagen

$714Scandinavian Airlines

Fri, Apr 9 - Sat, Apr 17

4:40 pm - 8:30 amORD Chicago O'Hare Intl-MXP Milan Malpensa

32h 50m1 stop Belgrade Nikola Tesla

8:50 pm - 9:15 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

31h 25m1 stop Belgrade Nikola Tesla

$715Air Serbia

Wed, Apr 14 - Fri, Apr 23

6:30 pm - 11:10 pmORD Chicago O'Hare Intl-LIN Milan Linate

21h 40m2 stops Reykjavik Keflavik Intl Rome Fiumicino

6:30 am - 5:20 pmLIN Milan Linate-ORD Chicago O'Hare Intl

17h 50m2 stops Rome Fiumicino Reykjavik Keflavik Intl

$716Multiple Airlines

Mon, Nov 30 - Wed, Dec 16

11:45 am - 9:05 amORD Chicago O'Hare Intl-MXP Milan Malpensa

14h 20m1 stop Istanbul

7:45 pm - 6:10 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

29h 25m1 stop Istanbul

$724Turkish Airlines

Sat, Feb 13 - Wed, Mar 31

8:05 pm - 8:50 amORD Chicago O'Hare Intl-MXP Milan Malpensa

29h 45m1 stop Istanbul

6:45 am - 9:35 amMXP Milan Malpensa-ORD Chicago O'Hare Intl

33h 50m1 stop Istanbul

$724Turkish Airlines

Mon, Apr 5 - Fri, Apr 16

8:10 pm - 4:55 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

13h 45m1 stop Lisbon Humberto Delgado

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

16h 10m1 stop Lisbon Humberto Delgado

$751TAP AIR PORTUGAL

Sun, Nov 15 - Fri, Nov 20

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

$755SWISS

Mon, Nov 30 - Wed, Dec 16

8:10 pm - 4:55 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

13h 45m1 stop Lisbon Humberto Delgado

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

16h 10m1 stop Lisbon Humberto Delgado

$756TAP AIR PORTUGAL

Sun, Nov 15 - Wed, Nov 18

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

16h 40m1 stop Zurich

6:45 am - 4:15 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

16h 30m1 stop Zurich

$756SWISS

Tue, Dec 29 - Thu, Jan 14

Cheap last minute flights

Enter your travel dates to find the best prices.

11:45 am - 5:50 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

23h 05m1 stop Istanbul

6:50 pm - 10:00 amMXP Milan Malpensa-ORD Chicago O'Hare Intl

22h 10m1 stop Istanbul

$712Turkish Airlines

Sun, Nov 8 - Tue, Nov 24

8:10 pm - 11:05 amORD Chicago O'Hare Intl-MXP Milan Malpensa

31h 55m1 stop Lisbon Humberto Delgado

5:45 pm - 3:30 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

28h 45m1 stop Lisbon Humberto Delgado

$718TAP AIR PORTUGAL

Sun, Nov 8 - Tue, Nov 24

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

20h 25m1 stop Lisbon Humberto Delgado

2:25 pm - 3:30 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

32h 05m2 stops Madrid Barajas Lisbon Humberto Delgado

$718Multiple Airlines

Sun, Nov 8 - Tue, Nov 24

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

20h 25m1 stop Lisbon Humberto Delgado

2:25 pm - 3:30 pmMXP Milan Malpensa-ORD Chicago O'Hare Intl

32h 05m2 stops Madrid Barajas Lisbon Humberto Delgado

$723Multiple Airlines

Sun, Nov 8 - Tue, Nov 24

11:45 am - 5:50 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

23h 05m1 stop Istanbul

6:50 pm - 10:00 amMXP Milan Malpensa-ORD Chicago O'Hare Intl

22h 10m1 stop Istanbul

$723Turkish Airlines

Sun, Nov 8 - Tue, Nov 24

7:00 pm - 11:45 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

21h 45m1 stop Lisbon Humberto Delgado

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

16h 10m1 stop Lisbon Humberto Delgado

$742TAP AIR PORTUGAL

Wed, Nov 4 - Wed, Nov 18

7:25 am - 10:30 amORD Chicago O'Hare Intl-MXP Milan Malpensa

20h 05m2 stops Boston Logan Intl Kastrup Copenhagen

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

12h 25m1 stop Kastrup Copenhagen

$813Scandinavian Airlines

Sun, Nov 8 - Wed, Nov 18

6:00 am - 10:30 amORD Chicago O'Hare Intl-MXP Milan Malpensa

21h 30m2 stops New York John F Kennedy Intl Kastrup Copenhagen

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

12h 25m1 stop Kastrup Copenhagen

$821Scandinavian Airlines

Mon, Nov 9 - Tue, Nov 24

7:00 am - 7:30 amORD Chicago O'Hare Intl-MXP Milan Malpensa

17h 30m1 stop Newark

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

10h 00mnonstop

$847United Airlines

Sun, Nov 8 - Tue, Nov 24

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

$847United Airlines

Sun, Nov 8 - Tue, Nov 24

Cheap direct flights

Enter your travel dates to find the best prices.

