Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Milan from $237

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 4/28. 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.
Scandinavian Airlines Logo
7:10 pm - 7:10 pm
ORD
-
MXP
17h 00m1 stop
Scandinavian Airlines Logo
11:15 am - 4:45 pm
MXP
-
ORD
12h 30m1 stop
$450Scandinavian Airlines
Sun, Feb 15 - Sat, Feb 21
Scandinavian Airlines Logo
7:20 pm - 9:45 am
ORD
-
MXP
31h 25m2 stops
Scandinavian Airlines Logo
10:10 pm - 4:55 pm
MXP
-
ORD
25h 45m2 stops
$451Scandinavian Airlines
Sat, Feb 14 - Sat, Feb 21
Scandinavian Airlines Logo
7:15 pm - 10:35 am
ORD
-
MXP
32h 20m1 stop
Scandinavian Airlines Logo
1:10 pm - 4:10 pm
MXP
-
ORD
34h 00m2 stops
$452Scandinavian Airlines
Sat, Apr 11 - Sun, Apr 19
Multiple Airlines Logo
7:20 pm - 9:30 pm
ORD
-
BGY
19h 10m2 stops
Multiple Airlines Logo
3:35 pm - 4:45 pm
BGY
-
ORD
32h 10m2 stops
$495Multiple Airlines
Mon, Feb 2 - Tue, Feb 17
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
$511Multiple Airlines
Thu, Feb 5 - Thu, Feb 12
KLM Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m1 stop
KLM Logo
10:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
$831KLM
Mon, Mar 9 - Tue, Mar 17
Delta Logo
12:47 pm - 8:45 am
MDW
-
LIN
13h 58m2 stops
Delta Logo
6:40 am - 5:54 pm
LIN
-
MDW
18h 14m2 stops
$843Delta
Mon, Mar 23 - Thu, Apr 2
KLM Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m1 stop
KLM Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m1 stop
$881KLM
Sun, Mar 22 - Mon, Mar 30
Delta Logo
1:10 pm - 8:45 am
MDW
-
MXP
13h 35m2 stops
Delta Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m1 stop
$885Delta
Sun, Mar 22 - Mon, Mar 30
Air France Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m1 stop
Air France Logo
10:05 am - 10:31 pm
MXP
-
MDW
18h 26m1 stop
$949Air France
Wed, Mar 11 - Tue, Mar 24

Scandinavian Airlines flights from Chicago to Milan

Our best Scandinavian Airlines deals on Chicago to Milan flight tickets
Scandinavian Airlines
Feb 15
ORD7:10 pmChicago O'Hare Intl
30h 15m
1 stop
MXP8:25 amMilan Malpensa
Feb 21
MXP11:15 amMilan Malpensa
12h 30m
1 stop
ORD4:45 pmChicago O'Hare Intl
$450
Scandinavian Airlines
Feb 14
ORD7:20 pmChicago O'Hare Intl
31h 25m
2 stops
MXP9:45 amMilan Malpensa
Feb 21
MXP10:10 pmMilan Malpensa
25h 45m
2 stops
ORD4:55 pmChicago O'Hare Intl
$451
Scandinavian Airlines
Apr 11
ORD7:15 pmChicago O'Hare Intl
32h 20m
1 stop
MXP10:35 amMilan Malpensa
Apr 19
MXP1:10 pmMilan Malpensa
34h 00m
2 stops
ORD4:10 pmChicago O'Hare Intl
$452

KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets
KLM
Mar 9
MDW12:47 pmChicago Midway
13h 18m
1 stop
MXP8:05 amMilan Malpensa
Mar 17
MXP10:05 amMilan Malpensa
18h 26m
1 stop
MDW10:31 pmChicago Midway
$831
KLM
Mar 22
MDW12:47 pmChicago Midway
13h 18m
1 stop
MXP8:05 amMilan Malpensa
Mar 30
MXP11:40 amMilan Malpensa
17h 51m
1 stop
MDW10:31 pmChicago Midway
$881
KLM
Feb 25
MDW12:45 pmChicago Midway
13h 20m
1 stop
MXP9:05 amMilan Malpensa
Mar 1
MXP11:05 amMilan Malpensa
18h 26m
1 stop
MDW10:31 pmChicago Midway
$1,031

