Can I fly direct from Chicago to Milan?

Direct flights from Chicago to Milan are not commonly available. Historically, only 3.1% of flights on this route have been direct. When connecting flights are necessary, travelers typically experience a median of 2 stopovers. This data is based on observations from the trailing 90 days.

How many hours is the flight from Chicago to Milan?

A direct flight from Chicago to Milan typically takes approximately 8 hours and 40 minutes, covering a distance of 7259 kilometers. For flights with one stop, the median duration increases to about 14 hours and 14 minutes. This difference highlights the convenience of direct routes when available.

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

Historically, good prices on flights from Chicago to Milan are frequently available. This route is classified as having frequent good price opportunities. Travelers can often find competitive deals when planning their trips.

Flights From Chicago

To Milan

Cheap Flights from Chicago to Milan

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Deals from

Chicago

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

Prices updated 1 day ago

461 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 14, 2026.)

Today’s best flight deals from Chicago to Milan

Explore current cheapest deals departing from Chicago to Milan

2026-11-04 – 2026-11-11
CHI - Milan
76% AI deal score
$553
$513
Round trip
2026-11-04 – 2026-11-13
CHI - Milan
75% AI deal score
$536
$513
Round trip
2026-11-17 – 2026-11-24
CHI - Milan
79% AI deal score
$556
$516
Round trip
2026-11-12 – 2026-11-16
CHI - Milan
77% AI deal score
$573
$520
Round trip
2026-11-12 – 2026-11-22
CHI - Milan
77% AI deal score
$538
$521
Round trip
2026-11-11 – 2026-11-24
CHI - Milan
77% AI deal score
$537
$525
Round trip
2026-11-11 – 2026-11-25
CHI - Milan
77% AI deal score
$537
$526
Round trip
2027-01-15 – 2027-01-24
CHI - Milan
89% AI deal score
$674
$527
Round trip
2026-11-16 – 2026-11-26
CHI - Milan
77% AI deal score
$541
$528
Round trip
2026-11-13 – 2026-11-22
CHI - Milan
77% AI deal score
$544
$529
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: $481 - $1,257

Prices are currently within the regular range.

The regular price range for flights from Chicago to Milan is $481 to $1257. The current lowest deal is $513 with Icelandair, for travel from Nov 4-Nov 11.

now $513

Low $481

High $1,257

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

Sun, Sep 27

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (LIN)

Aer Lingus

$844

$745

One-way

Sat, Oct 3

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$670

$600

One-way

Sun, Oct 4

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

Turkish Airlines

$659

$731

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

Aer Lingus

$662

$625

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

Air Canada

$679

$635

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (LIN)

Aer Lingus

$644

$666

One-way

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

2 nights

Dec 4 - Dec 6

$893 → $566

37%

7 nights

Dec 1 - Dec 8

$852 → $529

38%

3 nights

Dec 3 - Dec 6

$884 → $573

35%

6 nights

Dec 6 - Dec 12

$861 → $554

36%

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

January offers the lowest median prices

Historically, January, November, and April offer the lowest median prices for this route.

⏱️ Flight duration

Typically 32h 9m with stopovers

Flights from Chicago to Milan typically take 32h 9m, with a median of 2 stopovers.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 96.9% of recent bookings, with frequent deals available.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers offering direct flights on this long-haul route.

🎯 Booking tip

Consider Icelandair for deals

A recent deal from Icelandair was found for $513, for travel from Nov 4-Nov 11.

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

Chicago Midway International (MDW)

Chicago Midway International Airport is an option for travelers flying from Chicago to Milan.

📍 ~14 km from Chicago (reachable by car or train)

💸 Flights from ~$781

Chicago Rockford International (RFD)

Chicago Rockford International Airport provides an alternative departure choice for your trip to Milan.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$1,078

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)