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

$855United Airlines

Tue, Nov 17 - Thu, Nov 26

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

$880Lufthansa

Wed, Nov 18 - Wed, Nov 25

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

$980Lufthansa

Fri, Nov 13 - Mon, Nov 16

9:25 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 55mnonstop

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

9h 40mnonstop

$1,176Lufthansa

Tue, Mar 30 - Tue, Apr 6

9:25 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 55mnonstop

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

9h 40mnonstop

$1,271United Airlines

Tue, Mar 30 - Thu, Apr 15

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

Tue, Apr 20 - Thu, Apr 29

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

$1,366Multiple Airlines

Tue, Apr 20 - Sat, May 1

9:25 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 55mnonstop

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

9h 40mnonstop

$1,400Multiple Airlines

Tue, Mar 30 - Wed, Apr 14

9:25 pm - 1:20 pmORD Chicago O'Hare Intl-MXP Milan Malpensa

8h 55mnonstop

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

9h 40mnonstop

$1,551SWISS

Sun, Apr 4 - Sun, Apr 25

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

$2,225SWISS

Sun, Nov 15 - Wed, Nov 18

Save money when you book flights with momondo

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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

$714

Scandinavian Airlines

Jan 22

ORD7:10 pmChicago O'Hare Intl

17h 05m

1 stop

MXP7:15 pmMilan Malpensa

Jan 31

MXP11:20 amMilan Malpensa

12h 25m

1 stop

ORD4:45 pmChicago O'Hare Intl

$716

Scandinavian Airlines

Jan 22

ORD7:10 pmChicago O'Hare Intl

17h 05m

1 stop

MXP7:15 pmMilan Malpensa

Jan 31

MXP11:20 amMilan Malpensa

12h 25m

1 stop

ORD4:45 pmChicago O'Hare Intl

$728

Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets

Turkish Airlines

Nov 8

ORD11:45 amChicago O'Hare Intl

23h 05m

1 stop

MXP5:50 pmMilan Malpensa

Nov 24

MXP6:50 pmMilan Malpensa

22h 10m

1 stop

ORD10:00 amChicago O'Hare Intl

$712

Turkish Airlines

Nov 8

ORD11:45 amChicago O'Hare Intl

18h 25m

1 stop

MXP1:10 pmMilan Malpensa

Nov 18

MXP11:05 amMilan Malpensa

38h 15m

1 stop

ORD6:20 pmChicago O'Hare Intl

$723

Turkish Airlines

Nov 8

ORD11:45 amChicago O'Hare Intl

14h 20m

1 stop

MXP9:05 amMilan Malpensa

Nov 24

MXP6:50 pmMilan Malpensa

22h 10m

1 stop

ORD10:00 amChicago O'Hare Intl

$728

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

Fri 4/9

7:15 pm-10:35 am

1 stop32h 20m

Milan Malpensa

Sat 4/17

11:25 am-4:10 pm

1 stop11h 45m

$714

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

$714

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Wed 4/14

4:40 pm-8:30 am

1 stop32h 50m

Milan Malpensa

Fri 4/23

8:50 pm-9:15 pm

1 stop31h 25m

$715

ChicagoMilan

ORD Chicago O'Hare Intl - LIN Milan Linate

ORDLIN

Chicago O'Hare Intl

Mon 11/30

6:30 pm-11:10 pm

2 stops21h 40m

Milan Linate

Wed 12/16

6:30 am-5:20 pm

2 stops17h 50m

$716

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Sat 2/13

11:45 am-9:05 am

1 stop14h 20m

Milan Malpensa

Wed 3/31

7:45 pm-6:10 pm

1 stop29h 25m

$724

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Mon 4/5

8:05 pm-8:50 am

1 stop29h 45m

Milan Malpensa

Fri 4/16

6:45 am-9:35 am

1 stop33h 50m

$724

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Sun 11/15

8:10 pm-4:55 pm

1 stop13h 45m

Milan Malpensa

Fri 11/20

6:20 am-3:30 pm

1 stop16h 10m

$751

Quickest round-trip

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Mon 11/30

6:50 pm-6:30 pm

1 stop16h 40m

Milan Malpensa

Wed 12/16

10:30 am-4:15 pm

1 stop12h 45m

$755

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Sun 11/15

8:10 pm-4:55 pm

1 stop13h 45m

Milan Malpensa

Wed 11/18

6:20 am-3:30 pm

1 stop16h 10m

$756

ChicagoMilan

ORD Chicago O'Hare Intl - MXP Milan Malpensa

ORDMXP

Chicago O'Hare Intl

Tue 12/29

6:50 pm-6:30 pm

1 stop16h 40m

Milan Malpensa

Thu 1/14

6:45 am-4:15 pm

1 stop16h 30m

$756

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 $714.

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 $1,289. 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 $920 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 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	$216
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 $216. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $714.

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 54.29% of the total bookings. Other popular models include Boeing 787-10 Dreamliner with 32.47%, Boeing 787 Dreamliner with 9.87%, and Boeing 787-9 Dreamliner with 1.04%.
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 7%.

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 2,394 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $453	Free Cancellation	Rating 7.4 2,029 reviews	Search Scandinavian Airlines flights
Aer Lingus	PriceFrom $564	Free Cancellation	Rating 7.3 1,880 reviews	Search Aer Lingus flights
Turkish Airlines	PriceFrom $630	Free Cancellation	Rating 7.4 4,466 reviews	Search Turkish Airlines flights
SWISS	PriceFrom $779	Free Cancellation	Rating 7.5 2,107 reviews	Search SWISS flights
United Airlines	PriceFrom $780	Free Cancellation	Rating 7.3 10,462 reviews	Search United Airlines flights
Lufthansa	PriceFrom $823	Free Cancellation	Rating 6.8 8,299 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 2,107 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 7 flights to Milan from Chicago in an average week. Users have rated it 7.3/10 across 10,462 reviews.

Varenna

Bellagio

Stresa

Brescia

Livigno

Monza

Lecco

Menaggio

Cernobbio

Crema

Domodossola

Novara

Baveno

Bormio

Iseo

Levanto

Bellano

Assago

Rho

Lainate

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 $216

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 11/11. 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 one-way flights

Cheap last minute flights

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Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets

Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets

momondo Fare Finder

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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