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 January 8, 2026.
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 2/15

7:10 pm-7:10 pm

1 stop17h 00m

Milan Malpensa

Sat 2/21

11:15 am-4:45 pm

1 stop12h 30m

$450

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 2/14

7:20 pm-9:45 am

2 stops31h 25m

Milan Malpensa

Sat 2/21

10:10 pm-4:55 pm

2 stops25h 45m

$451

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 4/11

7:15 pm-10:35 am

1 stop32h 20m

Milan Malpensa

Sun 4/19

1:10 pm-4:10 pm

2 stops34h 00m

$452

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 2/2

7:20 pm-9:30 pm

2 stops19h 10m

Bergamo Orio Al Serio

Tue 2/17

3:35 pm-4:45 pm

2 stops32h 10m

$495

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Thu 2/5

6:30 pm-8:05 pm

2 stops18h 35m

Bergamo Orio Al Serio

Thu 2/12

5:45 am-5:20 pm

2 stops18h 35m

$511

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 3/9

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Tue 3/17

10:05 am-10:31 pm

1 stop18h 26m

$831

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Mon 3/23

12:47 pm-8:45 am

2 stops13h 58m

Milan Linate

Thu 4/2

6:40 am-5:54 pm

2 stops18h 14m

$843

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 3/22

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Mon 3/30

11:40 am-10:31 pm

1 stop17h 51m

$881

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 3/22

1:10 pm-8:45 am

2 stops13h 35m

Milan Malpensa

Mon 3/30

11:40 am-10:31 pm

1 stop17h 51m

$885

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 3/11

12:47 pm-8:05 am

1 stop13h 18m

Milan Malpensa

Tue 3/24

10:05 am-10:31 pm

1 stop18h 26m

$949

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 January is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $539. The month of March is another great option to travel to Milan, with average flight prices from Chicago averaging around $610.

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 $1,189. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,484.

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 $933 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 $711 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 11% 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 January 2026, prices for Chicago to Milan flights are approximately 11% 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

$838

Fastest flight time

8h 40m

Direct flights

Every day

Airports in Milan

2 airports
The best one-way flight to Milan from Chicago in the past 72 hours is $838. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $1,108.
The fastest flight from Chicago to Milan takes 8h 40m
Direct flights go from Chicago to Milan every day.
There are 2 airports in Milan. From Chicago there are direct flights to 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 8h 40m.

  • 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
2,111 reviews
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesPriceFrom $421Free CancellationRating
7.3
1,635 reviews
Search Scandinavian Airlines flights
British AirwaysPriceFrom $496Free CancellationRating
6.7
7,657 reviews
Search British Airways flights
Turkish AirlinesPriceFrom $518Free CancellationRating
7.3
4,150 reviews
Search Turkish Airlines flights
ITA AirwaysPriceFrom $584Free CancellationRating
6.7
1,126 reviews
Search ITA Airways flights
Aer LingusPriceFrom $626Free CancellationRating
7.2
1,427 reviews
Search Aer Lingus flights
IberiaPriceFrom $639Free CancellationRating
7.0
3,076 reviews
Search Iberia flights
American AirlinesPriceFrom $708Free CancellationRating
7.2
11,095 reviews
Search American Airlines flights
LOTPriceFrom $732Free CancellationRating
7.5
1,168 reviews
Search LOT flights
United AirlinesPriceFrom $788Free CancellationRating
7.4
9,139 reviews
Search United Airlines 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
Monza
Levanto
Livigno
Assago
Bellano
Domodossola
Lecco
Crema
Bormio
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 2/7
Sat 2/14
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