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Cheap flights from Chicago to Milan from $218

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 11/17. 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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0 bags

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Cheap round-trip flights

Scandinavian Airlines Logo
8:50 pm - 7:10 pmORD-MXP
16h 20m1 stop
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
$511Scandinavian Airlines
Find Deal
jeu., oct. 30 - sam., nov. 8
Scandinavian Airlines Logo
8:20 pm - 7:10 pmORD-MXP
16h 50m1 stop
Scandinavian Airlines Logo
8:00 pm - 4:45 pmMXP-ORD
27h 45m1 stop
$513Scandinavian Airlines
Find Deal
lun., oct. 27 - mar., nov. 11
Logo
3:35 pm - 2:10 pmORD-MXP
16h 35m2 stops
Logo
3:00 pm - 4:20 pmMXP-ORD
32h 20m2 stops
$514
Find Deal
mer., oct. 29 - mer., nov. 5
Scandinavian Airlines Logo
7:20 pm - 6:15 pmORD-LIN
39h 55m2 stops
Scandinavian Airlines Logo
12:55 pm - 4:45 pmLIN-ORD
34h 50m2 stops
$514Scandinavian Airlines
Find Deal
ven., nov. 7 - ven., nov. 14
Scandinavian Airlines Logo
7:20 pm - 10:25 amORD-MXP
32h 05m1 stop
Scandinavian Airlines Logo
8:15 pm - 4:55 pmMXP-ORD
27h 40m2 stops
$515Scandinavian Airlines
Find Deal
sam., janv. 10 - sam., janv. 17
Aer Lingus Logo
4:50 pm - 11:05 amORD-LIN
12h 15m1 stop
Aer Lingus Logo
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$522Aer Lingus
Find Deal
mer., oct. 29 - mer., nov. 5
TAP AIR PORTUGAL Logo
6:15 pm - 4:25 pmORD-MXP
15h 10m1 stop
TAP AIR PORTUGAL Logo
5:55 am - 12:35 pmMXP-ORD
13h 40m1 stop
$538TAP AIR PORTUGAL
Find Deal
sam., oct. 4 - jeu., oct. 23
Turkish Airlines Logo
7:50 pm - 6:10 pmORD-MXP
15h 20m1 stop
Turkish Airlines Logo
11:05 am - 11:05 amMXP-ORD
30h 00m1 stop
$550Turkish Airlines
Find Deal
mer., oct. 22 - ven., oct. 31
Aer Lingus Logo
4:50 pm - 11:05 amORD-LIN
12h 15m1 stop
Aer Lingus Logo
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$572Aer Lingus
Find Deal
jeu., oct. 30 - mer., nov. 5
ITA Airways Logo
8:45 am - 12:40 pmORD-LIN
20h 55m2 stops
ITA Airways Logo
8:00 am - 6:12 pmLIN-ORD
16h 12m2 stops
$673ITA Airways
Find Deal
mar., mars 3 - mer., mars 11

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets
Scandinavian Airlines
Oct 30
ORD8:50 pmChicago O'Hare Intl
16h 20m
1 stop
MXP7:10 pmMilan Malpensa
Nov 8
MXP11:15 amMilan Malpensa
12h 30m
1 stop
ORD4:45 pmChicago O'Hare Intl
$511
Find similar
Scandinavian Airlines
Oct 27
ORD8:20 pmChicago O'Hare Intl
16h 50m
1 stop
MXP7:10 pmMilan Malpensa
Nov 11
MXP8:00 pmMilan Malpensa
27h 45m
1 stop
ORD4:45 pmChicago O'Hare Intl
$513
Find similar
Scandinavian Airlines
Nov 7
ORD7:20 pmChicago O'Hare Intl
39h 55m
2 stops
LIN6:15 pmMilan Linate
Nov 14
LIN12:55 pmMilan Linate
34h 50m
2 stops
ORD4:45 pmChicago O'Hare Intl
$514
Find similar

