Cheap flights from Chicago (CHI) to Milan (MIL)

CHI — MIL
Feb 4 — Feb 111

The best prices from Chicago to Milan are usually found in February or March, booked 59 days in advance, depart on a Thursday or Monday and return on a Monday

How to find the cheapest flight from Chicago (CHI) to Milan (MIL)

All the information you need to plan the best CHI to MIL flight in 2023: compare Chicago to Milan flight prices with the expected peak season, weather and rainfall in Milan.

CHI - MIL

Price

$515 - $991

MIL

Temperature

33.8 - 71.6 °F

MIL

Rainfall

2.2 - 5.2 inches

Popular inJulyHigh demand for flights, 28% potential price rise
Cheapest inFebruaryBest time to find cheap flights, 27% potential price drop
Round-trip from$515From Chicago (CHI) to Milan (MIL)
One-way from$237One-way flight from Chicago (CHI) to Milan (MIL)

What is the cheapest day to fly round-trip from Chicago to Milan?

Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Milan. Check prices with Cheapflights to find a great deal for your trip.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 59 days in advance, which can save you up to 10% on flights from Chicago to Milan compared to booking the week you need them. Waiting 59 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $815. For sooner than that we have options available in the next 3 days from $900.

What is the cheapest month to fly from Chicago to Milan?

February is one of the best times of the year to fly to Milan from Chicago. Prices for February average $710 per person but you can even find prices for as low as $440. The most expensive prices can be found in the month of July. Opting for a February flight can save you 39% on your journey compared to booking in July

When is the cheapest time to fly from Chicago to Milan (CHI - MIL)?

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 15% on your trip compared to booking a flight in the evening.

Cheap flights from Chicago to Milan in January, February 2023

The best prices found for CHI to MIL flights for January, February
Feb 27 - Mar 6
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

18h 15m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

21h 10m
$402

TAP AIR PORTUGAL

Pick Dates

Deal found 1/28

Feb 24 - Mar 11
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

21h 05m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

21h 45m
$403

Scandinavian Airlines

Pick Dates

Deal found 1/29

Feb 16 - May 16
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

14h 05m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

24h 10m
$409

Scandinavian Airlines

Pick Dates

Deal found 1/28

Chicago to Milan 2023 flight deals

Cheap flights to Milan from Chicago found for this year
Feb 27 - Mar 6
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

18h 15m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

21h 10m
$402

TAP AIR PORTUGAL

Pick Dates

Deal found 1/28

Mar 3 - Mar 12
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

20h 35m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

27h 20m
$403

Scandinavian Airlines

Pick Dates

Deal found 1/28

Mar 5 - Mar 12
ORD

Chicago O'Hare Intl

LIN

Milan Linate

1 stop

13h 05m
LIN

Milan Linate

ORD

Chicago O'Hare Intl

1 stop

24h 30m
$404

Scandinavian Airlines

Pick Dates

Deal found 1/28

Cheap TAP AIR PORTUGAL flights from Chicago to Milan

Feb 27 - Mar 6
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

18h 15m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

21h 10m
$402

TAP AIR PORTUGAL

Pick Dates

Deal found 1/28

Apr 26 - May 3
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

19h 30m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

15h 30m
$407

TAP AIR PORTUGAL

Pick Dates

Deal found 1/28

Feb 27 - Mar 8
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

18h 15m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

15h 55m
$424

TAP AIR PORTUGAL

Pick Dates

Deal found 1/29

Cheap Scandinavian Airlines flights from Chicago to Milan

Mar 3 - Mar 12
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

20h 35m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

27h 20m
$403

Scandinavian Airlines

Pick Dates

Deal found 1/28

Mar 5 - Mar 12
ORD

Chicago O'Hare Intl

LIN

Milan Linate

1 stop

13h 05m
LIN

Milan Linate

ORD

Chicago O'Hare Intl

1 stop

24h 30m
$404

Scandinavian Airlines

Pick Dates

Deal found 1/28

May 8 - May 17
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

19h 20m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

13h 25m
$409

Scandinavian Airlines

Pick Dates

Deal found 1/28

Non-stop flights to Milan from Chicago

Save time with Chicago to Milan direct flight deals
May 1 - May 11
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

Nonstop

8h 55m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

Nonstop

9h 50m
$870

Lufthansa

Pick Dates

Deal found 1/28

Apr 26 - May 6
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

Nonstop

8h 55m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

Nonstop

9h 50m
$930

United Airlines

Pick Dates

Deal found 1/27

May 1 - Jun 14
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

Nonstop

8h 55m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

Nonstop

9h 50m
$1,240

United Airlines

Pick Dates

Deal found 1/30

Last minute flights from Chicago to Milan

Late deals on return flights to Milan from Chicago, departing today and this week
Feb 8 - Feb 28
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

