Can I fly direct from Chicago to Milan?

Direct flights from Chicago to Milan are not very common, historically making up only 3.1% of all flights. For travelers who opt for connecting flights, the median number of stopovers across the trailing 90 days was 2. This indicates that most travelers on this route typically make at least one connection.

How many hours is the flight from Chicago to Milan?

The average direct flight from Chicago to Milan typically takes 8 hours and 40 minutes. For flights with one stop, the median duration increases significantly to 14 hours and 14 minutes. The distance covered on this route is approximately 7259 kilometers.

Are there frequently good prices on flights from Chicago to Milan?

Historically, good prices on flights from Chicago to Milan have been frequent. This route is classified as one where deals appear often, based on pricing trends observed over the trailing 30 days. Travelers can typically find favorable pricing for this destination.

Flights From Chicago

To Milan

Cheap Flights from Chicago to Milan

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Milan

Prices updated 1 day ago

459 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Sep 8, 2026.)

Today’s best flight deals from Chicago to Milan

Explore current cheapest deals departing from Chicago to Milan

2026-10-03 – 2026-10-15
CHI - Milan
80% AI deal score
$670
$606
Round trip
2026-10-20 – 2026-10-28
CHI - Milan
76% AI deal score
$622
$609
Round trip
2026-11-03 – 2026-11-11
CHI - Milan
76% AI deal score
$630
$614
Round trip
2026-11-16 – 2026-11-19
CHI - Milan
76% AI deal score
$575
$619
Round trip
2026-11-01 – 2026-11-08
CHI - Milan
75% AI deal score
$556
$636
Round trip
2026-10-05 – 2026-10-21
CHI - Milan
80% AI deal score
$796
$638
Round trip
2026-11-08 – 2026-11-18
CHI - Milan
75% AI deal score
$540
$638
Round trip
2026-10-16 – 2026-10-21
CHI - Milan
74% AI deal score
$655
$651
Round trip
2026-10-07 – 2026-10-13
CHI - Milan
79% AI deal score
$708
$653
Round trip
2026-10-21 – 2026-10-28
CHI - Milan
79% AI deal score
$708
$653
Round trip

Chicago to Milan: Overview

Insights for flights from Chicago to Milan

Most itineraries for cheap flights from Chicago to Milan connect at least once, with only 3.1% of recent fares being non-stop. For connecting itineraries, the typical number of stopovers is 2. New deals appear almost daily, offering frequent opportunities to find suitable flights.

When is the cheapest time to fly from Chicago to Milan? The data indicates that January is typically the most affordable month, with a median fare of $585. November also presents a good value, with a median fare of $591. Additionally, April offers competitive prices, with a median fare of $653.

Fares for flights from Chicago to Milan typically range from $904–$1227, with a median of $1047. Right now, fares are near the typical level. Approximately 7% of recent fares were classified as a good price, suggesting that finding a deal requires some flexibility.

A typical journey from Chicago to Milan, including connections, takes about 32h 9m. This route covers a substantial distance of 7259 km, classifying it as a long-haul flight.

How much is a round trip from Chicago to Milan

Regular price: $482 - $1,235

Prices for flights from Chicago to Milan are currently within the regular range.

The regular price range for flights from Chicago to Milan is typically between $482 and $1235. The current lowest deal is $535 with Icelandair, for travel from Nov 4-Nov 11.

now $535

Low $482

High $1,235

The cheapest time to fly from Chicago to Milan

The cheapest month to fly from Chicago to Milan is January, with a median price of $585. The most expensive month is May, with a median price of $1295. Prices are generally lower from January to December.

January

Cheapest

Flights from $585

May

Most Expensive

Flights from $1,295

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Milan

United Airlines

Last-minute flights going from Chicago to Milan

Sat, Oct 3

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$670

$607

One-way

Sun, Oct 4

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$653

$664

One-way

Sun, Oct 4

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$657

$672

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (BGY)

Frontier Airlines

$780

$654

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (BGY)

Icelandair

$773

$675

One-way

Thu, Oct 8

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$727

$606

One-way

Biggest price drops on these dates for flights from Chicago to Milan

9 nights

Mar 24 - Apr 2

$1,049 → $801

24%

9 nights

Mar 17 - Mar 26

$1,039 → $801

23%

6 nights

Dec 4 - Dec 10

$865 → $667

23%

4 nights

Dec 8 - Dec 12

$897 → $709

21%

Popular Airports to fly from Chicago to Milan

Chicago - Milan route insights

💸 Price insights

Recent fares are near the typical level

Recent fares for Chicago to Milan are near the typical level, with a median price of $1047.

📅 Best time to fly

Fly in January for prices as low as $585

Historically, January, November, and April offer the lowest median prices for flights to Milan.

