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Cheap flights from Chicago to Milan from $195

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 1/26. 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.
Multiple Airlines Logo
6:30 pm - 8:15 pm
ORD
-
BGY
18h 45m2 stops
Multiple Airlines Logo
8:00 am - 5:20 pm
BGY
-
ORD
16h 20m2 stops
$477Multiple Airlines
Sun, Feb 8 - Sun, Feb 15
Multiple Airlines Logo
6:30 pm - 8:15 pm
ORD
-
BGY
18h 45m2 stops
Multiple Airlines Logo
8:00 am - 5:20 pm
BGY
-
ORD
16h 20m2 stops
$490Multiple Airlines
Sun, Jan 18 - Sun, Jan 25
Scandinavian Airlines Logo
7:35 pm - 8:30 am
ORD
-
MXP
29h 55m1 stop
Scandinavian Airlines Logo
11:45 am - 4:10 pm
MXP
-
ORD
35h 25m2 stops
$511Scandinavian Airlines
Wed, Apr 1 - Fri, Apr 10
Scandinavian Airlines Logo
7:15 pm - 7:10 pm
ORD
-
MXP
16h 55m1 stop
Scandinavian Airlines Logo
9:20 am - 4:10 pm
MXP
-
ORD
13h 50m1 stop
$512Scandinavian Airlines
Fri, Apr 10 - Sat, Apr 18
Scandinavian Airlines Logo
7:10 pm - 12:05 pm
ORD
-
LIN
33h 55m2 stops
Scandinavian Airlines Logo
12:55 pm - 4:45 pm
LIN
-
ORD
34h 50m2 stops
$514Scandinavian Airlines
Sun, Jan 18 - Fri, Jan 23
Turkish Airlines Logo
11:25 am - 2:00 pm
ORD
-
MXP
19h 35m1 stop
Turkish Airlines Logo
3:10 pm - 9:40 am
MXP
-
ORD
25h 30m1 stop
$523Turkish Airlines
Tue, Apr 14 - Sun, Apr 26
KLM Logo
10:46 am - 9:05 am
MDW
-
MXP
15h 19m1 stop
KLM Logo
11:05 am - 10:42 pm
MXP
-
MDW
18h 37m1 stop
$829KLM
Mon, Feb 9 - Wed, Feb 18
Delta Logo
1:26 pm - 11:40 am
MDW
-
MXP
15h 14m2 stops
Delta Logo
11:05 am - 10:42 pm
MXP
-
MDW
18h 37m1 stop
$833Delta
Sun, Feb 8 - Wed, Feb 18
Delta Logo
10:48 am - 9:05 am
MDW
-
MXP
15h 17m1 stop
Delta Logo
11:05 am - 10:42 pm
MXP
-
MDW
18h 37m1 stop
$879Delta
Fri, Jan 30 - Fri, Feb 13
KLM Logo
4:30 pm - 9:05 am
MDW
-
MXP
33h 35m1 stop
KLM Logo
11:05 am - 10:22 pm
MXP
-
MDW
18h 17m1 stop
$945KLM
Sat, Jan 31 - Sun, Feb 8

Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets
Turkish Airlines
Apr 14
ORD11:25 amChicago O'Hare Intl
19h 35m
1 stop
MXP2:00 pmMilan Malpensa
Apr 26
MXP6:50 amMilan Malpensa
18h 25m
1 stop
ORD6:15 pmChicago O'Hare Intl
$523
Find similar
Turkish Airlines
Mar 17
ORD12:50 pmChicago O'Hare Intl
18h 40m
1 stop
MXP1:30 pmMilan Malpensa
Mar 24
MXP6:55 amMilan Malpensa
18h 30m
1 stop
ORD7:25 pmChicago O'Hare Intl
$528
Find similar
Turkish Airlines
Jan 20
ORD8:20 pmChicago O'Hare Intl
18h 20m
1 stop
MXP9:40 pmMilan Malpensa
Jan 24
MXP6:55 amMilan Malpensa
34h 10m
1 stop
ORD10:05 amChicago O'Hare Intl
$532
Find similar

