Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Milan from $238

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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:30 pm - 8:05 pm
ORD
-
BGY
18h 35m2 stops
Multiple Airlines Logo
5:45 am - 5:20 pm
BGY
-
ORD
18h 35m2 stops
$463Multiple Airlines
Thu, Jan 22 - Thu, Feb 5
Multiple Airlines Logo
6:30 pm - 7:40 pm
ORD
-
BGY
18h 10m2 stops
Multiple Airlines Logo
8:00 am - 5:20 pm
BGY
-
ORD
16h 20m2 stops
$477Multiple Airlines
Fri, Jan 23 - Sun, Jan 25
Multiple Airlines Logo
6:30 pm - 6:35 pm
ORD
-
BGY
17h 05m2 stops
Multiple Airlines Logo
8:00 am - 5:20 pm
BGY
-
ORD
16h 20m2 stops
$486Multiple Airlines
Sun, Feb 1 - Sun, Feb 8
Scandinavian Airlines Logo
7:35 pm - 10:55 am
ORD
-
MXP
32h 20m2 stops
Scandinavian Airlines Logo
11:45 am - 4:10 pm
MXP
-
ORD
35h 25m2 stops
$508Scandinavian Airlines
Wed, Apr 1 - Fri, Apr 10
Scandinavian Airlines Logo
7:20 pm - 5:35 pm
ORD
-
MXP
39h 15m2 stops
Scandinavian Airlines Logo
8:00 pm - 4:45 pm
MXP
-
ORD
27h 45m1 stop
$511Scandinavian Airlines
Thu, Jan 29 - Tue, Feb 10
British Airways Logo
7:05 pm - 3:00 pm
ORD
-
LIN
12h 55m1 stop
British Airways Logo
11:10 am - 6:15 pm
LIN
-
ORD
14h 05m1 stop
$551British Airways
Sun, Apr 26 - Tue, May 5
KLM Logo
12:48 pm - 9:05 am
MDW
-
MXP
13h 17m1 stop
KLM Logo
11:05 am - 10:42 pm
MXP
-
MDW
18h 37m1 stop
$829KLM
Mon, Feb 2 - Fri, Feb 13
Delta Logo
12:48 pm - 9:05 am
MDW
-
MXP
13h 17m1 stop
Delta Logo
11:35 am - 10:22 pm
MXP
-
MDW
17h 47m2 stops
$831Delta
Sun, Jan 25 - Tue, Feb 10
Delta Logo
6:14 pm - 5:25 pm
MDW
-
MXP
16h 11m2 stops
Delta Logo
11:05 am - 10:42 pm
MXP
-
MDW
18h 37m1 stop
$833Delta
Sun, Feb 1 - Thu, Feb 12
KLM Logo
10:48 am - 9:05 am
MDW
-
MXP
15h 17m1 stop
KLM Logo
11:05 am - 10:22 pm
MXP
-
MDW
18h 17m1 stop
$879KLM
Sun, Feb 1 - Mon, Feb 9

Turkish Airlines flights from Chicago to Milan

Our best Turkish Airlines deals on Chicago to Milan flight tickets
Turkish Airlines
Apr 1
ORD7:50 pmChicago O'Hare Intl
35h 10m
1 stop
MXP2:00 pmMilan Malpensa
Apr 6
MXP3:05 pmMilan Malpensa
25h 35m
1 stop
ORD9:40 amChicago O'Hare Intl
$523
Find similar
Turkish Airlines
Apr 10
ORD11:25 amChicago O'Hare Intl
19h 10m
1 stop
MXP1:35 pmMilan Malpensa
Apr 18
MXP3:10 pmMilan Malpensa
25h 30m
1 stop
ORD9:40 amChicago O'Hare Intl
$532
Find similar
Turkish Airlines
Mar 20
ORD12:50 pmChicago O'Hare Intl
14h 15m
1 stop
MXP9:05 amMilan Malpensa
Mar 30
MXP10:20 amMilan Malpensa
30h 20m
1 stop
ORD9:40 amChicago O'Hare Intl
$560
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
Apr 5
ORD6:00 pmChicago O'Hare Intl
17h 50m
1 stop
MXP6:50 pmMilan Malpensa
Apr 12
MXP5:50 amMilan Malpensa
17h 10m
1 stop
ORD4:00 pmChicago O'Hare Intl
$533
Find similar
TAP AIR PORTUGAL
Mar 29
ORD6:00 pmChicago O'Hare Intl
23h 45m
1 stop
MXP12:45 amMilan Malpensa
Apr 7
MXP8:00 pmMilan Malpensa
27h 00m
1 stop
ORD4:00 pmChicago O'Hare Intl
$563
Find similar
TAP AIR PORTUGAL
Dec 14
ORD8:25 pmChicago O'Hare Intl
37h 30m
1 stop
MXP4:55 pmMilan Malpensa
Dec 23
MXP5:45 pmMilan Malpensa
28h 15m
1 stop
ORD3:00 pmChicago O'Hare Intl
$940
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 4, 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

