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$258+ 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
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
1 adult, Economy
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Find cheap flights from Chicago to Milan with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Milan are usually found in February or January, booked 74 days in advance, depart on a Monday or Tuesday and return on a Saturday

Cheap 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 9, 2026.

This Mytrip deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:25 pm
ORD
-
BGY
3 stops28h 00m
Multiple Airlines
Sun 9/67:00 am
BGY
-
ORD
2 stops18h 15m
Multiple Airlines
Deal found 6/8$724
This Kiwi.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:30 pm
ORD
-
BGY
1 stop20h 40m
Multiple Airlines
Tue 10/68:50 am
BGY
-
ORD
2 stops40h 00m
Multiple Airlines
Deal found 6/8$734
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:30 pm
ORD
-
BGY
1 stop20h 40m
Multiple Airlines
Thu 10/89:50 am
BGY
-
ORD
2 stops39h 00m
Multiple Airlines
Deal found 6/6$739
This Mytrip deal was found by Cheapflights users on 6/5. 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.
Sun 8/26:00 pm
ORD
-
BGY
2 stops18h 55m
Multiple Airlines
Tue 8/186:20 pm
BGY
-
ORD
2 stops28h 40m
Multiple Airlines
Deal found 6/5$751
This Mytrip deal was found by Cheapflights users on 6/8. 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 8/34:05 pm
ORD
-
BGY
3 stops20h 45m
Multiple Airlines
Wed 8/198:50 am
BGY
-
ORD
2 stops16h 25m
Multiple Airlines
Deal found 6/8$765
This Mytrip deal was found by Cheapflights users on 6/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:25 pm
ORD
-
BGY
2 stops18h 30m
Multiple Airlines
Wed 9/25:50 pm
BGY
-
ORD
2 stops34h 30m
Multiple Airlines
Deal found 6/6$767
This Mytrip deal was found by Cheapflights users on 6/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:15 pm
ORD
-
BGY
2 stops17h 50m
Multiple Airlines
Wed 10/148:40 pm
BGY
-
ORD
2 stops26h 30m
Multiple Airlines
Deal found 6/4$770
This Mytrip deal was found by Cheapflights users on 6/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:30 pm
ORD
-
BGY
2 stops19h 55m
Multiple Airlines
Tue 11/242:45 pm
BGY
-
ORD
2 stops31h 45m
Multiple Airlines
Deal found 6/6$772
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:30 pm
ORD
-
BGY
1 stop20h 40m
Multiple Airlines
Tue 10/68:50 am
BGY
-
ORD
2 stops40h 00m
Multiple Airlines
Deal found 6/7$777
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Thu 11/129:35 pm
ORD
-
MXP
Nonstop8h 30m
United Airlines
Tue 11/2411:20 am
MXP
-
ORD
1 stop15h 45m
United Airlines
Deal found 6/7$779
This Gotogate deal was found by Cheapflights users on 6/8. 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.
Thu 8/69:50 am
ORD
-
MXP
2 stops17h 30m
Multiple Airlines
Sun 8/306:30 am
MXP
-
ORD
2 stops34h 46m
Multiple Airlines
Deal found 6/8$780
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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.
Fri 8/143:35 pm
ORD
-
LIN
1 stop14h 25m
Lufthansa
Sun 8/236:50 am
LIN
-
ORD
1 stop13h 05m
Lufthansa
Deal found 6/8$780

Find 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 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$724
(Mytrip)

One-way from

$258
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$1,343

Good round-trip deal

$1,287 or less

Good one-way deal

$934 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. 28% potential increase in price ($333 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($48 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 9, 2026.
Use the filters below to find and compare flights from Chicago to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sun 11/8

9:35 pm-1:05 pm

Nonstop8h 30m

Milan Malpensa

Wed 11/11

11:20 am-8:05 pm

1 stop15h 45m

$779

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 8/23

7:15 pm-12:10 pm

2 stops33h 55m

Milan Linate

Wed 8/26

1:00 pm-4:10 pm

2 stops34h 10m

$781

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 11/8

1:05 pm-11:10 am

1 stop15h 05m

Milan Malpensa

Wed 11/11

1:05 pm-10:10 pm

1 stop16h 05m

$792

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 8/12

9:24 am-10:25 am

2 stops18h 01m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$796

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 10/10

7:15 pm-2:10 pm

1 stop11h 55m

Milan Malpensa

Sun 10/18

11:25 am-5:34 pm

2 stops37h 09m

$825

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 8/24

11:05 am-12:30 pm

3 stops18h 25m

Bergamo Orio Al Serio

Wed 9/2

5:50 pm-9:20 pm

2 stops34h 30m

$834

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Thu 11/26

1:00 pm-11:15 am

2 stops15h 15m

Milan Linate

Wed 12/16

6:30 am-4:50 pm

2 stops17h 20m

$853

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Fri 9/4

9:30 pm-11:50 pm

1 stop19h 20m

Bergamo Orio Al Serio

Fri 9/11

6:10 am-5:50 pm

2 stops18h 40m

$855

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 7/22

6:00 pm-7:05 pm

2 stops18h 05m

Bergamo Orio Al Serio

Wed 7/29

10:50 am-12:40 pm

2 stops32h 50m

$866

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 8/5

3:35 pm-8:05 pm

2 stops21h 30m

Bergamo Orio Al Serio

Thu 8/13

8:40 am-7:55 pm

2 stops18h 15m

$866

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 60 resultsSorted by cheapest first
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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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Milan flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Milan flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Milan flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Milan flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Milan flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Milan

