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Cheap flights from Chicago to Milan from $205

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 11/18. 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

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Scandinavian Airlines Logo
7:10 pm - 10:25 amORD-MXP
32h 15m1 stop
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
$442Scandinavian Airlines
Find Deal
Sun, Jan 25 - Wed, Feb 25
Scandinavian Airlines Logo
8:20 pm - 7:10 pmORD-MXP
16h 50m1 stop
Scandinavian Airlines Logo
8:40 pm - 4:10 pmMXP-ORD
26h 30m2 stops
$443Scandinavian Airlines
Find Deal
Sat, Mar 21 - Tue, Mar 31
TAP AIR PORTUGAL Logo
8:25 pm - 11:05 amORD-MXP
31h 40m1 stop
TAP AIR PORTUGAL Logo
5:45 pm - 3:00 pmMXP-ORD
28h 15m1 stop
$444TAP AIR PORTUGAL
Find Deal
Sun, Nov 9 - Tue, Nov 25
TAP AIR PORTUGAL Logo
7:10 pm - 4:55 pmORD-MXP
14h 45m1 stop
TAP AIR PORTUGAL Logo
6:20 am - 2:45 pmMXP-ORD
15h 25m1 stop
$445TAP AIR PORTUGAL
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Wed, Nov 5 - Sun, Nov 23
Aer Lingus Logo
3:50 pm - 11:05 amORD-LIN
12h 15m1 stop
Aer Lingus Logo
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$478Aer Lingus
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Mon, Nov 10 - Tue, Nov 25
Aer Lingus Logo
3:50 pm - 11:05 amORD-LIN
12h 15m1 stop
Aer Lingus Logo
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$486Aer Lingus
Find Deal
Sun, Nov 9 - Tue, Nov 25
ITA Airways Logo
1:10 pm - 10:10 amORD-LIN
15h 00m2 stops
ITA Airways Logo
7:00 pm - 1:10 pmLIN-ORD
25h 10m1 stop
$634ITA Airways
Find Deal
Tue, Mar 24 - Tue, Apr 7
ITA Airways Logo
3:00 pm - 3:10 pmORD-LIN
17h 10m1 stop
ITA Airways Logo
9:00 pm - 6:33 pmLIN-ORD
28h 33m2 stops
$638ITA Airways
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Wed, Apr 1 - Mon, Apr 6
Delta Logo
1:05 pm - 9:05 amMDW-MXP
13h 00m1 stop
Delta Logo
11:05 am - 9:46 pmMXP-MDW
17h 41m1 stop
$830Delta
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Sun, Jan 25 - Wed, Feb 25
Delta Logo
5:59 pm - 6:50 pmMDW-MXP
17h 51m2 stops
Delta Logo
11:05 am - 9:46 pmMXP-MDW
17h 41m1 stop
$833Delta
Find Deal
Wed, Jan 7 - Thu, Jan 15

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets
Scandinavian Airlines
Jan 25
ORD7:10 pmChicago O'Hare Intl
32h 15m
1 stop
MXP10:25 amMilan Malpensa
Feb 25
MXP11:15 amMilan Malpensa
12h 30m
1 stop
ORD4:45 pmChicago O'Hare Intl
$442
Find similar
Scandinavian Airlines
Mar 21
ORD8:20 pmChicago O'Hare Intl
16h 50m
1 stop
MXP7:10 pmMilan Malpensa
Mar 31
MXP8:40 pmMilan Malpensa
26h 30m
2 stops
ORD4:10 pmChicago O'Hare Intl
$443
Find similar
Scandinavian Airlines
Nov 16
ORD7:20 pmChicago O'Hare Intl
16h 50m
1 stop
MXP7:10 pmMilan Malpensa
Nov 19
MXP9:15 amMilan Malpensa
14h 30m
1 stop
ORD4:45 pmChicago O'Hare Intl
$446
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
Nov 9
ORD8:25 pmChicago O'Hare Intl
31h 40m
1 stop
MXP11:05 amMilan Malpensa
Nov 25
MXP5:45 pmMilan Malpensa
28h 15m
1 stop
ORD3:00 pmChicago O'Hare Intl
$444
Find similar
TAP AIR PORTUGAL
Nov 5
ORD7:10 pmChicago O'Hare Intl
14h 45m
1 stop
MXP4:55 pmMilan Malpensa
Nov 23
MXP6:20 amMilan Malpensa
15h 25m
1 stop
ORD2:45 pmChicago O'Hare Intl
$445
Find similar
TAP AIR PORTUGAL
Nov 5
ORD7:10 pmChicago O'Hare Intl
21h 25m
1 stop
MXP11:35 pmMilan Malpensa
Nov 11
MXP5:45 pmMilan Malpensa
28h 15m
1 stop
ORD3:00 pmChicago O'Hare Intl
$448
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 October 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

