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$222+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIL
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Milan are usually found in March or November, booked 47 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 July 31, 2025.

Round-trip from

$502
(oojo)

One-way from

$222
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$1,071

Good round-trip deal

$739 or less

Good one-way deal

$578 or less
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. 4% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Wed 11/124:45 pmORD - BGY
1 stop12h 20mMultiple Airlines
Wed 11/196:50 amBGY - ORD
1 stop14h 40mMultiple Airlines
Deal found 7/29$499
This oojo deal was found by Cheapflights users on 7/30. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/27:20 pmORD - MXP
2 stops16h 40mScandinavian Airlines
Tue 11/189:15 amMXP - ORD
2 stops39h 21mScandinavian Airlines
Deal found 7/30$503
This FlightHub deal was found by Cheapflights users on 7/29. 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.
Tue 10/147:50 pmORD - MXP
1 stop29h 55mTurkish Airlines
Sun 10/193:10 pmMXP - ORD
1 stop37h 50mTurkish Airlines
Deal found 7/29$506
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:00 pmORD - MXP
1 stop15h 25mTAP AIR PORTUGAL
Wed 10/296:20 amMXP - ORD
1 stop15h 40mTAP AIR PORTUGAL
Deal found 7/30$517
This oojo deal was found by Cheapflights users on 7/30. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/157:20 pmORD - LIN
2 stops33h 45mScandinavian Airlines
Thu 1/1512:55 pmLIN - ORD
2 stops34h 50mScandinavian Airlines
Deal found 7/30$517
This Mytrip deal was found by Cheapflights users on 7/31. 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.
Sun 9/146:00 pmORD - MXP
2 stops16h 25mMultiple Airlines
Sun 9/215:25 pmMXP - ORD
2 stops30h 15mMultiple Airlines
Deal found 7/31$546
This Cheapflightsfares deal was found by Cheapflights users on 7/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:45 pmORD - LIN
1 stop14h 00mMultiple Airlines
Tue 11/1111:25 amLIN - ORD
1 stop12h 35mMultiple Airlines
Deal found 7/30$590
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/63:45 pmORD - LIN
1 stop11h 55mAer Lingus
Fri 10/1711:20 amLIN - ORD
1 stop14h 40mAer Lingus
Deal found 7/29$620
This oojo deal was found by Cheapflights users on 7/31. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/113:00 pmORD - LIN
1 stop12h 10mITA Airways
Tue 8/197:00 pmLIN - ORD
1 stop25h 10mITA Airways
Deal found 7/31$669
This KLM deal was found by Cheapflights users on 7/31. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2710:35 amMDW - MXP
1 stop15h 30mKLM
Tue 11/1111:05 amMXP - MDW
1 stop17h 39mKLM
Deal found 7/31$817
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/199:30 amMDW - MXP
2 stops16h 35mDelta
Tue 12/211:05 amMXP - MDW
1 stop17h 39mDelta
Deal found 7/29$834
This Air France deal was found by Cheapflights users on 7/30. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2012:48 pmMDW - MXP
1 stop13h 37mAir France
Thu 10/306:55 amMXP - MDW
2 stops16h 48mAir France
Deal found 7/30$999

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 July 31, 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

Sat 9/27

11:45 pm-8:45 am

1 stop26h 00m

Milan Malpensa

Thu 10/2

6:50 am-9:40 am

1 stop33h 50m

$505

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 10/5

7:15 pm-7:15 pm

1 stop17h 00m

Milan Malpensa

Wed 10/15

3:30 pm-4:10 pm

1 stop31h 40m

$508

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 10/9

6:00 pm-7:15 pm

1 stop18h 15m

Milan Malpensa

Tue 10/14

5:25 pm-4:10 pm

1 stop29h 45m

$513

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 9/14

6:00 pm-5:25 pm

2 stops16h 25m

Milan Malpensa

Sun 9/21

5:25 pm-4:40 pm

2 stops30h 15m

$546

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sat 9/27

7:15 pm-12:10 pm

2 stops33h 55m

Milan Linate

Sat 10/4

2:50 pm-4:10 pm

1 stop32h 20m

$549

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 9/15

8:40 am-5:40 pm

2 stops26h 00m

Bergamo Orio Al Serio

Thu 9/25

6:20 am-5:33 pm

2 stops18h 13m

$561

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 10/6

3:45 pm-10:40 am

1 stop11h 55m

Milan Linate

Fri 10/17

11:20 am-7:00 pm

1 stop14h 40m

$620

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 9/21

7:25 pm-9:55 pm

2 stops19h 30m

Milan Linate

Thu 9/25

4:55 pm-9:15 pm

2 stops35h 20m

$641

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Mon 8/11

3:00 pm-10:10 am

1 stop12h 10m

Milan Linate

Tue 8/19

7:00 pm-1:10 pm

1 stop25h 10m

$669

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 8/17

4:00 pm-12:00 pm

1 stop13h 00m

Milan Linate

Tue 9/2

12:45 pm-7:55 pm

1 stop14h 10m

$725

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 29 results
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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 July 25, 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 $977). 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 July 31, 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 47% 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 July 31, 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 40% 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 Helsinki (HEL) have the shortest average one-way travel time for 1-stop routes: 13h 45m.

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 July 31, 2025.
Read through reviews of airlines operating flights from Chicago to Milan, such as Delta, KLM, and Air France. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,465 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Scandinavian Airlines
7.4
Good
1,457 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Turkish Airlines
7.3
Good
3,933 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $502, 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 $507 and $517, respectively. Users have found that Scandinavian Airlines is 40% 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 ITA Airways. According to our data, you can fly for as low as $243. Users have also found prices from $255 and $261 on TAP AIR PORTUGAL and Turkish 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 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 Air Canada (60%), Austrian Airlines (60%) or Brussels Airlines (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 $537. On average you can expect to pay $1,424. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $418.

  • 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 $63.

  • 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 $977). 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
Brescia
Assago
Bellagio
Stresa
Saronno

Browse thousands of different options on Cheapflights for your next trip

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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
IcelandairCheapest$382Average$708FlexibilityNo cancel feeOn-time76%
DeltaCheapest$419Average$929FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$423Average$608FlexibilityNo cancel feeOn-time77%
TAP AIR PORTUGALCheapest$470Average$694FlexibilityNo cancel feeOn-timeN/A
Turkish AirlinesCheapest$518Average$576FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$536Average$884FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$550Average$796FlexibilityNo cancel feeOn-time71%
Air FranceCheapest$575Average$961FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$584Average$915FlexibilityNo cancel feeOn-time81%
Aer LingusCheapest$623Average$822FlexibilityNo cancel feeOn-timeN/A

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