HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Milan

$206+ Cheap flights from Chicago (CHI) to Milan (MIL)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIL
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Milan with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Milan are usually found in January or March, booked 41 days in advance, depart on a Tuesday or Sunday and return on a Tuesday

Cheap flight deals from Chicago to Milan

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Milan (MIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septiembre 17, 2025.

Round-trip from

$486
(Mytrip)

One-way from

$206
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$778

Good round-trip deal

$845 or less

Good one-way deal

$683 or less
From Chicago (CHI) to Milan (MIL)
Search Deals
One-way flight from Chicago (CHI) to Milan (MIL)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Milan (MIL).
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Milan (MIL).
Search Deals

Find flight deals from Chicago to Milan

Cheapest flights from Chicago to Milan
Explore the most affordable flight options available from Chicago to Milan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.

This Mytrip deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/166:30 pmORD - BGY
2 stops18h 45mMultiple Airlines
dom. 11/238:00 amBGY - ORD
2 stops16h 20mMultiple Airlines
Deal found 9/17$486
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/56:30 pmORD - MXP
2 stops19h 40mMultiple Airlines
vie. 11/147:00 amMXP - ORD
2 stops17h 20mMultiple Airlines
Deal found 9/15$509
This oojo deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/247:20 pmORD - MXP
2 stops33h 45mScandinavian Airlines
vie. 1/98:50 pmMXP - ORD
2 stops26h 55mScandinavian Airlines
Deal found 9/15$510
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/56:20 pmORD - MXP
2 stops33h 05mScandinavian Airlines
mar. 11/118:00 pmMXP - ORD
1 stop27h 45mScandinavian Airlines
Deal found 9/15$511
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/59:18 amORD - MXP
2 stops17h 37mMultiple Airlines
mar. 11/111:05 pmMXP - ORD
2 stops25h 08mMultiple Airlines
Deal found 9/15$513
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/117:15 amORD - MXP
2 stops25h 45mMultiple Airlines
mar. 11/185:55 pmMXP - ORD
2 stops29h 25mMultiple Airlines
Deal found 9/15$514
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/123:45 pmORD - MXP
2 stops17h 25mMultiple Airlines
mar. 10/142:25 pmMXP - ORD
2 stops30h 35mMultiple Airlines
Deal found 9/15$515
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/610:40 amORD - BGY
2 stops20h 50mMultiple Airlines
lun. 10/1311:15 amBGY - ORD
2 stops33h 05mMultiple Airlines
Deal found 9/16$517
This FlightHub deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/47:05 amORD - MXP
2 stops42h 20mScandinavian Airlines
lun. 11/1011:15 amMXP - ORD
1 stop12h 30mScandinavian Airlines
Deal found 9/15$517
This oojo deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/97:20 pmORD - LIN
2 stops33h 45mScandinavian Airlines
vie. 11/1412:55 pmLIN - ORD
2 stops34h 50mScandinavian Airlines
Deal found 9/16$518
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/56:30 pmORD - BGY
2 stops19h 30mMultiple Airlines
mar. 11/115:45 amBGY - ORD
2 stops18h 35mMultiple Airlines
Deal found 9/15$519
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/196:00 pmORD - MXP
1 stop15h 25mTAP AIR PORTUGAL
sáb. 11/15:45 pmMXP - ORD
1 stop28h 00mTAP AIR PORTUGAL
Deal found 9/16$519

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated septiembre 17, 2025.
Use the filters below to find and compare flights from Chicago to Milan that are best for you.

