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$200+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MIL
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Milan are usually found in January or March, booked 47 days in advance, depart on a Tuesday or Sunday and return on a Tuesday

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 November 6, 2025.

This lol.travel deal was found by Cheapflights users on 11/5. 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.
Sun 11/167:10 amORD - MXP
2 stops29h 00mScandinavian Airlines
Tue 12/28:00 pmMXP - ORD
1 stop27h 45mScandinavian Airlines
Deal found 11/5$426
This Scandinavian Airlines deal was found by Cheapflights users on 11/5. 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.
Wed 12/36:30 pmORD - MXP
2 stops54h 55mScandinavian Airlines
Wed 12/101:00 pmMXP - ORD
2 stops34h 45mScandinavian Airlines
Deal found 11/5$436
This Scandinavian Airlines deal was found by Cheapflights users on 11/5. 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.
Wed 12/36:30 pmORD - MXP
2 stops54h 55mScandinavian Airlines
Thu 12/1111:15 amMXP - ORD
1 stop12h 30mScandinavian Airlines
Deal found 11/5$437
This oojo deal was found by Cheapflights users on 11/4. 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.
Wed 12/37:10 pmORD - MXP
1 stop14h 45mTAP AIR PORTUGAL
Sun 12/146:20 amMXP - ORD
1 stop15h 25mTAP AIR PORTUGAL
Deal found 11/4$445
This oojo deal was found by Cheapflights users on 11/5. 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 12/57:20 pmORD - MXP
1 stop30h 05mScandinavian Airlines
Mon 12/89:15 amMXP - ORD
1 stop14h 30mScandinavian Airlines
Deal found 11/5$451
This FlightHub deal was found by Cheapflights users on 11/6. 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 12/37:10 pmORD - MXP
1 stop14h 45mTAP AIR PORTUGAL
Wed 12/106:20 amMXP - ORD
1 stop15h 40mTAP AIR PORTUGAL
Deal found 11/6$458
This FlightHub deal was found by Cheapflights users on 11/6. 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 11/98:25 pmORD - MXP
1 stop31h 40mTAP AIR PORTUGAL
Tue 11/185:45 pmMXP - ORD
1 stop28h 15mTAP AIR PORTUGAL
Deal found 11/6$462
This Booking.com deal was found by Cheapflights users on 11/5. 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.
Fri 12/57:20 pmORD - MXP
1 stop30h 05mScandinavian Airlines
Tue 12/98:00 pmMXP - ORD
1 stop27h 45mScandinavian Airlines
Deal found 11/5$464
This CrystalTravel deal was found by Cheapflights users on 11/6. 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.
Sat 12/67:20 pmORD - MXP
1 stop16h 50mScandinavian Airlines
Sat 12/1311:15 amMXP - ORD
1 stop12h 30mScandinavian Airlines
Deal found 11/6$465
This CrystalTravel deal was found by Cheapflights users on 11/4. 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.
Sun 11/237:20 pmORD - MXP
1 stop16h 50mScandinavian Airlines
Thu 11/2711:15 amMXP - ORD
1 stop12h 30mScandinavian Airlines
Deal found 11/4$466
This Mytrip deal was found by Cheapflights users on 11/5. 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 12/46:30 pmORD - BGY
2 stops18h 35mMultiple Airlines
Thu 12/115:45 amBGY - ORD
2 stops18h 35mMultiple Airlines
Deal found 11/5$496
This Scandinavian Airlines deal was found by Cheapflights users on 11/5. 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.
Fri 12/57:20 pmORD - LIN
2 stops39h 55mScandinavian Airlines
Tue 12/912:55 pmLIN - ORD
2 stops34h 50mScandinavian Airlines
Deal found 11/5$496

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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$426
(lol.travel)

One-way from

$200
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$674

Good round-trip deal

$1,343 or less

Good one-way deal

$632 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. 3% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 6, 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