TAP AIR PORTUGAL flights from Chicago to Milan

Our best TAP AIR PORTUGAL deals on Chicago to Milan flight tickets
TAP AIR PORTUGAL
Oct 4
ORD6:15 pmChicago O'Hare Intl
15h 10m
1 stop
MXP4:25 pmMilan Malpensa
Oct 23
MXP5:55 amMilan Malpensa
13h 40m
1 stop
ORD12:35 pmChicago O'Hare Intl
$538
Find similar
TAP AIR PORTUGAL
Sep 15
ORD6:10 pmChicago O'Hare Intl
23h 35m
1 stop
MXP12:45 amMilan Malpensa
Sep 25
MXP5:55 amMilan Malpensa
13h 40m
1 stop
ORD12:35 pmChicago O'Hare Intl
$741
Find similar
TAP AIR PORTUGAL
Sep 25
ORD6:00 pmChicago O'Hare Intl
23h 45m
1 stop
MXP12:45 amMilan Malpensa
Oct 3
MXP5:35 amMilan Malpensa
17h 55m
1 stop
ORD4:30 pmChicago O'Hare Intl
$763
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 septembre 14, 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

jeu. 10/30

8:50 pm-7:10 pm

1 stop16h 20m

Milan Malpensa

sam. 11/8

11:15 am-4:45 pm

1 stop12h 30m

$511

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

lun. 10/27

8:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

mar. 11/11

8:00 pm-4:45 pm

1 stop27h 45m

$513

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

mer. 10/29

3:35 pm-2:10 pm

2 stops16h 35m

Milan Malpensa

mer. 11/5

3:00 pm-4:20 pm

2 stops32h 20m

$514

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

ven. 11/7

7:20 pm-6:15 pm

2 stops39h 55m

Milan Linate

ven. 11/14

12:55 pm-4:45 pm

2 stops34h 50m

$514

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

sam. 1/10

7:20 pm-10:25 am

1 stop32h 05m

Milan Malpensa

sam. 1/17

8:15 pm-4:55 pm

2 stops27h 40m

$515

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

mer. 10/29

4:50 pm-11:05 am

1 stop12h 15m

Milan Linate

mer. 11/5

11:45 am-5:55 pm

1 stop13h 10m

$522

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

sam. 10/4

6:15 pm-4:25 pm

1 stop15h 10m

Milan Malpensa

jeu. 10/23

5:55 am-12:35 pm

1 stop13h 40m

$538

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

mer. 10/22

7:50 pm-6:10 pm

1 stop15h 20m

Milan Malpensa

ven. 10/31

11:05 am-11:05 am

1 stop30h 00m

$550

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

jeu. 10/30

4:50 pm-11:05 am

1 stop12h 15m

Milan Linate

mer. 11/5

11:45 am-5:55 pm

1 stop13h 10m

$572

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

mar. 3/3

8:45 am-12:40 pm

2 stops20h 55m

Milan Linate

mer. 3/11

8:00 am-6:12 pm

2 stops16h 12m

$673

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 $640. 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 $1,179. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,498.

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 $1,345. 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 $944 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.

How have Chicago to Milan flight prices changed over time?

As of September 2025, prices for Chicago to Milan flights are approximately 14% 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

$663

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 $663. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $844.
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 55m.

  • 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
IcelandairPriceFrom $382Free CancellationRating
7.0
546 reviews
Search Icelandair flights
DeltaPriceFrom $419Free CancellationRating
7.9
7,956 reviews
Search Delta flights
Scandinavian AirlinesPriceFrom $420Free CancellationRating
7.4
1,484 reviews
Search Scandinavian Airlines flights
TAP AIR PORTUGALPriceFrom $447Free CancellationRating
7.1
1,977 reviews
Search TAP AIR PORTUGAL flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
3,968 reviews
Search Turkish Airlines flights
British AirwaysPriceFrom $536Free CancellationRating
6.6
7,361 reviews
Search British Airways flights
Air FrancePriceFrom $575Free CancellationRating
7.4
1,468 reviews
Search Air France flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,036 reviews
Search ITA Airways flights
Aer LingusPriceFrom $588Free CancellationRating
7.2
1,271 reviews
Search Aer Lingus flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • United Airlines Flights From Chicago to Milan

    United Airlines operates around 7 flights from Chicago to Milan every week. The average price of these flights found in the last 72 hours has been $1,281, but momondo users have found United Airlines deals from Chicago to Milan from as low as $782 round-trip. United Airlines has been scored 7.4/10 in 8,931 reviews.

Traveling to a place near Milan?

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

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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