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

Flights via Reykjavik (KEF) offer the lowest average round-trip price of $395.

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

British Airways, United Airlines, and Air Canada are the most popular carriers operating from Chicago to Milan

What airlines fly to Milan?

United Airlines, Scandinavian Airlines and TAP AIR PORTUGAL 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 41% of people opting to fly with this airline when traveling to Milan. Keep in mind that there are 10 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 Paris (CDG) have the shortest average one-way travel time: 10h 55m.

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

Copenhagen (CPH) was the most common stop: 24% of momondo users choosing 1-stop flights on this route connected there.

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

As of May 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 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 week?

As of May 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.

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 10 as of May 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.

$330 Cheap Flights from Chicago to Milan in 2026

Q: 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 $1,607 to $776. The lowest price recently found on this route was $732.

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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.

7:00 am - 10:25 am

ORD

MXP

20h 25m

2 stops

11:15 am - 4:45 pm

MXP

ORD

12h 30m

1 stop

$732Scandinavian Airlines

Mon, Nov 2 - Wed, Dec 2

7:20 pm - 7:10 pm

ORD

MXP

16h 50m

1 stop

12:55 pm - 4:45 pm

MXP

ORD

34h 50m

2 stops

$733Scandinavian Airlines

Wed, Nov 4 - Wed, Nov 18

4:40 pm - 8:30 am

ORD

MXP

32h 50m

1 stop

8:50 pm - 9:15 pm

MXP

ORD

31h 25m

1 stop

$734Air Serbia

Mon, Sep 14 - Fri, Oct 2

2:20 pm - 8:05 pm

ORD

BGY

22h 45m

2 stops

8:40 am - 7:55 pm

BGY

ORD

18h 15m

2 stops

$735Multiple Airlines

Mon, Aug 3 - Wed, Aug 19

7:15 pm - 10:40 am

ORD

MXP

32h 25m

2 stops

11:25 am - 10:06 pm

MXP

ORD

41h 41m

2 stops

$736Scandinavian Airlines

Thu, Sep 10 - Tue, Sep 22

7:20 pm - 12:05 pm

ORD

LIN

33h 45m

2 stops

12:55 pm - 4:45 pm

LIN

ORD

34h 50m

2 stops

$736Scandinavian Airlines

Mon, Nov 2 - Tue, Dec 1

11:05 am - 11:45 pm

ORD

BGY

29h 40m

3 stops

6:10 am - 7:55 pm

BGY

ORD

20h 45m

2 stops

$746Multiple Airlines

Mon, Aug 3 - Wed, Aug 19

3:35 pm - 9:10 am

ORD

LIN

10h 35m

1 stop

10:35 am - 7:55 pm

LIN

ORD

16h 20m

1 stop

$767Lufthansa

Mon, Aug 3 - Wed, Aug 19

3:00 pm - 10:10 am

ORD

LIN

12h 10m

1 stop

9:00 pm - 1:10 pm

LIN

ORD

23h 10m

1 stop

$770ITA Airways

Tue, Aug 11 - Tue, Aug 18

3:00 pm - 10:10 am

ORD

LIN

12h 10m

1 stop

9:00 pm - 1:10 pm

LIN

ORD

23h 10m

1 stop

$771ITA Airways

Tue, Aug 11 - Tue, Aug 18

Air Serbia flights from Chicago to Milan

Our best Air Serbia deals on Chicago to Milan flight tickets

Air Serbia

Sep 14

ORD4:40 pmChicago O'Hare Intl

32h 50m

1 stop

MXP8:30 amMilan Malpensa

Oct 2

MXP8:50 pmMilan Malpensa

31h 25m

1 stop

ORD9:15 pmChicago O'Hare Intl

$734

Air Serbia

Oct 3

ORD11:20 pmChicago O'Hare Intl

13h 45m

1 stop

MXP8:05 pmMilan Malpensa

Oct 10

MXP9:20 amMilan Malpensa

18h 55m

1 stop

ORD9:15 pmChicago O'Hare Intl

$764

Air Serbia

May 9

ORD11:20 pmChicago O'Hare Intl

26h 10m

1 stop

MXP8:30 amMilan Malpensa

May 15

MXP8:50 pmMilan Malpensa

31h 25m

1 stop

ORD9:15 pmChicago O'Hare Intl

$800

SWISS flights from Chicago to Milan

Our best SWISS deals on Chicago to Milan flight tickets

SWISS

Aug 11

ORD7:05 pmChicago O'Hare Intl

31h 45m

1 stop

MXP9:50 amMilan Malpensa

Aug 18

MXP7:25 pmMilan Malpensa

24h 10m

1 stop

ORD12:35 pmChicago O'Hare Intl

$743

SWISS

Aug 13

ORD2:20 pmChicago O'Hare Intl

12h 30m

1 stop

MXP9:50 amMilan Malpensa

Aug 23

MXP5:50 amMilan Malpensa

13h 45m

1 stop

ORD12:35 pmChicago O'Hare Intl

$751

SWISS

Aug 11

ORD7:05 pmChicago O'Hare Intl

31h 45m

1 stop

MXP9:50 amMilan Malpensa

Aug 18

MXP7:25 pmMilan Malpensa

24h 10m

1 stop

ORD12:35 pmChicago O'Hare Intl

$770

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 11/2

7:00 am-10:25 am

2 stops20h 25m

Milan Malpensa

Wed 12/2

11:15 am-4:45 pm

1 stop12h 30m

$732

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 11/4

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Wed 11/18

12:55 pm-4:45 pm

2 stops34h 50m

$733

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 9/14

4:40 pm-8:30 am

1 stop32h 50m

Milan Malpensa

Fri 10/2

8:50 pm-9:15 pm

1 stop31h 25m

$734

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 8/3

2:20 pm-8:05 pm

2 stops22h 45m

Bergamo Orio Al Serio

Wed 8/19

8:40 am-7:55 pm

2 stops18h 15m

$735

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 9/10

7:15 pm-10:40 am

2 stops32h 25m

Milan Malpensa

Tue 9/22

11:25 am-10:06 pm

2 stops41h 41m

$736