⏱️ Flight duration

Flights to Milan typically take 32h 9m

The median flight duration from Chicago to Milan is 32 hours and 9 minutes, including layovers.

✈️ Airlines & availability

Connecting flights are dominant on this route

Only 3.1% of flights are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers providing direct flight options on this long-haul route.

🎯 Booking tip

Deals appear frequently for this route

Deals for flights from Chicago to Milan are frequent, appearing often within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a convenient departure point for flights from Chicago to Milan.

📍 ~25 km from Chicago (reachable by car or train)

💸 Flights from ~$610

Milan main airports to arrive at

Milan–Malpensa (MXP)

Cheapest

Milan–Malpensa is a good option for flights from Chicago to Milan, offering competitive prices.

📍 ~40 km from Milan (reachable by car)

💸 Flights from ~$620

Airports nearby Milan used as alternative

Turin (TRN)

Turin offers a reliable alternative for domestic and European routes, despite a smaller flight network than Milan Malpensa.

📍 ~135 km from Milan (reachable by high-speed rail and motorway).

💸 Flights from ~$694

Business & First Class Flight Deals to Milan

Discover luxury on the budget with premium cabin class on flights from Chicago to Milan.

Elite

Best Elite deals to Milan

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From ORD

Elite

Nov 01

Milan, Italy

92% AI deal score

$2,268

$1,525

Save $743

Scandinavian Airlines

Business Class

From ORD

Elite

Nov 02

Milan, Italy

92% AI deal score

$2,295

$1,525

Save $770

Scandinavian Airlines

Business Class

From ORD

Elite

Oct 06

Milan, Italy

92% AI deal score

$2,300

$1,526

Save $774

Scandinavian Airlines

Business Class

From ORD

Elite

Dec 01

Milan, Italy

92% AI deal score

$2,567

$1,762

Save $805

Scandinavian Airlines

Business Class

From ORD

Elite

Dec 16

Milan, Italy

92% AI deal score

$2,603

$1,809

Save $794

TAP Portugal

Business Class

From ORD

Elite

Nov 11

Milan, Italy

91% AI deal score

$4,437

$3,038

Save $1,399

Icelandair, +1

Business Class

From ORD

Elite

Nov 08

Milan, Italy

91% AI deal score

$4,433

$3,038

Save $1,395

Icelandair, +1

Business Class

From ORD

Elite

Nov 08

Milan, Italy

91% AI deal score

$4,437

$3,042

Save $1,395

Icelandair, +1

Business Class

From ORD

Elite

Nov 11

Milan, Italy

91% AI deal score

$4,428

$3,042

Save $1,386

Icelandair, +1

Business Class

From ORD

Elite

Nov 14

Milan, Italy

91% AI deal score

$4,545

$3,093

Save $1,452

Icelandair, +1

Business Class

From ORD

Elite

Nov 16

Milan, Italy

91% AI deal score

$4,684

$3,103

Save $1,581

Icelandair, +1

Business Class

From ORD

Elite

Nov 15

Milan, Italy

91% AI deal score

$4,626

$3,103

Save $1,523

Icelandair, +1

Business Class

Frequently Asked Questions About Flights to Milan

Historically, the lowest average prices for flights from Chicago to Milan are found when booking between 14 and 27 days in advance. During this period, the average price was around $737. Prices tend to increase outside this window, with flights booked 7-13 days out averaging $843, and those booked 28-59 days out averaging $986. Booking more than 60 days in advance typically results in higher prices, averaging $1072.

Across the trailing quarter, a good price for a flight from Chicago to Milan was considered to be $904 or less. The median price for this route during the same period was $1047. Prices tended to increase for a significant portion of flights, with 75% of prices being $1227 or less.

Historically, the cheapest months to fly from Chicago to Milan include January, with a median price of $585, and November, with a median price of $591. April also offered relatively lower prices, with a median of $653. These prices are notably lower than the annual median price of $1047 for this route.

Chicago to Milan: Overview

Insights for flights from Chicago to Milan

A typical journey from Chicago to Milan, including connections, takes about 32h 9m. This route covers a substantial distance of 7259 km, classifying it as a long-haul flight.

How much is a round trip from Chicago to Milan

Regular price: $482 - $1,235

Prices for flights from Chicago to Milan are currently within the regular range.