Fly from

Chicago

Fly to

Milan

Route

Depart

Return

Price

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

dom. 11/16

6:30 pm-8:15 pm

2 stops18h 45m

Bergamo Orio Al Serio

dom. 11/23

8:00 am-5:20 pm

2 stops16h 20m

$486

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

lun. 10/6

10:40 am-2:30 pm

2 stops20h 50m

Bergamo Orio Al Serio

lun. 10/13

11:15 am-1:20 pm

2 stops33h 05m

$517

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

mié. 11/5

7:00 am-10:25 am

2 stops20h 25m

Milan Malpensa

lun. 11/10

9:15 am-4:45 pm

1 stop14h 30m

$536

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

lun. 12/15

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

jue. 12/25

11:15 am-4:45 pm

1 stop12h 30m

$548

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

lun. 11/10

3:35 pm-6:40 pm

2 stops20h 05m

Bergamo Orio Al Serio

lun. 11/17

8:25 am-8:00 pm

2 stops18h 35m

$565

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

vie. 11/7

8:15 pm-12:40 am

2 stops21h 25m

Bergamo Orio Al Serio

sáb. 11/15

10:20 pm-2:45 pm

2 stops23h 25m

$569

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

mar. 10/21

7:15 pm-8:15 pm

2 stops18h 00m

Bergamo Orio Al Serio

mié. 10/29

8:25 am-9:05 pm

2 stops18h 40m

$580

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

vie. 10/31

10:55 pm-9:50 pm

2 stops16h 55m

Bergamo Orio Al Serio

vie. 11/7

7:40 am-8:00 pm

2 stops19h 20m

$593

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

jue. 10/30

5:45 pm-11:35 am

1 stop11h 50m

Bergamo Orio Al Serio

jue. 11/6

6:50 am-2:30 pm

1 stop14h 40m

$613

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

dom. 11/9

9:55 pm-10:40 pm

1 stop17h 45m

Bergamo Orio Al Serio

mar. 11/25

8:05 am-8:00 pm

2 stops18h 55m

$616

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
1
2
3
...
6

The best insider tips for Chicago to Milan flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Milan trip
Airports
ORD

For a smooth departure from ORD, consider using the 'L' train for reliable access, avoiding Chicago's notorious traffic delays.

Read more about ORDby Ramsey Qubein
MXP

Upon arrival at MXP, the Malpensa Express train offers a convenient 45-minute ride to Milan's city center.

Read more about MXPby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MXP

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Best time to book a flight from Chicago to Milan

Have a flexible travel schedule? Discover the best time to fly to Milan from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Milan

How far ahead should I book a flight from Chicago to Milan?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Milan. Price data was last updated on September 12, 2025.

The price you pay for your flight from Chicago to Milan may vary depending on when you book. For the best chance of a lower fare, look to book 41 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Milan?

Currently, January is the cheapest month in which you can book a flight from Chicago to Milan (average of $594). Flying from Chicago to Milan in June is currently the most expensive (average of $970). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to MIL?

Find hourly flight availability from Chicago to Milan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 17, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Milan in the morning. If you’re flexible enough to do this you can expect to save up to 48% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Chicago to Milan?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Milan. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Milan flight should consider departing on Monday mornings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Milan

Explore weekly flight availability from Chicago to Milan. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated septiembre 17, 2025.

The most flights from CHI to MIL are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).

How much does it cost to fly round-trip from Chicago to Milan?

What’s the top layover airport for flights from Chicago to Milan?

Share of 1-stop round-trip flights from Chicago to Milan chosen by Cheapflights users in the past 12 months, using the same layover each way.

Copenhagen (CPH) – chosen by Cheapflights users on 38% of 1-stop itineraries from Chicago to Milan on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Milan?

Average round-trip fare for 1-stop flights from Chicago to Milan, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Copenhagen (CPH) is the most affordable 1-stop option, with an average round-trip price of $515.

What’s the fastest layover option from Chicago to Milan?

Shortest average travel time for 1-stop one-way flights from Chicago to Milan, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Montreal (YUL) have the shortest average one-way travel time for 1-stop routes: 11h 20m.

Which airport typically offers the quickest layover for flights from Chicago to Milan?

Average layover duration for 1-stop one-way flights from Chicago to Milan, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Helsinki (HEL) offer the fastest connection on this route, with an average layover time of 1h 38m.

Reviews of airlines servicing Milan

Get insights into the airlines that provide service to Milan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milan. Reviews last updated septiembre 17, 2025.
Read through reviews of airlines operating flights from Chicago to Milan, such as Scandinavian Airlines, United Airlines, and Aer Lingus. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Scandinavian Airlines
7.4
Good
1,486 reviews

Comfort

7.3

Boarding

7.6

Food

6.7

Crew

8.0

Entertainment

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
Scandinavian Airlines
7.4
Good
1,486 reviews
Scandinavian Airlines
7.4
Good
1,486 reviews

Comfort

7.3

Boarding

7.6

Food

6.7

Crew

8.0

Entertainment

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
United Airlines
7.4
Good
8,926 reviews
Scandinavian Airlines
7.4
Good
1,486 reviews

Comfort

7.3

Boarding

7.6

Food

6.7

Crew

8.0

Entertainment

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
Aer Lingus
7.2
Good
1,277 reviews
Scandinavian Airlines
7.4
Good
1,486 reviews

Comfort

7.3

Boarding

7.6

Food

6.7

Crew

8.0

Entertainment

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
TAP AIR PORTUGAL
7.1
Good
1,977 reviews
Scandinavian Airlines
7.4
Good
1,486 reviews

Comfort

7.3

Boarding

7.6

Food

6.7

Crew

8.0

Entertainment

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
British Airways
6.7
Okay
7,367 reviews
Scandinavian Airlines
7.4
Good
1,486 reviews

Comfort

7.3

Boarding

7.6

Food

6.7

Crew

8.0

Entertainment

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Milan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Milan?

    Departing from Chicago to Milan will take you 13h. The distance between Chicago and Milan is about 4510 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Milan round-trip?

    Currently priced at $382, Icelandair will fly you from Chicago to Milan and back. In addition to Icelandair, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and Scandinavian Airlines - these airlines can fly you to your destination from $419 and $420, respectively. Users have found that Icelandair is 53% cheaper than the other options available to this destination.

  • What are the most popular routes from Chicago to Milan?

    Most travelers choose Chicago O'Hare Intl - Milan Malpensa, Chicago O'Hare Intl - Milan Linate or Chicago Midway - Milan Malpensa when deciding on the best route from Chicago to Milan.

  • What are the most reliable airlines from Chicago to Milan?

    No one likes to see their flight delayed. When booking a flight from Chicago to Milan consider choosing Qatar Airways (75%), Lufthansa (60%) or Air Canada (60%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Milan?

    The cheapest flight price from Chicago to Milan is $659. On average you can expect to pay $1,121. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $374.

  • Where are the most common layover locations when flying from Chicago to Milan?

    Chicago to Milan flights have a layover in Copenhagen most often.

  • What are some popular things to do or see while on a layover in Copenhagen?

    Most Copenhagen visitors opt to spend their time experiencing Tivoli, Rådhuspladsen, and Kongens Nytorv. Tivoli, Rådhuspladsen, and Kongens Nytorv are located about 5.3 mi, 5.2 mi, and 5.1 mi, respectively from Kastrup Copenhagen. Those on a layover in Copenhagen in need of a rental car can book one at Kastrup Copenhagen for about $53.

  • Where are the least popular layover locations for Chicago to Milan flights?

    Chicago to Milan flights that have layovers will least frequently stop in Dublin.

  • Can I find deals for flights from Chicago to Milan that include hotel bookings?

    Yes. In addition to deals on Chicago to Milan flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Milan?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Milan.

  • Can I find deals for business class flights from Chicago to Milan?

    Yes. Cheapflights offers flight deals from Chicago to Milan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Milan?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Milan (average of $594). Flying from Chicago to Milan in June is currently the most expensive (average of $970). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Monza
Menaggio
Rho
Lainate
Porlezza
Novara
Lecco
Assago
Brescia
Bellagio
Stresa

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 10 airlines flying from Chicago to Milan

Discover the top 10 airlines that operate flights from Chicago to Milan. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest$382Average$722FlexibilityNo cancel feeOn-time76%
DeltaCheapest$419Average$929FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$420Average$567FlexibilityNo cancel feeOn-time77%
TAP AIR PORTUGALCheapest$447Average$690FlexibilityNo cancel feeOn-timeN/A
Turkish AirlinesCheapest$518Average$574FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$536Average$881FlexibilityNo cancel feeOn-time70%
Air FranceCheapest$575Average$961FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$584Average$915FlexibilityNo cancel feeOn-time81%
Aer LingusCheapest$588Average$822FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$624Average$867FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.