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 Thursday and return on a Friday

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 2022: 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
Rainfall
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

$333

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 day to fly round-trip from Chicago to Milan?

Flying to your destination on a Friday 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.

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 December

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 morning. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight in the evening.

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.

Cheap flights from Chicago to Milan in May, June 2022

The best prices found for CHI to MIL flights for May, June
15 Jun - 25 Jun
$547pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
MXP
Milan Malpensa
MXP
Milan Malpensa
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
15 Jun - 25 Jun
$550pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
MXP
Milan Malpensa
MXP
Milan Malpensa
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
15 Jun - 25 Jun
$554pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
MXP
Milan Malpensa
MXP
Milan Malpensa
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Chicago to Milan 2022 flight deals

Cheap flights to Milan from Chicago found for this year
10 Sep - 27 Sep
$391pp
ORD
Chicago O'Hare Intl
Scandinavian Airlines
   
2 STOPS
MXP
Milan Malpensa
MXP
Milan Malpensa
Scandinavian Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
10 Sep - 27 Sep
$393pp
ORD
Chicago O'Hare Intl
Scandinavian Airlines
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
Scandinavian Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
10 Sep - 27 Sep
$397pp
ORD
Chicago O'Hare Intl
Scandinavian Airlines
 
1 STOP
LIN
Milan Linate
LIN
Milan Linate
Scandinavian Airlines
   
2 STOPS
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
27 May - 4 Jun
$581pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
LIN
Milan Linate
LIN
Milan Linate
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
27 May - 8 Jun
$627pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
LIN
Milan Linate
LIN
Milan Linate
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
23 May - 10 Sep
$669pp
ORD
Chicago O'Hare Intl
Scandinavian Airlines
 
1 STOP
MXP
Milan Malpensa
MXP
Milan Malpensa
Scandinavian Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

One-way flights to Milan from Chicago

The cheapest one-way flights from Chicago to Milan
6:05 pm - 8:05 am
Scandinavian Airlines
2 Stops
31h 00m
ORD - LIN
Scandinavian Airlines
$333
ChatDeal
6:05 pm - 3:35 pm
TAP AIR PORTUGAL
1 Stop
14h 30m
ORD - MXP
TAP AIR PORTUGAL
4:10 am - 2:55 pm
Multiple Airlines
3 Stops
27h 45m
ORD - LIN
Multiple Airlines
$350
Kiwi.com

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. United Airlines, Scandinavian Airlines, and TAP AIR PORTUGAL 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 $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Milan for under $400. The cheapest flight booked recently is on Scandinavian Airlines for just $391, but on average you can expect to pay $427.

Are there last-minute flights available from Chicago to Milan for under $600?

There are currently 20+ open flights from Chicago to Milan within the next 7 days for less than $600.

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

Currently priced at $391, Scandinavian Airlines will fly you from Chicago to Milan and back. In addition to Scandinavian Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on TAP AIR PORTUGAL for as low as $437. Users have found that Scandinavian Airlines is 46% cheaper than the other options available to this destination.

What are the most popular airlines that fly from Chicago to Milan?

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

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 cheapest flights from Chicago to Milan?

The cheapest flight price from Chicago to Milan is $428. On average you can expect to pay $1,174. The most popular route, (Chicago O'Hare Intl - Milan Malpensa), can usually be booked for $413.

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 RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours for RT-PCR (NAAT) and 48 hours for Antigen (quick-test) before departing to Milan.

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

Documents
COVID-19 Green Certificate - Mandatory to access the inpatient departments of hospitals and nursing homes as visitors. It is useful for staying as carers for non-Covid-19 patients in emergency rooms, health, and social health facilities.


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 1 day for RT-PCR (NAAT) and 1 day for Antigen (quick-test) 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 = €0.96
Average temperature for May in Milan
75.2 °F
Avg rainfall for May in Milan
2.8 ″

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Milan

Milan Linate (LIN)

Top 8 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
$269 $451 No cancel fee N/A
SWISS
$392 $785 No cancel fee 79%
Scandinavian Airlines
$414 $577 No cancel fee 77%
Delta
$421 $565 No cancel fee N/A
Lufthansa
$437 $785 No cancel fee 76%
American Airlines
$503 $750 No cancel fee 71%
United Airlines
$532 $816 No cancel fee 69%
British Airways
$643 $793 No cancel fee 70%

Hourly flight availability from Chicago to Milan

See what time of day planes typically take off from Chicago towards Milan.
Evening 6 PM to midnight 100% of CHI to MIL departures
Early morning Midnight to 6 AM 0% of CHI to MIL departures
Morning 6 AM to noon 0% of CHI to MIL departures
Afternoon Noon to 6 PM 0% of CHI to MIL departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to Milan
See how many times per day planes take to the skies headed from Chicago to Milan.
Sunday
2 daily flights
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
2 daily flights
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