The regular price range for flights from Chicago to Milan is typically between $482 and $1235. The current lowest deal is $535 with Icelandair, for travel from Nov 4-Nov 11.

now $535

Low $482

High $1,235

The cheapest time to fly from Chicago to Milan

January

Cheapest

Flights from $585

May

Most Expensive

Flights from $1,295

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Milan

United Airlines

Last-minute flights going from Chicago to Milan

Sat, Oct 3

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$670

$607

One-way

Sun, Oct 4

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$653

$664

One-way

Sun, Oct 4

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$657

$672

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (BGY)

Frontier Airlines

$780

$654

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (BGY)

Icelandair

$773

$675

One-way

Thu, Oct 8

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$727

$606

One-way

Biggest price drops on these dates for flights from Chicago to Milan

9 nights

Mar 24 - Apr 2

$1,049 → $801

24%

9 nights

Mar 17 - Mar 26

$1,039 → $801

23%

6 nights

Dec 4 - Dec 10

$865 → $667

23%

4 nights

Dec 8 - Dec 12

$897 → $709

21%

Popular Airports to fly from Chicago to Milan

Chicago - Milan route insights

💸 Price insights

Recent fares are near the typical level

Recent fares for Chicago to Milan are near the typical level, with a median price of $1047.

📅 Best time to fly

Fly in January for prices as low as $585

Historically, January, November, and April offer the lowest median prices for flights to Milan.

⏱️ Flight duration

Flights to Milan typically take 32h 9m

The median flight duration from Chicago to Milan is 32 hours and 9 minutes, including layovers.

✈️ Airlines & availability

Connecting flights are dominant on this route

Only 3.1% of flights are direct, with connecting flights typically having 2 stopovers.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers providing direct flight options on this long-haul route.

🎯 Booking tip

Deals appear frequently for this route

Deals for flights from Chicago to Milan are frequent, appearing often within a 30-day window.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

O'Hare International Airport offers a convenient departure point for flights from Chicago to Milan.

📍 ~25 km from Chicago (reachable by car or train)

💸 Flights from ~$610

Milan main airports to arrive at

Milan–Malpensa (MXP)

Cheapest

Milan–Malpensa is a good option for flights from Chicago to Milan, offering competitive prices.

📍 ~40 km from Milan (reachable by car)

💸 Flights from ~$620

Airports nearby Milan used as alternative

Turin (TRN)

Turin offers a reliable alternative for domestic and European routes, despite a smaller flight network than Milan Malpensa.

Milan, Italy

91% AI deal score

$4,626

$3,103

Save $1,523

Icelandair, +1

Business Class

Frequently Asked Questions About Flights to Milan

Cheap Flights from Chicago to Milan

Today’s best flight deals from Chicago to Milan

Chicago to Milan: Overview

Insights for flights from Chicago to Milan

How much is a round trip from Chicago to Milan

The cheapest time to fly from Chicago to Milan

Direct flights from Chicago to Milan

Last-minute flights going from Chicago to Milan

Biggest price drops on these dates for flights from Chicago to Milan

Popular Airports to fly from Chicago to Milan

Chicago - Milan route insights

Recent fares are near the typical level

Fly in January for prices as low as $585

Flights to Milan typically take 32h 9m

Connecting flights are dominant on this route

United Airlines offers direct flights

Deals appear frequently for this route

Chicago main airports to depart from

Milan main airports to arrive at

Airports nearby Milan used as alternative

Business & First Class Flight Deals to Milan

Best Elite deals to Milan

Nov 01

Nov 02

Oct 06

Dec 01

Dec 16

Nov 11

Nov 08

Nov 08

Nov 11

Nov 14

Nov 16

Nov 15

Frequently Asked Questions About Flights to Milan

How early should I book Chicago to Milan flights to get the cheapest price?

How much should a flight from Chicago to Milan cost?

Which months have the cheapest flights from Chicago to Milan?

Can I fly direct from Chicago to Milan?

How many hours is the flight from Chicago to Milan?

Are there frequently good prices on flights from Chicago to Milan?

Related routes

More routes from Chicago

Flights to Milan from other cities

Chicago to Milan: Overview

Insights for flights from Chicago to Milan

How much is a round trip from Chicago to Milan

The cheapest time to fly from Chicago to Milan

Direct flights from Chicago to Milan

Last-minute flights going from Chicago to Milan

Biggest price drops on these dates for flights from Chicago to Milan

Popular Airports to fly from Chicago to Milan

Chicago - Milan route insights

Recent fares are near the typical level

Fly in January for prices as low as $585

Flights to Milan typically take 32h 9m

Connecting flights are dominant on this route

United Airlines offers direct flights

Deals appear frequently for this route

Chicago main airports to depart from

Milan main airports to arrive at

Airports nearby Milan used as alternative

Business & First Class Flight Deals to Milan

Best Elite deals to Milan

Nov 01

Nov 02

Oct 06

Dec 01

Dec 16

Nov 11

Nov 08

Nov 08

Nov 11

Nov 14

Nov 16

Nov 15

Frequently Asked Questions About Flights to Milan

How early should I book Chicago to Milan flights to get the cheapest price?

How much should a flight from Chicago to Milan cost?

Which months have the cheapest flights from Chicago to Milan?