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Cheap flights from Chicago to Milan from $213

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 2/2. 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

Enter your travel dates to find the best prices.
Scandinavian Airlines Logo
7:15 pm - 3:05 pm
ORD
-
MXP
12h 50m
1 stop
Scandinavian Airlines Logo
3:55 pm - 4:10 pm
MXP
-
ORD
31h 15m
1 stop
$422Scandinavian Airlines
Wed, Apr 15 - Fri, Apr 24
TAP AIR PORTUGAL Logo
7:10 pm - 4:55 pm
ORD
-
MXP
14h 45m
1 stop
TAP AIR PORTUGAL Logo
5:45 pm - 3:00 pm
MXP
-
ORD
28h 15m
1 stop
$428TAP AIR PORTUGAL
Wed, Feb 4 - Tue, Feb 10
TAP AIR PORTUGAL Logo
6:00 pm - 4:25 pm
ORD
-
MXP
15h 25m
1 stop
TAP AIR PORTUGAL Logo
5:50 am - 4:00 pm
MXP
-
ORD
17h 10m
1 stop
$429TAP AIR PORTUGAL
Wed, Apr 22 - Fri, May 8
Scandinavian Airlines Logo
7:20 pm - 7:10 pm
ORD
-
MXP
16h 50m
1 stop
Scandinavian Airlines Logo
8:00 pm - 4:45 pm
MXP
-
ORD
27h 45m
1 stop
$430Scandinavian Airlines
Wed, Feb 18 - Wed, Feb 25
Scandinavian Airlines Logo
7:15 pm - 3:05 pm
ORD
-
MXP
12h 50m
1 stop
Scandinavian Airlines Logo
9:20 am - 4:10 pm
MXP
-
ORD
13h 50m
1 stop
$431Scandinavian Airlines
Wed, Apr 15 - Sat, Apr 25
Aer Lingus Logo
3:50 pm - 11:05 am
ORD
-
LIN
12h 15m
1 stop
Aer Lingus Logo
11:45 am - 6:55 pm
LIN
-
ORD
13h 10m
1 stop
$490Aer Lingus
Mon, Mar 2 - Wed, Mar 11
KLM Logo
10:45 am - 8:05 am
MDW
-
MXP
15h 20m
1 stop
KLM Logo
10:05 am - 10:31 pm
MXP
-
MDW
18h 26m
1 stop
$830KLM
Mon, Mar 9 - Tue, Mar 17
KLM Logo
10:45 am - 8:05 am
MDW
-
MXP
15h 20m
1 stop
KLM Logo
10:05 am - 10:31 pm
MXP
-
MDW
18h 26m
1 stop
$881KLM
Mon, Mar 9 - Tue, Mar 24
Delta Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m
1 stop
Delta Logo
6:45 am - 4:55 pm
MXP
-
MDW
17h 10m
2 stops
$892Delta
Sun, Mar 22 - Mon, Mar 30
Delta Logo
6:34 pm - 5:35 pm
MDW
-
MXP
16h 01m
2 stops
Delta Logo
11:40 am - 10:29 pm
MXP
-
MDW
17h 49m
1 stop
$979Delta
Mon, Apr 6 - Thu, Apr 16

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets
Scandinavian Airlines
Apr 15
ORD7:15 pmChicago O'Hare Intl
12h 50m
1 stop
MXP3:05 pmMilan Malpensa
Apr 24
MXP3:55 pmMilan Malpensa
31h 15m
1 stop
ORD4:10 pmChicago O'Hare Intl
$422
Scandinavian Airlines
Feb 2
ORD7:20 pmChicago O'Hare Intl
16h 50m
1 stop
MXP7:10 pmMilan Malpensa
Feb 18
MXP8:00 pmMilan Malpensa
27h 45m
1 stop
ORD4:45 pmChicago O'Hare Intl
$430
Scandinavian Airlines
Apr 15
ORD7:15 pmChicago O'Hare Intl
12h 50m
1 stop
MXP3:05 pmMilan Malpensa
Apr 25
MXP9:20 amMilan Malpensa
13h 50m
1 stop
ORD4:10 pmChicago O'Hare Intl
$431

