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Cheap flights from Chicago to Milan from $249

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 3/1. 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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Find the cheapest flights from Chicago to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Scandinavian Airlines Logo
7:10 pm - 8:25 am
ORD
-
MXP
30h 15m1 stop
Scandinavian Airlines Logo
11:15 am - 4:45 pm
MXP
-
ORD
12h 30m1 stop
$475Scandinavian Airlines
Sun, Jan 11 - Thu, Jan 15
Scandinavian Airlines Logo
7:20 pm - 3:00 pm
ORD
-
MXP
36h 40m2 stops
Scandinavian Airlines Logo
10:00 pm - 4:45 pm
MXP
-
ORD
25h 45m1 stop
$476Scandinavian Airlines
Sat, Feb 7 - Sun, Feb 15
Scandinavian Airlines Logo
7:10 pm - 7:10 pm
ORD
-
MXP
17h 00m1 stop
Scandinavian Airlines Logo
3:45 pm - 4:45 pm
MXP
-
ORD
32h 00m2 stops
$477Scandinavian Airlines
Fri, Jan 30 - Tue, Feb 3
Scandinavian Airlines Logo
7:20 pm - 8:25 am
ORD
-
MXP
30h 05m1 stop
Scandinavian Airlines Logo
12:55 pm - 4:45 pm
MXP
-
ORD
34h 50m2 stops
$478Scandinavian Airlines
Mon, Feb 16 - Fri, Feb 20
Multiple Airlines Logo
6:30 pm - 8:15 pm
ORD
-
BGY
18h 45m2 stops
Multiple Airlines Logo
10:35 pm - 5:20 pm
BGY
-
ORD
25h 45m2 stops
$542Multiple Airlines
Sun, Jan 11 - Thu, Jan 15
Multiple Airlines Logo
7:20 pm - 7:45 pm
ORD
-
BGY
17h 25m2 stops
Multiple Airlines Logo
5:15 pm - 4:45 pm
BGY
-
ORD
30h 30m2 stops
$566Multiple Airlines
Wed, Feb 18 - Sat, Feb 28
KLM Logo
11:01 am - 9:05 am
MDW
-
MXP
15h 04m1 stop
KLM Logo
11:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
$830KLM
Sun, Feb 15 - Wed, Feb 25
Delta Logo
9:34 am - 9:05 am
MDW
-
MXP
16h 31m2 stops
Delta Logo
11:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
$834Delta
Sun, Feb 15 - Wed, Feb 25
KLM Logo
10:49 am - 9:05 am
MDW
-
MXP
15h 16m1 stop
KLM Logo
10:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
$880KLM
Thu, Mar 5 - Tue, Mar 17
Delta Logo
9:34 am - 9:05 am
MDW
-
MXP
16h 31m2 stops
Delta Logo
11:00 am - 10:31 pm
MXP
-
MDW
17h 31m2 stops
$884Delta
Thu, Mar 5 - Tue, Mar 17

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets
Scandinavian Airlines
Jan 11
ORD7:10 pmChicago O'Hare Intl
30h 15m
1 stop
MXP8:25 amMilan Malpensa
Jan 15
MXP11:15 amMilan Malpensa
12h 30m
1 stop
ORD4:45 pmChicago O'Hare Intl
$475
Find similar
Scandinavian Airlines
Feb 7
ORD7:20 pmChicago O'Hare Intl
36h 40m
2 stops
MXP3:00 pmMilan Malpensa
Feb 16
MXP11:15 amMilan Malpensa
12h 30m
1 stop
ORD4:45 pmChicago O'Hare Intl
$476
Find similar
Scandinavian Airlines
Jan 30
ORD7:10 pmChicago O'Hare Intl
17h 00m
1 stop
MXP7:10 pmMilan Malpensa
Feb 3
MXP3:45 pmMilan Malpensa
32h 00m
2 stops
ORD4:45 pmChicago O'Hare Intl
$477
Find similar