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 11/2

7:20 pm-12:05 pm

2 stops33h 45m

Milan Linate

Tue 12/1

12:55 pm-4:45 pm

2 stops34h 50m

$736

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 8/3

11:05 am-11:45 pm

3 stops29h 40m

Bergamo Orio Al Serio

Wed 8/19

6:10 am-7:55 pm

2 stops20h 45m

$746

Quickest round-trip

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 8/3

3:35 pm-9:10 am

1 stop10h 35m

Milan Linate

Wed 8/19

10:35 am-7:55 pm

1 stop16h 20m

$767

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 8/11

3:00 pm-10:10 am

1 stop12h 10m

Milan Linate

Tue 8/18

9:00 pm-1:10 pm

1 stop23h 10m

$770

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 8/11

3:00 pm-10:10 am

1 stop12h 10m

Milan Linate

Tue 8/18

9:00 pm-1:10 pm

1 stop23h 10m

$771

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?

What is the cheapest month to fly to Milan?

The month of June is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $115. The month of October is another great option to travel to Milan, with average flight prices from Chicago averaging around $266.

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 $1,226. The most expensive day to fly to Milan is Wednesday, with ticket prices averaging around $1,473.

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 $864 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.

Can stopping save me money on Chicago to Milan flights?

You could potentially save up to 33% 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 May 2026, prices for Chicago to Milan flights are approximately 16% 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	$898
Fastest flight time	8h 30m
Direct flights	Every day
Airports in Milan	2 airports

The best one-way flight to Milan from Chicago in the past 72 hours is $898. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,273.

The fastest flight from Chicago to Milan takes 8h 30m

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 30m.
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 10 as of May 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 787-10 Dreamliner, making up 62.60% of the total bookings. Other popular models include Boeing 787 Dreamliner with 31.51%, Boeing 787-8 Dreamliner with 4.79%, and Boeing 737 MAX 8 with 0.14%.
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 United Airlines, representing 31% of all bookings. The subsequent popular airlines are Scandinavian Airlines at 29%, Lufthansa at 9%, and TAP AIR PORTUGAL at 9%.

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 $401	Free Cancellation	Rating 7.2 2,245 reviews	Search TAP AIR PORTUGAL flights
Scandinavian Airlines	PriceFrom $410	Free Cancellation	Rating 7.4 1,770 reviews	Search Scandinavian Airlines flights
British Airways	PriceFrom $493	Free Cancellation	Rating 6.7 7,952 reviews	Search British Airways flights
Turkish Airlines	PriceFrom $534	Free Cancellation	Rating 7.4 4,355 reviews	Search Turkish Airlines flights
American Airlines	PriceFrom $624	Free Cancellation	Rating 7.1 11,667 reviews	Search American Airlines flights
Aer Lingus	PriceFrom $627	Free Cancellation	Rating 7.3 1,550 reviews	Search Aer Lingus flights
ITA Airways	PriceFrom $644	Free Cancellation	Rating 6.7 1,208 reviews	Search ITA Airways flights
SWISS	PriceFrom $759	Free Cancellation	Rating 7.6 1,937 reviews	Search SWISS flights
United Airlines	PriceFrom $764	Free Cancellation	Rating 7.4 9,694 reviews	Search United Airlines flights
Lufthansa	PriceFrom $840	Free Cancellation	Rating 6.8 7,980 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 $759 round-trip. SWISS has been scored 7.6/10 in 1,937 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 $764 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $1,234. United Airlines operates 7 flights to Milan from Chicago in an average week. Users have rated it 7.4/10 across 9,694 reviews.

Bellagio

Varenna

Menaggio

Stresa

Brescia

Livigno

Levanto

Monza

Bellano

Lecco

Crema

Domodossola

Assago

Cernobbio

Moltrasio

Bormio

Rho

Baveno

Novara

Iseo

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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Cheap flights from Chicago to Milan from $347

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 7/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Air Serbia flights from Chicago to Milan

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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?

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

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

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

SWISS Flights From Chicago to Milan

United Airlines Flights From Chicago to Milan

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

Fly your favorite airline to Milan

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List of cabin classes available on flights landing in Milan. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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