Have a flexible travel schedule? Discover the best time to fly to Milan from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Milan

What is the cheapest month to book a flight from Chicago to Milan?

Currently, July is the cheapest month in which you can book a flight from Chicago to Milan (average of $187). Flying from Chicago to Milan in June is currently the most expensive (average of $671). 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 9, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Milan as you normally would.

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 9, 2026.

The most flights from CHI to MIL are scheduled on a Tuesday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 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 50% 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.

Montreal (YUL) is the most affordable 1-stop option, with an average round-trip price of $613.

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 Montreal (YUL) offer the fastest connection on this route, with an average layover time of 1h 48m.

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

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 9 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

The best insider tips for Chicago to Milan flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Milan trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MXP

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 June 9, 2026.
Read through reviews of airlines operating flights from Chicago to Milan, such as Scandinavian Airlines,United Airlines, andAer Lingus. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Scandinavian Airlines
7.4
Good
1,812 reviews

Crew

8.0

Entertainment

6.7

Food

6.7

Boarding

7.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2026

OSL - CPH

The flight was very short. The seats were very comfortable. No television or entertainment.
Scandinavian Airlines
7.4
Good
1,812 reviews
Scandinavian Airlines
7.4
Good
1,812 reviews

Crew

8.0

Entertainment

6.7

Food

6.7

Boarding

7.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2026

OSL - CPH

The flight was very short. The seats were very comfortable. No television or entertainment.
United Airlines
7.4
Good
9,795 reviews
Scandinavian Airlines
7.4
Good
1,812 reviews

Crew

8.0

Entertainment

6.7

Food

6.7

Boarding

7.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2026

OSL - CPH

The flight was very short. The seats were very comfortable. No television or entertainment.
Aer Lingus
7.3
Good
1,599 reviews
Scandinavian Airlines
7.4
Good
1,812 reviews

Crew

8.0

Entertainment

6.7

Food

6.7

Boarding

7.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2026

OSL - CPH

The flight was very short. The seats were very comfortable. No television or entertainment.
TAP AIR PORTUGAL
7.2
Good
2,275 reviews
Scandinavian Airlines
7.4
Good
1,812 reviews

Crew

8.0

Entertainment

6.7

Food

6.7

Boarding

7.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2026

OSL - CPH

The flight was very short. The seats were very comfortable. No television or entertainment.
Lufthansa
6.8
Okay
8,048 reviews
Scandinavian Airlines
7.4
Good
1,812 reviews

Crew

8.0

Entertainment

6.7

Food

6.7

Boarding

7.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Mar 2026

OSL - CPH

The flight was very short. The seats were very comfortable. No television or entertainment.

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 8h 30m. The distance between Chicago and Milan is about 4508 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 $401, 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 Scandinavian Airlines and Turkish Airlines - these airlines can fly you to your destination from $420 and $534, 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 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 Austrian Airlines (63%), Brussels Airlines (63%) or United Airlines (63%) 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 $728. On average you can expect to pay $1,305. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $606.

  • 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, July is the cheapest month in which you can book a flight from Chicago to Milan (average of $187). Flying from Chicago to Milan in June is currently the most expensive (average of $671). 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
Menaggio
Rho
Brescia
Porlezza
Assago
Stresa
Bellagio
Domodossola

Browse thousands of different options on Cheapflights for your next trip

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Top 8 airlines flying from Chicago to Milan

Discover the top 8 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 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
TAP AIR PORTUGALCheapest$401Average$629FlexibilityNo cancel feeOn-timeN/A
Scandinavian AirlinesCheapest$420Average$597FlexibilityNo cancel feeOn-time77%
Turkish AirlinesCheapest$534Average$689FlexibilityNo cancel feeOn-time77%
Aer LingusCheapest$627Average$828FlexibilityNo cancel feeOn-timeN/A
British AirwaysCheapest$644Average$856FlexibilityNo cancel feeOn-time70%
ITA AirwaysCheapest$644Average$968FlexibilityNo cancel feeOn-time81%
United AirlinesCheapest$774Average$1,290FlexibilityNo cancel feeOn-time69%
LufthansaCheapest$840Average$1,235FlexibilityNo cancel feeOn-time76%

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