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Cheap flights from Chicago to Milan from $244

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 2/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

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Multiple Airlines Logo
6:30 pm - 9:00 pmORD-BGY
19h 30m2 stops
Multiple Airlines Logo
10:10 pm - 5:20 pmBGY-ORD
26h 10m2 stops
$473Multiple Airlines
Find Deal
mer., déc. 10 - lun., déc. 15
Multiple Airlines Logo
6:30 pm - 12:10 amORD-BGY
22h 40m2 stops
Multiple Airlines Logo
6:45 am - 5:20 pmBGY-ORD
17h 35m2 stops
$474Multiple Airlines
Find Deal
mer., janv. 14 - mer., janv. 21
Scandinavian Airlines Logo
7:00 am - 1:10 pmORD-MXP
24h 10m2 stops
Scandinavian Airlines Logo
8:40 pm - 4:10 pmMXP-ORD
26h 30m2 stops
$494Scandinavian Airlines
Find Deal
sam., mars 28 - mar., avr. 7
Icelandair Logo
7:25 pm - 3:10 pmORD-MXP
12h 45m1 stop
Icelandair Logo
4:20 pm - 9:40 pmMXP-ORD
12h 20m1 stop
$495Icelandair
Find Deal
jeu., mai 14 - sam., mai 23
Scandinavian Airlines Logo
7:01 am - 10:25 amORD-MXP
20h 24m2 stops
Scandinavian Airlines Logo
12:55 pm - 4:45 pmMXP-ORD
34h 50m2 stops
$496Scandinavian Airlines
Find Deal
jeu., févr. 19 - mer., mars 4
Scandinavian Airlines Logo
7:20 pm - 7:10 pmORD-MXP
16h 50m1 stop
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
$497Scandinavian Airlines
Find Deal
mer., janv. 7 - jeu., janv. 15
Scandinavian Airlines Logo
7:05 am - 10:25 amORD-MXP
20h 20m2 stops
Scandinavian Airlines Logo
8:00 pm - 4:10 pmMXP-ORD
27h 10m1 stop
$498Scandinavian Airlines
Find Deal
dim., janv. 18 - dim., mai 10
TAP AIR PORTUGAL Logo
8:25 pm - 4:55 pmORD-MXP
13h 30m1 stop
TAP AIR PORTUGAL Logo
6:20 am - 3:00 pmMXP-ORD
15h 40m1 stop
$499TAP AIR PORTUGAL
Find Deal
dim., nov. 30 - mer., déc. 10
ITA Airways Logo
3:00 pm - 11:40 amORD-LIN
13h 40m1 stop
ITA Airways Logo
7:00 am - 1:10 pmLIN-ORD
13h 10m1 stop
$523ITA Airways
Find Deal
mer., avr. 1 - ven., avr. 24
ITA Airways Logo
10:40 am - 10:10 amORD-LIN
16h 30m2 stops
ITA Airways Logo
7:00 am - 1:10 pmLIN-ORD
13h 10m1 stop
$527ITA Airways
Find Deal
mer., mai 6 - mer., mai 27

KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets
KLM
Feb 9
MDW12:48 pmChicago Midway
13h 17m
1 stop
MXP9:05 amMilan Malpensa
Feb 18
MXP11:05 amMilan Malpensa
18h 39m
1 stop
MDW10:44 pmChicago Midway
$829
Find similar
KLM
Feb 10
MDW12:48 pmChicago Midway
13h 17m
1 stop
MXP9:05 amMilan Malpensa
Feb 17
MXP11:05 amMilan Malpensa
18h 39m
1 stop
MDW10:44 pmChicago Midway
$887
Find similar
KLM
Feb 19
MDW12:46 pmChicago Midway
13h 19m
1 stop
MXP9:05 amMilan Malpensa
Mar 2
MXP11:05 amMilan Malpensa
18h 39m
1 stop
MDW10:44 pmChicago Midway
$929
Find similar

Delta flights from Chicago to Milan

Our best Delta deals on Chicago to Milan flight tickets
Delta
Feb 9
MDW1:49 pmChicago Midway
14h 51m
2 stops
MXP11:40 amMilan Malpensa
Feb 18
MXP11:05 amMilan Malpensa
18h 39m
1 stop
MDW10:44 pmChicago Midway
$833
Find similar
Delta
Feb 19
MDW12:46 pmChicago Midway
13h 19m
1 stop
MXP9:05 amMilan Malpensa
Mar 4
MXP11:05 amMilan Malpensa
18h 39m
1 stop
MDW10:44 pmChicago Midway
$879
Find similar
Delta
Feb 20
MDW1:28 pmChicago Midway
13h 17m
2 stops
MXP9:45 amMilan Malpensa
Mar 4
MXP11:05 amMilan Malpensa
18h 39m
1 stop
MDW10:44 pmChicago Midway
$884
Find similar