14h 05m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

29h 10m
$415

Scandinavian Airlines

Pick Dates

Deal found 1/28

Feb 8 - Mar 1
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

18h 15m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

15h 55m
$466

TAP AIR PORTUGAL

Pick Dates

Deal found 1/28

Feb 4 - Feb 11
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

18h 15m
MXP

Milan Malpensa

ORD

Chicago O'Hare Intl

1 stop

21h 10m
$496

TAP AIR PORTUGAL

Pick Dates

Deal found 1/29

One-way flights to Milan from Chicago

The cheapest one-way flights from Chicago to Milan
Feb 20
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

2 stops

19h 05m
$229

Multiple Airlines

Pick Dates

Deal found 1/28

Mar 26
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

2 stops

35h 15m
$235

Multiple Airlines

Pick Dates

Deal found 1/28

Mar 29
ORD

Chicago O'Hare Intl

MXP

Milan Malpensa

1 stop

14h 30m
$237

TAP AIR PORTUGAL

Pick Dates

Deal found 1/29

Reviews of Airlines Servicing Milan

Delta
8.0
Very good
2,019 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.0

Food

7.2

Reviews

1 / 10

Great flight. Left gate early and arrived in Baton Rouge 6 minutes early.

Delta
8.0
Very good
2,019 reviews
Delta
8.0
Very good
2,019 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.0

Food

7.2

Reviews

1 / 10

Great flight. Left gate early and arrived in Baton Rouge 6 minutes early.

Air France
7.8
Good
113 reviews
Delta
8.0
Very good
2,019 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.0

Food

7.2

Reviews

1 / 10

Great flight. Left gate early and arrived in Baton Rouge 6 minutes early.

KLM
7.5
Good
115 reviews
Delta
8.0
Very good
2,019 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.0

Food

7.2

Reviews

1 / 10

Great flight. Left gate early and arrived in Baton Rouge 6 minutes early.

Scandinavian Airlines
6.9
Okay
103 reviews
Delta
8.0
Very good
2,019 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.0

Food

7.2

Reviews

1 / 10

Great flight. Left gate early and arrived in Baton Rouge 6 minutes early.

Aer Lingus
6.6
Okay
239 reviews
Delta
8.0
Very good
2,019 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.0

Food

7.2

Reviews

1 / 10

Great flight. Left gate early and arrived in Baton Rouge 6 minutes early.

Related info for your journey

Useful info, stats and facts about Chicago to Milan flights.

Which airlines flying from Chicago to Milan have flexible cancellations due to COVID-19?

Some of our airline partners flying from Chicago to Milan have new flexible policies in place due to COVID-19. United Airlines, Scandinavian Airlines, and Lufthansa are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like United Airlines with this kind of flexibility.

Can I find flights from Chicago to Milan for under $500 on Cheapflights?

Yes, there are multiple flights from Chicago to Milan for under $500. The cheapest flight booked recently is on TAP AIR PORTUGAL for just $402, but on average you can expect to pay $440.

Are there nonstop flights from Chicago to Milan for under $900 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Milan under $900. A good price for a nonstop flight from Chicago to Milan is less than $1,470.

Are there last-minute flights available from Chicago to Milan for under $500?

There are currently 20+ open flights from Chicago to Milan within the next 7 days for less than $500.

What are the cheapest airlines flying from Chicago to Milan round-trip?

Currently priced at $402, 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. Check Cheapflights for deals on Scandinavian Airlines for as low as $403. Users have found that TAP AIR PORTUGAL is 43% 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 popular airlines that fly from Chicago to Milan?

Consider American Airlines, Air Canada or Air France when booking your flight. These represent the most popular airlines when flying from Chicago to Milan.

What are the cheapest flights from Chicago to Milan?

The cheapest flight price from Chicago to Milan is $195. On average you can expect to pay $1,026. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $402.

Top 10 airlines flying from Chicago to Milan

The chart below displays the airlines Cheapflights users traveling from Chicago to Milan choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$12Average$18FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
KLMCheapest$371Average$669FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search KLM flights
TAP AIR PORTUGALCheapest$381Average$416FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesCheapest$392Average$508FlexibilityNo cancel feeOn-time77%COVID-19 safety
Search Scandinavian Airlines flights
DeltaCheapest$421Average$601FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
SWISSCheapest$439Average$789FlexibilityNo cancel feeOn-time79%COVID-19 safety
Search SWISS flights
LufthansaCheapest$446Average$754FlexibilityNo cancel feeOn-time76%COVID-19 safety
Search Lufthansa flights
British AirwaysCheapest$475Average$810FlexibilityNo cancel feeOn-time70%COVID-19 safety
Search British Airways flights
Air CanadaCheapest$492Average$787FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
American AirlinesCheapest$499Average$687FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
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