Milan, Italy

92% AI deal score

$2,593

$1,409

Save $1,184

TAP Portugal

Business Class

From ORD

Elite

Dec 27

Milan, Italy

92% AI deal score

$2,581

$1,413

Save $1,168

TAP Portugal

Business Class

From ORD

Elite

Oct 14

Milan, Italy

92% AI deal score

$2,300

$1,518

Save $782

Scandinavian Airlines

Business Class

From ORD

Elite

Dec 09

Milan, Italy

92% AI deal score

$2,566

$1,763

Save $803

Scandinavian Airlines

Business Class

From ORD

Elite

Nov 09

Milan, Italy

91% AI deal score

$4,419

$2,954

Save $1,465

Icelandair, +1

Business Class

From ORD

Elite

Nov 08

Milan, Italy

91% AI deal score

$4,415

$3,031

Save $1,384

Icelandair, +1

Business Class

From ORD

Elite

Nov 08

Milan, Italy

91% AI deal score

$4,419

$3,036

Save $1,383

Icelandair, +1

Business Class

From ORD

Elite

Nov 14

Milan, Italy

91% AI deal score

$4,522

$3,087

Save $1,435

Icelandair, +1

Business Class

From ORD

Elite

Nov 15

Milan, Italy

91% AI deal score

$4,606

$3,096

Save $1,510

Icelandair, +1

Business Class

From ORD

Elite

Nov 16

Milan, Italy

91% AI deal score

$4,668

$3,096

Save $1,572

Icelandair, +1

Business Class

From ORD

Elite

Nov 02

Milan, Italy

91% AI deal score

$4,604

$3,148

Save $1,456

Icelandair, +1

Business Class

Frequently Asked Questions About Flights to Milan

Historically, the best prices for flights from Chicago to Milan are found when booking between 14 and 27 days in advance. During this period, the average price is typically around $737. Booking within 6 days of departure sees the average price rise to approximately $977. For those planning further ahead, booking 60 or more days out usually results in an average price of $1072.

Based on historical data from the trailing 90 days, a good price for a flight from Chicago to Milan is considered to be $904 or less. The median price for this route has been $1047. Prices can vary, with 75% of flights typically costing $1227 or less.

Historically, the cheapest months to fly from Chicago to Milan are January, with a median price of $585, and November, with a median price of $591. April also offers competitive prices, with a median of $653. Across the trailing quarter, the annual median price for this route was $1047, indicating significant savings during these months.

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: $481 - $1,257

Prices are currently within the regular range.

The regular price range for flights from Chicago to Milan is $481 to $1257. The current lowest deal is $513 with Icelandair, for travel from Nov 4-Nov 11.

now $513

Low $481

High $1,257

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

Sun, Sep 27

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (LIN)

Aer Lingus

$844

$745

One-way

Sat, Oct 3

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

TAP Portugal

$670

$600

One-way

Sun, Oct 4

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

Turkish Airlines

$659

$731

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

Aer Lingus

$662

$625

One-way

Mon, Oct 5

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (MXP)

Air Canada

$679

$635

One-way

Tue, Oct 6

⌛ Last-Minute

ORD - Milan

Chicago (ORD) - Milan (LIN)

Aer Lingus

$644

$666

One-way

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

2 nights

Dec 4 - Dec 6

$893 → $566

37%

7 nights

Dec 1 - Dec 8

$852 → $529

38%

3 nights

Dec 3 - Dec 6

$884 → $573

35%

6 nights

Dec 6 - Dec 12

$861 → $554

36%

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

January offers the lowest median prices

Historically, January, November, and April offer the lowest median prices for this route.

⏱️ Flight duration

Typically 32h 9m with stopovers

Flights from Chicago to Milan typically take 32h 9m, with a median of 2 stopovers.

✈️ Airlines & availability

Connecting flights are dominant

Connecting flights make up 96.9% of recent bookings, with frequent deals available.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers offering direct flights on this long-haul route.

🎯 Booking tip

Consider Icelandair for deals

A recent deal from Icelandair was found for $513, for travel from Nov 4-Nov 11.

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

Chicago Midway International (MDW)

Chicago Midway International Airport is an option for travelers flying from Chicago to Milan.

📍 ~14 km from Chicago (reachable by car or train)

💸 Flights from ~$781

Chicago Rockford International (RFD)

Chicago Rockford International Airport provides an alternative departure choice for your trip to Milan.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$1,078

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

$4,604

$3,148

Save $1,456

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

January offers the lowest median prices

Typically 32h 9m with stopovers

Connecting flights are dominant

United Airlines offers direct flights

Consider Icelandair for deals

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

Dec 30

Dec 16

Dec 27

Oct 14

Dec 09

Nov 09

Nov 08

Nov 08

Nov 14

Nov 15

Nov 16

Nov 02

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

January offers the lowest median prices

Typically 32h 9m with stopovers

Connecting flights are dominant

United Airlines offers direct flights

Consider Icelandair for deals

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

Dec 30

Dec 16

Dec 27

Oct 14

Dec 09

Nov 09

Nov 08

Nov 08

Nov 14

Nov 15

Nov 16

Nov 02

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?