TAP AIR PORTUGAL flights from Chicago to Milan

Our best TAP AIR PORTUGAL deals on Chicago to Milan flight tickets
TAP AIR PORTUGAL
Feb 4
ORD7:10 pmChicago O'Hare Intl
14h 45m
1 stop
MXP4:55 pmMilan Malpensa
Feb 10
MXP5:45 pmMilan Malpensa
28h 15m
1 stop
ORD3:00 pmChicago O'Hare Intl
$428
TAP AIR PORTUGAL
Apr 22
ORD6:00 pmChicago O'Hare Intl
15h 25m
1 stop
MXP4:25 pmMilan Malpensa
May 8
MXP5:50 amMilan Malpensa
17h 10m
1 stop
ORD4:00 pmChicago O'Hare Intl
$429
TAP AIR PORTUGAL
Jan 23
ORD8:15 pmChicago O'Hare Intl
20h 20m
1 stop
MXP11:35 pmMilan Malpensa
Jan 31
MXP5:45 pmMilan Malpensa
28h 00m
1 stop
ORD2:45 pmChicago O'Hare Intl
$519

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 January 19, 2026.
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

Wed 4/15

7:15 pm-3:05 pm

1 stop12h 50m

Milan Malpensa

Fri 4/24

3:55 pm-4:10 pm

1 stop31h 15m

$422

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 2/4

7:10 pm-4:55 pm

1 stop14h 45m

Milan Malpensa

Tue 2/10

5:45 pm-3:00 pm

1 stop28h 15m

$428

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 4/22

6:00 pm-4:25 pm

1 stop15h 25m

Milan Malpensa

Fri 5/8

5:50 am-4:00 pm

1 stop17h 10m

$429

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 2/18

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Wed 2/25

8:00 pm-4:45 pm

1 stop27h 45m

$430

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 4/15

7:15 pm-3:05 pm

1 stop12h 50m

Milan Malpensa

Sat 4/25

9:20 am-4:10 pm

1 stop13h 50m

$431

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 3/2

3:50 pm-11:05 am

1 stop12h 15m

Milan Linate

Wed 3/11

11:45 am-6:55 pm

1 stop13h 10m

$490

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/9

10:45 am-8:05 am

1 stop15h 20m

Milan Malpensa

Tue 3/17

10:05 am-10:31 pm

1 stop18h 26m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/9

10:45 am-8:05 am

1 stop15h 20m

Milan Malpensa

Tue 3/24

10:05 am-10:31 pm

1 stop18h 26m

$881

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 3/22

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Mon 3/30

6:45 am-4:55 pm

2 stops17h 10m

$892

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 4/6

6:34 pm-5:35 pm

2 stops16h 01m

Milan Malpensa

Thu 4/16

11:40 am-10:29 pm

1 stop17h 49m

$979

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 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 $539. The month of October is another great option to travel to Milan, with average flight prices from Chicago averaging around $615.

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 $1,479.

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 $923 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 $711 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 5% 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 January 2026, prices for Chicago to Milan flights are approximately 11% 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

$764

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 $764. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,104.
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
7.1
2,122 reviews
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesPriceFrom $421Free CancellationRating
7.3
1,655 reviews
Search Scandinavian Airlines flights
British AirwaysPriceFrom $496Free CancellationRating
6.7
7,689 reviews
Search British Airways flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
4,193 reviews
Search Turkish Airlines flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,129 reviews
Search ITA Airways flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
11,159 reviews
Search American Airlines flights
Aer LingusPriceFrom $626Free CancellationRating
7.2
1,435 reviews
Search Aer Lingus flights
IberiaPriceFrom $639Free CancellationRating
7.0
3,091 reviews
Search Iberia flights
LOTPriceFrom $732Free CancellationRating
7.5
1,174 reviews
Search LOT flights
United AirlinesPriceFrom $793Free CancellationRating
7.4
9,176 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
Livigno
Assago
Bellano
Domodossola
Lecco
Crema
Rho
Cernobbio
Bormio
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