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$214+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIL
Mar 29 — Apr 51
Sun 3/29
Sun 4/5
1 adult, Economy
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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”

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Cheapflights Tip: The best prices from Chicago to Milan are usually found in January or February, booked 19 days in advance, depart on a Tuesday or Sunday and return on a Saturday

Cheap 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 February 27, 2026.

This CrystalTravel deal was found by Cheapflights users on 2/24. 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 CrystalTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:20 pm
ORD
-
MXP
2 stops33h 50m
Scandinavian Airlines
Wed 11/119:15 am
MXP
-
ORD
1 stop14h 30m
Scandinavian Airlines
Deal found 2/24$439
This oojo deal was found by Cheapflights users on 2/24. 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.
Fri 11/277:20 pm
ORD
-
MXP
2 stops34h 35m
Scandinavian Airlines
Fri 12/48:00 pm
MXP
-
ORD
1 stop27h 45m
Scandinavian Airlines
Deal found 2/24$441
This Mytrip deal was found by Cheapflights users on 2/27. 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.
Sun 11/17:20 pm
ORD
-
MXP
1 stop30h 05m
Scandinavian Airlines
Mon 11/911:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 2/27$443
This Kiwi.com deal was found by Cheapflights users on 2/25. 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.
Sun 8/237:15 pm
ORD
-
MXP
1 stop12h 50m
Scandinavian Airlines
Tue 9/88:00 pm
MXP
-
ORD
1 stop27h 10m
Scandinavian Airlines
Deal found 2/25$444
This oojo deal was found by Cheapflights users on 2/25. 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.
Sat 11/217:20 pm
ORD
-
MXP
1 stop32h 05m
Scandinavian Airlines
Sat 11/289:15 am
MXP
-
ORD
1 stop14h 30m
Scandinavian Airlines
Deal found 2/25$445
This Gotogate deal was found by Cheapflights users on 2/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:20 pm
ORD
-
MXP
1 stop32h 05m
Scandinavian Airlines
Wed 1/1312:55 pm
MXP
-
ORD
2 stops34h 50m
Scandinavian Airlines
Deal found 2/26$446
This FlightHub deal was found by Cheapflights users on 2/24. 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.
Sun 10/258:20 pm
ORD
-
MXP
2 stops57h 50m
Scandinavian Airlines
Thu 11/1211:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 2/24$448
This lol.travel deal was found by Cheapflights users on 2/27. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:15 pm
ORD
-
MXP
1 stop12h 50m
Scandinavian Airlines
Mon 4/209:20 am
MXP
-
ORD
1 stop13h 50m
Scandinavian Airlines
Deal found 2/27$449
This oojo deal was found by Cheapflights users on 2/25. 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.
Sat 11/217:20 pm
ORD
-
LIN
2 stops15h 55m
Scandinavian Airlines
Sat 11/2812:55 pm
LIN
-
ORD
2 stops34h 50m
Scandinavian Airlines
Deal found 2/25$449
This FlightHub deal was found by Cheapflights users on 2/24. 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.
Sun 10/258:20 pm
ORD
-
MXP
1 stop30h 05m
Scandinavian Airlines
Wed 11/1111:15 am
MXP
-
ORD
1 stop12h 30m
Scandinavian Airlines
Deal found 2/24$450
This oojo deal was found by Cheapflights users on 2/25. 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.
Sun 9/137:15 pm
ORD
-
MXP
2 stops33h 10m
Scandinavian Airlines
Wed 9/238:00 pm
MXP
-
ORD
1 stop27h 10m
Scandinavian Airlines
Deal found 2/25$452
This FlightHub deal was found by Cheapflights users on 2/25. 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.
Mon 11/27:20 pm
ORD
-
LIN
2 stops33h 45m
Scandinavian Airlines
Wed 11/1812:55 pm
LIN
-
ORD
2 stops34h 50m
Scandinavian Airlines
Deal found 2/25$457

Find 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 February 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$444
(Kiwi.com)

One-way from

$214
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$600

Good round-trip deal

$1,227 or less

Good one-way deal

$764 or less
Provider with most accurate pricing for Chicago (CHI)-Milan (MIL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Milan (MIL) flights.
Search Deals
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. 26% potential increase in price ($298 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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

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 February 27, 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

Mon 3/9

8:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Fri 3/13

9:15 am-5:55 pm

1 stop14h 40m

$653

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Fri 5/8

10:25 pm-10:55 pm

2 stops17h 30m

Bergamo Orio Al Serio

Tue 5/19

9:45 am-9:25 pm

2 stops18h 40m

$670

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Fri 5/8

10:25 pm-10:20 pm

2 stops40h 55m

Bergamo Orio Al Serio

Mon 5/18

8:20 pm-2:25 pm

1 stop25h 05m

$670

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 8/26

7:15 pm-4:15 pm

1 stop14h 00m

Bergamo Orio Al Serio

Wed 9/9

9:20 am-4:10 pm

1 stop13h 50m

$701

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 3/28

5:30 pm-7:35 am

1 stop32h 05m

Milan Malpensa

Tue 4/7

9:25 am-2:30 pm

1 stop36h 05m

$793

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 3/22

3:55 pm-8:10 pm

2 stops22h 15m

Milan Linate

Mon 3/30

9:00 am-7:25 pm

2 stops17h 25m

$820

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 5/17

9:55 am-11:20 pm

3 stops30h 25m

Bergamo Orio Al Serio

Mon 5/25

8:55 pm-10:05 pm

3 stops32h 10m

$843

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 7/26

3:45 pm-12:10 pm

1 stop13h 25m

Bergamo Orio Al Serio

Sat 8/8

6:25 pm-11:50 am

1 stop24h 25m

$843

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Tue 5/12

9:00 pm-9:45 pm

1 stop17h 45m

Bergamo Orio Al Serio

Fri 5/22

6:10 am-5:50 pm

2 stops18h 40m

$848

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 5/13

7:25 pm-8:30 pm

3 stops18h 05m

Bergamo Orio Al Serio

Mon 5/18

9:45 pm-5:50 pm

3 stops27h 05m

$852

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Milan

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Milan in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Milan flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Milan flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Milan flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Milan flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Milan flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 February 20, 2026.

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 19 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, February is the cheapest month in which you can book a flight from Chicago to Milan (average of $398). Flying from Chicago to Milan in July is currently the most expensive (average of $774). 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.

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.

Montreal (YUL) – chosen by Cheapflights users on 29% 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 $566.

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 Montreal (YUL) offer the fastest connection on this route, with an average layover time of 1h 48m.

The best insider tips for Chicago to Milan flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Milan trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MXP

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

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 February 27, 2026.
Read through reviews of airlines operating flights from Chicago to Milan, such as United Airlines, Scandinavian Airlines, and Aer Lingus. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,362 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,362 reviews
United Airlines
7.4
Good
9,362 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Scandinavian Airlines
7.3
Good
1,700 reviews
United Airlines
7.4
Good
9,362 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Aer Lingus
7.2
Good
1,464 reviews
United Airlines
7.4
Good
9,362 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
TAP AIR PORTUGAL
7.1
Good
2,152 reviews
United Airlines
7.4
Good
9,362 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Lufthansa
6.8
Okay
7,817 reviews
United Airlines
7.4
Good
9,362 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 14h 56m. The distance between Chicago and Milan is about 4539 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 $398, TAP AIR PORTUGAL will fly you from Chicago to Milan and back. In addition to TAP AIR PORTUGAL, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Scandinavian Airlines and British Airways - these airlines can fly you to your destination from $410 and $496, respectively. Users have found that TAP AIR PORTUGAL is 51% 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 cheapest flights from Chicago to Milan?

    The cheapest flight price from Chicago to Milan is $584. On average you can expect to pay $1,131. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $449.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Milan (average of $398). Flying from Chicago to Milan in July is currently the most expensive (average of $774). 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
Porlezza
Brescia
Novara
Assago
Stresa
Bellagio
Domodossola

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 February 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$398Average$470FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$410Average$553FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$496Average$852FlexibilityNo cancel feeOn-time70%
Turkish AirlinesCheapest$534Average$745FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$564Average$1,052FlexibilityNo cancel feeOn-timeN/A
ITA AirwaysCheapest$584Average$915FlexibilityNo cancel feeOn-time81%
American AirlinesCheapest$624Average$1,569FlexibilityNo cancel feeOn-time71%
IberiaCheapest$639Average$1,029FlexibilityNo cancel feeOn-time77%
SWISSCheapest$759Average$1,131FlexibilityNo cancel feeOn-time79%
United AirlinesCheapest$789Average$1,239FlexibilityNo cancel feeOn-time69%

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