Cheap flights from Chicago to Milan from $319
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Milan departing on 1/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
ChicagoBergamo
ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio
ORDBGY
Chicago O'Hare Intl
Tue 11/3
7:10 pm-12:25 am
2 stops22h 15m
Bergamo Orio Al Serio
Tue 11/10
8:05 pm-4:45 pm
2 stops27h 40m
ChicagoBergamo
ORD Chicago O'Hare Intl - BGY Bergamo Orio Al Serio
ORDBGY
Chicago O'Hare Intl
Tue 11/3
7:10 pm-12:25 am
2 stops22h 15m
Bergamo Orio Al Serio
Tue 11/10
8:05 pm-4:45 pm
2 stops27h 40m
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Fri 1/22
7:10 pm-10:30 am
1 stop32h 20m
Milan Malpensa
Sun 1/31
11:20 am-4:45 pm
1 stop12h 25m
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Fri 11/27
7:10 pm-10:30 am
1 stop32h 20m
Milan Malpensa
Wed 12/2
8:05 pm-4:45 pm
1 stop27h 40m
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Fri 10/30
9:10 pm-11:35 pm
1 stop20h 25m
Milan Malpensa
Thu 11/12
5:45 pm-3:30 pm
1 stop28h 45m
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Sun 11/8
8:10 pm-4:55 pm
1 stop13h 45m
Milan Malpensa
Tue 11/24
5:45 pm-3:30 pm
1 stop28h 45m
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Sun 11/8
3:55 pm-11:05 am
1 stop12h 10m
Milan Linate
Tue 11/24
11:45 am-6:20 pm
1 stop13h 35m
ChicagoMilan
ORD Chicago O'Hare Intl - LIN Milan Linate
ORDLIN
Chicago O'Hare Intl
Sun 11/8
3:55 pm-11:05 am
1 stop12h 10m
Milan Linate
Tue 11/24
11:45 am-6:20 pm
1 stop13h 35m
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Sun 11/8
9:35 pm-1:15 pm
Nonstop8h 40m
Milan Malpensa
Tue 11/24
3:15 pm-6:15 pm
Nonstop10h 00m
ChicagoMilan
ORD Chicago O'Hare Intl - MXP Milan Malpensa
ORDMXP
Chicago O'Hare Intl
Sun 11/8
9:48 pm-7:30 am
1 stop26h 42m
Milan Malpensa
Tue 11/24
1:05 pm-8:00 am
1 stop25h 55m
See travel insights to Milan from
How to get the cheapest flight ticket from Chicago to Milan
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago and Milan?
Prices are currently low for flights on this route.
Typical prices usually range from $609 to $961.The lowest price recently found on this route was $562.
What is the cheapest month to fly to Milan?
The month of January is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $551. The month of February is another great option to travel to Milan, with average flight prices from Chicago averaging around $587.
What is the cheapest day to depart on your flight to Milan?
Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,253. The most expensive day to fly to Milan is Sunday, with ticket prices averaging around $1,526.
What is the cheapest Chicago to Milan flight route?
Fly from Chicago O'Hare Intl to Milan Malpensa for the best Chicago - Milan flight prices
How far in advance should I book a flight from Chicago to Milan?
You are more likely to see cheaper flights to Milan from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Milan for around $884 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan from Chicago for as low as $561 on momondo.
What cabin class options are available on Chicago to Milan flights?
There are 4 cabin classes available to choose from on Chicago to Milan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to Milan flights?
You could potentially save up to 4% on your flight if you consider stops on a Chicago to Milan flight.
What is the cheapest airline that flies from Chicago to Milan?
Air Serbia, Aer Lingus, and Turkish Airlines are the most popular carriers operating from Chicago to Milan
What airlines fly to Milan?
United Airlines, Scandinavian Airlines and TAP AIR PORTUGAL are the top three most popular airlines that fly to Milan from Chicago according to our data. United Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Milan. Keep in mind that there are 5 different airlines that fly to Milan on a routine basis, so you have a few additional options to choose from.