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets
Scandinavian Airlines
Feb 14
ORD7:20 pmChicago O'Hare Intl
18h 50m
1 stop
MXP9:10 pmMilan Malpensa
Feb 17
MXP3:45 pmMilan Malpensa
32h 00m
2 stops
ORD4:45 pmChicago O'Hare Intl
$511
Find similar
Scandinavian Airlines
Apr 10
ORD7:15 pmChicago O'Hare Intl
16h 55m
1 stop
MXP7:10 pmMilan Malpensa
Apr 18
MXP9:20 amMilan Malpensa
13h 50m
1 stop
ORD4:10 pmChicago O'Hare Intl
$512
Find similar
Scandinavian Airlines
Jan 18
ORD7:10 pmChicago O'Hare Intl
33h 55m
2 stops
LIN12:05 pmMilan Linate
Jan 23
LIN12:55 pmMilan Linate
34h 50m
2 stops
ORD4:45 pmChicago O'Hare Intl
$514
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 8, 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

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 2/8

6:30 pm-8:15 pm

2 stops18h 45m

Bergamo Orio Al Serio

Sun 2/15

8:00 am-5:20 pm

2 stops16h 20m

$477

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 1/18

6:30 pm-8:15 pm

2 stops18h 45m

Bergamo Orio Al Serio

Sun 1/25

8:00 am-5:20 pm

2 stops16h 20m

$490

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 4/1

7:35 pm-8:30 am

1 stop29h 55m

Milan Malpensa

Fri 4/10

11:45 am-4:10 pm

2 stops35h 25m

$511

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 4/10

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Sat 4/18

9:20 am-4:10 pm

1 stop13h 50m

$512

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 1/18

7:10 pm-12:05 pm

2 stops33h 55m

Milan Linate

Fri 1/23

12:55 pm-4:45 pm

2 stops34h 50m

$514

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 4/14

11:25 am-2:00 pm

1 stop19h 35m

Milan Malpensa

Sun 4/26

3:10 pm-9:40 am

1 stop25h 30m

$523

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 2/9

10:46 am-9:05 am

1 stop15h 19m

Milan Malpensa

Wed 2/18

11:05 am-10:42 pm

1 stop18h 37m

$829

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/8

1:26 pm-11:40 am

2 stops15h 14m

Milan Malpensa

Wed 2/18

11:05 am-10:42 pm

1 stop18h 37m

$833

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Fri 1/30

10:48 am-9:05 am

1 stop15h 17m

Milan Malpensa

Fri 2/13

11:05 am-10:42 pm

1 stop18h 37m

$879

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 1/31

4:30 pm-9:05 am

1 stop33h 35m

Milan Malpensa

Sun 2/8

11:05 am-10:22 pm

1 stop18h 17m

$945

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 $621. 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 $1,494.

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 $1,349. 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 $908 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 26% 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 3% 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

$550

Fastest flight time

8h 40m

Direct flights

Tue, 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 $550. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,224.
The fastest flight from Chicago to Milan takes 8h 40m
Direct flights go from Chicago to Milan on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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
TAP AIR PORTUGALPriceFrom $398Free CancellationRating
7.2
2,083 reviews
Search TAP AIR PORTUGAL flights
DeltaPriceFrom $419Free CancellationRating
7.9
8,013 reviews
Search Delta flights
Scandinavian AirlinesPriceFrom $420Free CancellationRating
7.4
1,597 reviews
Search Scandinavian Airlines flights
IcelandairPriceFrom $457Free CancellationRating
7.0
586 reviews
Search Icelandair flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
4,084 reviews
Search Turkish Airlines flights
British AirwaysPriceFrom $536Free CancellationRating
6.7
7,564 reviews
Search British Airways flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,098 reviews
Search ITA Airways flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
Aer LingusPriceFrom $626Free CancellationRating
7.2
1,389 reviews
Search Aer Lingus flights
IberiaPriceFrom $639Free CancellationRating
7.0
3,042 reviews
Search Iberia 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
Assago
Levanto
Monza
Livigno
Domodossola
Bellano
Lecco
Bormio
Crema
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