Fri 12/5

7:20 pm-8:25 am

1 stop30h 05m

Milan Malpensa

Wed 12/10

8:00 pm-4:45 pm

1 stop27h 45m

$467

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 1/9

7:20 pm-12:55 pm

2 stops34h 35m

Milan Malpensa

Thu 4/23

8:40 pm-4:10 pm

2 stops26h 30m

$475

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 11/27

7:20 pm-7:10 pm

1 stop16h 50m

Milan Malpensa

Tue 12/2

8:00 pm-4:45 pm

1 stop27h 45m

$475

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 1/7

7:20 pm-7:40 pm

2 stops17h 20m

Milan Malpensa

Wed 1/14

12:55 pm-4:45 pm

2 stops34h 50m

$480

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 12/3

6:30 pm-8:25 am

2 stops54h 55m

Milan Malpensa

Tue 12/9

11:15 am-9:39 pm

2 stops41h 24m

$492

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 12/3

6:30 pm-10:10 pm

2 stops20h 40m

Bergamo Orio Al Serio

Sun 12/14

8:00 am-5:20 pm

2 stops16h 20m

$499

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 1/30

7:20 pm-12:55 pm

2 stops34h 35m

Milan Malpensa

Mon 3/9

11:15 am-5:45 pm

1 stop12h 30m

$562

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sun 11/16

6:30 pm-11:59 pm

2 stops22h 29m

Bergamo Orio Al Serio

Tue 12/2

2:35 pm-3:00 pm

2 stops31h 25m

$598

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Sat 12/6

6:30 pm-6:25 pm

2 stops16h 55m

Bergamo Orio Al Serio

Sat 12/13

2:40 pm-2:45 pm

2 stops31h 05m

$613

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Fri 12/5

7:20 pm-8:10 pm

1 stop17h 50m

Bergamo Orio Al Serio

Thu 12/11

6:15 am-4:45 pm

1 stop17h 30m

$633

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 60 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
AranGrantPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy3 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Milan flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 31, 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, 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 June is currently the most expensive (average of $932). 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 November 6, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Milan in the afternoon. If you’re flexible enough to do this you can expect to save up to 45% 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 Thursday mornings when fares are most often at their lowest. Monday at noon 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 November 6, 2025.

The most flights from CHI to MIL are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

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 38% 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 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 Helsinki (HEL) offer the fastest connection on this route, with an average layover time of 1h 38m.

The best insider tips for Chicago to Milan flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Milan trip
Airports
ORD

For a smooth departure from ORD, consider using the 'L' train for reliable access, avoiding Chicago's notorious traffic delays.

Read more about ORDby Ramsey Qubein
MXP

Upon arrival at MXP, the Malpensa Express train offers a convenient 45-minute ride to Milan's city center.

Read more about MXPby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MXP

Ramsey Qubein

Ramsey Qubein

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 November 6, 2025.
Read through reviews of airlines operating flights from Chicago to Milan, such as Scandinavian Airlines, United Airlines, and Aer Lingus. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Scandinavian Airlines
7.4
Good
1,564 reviews

Crew

8.0

Food

6.6

Entertainment

6.6

Boarding

7.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
Scandinavian Airlines
7.4
Good
1,564 reviews
Scandinavian Airlines
7.4
Good
1,564 reviews

Crew

8.0

Food

6.6

Entertainment

6.6

Boarding

7.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
United Airlines
7.4
Good
9,007 reviews
Scandinavian Airlines
7.4
Good
1,564 reviews

Crew

8.0

Food

6.6

Entertainment

6.6

Boarding

7.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
Aer Lingus
7.2
Good
1,365 reviews
Scandinavian Airlines
7.4
Good
1,564 reviews

Crew

8.0

Food

6.6

Entertainment

6.6

Boarding

7.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
TAP AIR PORTUGAL
7.1
Good
2,047 reviews
Scandinavian Airlines
7.4
Good
1,564 reviews

Crew

8.0

Food

6.6

Entertainment

6.6

Boarding

7.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.
British Airways
6.7
Okay
7,500 reviews
Scandinavian Airlines
7.4
Good
1,564 reviews

Crew

8.0

Food

6.6

Entertainment

6.6

Boarding

7.6

Comfort

7.3

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Scott,Sep 2025

CPH - LAX

Unfortunately, usual rubbish at the gate for SAS reporting that boarding is underway, but clearly that was not the case. Internet worked to start with, but at some point it wouldn't connect using any of the devices I had with me and remained that way for the rest of the trip; could not even blame being out of network coverage, for all of that, as surely it should work across continental USA - worked for so little of the flight for me that I wouldn't have advertised that such a service was actually available; if I had had to pay extra for internet, I would have been demanding that money back.

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 12h 15m. The distance between Chicago and Milan is about 4536 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 Delta and Scandinavian Airlines - these airlines can fly you to your destination from $419 and $420, 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 O'Hare Intl - Bergamo Orio Al Serio 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 Austrian Airlines (73%), United Airlines (73%) or SWISS (73%) 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 $551. On average you can expect to pay $1,179. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $387.

  • 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 Tøjhusmuseet. Tivoli, Rådhuspladsen, and Tøjhusmuseet are located about 5.3 mi, 5.2 mi, and 4.8 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 $33.

  • 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, 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 June is currently the most expensive (average of $932). 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
Assago
Bellagio
Stresa
Domodossola

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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$398Average$653FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$419Average$745FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$420Average$565FlexibilityNo cancel feeOn-time77%
IcelandairCheapest$484Average$722FlexibilityNo cancel feeOn-time76%
Turkish AirlinesCheapest$518Average$574FlexibilityNo cancel feeOn-time77%
British AirwaysCheapest$536Average$881FlexibilityNo cancel feeOn-time70%
ITA AirwaysCheapest$584Average$915FlexibilityNo cancel feeOn-time81%
Aer LingusCheapest$623Average$822FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$624Average$878FlexibilityNo cancel feeOn-time71%
IberiaCheapest$639Average$1,029FlexibilityNo cancel feeOn-time77%

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