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$502+ Cheap flights from Milan (MIL) to Chicago (CHI)

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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
MIL — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Milan to Chicago are usually found in November or February, booked 55 days in advance, depart on a Saturday or Monday and return on a Tuesday

Cheap flight deals from Milan to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Milan (MIL) to Chicago (CHI). 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

$600
(Gotogate)

One-way from

$502
(FlightHub)

Popular in

July

Cheapest in

November

Average price

$748

Good round-trip deal

$664 or less

Good one-way deal

$787 or less
From Milan (MIL) to Chicago (CHI)
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One-way flight from Milan (MIL) to Chicago (CHI)
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Highest demand for flights based on searches. 18% potential increase in price ($156 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($19 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 Milan (MIL) to Chicago (CHI).
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Price to beat on a one-way flight from Milan (MIL) to Chicago (CHI).
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Find flight deals from Milan to Chicago

Cheapest flights from Milan to Chicago
Explore the most affordable flight options available from Milan to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

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 9/155:55 amMXP - ORD
1 stop17h 45mTAP AIR PORTUGAL
Wed 10/16:00 pmORD - MXP
1 stop18h 15mTAP AIR PORTUGAL
Deal found 6/9$600
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:30 pmLIN - ORD
1 stop25h 25mBritish Airways
Thu 10/910:35 pmORD - LIN
1 stop13h 20mBritish Airways
Deal found 6/11$606
This Scandinavian Airlines deal was found by Cheapflights users on 6/12. 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.
Sat 9/207:15 pmMXP - ORD
1 stop27h 55mScandinavian Airlines
Mon 10/207:15 pmORD - MXP
1 stop17h 00mScandinavian Airlines
Deal found 6/12$607
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:15 amMXP - ORD
2 stops16h 35mAmerican Airlines
Wed 1/76:45 pmORD - MXP
1 stop12h 55mAmerican Airlines
Deal found 6/10$609
This Iberia 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 Iberia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:55 amLIN - ORD
2 stops18h 50mMultiple Airlines
Mon 11/249:45 pmORD - LIN
1 stop13h 05mMultiple Airlines
Deal found 6/11$617
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:15 amLIN - ORD
2 stops17h 22mAmerican Airlines
Thu 11/136:45 pmORD - LIN
1 stop11h 35mAmerican Airlines
Deal found 6/12$621
This ITA Airways 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 ITA Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/157:00 amLIN - ORD
1 stop13h 10mITA Airways
Sun 9/283:00 pmORD - LIN
1 stop21h 10mITA Airways
Deal found 6/10$626
This Booking.com deal was found by Cheapflights users on 6/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/179:30 pmMXP - ORD
3 stops30h 45mMultiple Airlines
Sun 9/217:25 pmORD - MXP
2 stops19h 10mMultiple Airlines
Deal found 6/12$627
This Delta deal was found by Cheapflights users on 6/12. 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.
Thu 11/611:05 amMXP - MDW
1 stop17h 39mDelta
Thu 11/131:00 pmMDW - MXP
2 stops15h 40mDelta
Deal found 6/12$633
This Delta deal was found by Cheapflights users on 6/12. 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.
Thu 11/66:30 amLIN - ORD
2 stops18h 06mDelta
Thu 11/1310:40 amORD - LIN
2 stops15h 05mDelta
Deal found 6/12$635
This lol.travel deal was found by Cheapflights users on 6/12. 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.
Tue 9/3011:15 amMXP - ORD
2 stops15h 56mAir Canada
Wed 10/812:00 pmORD - MXP
2 stops15h 00mAir Canada
Deal found 6/12$635
This lol.travel 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:00 amLIN - ORD
2 stops14h 55mAir Canada
Sun 10/192:08 pmORD - LIN
2 stops14h 52mAir Canada
Deal found 6/10$636

Cheapflights Fare Finder

Customize your flight search to find flights from Milan to Chicago 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 Milan to Chicago that are best for you.

