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  1. Flights
  2. Italy
  3. Milan
  4. Chicago - Milan

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

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Discover the cheapest flights from Chicago to Milan
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Sat, Apr 25 - Fri, May 1
Turkish Airlines
Turkish Airlines1 stop
CHI - MIL
Turkish Airlines
Turkish Airlines1 stop
MIL - CHI
433$
422$
Prime price per passenger
Thu, May 7 - Sat, May 9
Icelandair
Icelandair2 stops
CHI - MIL
Air Serbia
Air Serbia1 stop
MIL - CHI
761$
739$
Prime price per passenger
Sun, May 24 - