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$288+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIL
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Milan are usually found in November or March, booked 47 days in advance, depart on a Tuesday or Monday and return on a Saturday

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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$524
(FlightHub)

One-way from

$288
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$733

Good round-trip deal

$1,207 or less

Good one-way deal

$788 or less
Provider with most accurate pricing for Chicago (CHI)-Milan (MIL) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Milan (MIL) flights.
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From Chicago (CHI) to Milan (MIL)
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One-way flight from Chicago (CHI) to Milan (MIL)
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Highest demand for flights based on searches. 1% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($37 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Milan (MIL).
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Price to beat on a one-way flight from Chicago (CHI) to Milan (MIL).
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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 April 1, 2025.

This FlightHub deal was found by Cheapflights users on 3/31. 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 4/147:15 pmORD - MXP
1 stop30h 20mScandinavian Airlines
Wed 4/308:05 pmMXP - ORD
1 stop27h 05mScandinavian Airlines
Deal found 3/31$524
This FlightHub deal was found by Cheapflights users on 3/31. 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 10/268:30 pmORD - LIN
2 stops33h 35mScandinavian Airlines
Thu 11/612:55 pmLIN - ORD
2 stops34h 50mScandinavian Airlines
Deal found 3/31$527
This FlightHub deal was found by Cheapflights users on 3/31. 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.
Wed 9/311:45 pmORD - MXP
1 stop26h 00mTurkish Airlines
Tue 9/98:10 pmMXP - ORD
1 stop20h 30mTurkish Airlines
Deal found 3/31$558
This Mytrip deal was found by Cheapflights users on 3/31. 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.
Wed 4/307:25 pmORD - MXP
2 stops17h 25mMultiple Airlines
Wed 5/76:35 pmMXP - ORD
2 stops35h 54mMultiple Airlines
Deal found 3/31$601
This TAP AIR PORTUGAL deal was found by Cheapflights users on 3/31. 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 TAP AIR PORTUGAL is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/136:00 pmORD - MXP
1 stop18h 15mTAP AIR PORTUGAL
Tue 4/295:25 pmMXP - ORD
1 stop29h 45mTAP AIR PORTUGAL
Deal found 3/31$614
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Tue 5/139:15 pmORD - BGY
1 stop18h 20mMultiple Airlines
Tue 5/2011:10 amBGY - ORD
1 stop14h 50mMultiple Airlines
Deal found 3/31$663
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Tue 5/137:47 amORD - LIN
2 stops27h 53mMultiple Airlines
Tue 5/207:00 amLIN - ORD
2 stops31h 27mMultiple Airlines
Deal found 3/30$691
This Orbitz deal was found by Cheapflights users on 3/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/143:45 pmORD - LIN
1 stop11h 55mAer Lingus
Wed 5/2111:20 amLIN - ORD
1 stop14h 40mAer Lingus
Deal found 3/31$704
This Ovago deal was found by Cheapflights users on 3/31. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/73:00 pmORD - LIN
1 stop23h 10mITA Airways
Sun 5/117:00 amLIN - ORD
1 stop13h 10mITA Airways
Deal found 3/31$756
This Gurufare deal was found by Cheapflights users on 3/31. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:45 pmORD - LIN
1 stop13h 05mBritish Airways
Mon 1/124:35 pmLIN - ORD
1 stop28h 20mBritish Airways
Deal found 3/31$907
This United deal was found by Cheapflights users on 3/31. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:04 pmORD - LIN
2 stops13h 11mUnited Airlines
Mon 1/122:55 pmLIN - ORD
1 stop27h 15mUnited Airlines
Deal found 3/31$919
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/294:00 pmORD - LIN
2 stops15h 15mAir Canada
Mon 1/126:15 amLIN - ORD
2 stops15h 30mAir Canada
Deal found 3/31$940

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 April 1, 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

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 4/14

7:15 pm-8:35 am

1 stop30h 20m

Milan Malpensa

Wed 4/30

8:05 pm-4:10 pm

1 stop27h 05m

$524

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 4/13

6:00 pm-7:15 pm

1 stop18h 15m

Milan Malpensa

Tue 4/29

5:25 pm-4:10 pm

1 stop29h 45m

$614

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 5/13

9:08 pm-2:45 pm

3 stops34h 37m

Milan Malpensa

Tue 5/20

9:15 am-7:27 am

2 stops29h 12m

$615

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 4/20

11:25 am-6:10 pm

1 stop23h 45m

Milan Malpensa

Tue 5/6

3:10 pm-9:40 am

1 stop25h 30m

$637

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Tue 5/13

9:15 pm-10:35 pm

1 stop18h 20m

Bergamo Orio Al Serio

Tue 5/20

11:10 am-7:00 pm

1 stop14h 50m

$663

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 5/13

7:47 am-6:40 pm

2 stops27h 53m

Milan Linate

Tue 5/20

7:00 am-7:27 am

2 stops31h 27m

$691

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 5/14

3:45 pm-10:40 am

1 stop11h 55m

Milan Linate

Wed 5/21

11:20 am-7:00 pm

1 stop14h 40m

$704

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sat 4/19

7:15 pm-12:10 pm

2 stops33h 55m

Milan Linate

Wed 4/30

1:00 pm-4:10 pm

2 stops34h 10m

$718

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 5/7

3:00 pm-9:10 pm

1 stop23h 10m

Milan Linate

Sun 5/11

7:00 am-1:10 pm

1 stop13h 10m

$756

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Fri 5/9

9:15 pm-9:40 pm

1 stop17h 25m

Milan Linate

Mon 5/12

7:25 am-3:55 pm

1 stop15h 30m

$1,088

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 47 results
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 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 March 28, 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 47 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 $1,063). 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 April 1, 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 49% 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.

Rainfall in Milan by month

Plan your trip to Milan by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Milan ranges from 2.2 - 5.2 inches per month. May is typically the wettest month, when rainfall can reach 5.2 in. December is typically the driest time to visit Milan when rainfall is around 2.2 in.

Temperature in Milan by month

Plan your trip to Milan by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Milan, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

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 April 1, 2025.
To help decide which airline to fly from Chicago to Milan, see what other customers have to say about Delta, KLM and Air France. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
KLM
7.8
Good
1,321 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air France
7.4
Good
1,425 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,615 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Turkish Airlines
7.3
Good
3,748 reviews
Delta
8.0
Very good
7,899 reviews

Crew

8.5

Comfort

8.0

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    Currently priced at $524, Scandinavian Airlines will fly you from Chicago to Milan and back. In addition to Scandinavian Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Turkish Airlines and TAP AIR PORTUGAL - these airlines can fly you to your destination from $558 and $614, respectively. Users have found that Scandinavian Airlines is 37% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago to Milan one-way?

    For one-way options, check prices for Aer Lingus. According to our data, you can fly for as low as $375. Users have also found prices from $423 and $447 on TAP AIR PORTUGAL and Scandinavian Airlines, respectively.

  • 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 $603. On average you can expect to pay $3,793. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $423.

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

    Chicago to Milan flights have a layover in Stockholm most often. Copenhagen sees the second most layovers for non-direct flights flying from Chicago to Milan.

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

    Most Stockholm visitors opt to spend their time experiencing Stockholms Centralstation, Sergels Torg, and Stureplan. Stockholms Centralstation, Sergels Torg, and Stureplan are located about 22.7 mi, 22.5 mi, and 22.4 mi, respectively from Stockholm Arlanda. Those on a layover in Stockholm in need of a rental car can book one at Stockholm Arlanda for about $34.

  • What are some popular points of interest to see during a layover in Copenhagen?

    If you're on a layover in Copenhagen and looking for things to do, consider visiting Tivoli, Kongens Nytorv, or Rådhuspladsen. Tivoli, Kongens Nytorv, and Rådhuspladsen are located about 5.3 mi, 5.1 mi, and 5.2 mi, respectively from Kastrup Copenhagen. Those landing in Copenhagen looking to spend some time exploring during their layover can rent a car for about $34 per day.

  • 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 $1,063). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Scandinavian AirlinesCheapest$443Average$635FlexibilityNo cancel feeOn-time77%
IcelandairCheapest$485Average$746FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$499Average$701FlexibilityNo cancel feeOn-timeN/A
Turkish AirlinesCheapest$518Average$576FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$519Average$808FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$550Average$796FlexibilityNo cancel feeOn-time71%
DeltaCheapest$567Average$961FlexibilityNo cancel feeOn-timeN/A
Air FranceCheapest$575Average$961FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$661Average$953FlexibilityNo cancel feeOn-time70%
ITA AirwaysCheapest$715Average$746FlexibilityNo cancel feeOn-time81%
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