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$231+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIL
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Milan are usually found in November or March, booked 54 days in advance, depart on a Tuesday or Sunday 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 June 12, 2025.

Round-trip from

$546
(Mytrip)

One-way from

$231
(Booking.com)

Popular in

December

Cheapest in

November

Average price

$1,147

Good round-trip deal

$923 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. 3% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($38 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. 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.
Mon 9/16:10 pmORD - BGY
2 stops22h 00mMultiple Airlines
Sun 9/79:25 pmBGY - ORD
2 stops26h 15mMultiple Airlines
Deal found 6/11$546
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Fri 9/197:15 amORD - MXP
3 stops28h 10mMultiple Airlines
Fri 10/38:45 pmMXP - ORD
2 stops33h 25mMultiple Airlines
Deal found 6/11$658
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 9/64:20 pmORD - LIN
1 stop16h 35mDelta
Sat 9/1312:20 pmLIN - ORD
2 stops16h 26mDelta
Deal found 6/11$659
This Scandinavian Airlines deal was found by Cheapflights users on 6/11. 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 Scandinavian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:15 pmORD - MXP
1 stop12h 30mScandinavian Airlines
Mon 10/208:05 pmMXP - ORD
1 stop27h 05mScandinavian Airlines
Deal found 6/11$661
This Turkish Airlines deal was found by Cheapflights users on 6/11. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1011:25 amORD - MXP
1 stop23h 45mTurkish Airlines
Sun 10/193:10 pmMXP - ORD
1 stop37h 50mTurkish Airlines
Deal found 6/11$663
This FlightHub deal was found by Cheapflights users on 6/10. 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 11/25:55 pmORD - LIN
1 stop16h 55mBrussels Airlines
Wed 11/197:00 amLIN - ORD
1 stop12h 10mBrussels Airlines
Deal found 6/10$665
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Thu 8/287:25 pmORD - LIN
2 stops16h 30mMultiple Airlines
Mon 9/17:30 pmLIN - ORD
2 stops32h 45mMultiple Airlines
Deal found 6/11$667
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Thu 9/2510:35 pmORD - LIN
1 stop11h 40mBritish Airways
Thu 10/211:05 amLIN - ORD
1 stop14h 10mBritish Airways
Deal found 6/9$671
This United Airlines deal was found by Cheapflights users on 6/10. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2610:30 pmORD - MXP
Nonstop8h 20mUnited Airlines
Thu 11/61:05 pmMXP - ORD
1 stop14h 20mUnited Airlines
Deal found 6/10$674
This Gotogate deal was found by Cheapflights users on 6/9. 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.
Mon 7/2110:15 pmORD - MXP
1 stop16h 45mIcelandair
Sat 10/43:10 pmMXP - ORD
1 stop34h 05mIcelandair
Deal found 6/9$675
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 9/61:08 pmMDW - LIN
2 stops15h 52mDelta
Sat 9/136:40 amLIN - MDW
2 stops18h 56mDelta
Deal found 6/11$677
This KLM deal was found by Cheapflights users on 6/11. 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.
Fri 8/81:26 pmORD - MXP
1 stop12h 59mKLM
Fri 8/159:00 amMXP - ORD
1 stop15h 41mKLM
Deal found 6/11$680

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 June 12, 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

Mon 9/1

6:10 pm-11:10 pm

2 stops22h 00m

Bergamo Orio Al Serio

Sun 9/7

9:25 pm-4:40 pm

2 stops26h 15m

$546

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 9/19

7:15 am-6:25 pm

3 stops28h 10m

Milan Malpensa

Fri 10/3

8:45 pm-11:10 pm

2 stops33h 25m

$658

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sat 9/6

4:20 pm-3:55 pm

1 stop16h 35m

Milan Linate

Sat 9/13

12:20 pm-9:46 pm

2 stops16h 26m

$659

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Tue 10/14

7:15 pm-2:45 pm

1 stop12h 30m

Milan Malpensa

Mon 10/20

8:05 pm-4:10 pm

1 stop27h 05m

$661

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 10/10

11:25 am-6:10 pm

1 stop23h 45m

Milan Malpensa

Fri 10/17

10:45 am-9:40 am

1 stop29h 55m

$663

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 11/2

5:55 pm-5:50 pm

1 stop16h 55m

Milan Linate

Wed 11/19

7:00 am-12:10 pm

1 stop12h 10m

$665

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Thu 8/28

7:25 pm-6:55 pm

2 stops16h 30m

Milan Linate

Mon 9/1

7:30 pm-9:15 pm

2 stops32h 45m

$667

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Thu 9/25

10:35 pm-5:15 pm

1 stop11h 40m

Milan Linate

Thu 10/2

11:05 am-6:15 pm

1 stop14h 10m

$671

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 11/2

9:30 pm-12:50 pm

Nonstop8h 20m

Milan Malpensa

Tue 11/18

3:05 pm-6:05 pm

Nonstop10h 00m

$674

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Wed 9/10

10:30 pm-5:35 pm

1 stop12h 05m

Milan Linate

Sun 9/14

7:00 am-12:55 pm

1 stop12h 55m

$674

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 60 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 June 9, 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 54 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 $989). 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 June 12, 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 June 12, 2025.

The most flights from CHI to MIL are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

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 June 12, 2025.
To help decide which airline to fly from Chicago to Milan, see what other customers have to say about Delta, KLM and LOT. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
1,358 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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!
LOT
7.6
Good
1,077 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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!
Austrian Airlines
7.6
Good
802 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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
1,463 reviews
Delta
8.0
Very good
7,950 reviews

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

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 $659, Delta will fly you from Chicago to Milan and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Scandinavian Airlines and Icelandair - these airlines can fly you to your destination from $666 and $675, respectively. Users have found that Delta is 21% 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 Icelandair. According to our data, you can fly for as low as $231. Users have also found prices from $300 and $334 on TAP AIR PORTUGAL and Air Serbia, 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 (64%), Austrian Airlines (64%) or Brussels Airlines (64%) 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 $474. On average you can expect to pay $4,692. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $375.

  • 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 $48.

  • 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 $989). 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?

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$419Average$941FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$423Average$618FlexibilityNo cancel feeOn-time77%
IcelandairCheapest$484Average$708FlexibilityNo cancel feeOn-time76%
TAP AIR PORTUGALCheapest$499Average$699FlexibilityNo cancel feeOn-timeN/A
Turkish AirlinesCheapest$518Average$576FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$536Average$886FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$550Average$788FlexibilityNo cancel feeOn-time71%
Air FranceCheapest$575Average$961FlexibilityNo cancel feeOn-time77%
ITA AirwaysCheapest$584Average$741FlexibilityNo cancel feeOn-time81%
Aer LingusCheapest$594Average$820FlexibilityNo cancel feeOn-timeN/A

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