Thu 1/22

6:30 pm-8:05 pm

2 stops18h 35m

Bergamo Orio Al Serio

Thu 2/5

5:45 am-5:20 pm

2 stops18h 35m

$463

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Fri 1/23

6:30 pm-7:40 pm

2 stops18h 10m

Bergamo Orio Al Serio

Sun 1/25

8:00 am-5:20 pm

2 stops16h 20m

$477

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 2/1

6:30 pm-6:35 pm

2 stops17h 05m

Bergamo Orio Al Serio

Sun 2/8

8:00 am-5:20 pm

2 stops16h 20m

$486

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 4/1

7:35 pm-10:55 am

2 stops32h 20m

Milan Malpensa

Fri 4/10

11:45 am-4:10 pm

2 stops35h 25m

$508

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 1/29

7:20 pm-5:35 pm

2 stops39h 15m

Milan Malpensa

Tue 2/10

8:00 pm-4:45 pm

1 stop27h 45m

$511

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 4/26

7:05 pm-3:00 pm

1 stop12h 55m

Milan Linate

Tue 5/5

11:10 am-6:15 pm

1 stop14h 05m

$551

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 2/2

12:48 pm-9:05 am

1 stop13h 17m

Milan Malpensa

Fri 2/13

11:05 am-10:42 pm

1 stop18h 37m

$829

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 1/25

12:48 pm-9:05 am

1 stop13h 17m

Milan Malpensa

Tue 2/10

11:35 am-10:22 pm

2 stops17h 47m

$831

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/1

6:14 pm-5:25 pm

2 stops16h 11m

Milan Malpensa

Thu 2/12

11:05 am-10:42 pm

1 stop18h 37m

$833

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/1

10:48 am-9:05 am

1 stop15h 17m

Milan Malpensa

Mon 2/9

11:05 am-10:22 pm

1 stop18h 17m

$879

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 March is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $627. The month of January is another great option to travel to Milan, with average flight prices from Chicago averaging around $636.

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 $1,186. 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 $916 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 23% 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 39% 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

$765

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 $765. 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 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 35m.

  • 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
2,081 reviews
Search TAP AIR PORTUGAL flights
DeltaPriceFrom $419Free CancellationRating
7.9
8,011 reviews
Search Delta flights
Scandinavian AirlinesPriceFrom $420Free CancellationRating
7.4
1,592 reviews
Search Scandinavian Airlines flights
IcelandairPriceFrom $484Free CancellationRating
7.0
584 reviews
Search Icelandair flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
4,077 reviews
Search Turkish Airlines flights
British AirwaysPriceFrom $536Free CancellationRating
6.7
7,562 reviews
Search British Airways flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,097 reviews
Search ITA Airways flights
American AirlinesPriceFrom $624Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
Aer LingusPriceFrom $626Free CancellationRating
7.2
1,384 reviews
Search Aer Lingus flights
IberiaPriceFrom $639Free CancellationRating
7.0
3,040 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.

An easier way to manage your Milan trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 1/3
Sat 1/10
By creating a price alert you accept our terms of use and privacy policy.

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