Fly from

Milan

Fly to

Chicago

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 9/15

5:55 am-4:40 pm

1 stop17h 45m

Chicago O'Hare Intl

Wed 10/1

6:00 pm-7:15 pm

1 stop18h 15m

$600

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 10/1

7:30 pm-1:55 pm

1 stop25h 25m

Chicago O'Hare Intl

Thu 10/9

10:35 pm-6:55 pm

1 stop13h 20m

$606

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 9/20

7:15 pm-4:10 pm

1 stop27h 55m

Chicago O'Hare Intl

Mon 10/20

7:15 pm-7:15 pm

1 stop17h 00m

$607

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 11/6

10:15 am-7:50 pm

2 stops16h 35m

Chicago O'Hare Intl

Thu 11/13

9:45 pm-8:25 pm

1 stop15h 40m

$611

MilanChicago

LIN - ORD

LINORD

Milan Linate

Sat 11/15

7:55 am-7:45 pm

2 stops18h 50m

Chicago O'Hare Intl

Mon 11/24

9:45 pm-5:50 pm

1 stop13h 05m

$617

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 11/6

7:15 am-5:37 pm

2 stops17h 22m

Chicago O'Hare Intl

Thu 11/13

6:45 pm-1:20 pm

1 stop11h 35m

$621

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 9/15

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Sun 9/28

3:00 pm-7:10 pm

1 stop21h 10m

$626

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 9/17

9:30 pm-9:15 pm

3 stops30h 45m

Chicago O'Hare Intl

Sun 9/21

7:25 pm-9:35 pm

2 stops19h 10m

$627

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 11/6

11:05 am-9:44 pm

1 stop17h 39m

Chicago Midway

Thu 11/13

1:00 pm-11:40 am

2 stops15h 40m

$633

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 9/30

11:15 am-8:11 pm

2 stops15h 56m

Chicago O'Hare Intl

Wed 10/8

12:00 pm-10:00 am

2 stops15h 00m

$635

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 Milan to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Milan 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 Milan to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Milan to Chicago. Price data was last updated on June 9, 2025.

The price you pay for your flight from Milan to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 55 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 Milan to Chicago?

Currently, August is the cheapest month in which you can book a flight from Milan to Chicago (average of $245). Flying from Milan to Chicago in March is currently the most expensive (average of $321). 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 MIL to CHI?

Find hourly flight availability from Milan to Chicago. 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.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 39% on flights from Milan to Chicago by exploring options for tickets in the evening.

Weekly flight availability from Milan to Chicago

Explore weekly flight availability from Milan to Chicago. 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 MIL to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 12, 2025.
Get a feel of what it's like to fly with Emirates, Delta and KLM from Milan to Chicago by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Emirates
8.1
Very good
3,264 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Overall

8.1

Food

7.8

Crew

8.3

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
Emirates
8.1
Very good
3,264 reviews
Emirates
8.1
Very good
3,264 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Overall

8.1

Food

7.8

Crew

8.3

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
Delta
8.0
Very good
7,946 reviews
Emirates
8.1
Very good
3,264 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Overall

8.1

Food

7.8

Crew

8.3

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
KLM
7.8
Good
1,358 reviews
Emirates
8.1
Very good
3,264 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Overall

8.1

Food

7.8

Crew

8.3

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
LOT
7.6
Good
1,077 reviews
Emirates
8.1
Very good
3,264 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Overall

8.1

Food

7.8

Crew

8.3

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.
Austrian Airlines
7.6
Good
802 reviews
Emirates
8.1
Very good
3,264 reviews

Boarding

8.1

Comfort

8.0

Entertainment

8.2

Overall

8.1

Food

7.8

Crew

8.3

Reviews

1 / 20
2.0
Mediocre

Anonymous,Jun 2024

DXB - IAH

It was not a good experience the seats were small and uncomfortable the food was not good and they forgot to serve me my breakfast - there were 5 us in 2 rows that they just completely skipped us. Very disappointed.

Related info for your journey

Find useful and relevant information for your journey from Milan to Chicago. 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 Milan to Chicago round-trip?

    Currently priced at $600, TAP AIR PORTUGAL will fly you from Milan to Chicago and back. In addition to TAP AIR PORTUGAL, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from British Airways and Scandinavian Airlines - these airlines can fly you to your destination from $606 and $607, respectively. TAP AIR PORTUGAL is currently priced 11% below the average price you’ll pay for this route.

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

    $502 is the cheapest one-way deal found within the past few days, from Icelandair. You may also be able to find cheap deals on Air Serbia and Aer Lingus, with prices starting from $510 and $516, respectively.

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

    The most popular flight routes from Milan to Chicago are Milan Malpensa - Chicago O'Hare Intl, Milan Linate - Chicago O'Hare Intl and Milan Linate - Chicago Midway.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Milan to Chicago on time: Brussels Airlines (80%), Air Canada (76%), Austrian Airlines (76%).

  • What are the cheapest flights from Milan to Chicago?

    Looking for the cheapest flight from Milan to Chicago? While on average our users pay $1,988, our data indicates the cheapest price to be $650. The most popular route (Milan Malpensa - Chicago O'Hare Intl), is priced around $371.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milan to Chicago 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 Milan to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Milan to Chicago (average of $245). Flying from Milan to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Milan to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Malpensa to O'Hare Intl flights
Linate to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Malpensa to St. Louis flights
Verona to O'Hare Intl flights
Malpensa to Moline flights

Top 3 airlines flying from Milan to Chicago

Discover the top 3 airlines that operate flights from Milan to Chicago. 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
British AirwaysCheapest$525Average$716FlexibilityNo cancel feeOn-time70%
TAP AIR PORTUGALCheapest$537Average$564FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$626Average$943FlexibilityNo cancel feeOn-time69%

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