Sun 1/25

7:10 pm-10:25 am

1 stop32h 15m

Milan Malpensa

Wed 2/25

11:15 am-4:45 pm

1 stop12h 30m

$442

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 3/21

8:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Tue 3/31

8:40 pm-4:10 pm

2 stops26h 30m

$443

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 11/9

8:25 pm-11:05 am

1 stop31h 40m

Milan Malpensa

Tue 11/25

5:45 pm-3:00 pm

1 stop28h 15m

$444

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 11/5

7:10 pm-4:55 pm

1 stop14h 45m

Milan Malpensa

Sun 11/23

6:20 am-2:45 pm

1 stop15h 25m

$445

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 11/10

3:50 pm-11:05 am

1 stop12h 15m

Milan Linate

Tue 11/25

11:45 am-5:55 pm

1 stop13h 10m

$478

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 11/9

3:50 pm-11:05 am

1 stop12h 15m

Milan Linate

Tue 11/25

11:45 am-5:55 pm

1 stop13h 10m

$486

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 3/24

1:10 pm-10:10 am

2 stops15h 00m

Milan Linate

Tue 4/7

7:00 pm-1:10 pm

1 stop25h 10m

$634

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 4/1

3:00 pm-3:10 pm

1 stop17h 10m

Milan Linate

Mon 4/6

9:00 pm-6:33 pm

2 stops28h 33m

$638

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 1/25

1:05 pm-9:05 am

1 stop13h 00m

Milan Malpensa

Wed 2/25

11:05 am-9:46 pm

1 stop17h 41m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 1/7

5:59 pm-6:50 pm

2 stops17h 51m

Milan Malpensa

Thu 1/15

11:05 am-9:46 pm

1 stop17h 41m

$833

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 $638. The month of March is another great option to travel to Milan, with average flight prices from Chicago averaging around $639.

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 $1,191. 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 $1,350. 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 $949 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 October 2025, prices for Chicago to Milan flights are approximately 1% more expensive 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

$698

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 $698. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,305.
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)
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  • 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
TAP AIR PORTUGALPriceFrom $398Free CancellationRating
7.1
2,015 reviews
Search TAP AIR PORTUGAL flights
DeltaPriceFrom $419Free CancellationRating
7.9
7,975 reviews
Search Delta flights
Scandinavian AirlinesPriceFrom $420Free CancellationRating
7.4
1,532 reviews
Search Scandinavian Airlines flights
IcelandairPriceFrom $484Free CancellationRating
7.0
556 reviews
Search Icelandair flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
4,010 reviews
Search Turkish Airlines flights
British AirwaysPriceFrom $536Free CancellationRating
6.7
7,456 reviews
Search British Airways flights
Air FrancePriceFrom $575Free CancellationRating
7.4
1,475 reviews
Search Air France flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,065 reviews
Search ITA Airways flights
Aer LingusPriceFrom $623Free CancellationRating
7.2
1,336 reviews
Search Aer Lingus flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
11,042 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 $1,278, but momondo users have found United Airlines deals from Chicago to Milan from as low as $790 round-trip. United Airlines has been scored 7.4/10 in 8,976 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
Assago
Monza
Levanto
Livigno
Bellano
Rho
Domodossola
Lecco
Bormio
Crema
Cernobbio
Novara
Moltrasio
Saronno
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.

An easier way to manage your Milan trip

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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