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 novembre 17, 2025.
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

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

mer. 12/10

6:30 pm-9:00 pm

2 stops19h 30m

Bergamo Orio Al Serio

lun. 12/15

10:10 pm-5:20 pm

2 stops26h 10m

$473

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

mer. 1/14

6:30 pm-12:10 am

2 stops22h 40m

Bergamo Orio Al Serio

mer. 1/21

6:45 am-5:20 pm

2 stops17h 35m

$474

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

sam. 3/28

7:00 am-1:10 pm

2 stops24h 10m

Milan Malpensa

mar. 4/7

8:40 pm-4:10 pm

2 stops26h 30m

$494

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

jeu. 5/14

7:25 pm-3:10 pm

1 stop12h 45m

Milan Malpensa

sam. 5/23

4:20 pm-9:40 pm

1 stop12h 20m

$495

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

jeu. 2/19

7:01 am-10:25 am

2 stops20h 24m

Milan Malpensa

mer. 3/4

12:55 pm-4:45 pm

2 stops34h 50m

$496

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

mer. 1/7

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

jeu. 1/15

11:15 am-4:45 pm

1 stop12h 30m

$497

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

dim. 1/18

7:05 am-10:25 am

2 stops20h 20m

Milan Malpensa

dim. 5/10

8:00 pm-4:10 pm

1 stop27h 10m

$498

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

dim. 11/30

8:25 pm-4:55 pm

1 stop13h 30m

Milan Malpensa

mer. 12/10

6:20 am-3:00 pm

1 stop15h 40m

$499

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

mer. 4/1

3:00 pm-11:40 am

1 stop13h 40m

Milan Linate

ven. 4/24

7:00 am-1:10 pm

1 stop13h 10m

$523

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

mer. 5/6

10:40 am-10:10 am

2 stops16h 30m

Milan Linate

mer. 5/27

7:00 am-1:10 pm

1 stop13h 10m

$527

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?

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 $636. The month of March is another great option to travel to Milan, with average flight prices from Chicago averaging around $640.

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 $1,189. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,492.

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

In the morning is the cheapest time of day to fly from Chicago to Milan when you can find flight prices for as low as $703. Flying to Milan in the morning is an ideal time because this is during off-peak travel hours. Flights to Milan are more costly in the evening, with an average ticket price of $1,351. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

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 $925 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 $650 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.

Can stopping save me money on Chicago to Milan flights?

You could potentially save up to 17% 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 2025, prices for Chicago to Milan flights are approximately 2% 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

$632

Fastest flight time

8h 30m

Direct flights

Every day

Airports in Milan

1 airport
The best one-way flight to Milan from Chicago in the past 72 hours is $632. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,343.
The fastest flight from Chicago to Milan takes 8h 30m
Direct flights go from Chicago to Milan every day.
There is 1 airport near Milan: 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 11h 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?

  • 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
2,065 reviews
Search TAP AIR PORTUGAL flights
DeltaPriceFrom $419Free CancellationRating
7.9
8,007 reviews
Search Delta flights
Scandinavian AirlinesPriceFrom $420Free CancellationRating
7.4
1,582 reviews
Search Scandinavian Airlines flights
IcelandairPriceFrom $484Free CancellationRating
7.0
580 reviews
Search Icelandair flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
4,047 reviews
Search Turkish Airlines flights
British AirwaysPriceFrom $536Free CancellationRating
6.7
7,528 reviews
Search British Airways flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,083 reviews
Search ITA Airways flights
Aer LingusPriceFrom $623Free CancellationRating
7.2
1,373 reviews
Search Aer Lingus flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
IberiaPriceFrom $639Free CancellationRating
7.0
3,020 reviews
Search Iberia flights

  • United Airlines Flights From Chicago to Milan

    United Airlines operates around 6 flights from Chicago to Milan every week. The average price of these flights found in the last 72 hours has been $1,281, but momondo users have found United Airlines deals from Chicago to Milan from as low as $789 round-trip. United Airlines has been scored 7.4/10 in 9,015 reviews.

Traveling to a place near Milan?

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

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