Which airport is the most popular layover for flights between Chicago and Milan?
Copenhagen (CPH) was the most common stop: 39% of momondo users choosing 1-stop flights on this route connected there.
Which layover airport offers the lowest fares from Chicago to Milan?
Flights via Reykjavik (KEF) offer the lowest average round-trip price of $403.
Which layover airport has the shortest travel time from Chicago to Milan?
Flights connecting via Frankfurt am Main (FRA) have the shortest average one-way travel time: 11h 58m.
Which layover airport has the shortest connection time from Chicago to Milan?
Rome (FCO) has the shortest average layover time for this route: 1h 25m.
How many flights depart from Chicago to Milan on average per day?
As of October 2026, there are 5 flights per day flying from Chicago to Milan. The most common time of day flights depart is 9:00PM, with 100% of flights taking off in the evening.
How many flights depart from Chicago to Milan on average per week?
As of October 2026, there are 35 flights per week flying from Chicago to Milan. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.
When to book flights from Chicago to Milan
Cheap Chicago to Milan (CHI to MIL) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Milan
Frequently asked questions about flying from Chicago to Milan
How far is Chicago to Milan by plane?
There are 4526.2 mi between Chicago and Milan. By plane, this route typically takes 8h 40m.
When did momondo last update prices for flights from Chicago to Milan?
Prices for flights from Chicago to Milan are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Milan?
The number of operators available for flights from Chicago to Milan is 5 as of October 2026.
How old do you have to be to fly from Chicago to Milan?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Milan.
What documentation or ID do you need to fly to Milan?
The required travel and health documents for your Milan trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Milan. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago to Milan?
Based on momondo bookings for flights between Chicago and Milan, the leading plane model is Boeing 787-10 Dreamliner, making up 52.58% of the total bookings. Other popular models include Boeing 787-8 Dreamliner with 35.41%, Boeing 787 Dreamliner with 9.23%, and Boeing 787-9 Dreamliner with 0.86%.
What is the most popular airline from Chicago to Milan?
momondo data reveals that the most frequently booked airline on the route from Chicago to Milan is Scandinavian Airlines, representing 33% of all bookings. The subsequent popular airlines are United Airlines at 29%, Lufthansa at 12%, and Aer Lingus at 8%.
Best airlines flying from Chicago to Milan
Compare and see reviews for airlines that fly from Chicago to Milan with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $408 | Free Cancellation | Rating 7.2 2,383 reviews | |||
| PriceFrom $445 | Free Cancellation | Rating 7.4 2,007 reviews | |||
| PriceFrom $627 | Free Cancellation | Rating 7.3 1,818 reviews | |||
| PriceFrom $780 | Free Cancellation | Rating 7.4 10,295 reviews | |||
| PriceFrom $786 | Free Cancellation | Rating 6.8 8,263 reviews |
United Airlines Flights From Chicago to Milan
United Airlines operates around 7 flights from Chicago to Milan every week. The average price of these flights found in the last 72 hours has been $1,236, but momondo users have found United Airlines deals from Chicago to Milan from as low as $780 round-trip. United Airlines has been scored 7.4/10 in 10,295 reviews.
Lufthansa Flights From Chicago to Milan
Lufthansa is also a popular choice for this route. Lufthansa flight deals for Chicago to Milan start from as low as $786 round-trip, depending on your selected dates, with average Lufthansa deals seen on momondo around $1,193. Lufthansa operates 7 flights to Milan from Chicago in an average week. Users have rated it 6.8/10 across 8,263 reviews.
Traveling to a place near Milan?
Book flights to Milan if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Milan?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Milan from Chicago.
Can I find flights from Chicago to Milan with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.
How can momondo help me find flights from Chicago to Milan?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Milan.
I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Milan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.