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

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The best prices from Chicago to Milan are usually found in February or January, booked 58 days in advance, depart on a Monday or Wednesday and return on a Tuesday

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 2021: compare Chicago to Milan flight prices with the expected peak season, weather and rainfall in Milan.
CHI - MIL
Price
$613 - $901
MIL
Temperature
33.8 - 71.6 °F
MIL
Precipitation
2.2 - 5.2 inches

Popular in

December

High demand for flights, 19% potential price rise

Cheapest in

February

Best time to find cheap flights, 16% potential price drop

Round-trip from

$613

From Chicago (CHI) to Milan (MIL)

One-way from

$393

One-way flight from Chicago (CHI) to Milan (MIL)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
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 $730 per person but you can even find prices for as low as $471. The most expensive prices can be found in the month of December. Opting for a February flight can save you 23% on your journey compared to booking in February

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 58 days in advance, which can save you up to 63% on flights from Chicago to Milan compared to booking the week you need them. Waiting 58 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 $974. For sooner than that we have options available in the next 3 days from $1,407.

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

Flying to your destination on a Thursday 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.

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 18% on your trip compared to booking a flight in the morning.

Cheap flights from Chicago to Milan in October, November 2021

The best prices found for CHI to MIL flights for October, November
3 Nov - 26 Nov
$353pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
3 Nov - 21 Nov
$360pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
7 Nov - 21 Nov
$361pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Milan 2021 flight deals

Cheap flights to Milan from Chicago found for this year
3 Nov - 26 Nov
$353pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
3 Nov - 21 Nov
$360pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
7 Nov - 21 Nov
$361pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Milan

Late deals on round-trip flights to Milan from Chicago, departing today and this week
28 Oct - 10 Nov
$363pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
28 Oct - 11 Nov
$366pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl
28 Oct - 10 Nov
$377pp
ORD
Chicago O'Hare Intl
TAP AIR PORTUGAL
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
TAP AIR PORTUGAL
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Milan from Chicago

The cheapest one-way flights from Chicago to Milan
5:30 am - 3:15 am
Multiple Airlines
3 Stops
38h 45m
MDW - LIN
Multiple Airlines
$393
Kiwi.com
5:15 pm - 6:30 pm
TAP AIR PORTUGAL
1 Stop
18h 15m
ORD - MXP
TAP AIR PORTUGAL
$396
mytrip.com
7:05 pm - 8:45 am
SAS
2 Stops
31h 40m
ORD - LIN
SAS
$398
KAYAK

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Milan</span> flights.

Flight FAQs

From Chicago to Milan

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. SAS, Aer Lingus, and American Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like SAS with this kind of flexibility.

Can I find flights from Chicago to Milan for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Milan for under $400. The cheapest flight booked recently is on TAP AIR PORTUGAL for just $353, but on average you can expect to pay $383.

Are there last-minute flights available from Chicago to Milan for under $400?

There are currently 20+ open flights from Chicago to Milan within the next 7 days for less than $400.

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

Currently priced at $353, 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 SAS for as low as $388. 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 popular airlines that fly from Chicago to Milan?

Consider American Airlines, Air Canada or British Airways 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 $288. On average you can expect to pay $1,784. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $353.

COVID Restrictions

View COVID Travel Restrictions for Milan, Italy

Do I need a COVID test to fly to Milan from Chicago?

Information is based on travel restrictions from Chicago to Milan

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Milan.

COVID-19 testing requirements
Visitors from Chicago must present a negative Antigen (quick-test) test taken 72 or 48 hours before departing to Milan.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Milan.

Do I need a test to fly back to Chicago from Milan?

Returning to Chicago from Milan

COVID-19 testing requirements
Visitors from Milan must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Milan are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Milan, Italy

Destination information for Milan

Things to know before you go - useful duration and weather info for your trip from Chicago to Milan.
Today's exchange rate
$1 = €0.86
Average temperature for October in Milan
66.2 °F
Avg rainfall for October in Milan
3.5 ″

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Milan

Milan Linate (LIN)

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.
Airline Cheapest Average Flexibility On-time COVID-19 safety
TAP AIR PORTUGAL
$335 $660 No cancel fee N/A
Turkish Airlines
$410 $604 No cancel fee 77%
British Airways
$476 $832 No cancel fee 70%
SAS
$497 $827 No cancel fee 77%
Lufthansa
$512 $945 No cancel fee 76%
American Airlines
$515 $615 No cancel fee 71%
United Airlines
$561 $889 No cancel fee 69%
Air Canada
$566 $892 No cancel fee 67%
Aer Lingus
$594 $848 No cancel fee N/A
SWISS
$663 $1,036 No cancel fee 79%
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