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.
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CHI - MIL Price
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$613 - $901
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MIL Temperature
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33.8 - 71.6 °F
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MIL Precipitation
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2.2 - 5.2 inches
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Popular in December High demand for flights, 19% potential price rise |
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Cheapest in February Best time to find cheap flights, 16% potential price drop |
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Round-trip from $613 From Chicago (CHI) to Milan (MIL) |
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One-way from $393 One-way flight from Chicago (CHI) to Milan (MIL) |
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
$393
Kiwi.com
5:15 pm - 6:30 pm
TAP AIR PORTUGAL
1 Stop
18h 15m
ORD - MXP
$396
mytrip.com
7:05 pm - 8:45 am
SAS
2 Stops
31h 40m
ORD - LIN
$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.
COVID Restrictions
View COVID Travel Restrictions for Milan, Italy
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 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 | |
|---|---|---|---|---|---|---|
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$335 | $660 | No cancel fee | N/A | ||
|
$410 | $604 | No cancel fee | 77% | ||
|
$476 | $832 | No cancel fee | 70% | ||
|
$497 | $827 | No cancel fee | 77% | ||
|
$512 | $945 | No cancel fee | 76% | ||
|
$515 | $615 | No cancel fee | 71% | ||
|
$561 | $889 | No cancel fee | 69% | ||
|
$566 | $892 | No cancel fee | 67% | ||
|
$594 | $848 | No cancel fee | N/A | ||
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$663 | $1,036 | No cancel fee | 79% |