LOT flights from Chicago to Milan

Our best LOT deals on Chicago to Milan flight tickets
LOT
Dec 30
ORD9:55 pmChicago O'Hare Intl
14h 10m
1 stop
MXP7:05 pmMilan Malpensa
Jan 13
MXP10:25 amMilan Malpensa
16h 35m
1 stop
ORD8:00 pmChicago O'Hare Intl
$710
Find similar
LOT
Dec 30
ORD9:55 pmChicago O'Hare Intl
28h 50m
1 stop
MXP9:45 amMilan Malpensa
Jan 20
MXP7:50 pmMilan Malpensa
31h 10m
1 stop
ORD8:00 pmChicago O'Hare Intl
$828
Find similar
LOT
Dec 29
ORD9:55 pmChicago O'Hare Intl
28h 50m
1 stop
MXP9:45 amMilan Malpensa
Jan 20
MXP7:50 pmMilan Malpensa
31h 10m
1 stop
ORD8:00 pmChicago O'Hare Intl
$873
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 December 28, 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

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 1/11

7:10 pm-8:25 am

1 stop30h 15m

Milan Malpensa

Thu 1/15

11:15 am-4:45 pm

1 stop12h 30m

$475

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 2/7

7:20 pm-3:00 pm

2 stops36h 40m

Milan Malpensa

Sun 2/15

10:00 pm-4:45 pm

1 stop25h 45m

$476

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 1/30

7:10 pm-7:10 pm

1 stop17h 00m

Milan Malpensa

Tue 2/3

3:45 pm-4:45 pm

2 stops32h 00m

$477

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 2/16

7:20 pm-8:25 am

1 stop30h 05m

Milan Malpensa

Fri 2/20

12:55 pm-4:45 pm

2 stops34h 50m

$478

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 1/11

6:30 pm-8:15 pm

2 stops18h 45m

Bergamo Orio Al Serio

Thu 1/15

10:35 pm-5:20 pm

2 stops25h 45m

$542

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 2/18

7:20 pm-7:45 pm

2 stops17h 25m

Bergamo Orio Al Serio

Sat 2/28

5:15 pm-4:45 pm

2 stops30h 30m

$566

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/15

11:01 am-9:05 am

1 stop15h 04m

Milan Malpensa

Wed 2/25

11:05 am-10:31 pm

1 stop18h 26m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/15

9:34 am-9:05 am

2 stops16h 31m

Milan Malpensa

Wed 2/25

11:05 am-10:31 pm

1 stop18h 26m

$834

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/5

10:49 am-9:05 am

1 stop15h 16m

Milan Malpensa

Tue 3/17

10:05 am-10:31 pm

1 stop18h 26m

$880

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 3/5

9:34 am-9:05 am

2 stops16h 31m

Milan Malpensa

Tue 3/17

11:00 am-10:31 pm

2 stops17h 31m

$884

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 $548. The month of March is another great option to travel to Milan, with average flight prices from Chicago averaging around $621.

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 $1,183. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,485.

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 $1,349. 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 $904 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 6% 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 December 2025, prices for Chicago to Milan flights are approximately 0% 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

$838

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 $838. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,365.
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

  • 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 $398Free CancellationRating
7.2
2,098 reviews
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesPriceFrom $421Free CancellationRating
7.4
1,630 reviews
Search Scandinavian Airlines flights
British AirwaysPriceFrom $496Free CancellationRating
6.7
7,617 reviews
Search British Airways flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
4,126 reviews
Search Turkish Airlines flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,114 reviews
Search ITA Airways flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
11,071 reviews
Search American Airlines flights
Aer LingusPriceFrom $626Free CancellationRating
7.2
1,413 reviews
Search Aer Lingus flights
IberiaPriceFrom $639Free CancellationRating
7.0
3,059 reviews
Search Iberia flights
LOTPriceFrom $732Free CancellationRating
7.5
1,155 reviews
Search LOT flights
United AirlinesPriceFrom $789Free CancellationRating
7.4
9,114 reviews
Search United Airlines flights

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
Levanto
Assago
Livigno
Bellano
Lecco
Domodossola
Crema
Bormio
Rho
Cernobbio
Moltrasio
Saronno
Baveno
Novara

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