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Cheap flights from Chicago to Milan from $186

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 1/27. 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
7:20 pm - 8:00 pmORD-MXP
17h 40m2 stops
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
$446Scandinavian Airlines
Find Deal
Thu, Jan 8 - Sat, Jan 17
Scandinavian Airlines Logo
7:20 pm - 12:05 pmORD-LIN
33h 45m2 stops
Scandinavian Airlines Logo
12:55 pm - 4:45 pmLIN-ORD
34h 50m2 stops
$446Scandinavian Airlines
Find Deal
Thu, Jan 8 - Fri, Jan 16
TAP AIR PORTUGAL Logo
7:10 pm - 11:05 amORD-MXP
32h 55m1 stop
TAP AIR PORTUGAL Logo
5:45 pm - 3:00 pmMXP-ORD
28h 15m1 stop
$450TAP AIR PORTUGAL
Find Deal
Wed, Nov 12 - Tue, Nov 18
TAP AIR PORTUGAL Logo
8:25 pm - 11:35 pmORD-MXP
20h 10m1 stop
TAP AIR PORTUGAL Logo
5:45 pm - 3:00 pmMXP-ORD
28h 15m1 stop
$460TAP AIR PORTUGAL
Find Deal
Sun, Nov 9 - 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
$492Aer Lingus
Find Deal
Mon, Nov 17 - Fri, Nov 21
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
$495Aer Lingus
Find Deal
Mon, Dec 1 - Tue, Dec 9
Turkish Airlines Logo
11:50 am - 9:05 amORD-MXP
14h 15m1 stop
Turkish Airlines Logo
6:40 pm - 6:25 pmMXP-ORD
30h 45m1 stop
$496Turkish Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
Turkish Airlines Logo
11:50 am - 4:35 pmORD-MXP
21h 45m1 stop
Turkish Airlines Logo
3:10 pm - 9:40 amMXP-ORD
25h 30m1 stop
$506Turkish Airlines
Find Deal
Mon, Jan 19 - Sat, May 9
ITA Airways Logo
10:48 am - 10:10 amORD-LIN
16h 22m2 stops
ITA Airways Logo
8:00 pm - 6:10 pmLIN-ORD
29h 10m2 stops
$586ITA Airways
Find Deal
Wed, Nov 12 - Tue, Nov 18
ITA Airways Logo
11:00 am - 10:10 amORD-LIN
17h 10m2 stops
ITA Airways Logo
9:30 pm - 6:45 pmLIN-ORD
27h 15m2 stops
$618ITA Airways
Find Deal
Wed, Mar 11 - Mon, Mar 23

TAP AIR PORTUGAL flights from Chicago to Milan

Our best TAP AIR PORTUGAL deals on Chicago to Milan flight tickets
TAP AIR PORTUGAL
Nov 12
ORD7:10 pmChicago O'Hare Intl
32h 55m
1 stop
MXP11:05 amMilan Malpensa
Nov 18
MXP5:45 pmMilan Malpensa
28h 15m
1 stop
ORD3:00 pmChicago O'Hare Intl
$450
Find similar
TAP AIR PORTUGAL
Nov 9
ORD8:25 pmChicago O'Hare Intl
20h 10m
1 stop
MXP11:35 pmMilan Malpensa
Nov 25
MXP5:45 pmMilan Malpensa
28h 15m
1 stop
ORD3:00 pmChicago O'Hare Intl
$460
Find similar
TAP AIR PORTUGAL
Nov 9
ORD8:25 pmChicago O'Hare Intl
20h 10m
1 stop
MXP11:35 pmMilan Malpensa
Nov 19
MXP6:20 amMilan Malpensa
15h 40m
1 stop
ORD3:00 pmChicago O'Hare Intl
$489
Find similar

Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets
Turkish Airlines
Nov 5
ORD11:50 amChicago O'Hare Intl
18h 40m
1 stop
MXP1:30 pmMilan Malpensa
Nov 10
MXP6:55 amMilan Malpensa
18h 30m
1 stop
ORD6:25 pmChicago O'Hare Intl
$496
Find similar
Turkish Airlines
Nov 4
ORD11:50 amChicago O'Hare Intl
18h 40m
1 stop
MXP1:30 pmMilan Malpensa
Nov 9
MXP10:40 amMilan Malpensa
38h 45m
1 stop
ORD6:25 pmChicago O'Hare Intl
$505
Find similar
Turkish Airlines
Jan 19
ORD11:50 amChicago O'Hare Intl
21h 45m
1 stop
MXP4:35 pmMilan Malpensa
May 9
MXP3:10 pmMilan Malpensa
25h 30m
1 stop
ORD9:40 amChicago O'Hare Intl
$506
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 30, 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

Thu 1/8

7:20 pm-8:00 pm

2 stops17h 40m

Milan Malpensa

Sat 1/17

11:15 am-4:45 pm

1 stop12h 30m

$446

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Thu 1/8

7:20 pm-12:05 pm

2 stops33h 45m

Milan Linate

Fri 1/16

12:55 pm-4:45 pm

2 stops34h 50m

$446

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 11/12

7:10 pm-11:05 am

1 stop32h 55m

Milan Malpensa

Tue 11/18

5:45 pm-3:00 pm

1 stop28h 15m

$450

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 11/9

8:25 pm-11:35 pm

1 stop20h 10m

Milan Malpensa

Tue 11/25

5:45 pm-3:00 pm

1 stop28h 15m

$460

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 11/17

3:50 pm-11:05 am

1 stop12h 15m

Milan Linate

Fri 11/21

11:45 am-5:55 pm

1 stop13h 10m

$492

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 12/1

3:50 pm-11:05 am

1 stop12h 15m

Milan Linate

Tue 12/9

11:45 am-5:55 pm

1 stop13h 10m

$495

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 11/14

11:50 am-9:05 am

1 stop14h 15m

Milan Malpensa

Mon 11/17

6:40 pm-6:25 pm

1 stop30h 45m

$496

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 1/19

11:50 am-4:35 pm

1 stop21h 45m

Milan Malpensa

Sat 5/9

3:10 pm-9:40 am

1 stop25h 30m

$506

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 11/12

10:48 am-10:10 am

2 stops16h 22m

Milan Linate

Tue 11/18

8:00 pm-6:10 pm

2 stops29h 10m

$586

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 3/11

11:00 am-10:10 am

2 stops17h 10m

Milan Linate

Mon 3/23

9:30 pm-6:45 pm

2 stops27h 15m

$618

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 $1,494.

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 $1,352. 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 $941 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

$651

Fastest flight time

8h 30m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun

Airports in Milan

1 airport
The best one-way flight to Milan from Chicago in the past 72 hours is $651. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,310.
The fastest flight from Chicago to Milan takes 8h 30m
Direct flights go from Chicago to Milan on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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 25m.

  • 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
2,040 reviews
Search TAP AIR PORTUGAL flights
DeltaPriceFrom $419Free CancellationRating
7.9
7,998 reviews
Search Delta flights
Scandinavian AirlinesPriceFrom $420Free CancellationRating
7.4
1,548 reviews
Search Scandinavian Airlines flights
IcelandairPriceFrom $484Free CancellationRating
7.1
562 reviews
Search Icelandair flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
4,033 reviews
Search Turkish Airlines flights
British AirwaysPriceFrom $536Free CancellationRating
6.7
7,488 reviews
Search British Airways flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,078 reviews
Search ITA Airways flights
Aer LingusPriceFrom $623Free CancellationRating
7.2
1,365 reviews
Search Aer Lingus flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
11,034 reviews
Search American Airlines flights
IberiaPriceFrom $639Free CancellationRating
7.0
3,004 reviews
Search Iberia flights

  • United Airlines Flights From Chicago to Milan

    United Airlines operates around 4 flights from Chicago to Milan every week. The average price of these flights found in the last 72 hours has been $1,279, 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 8,996 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
Bellano
Lecco
Rho
Domodossola
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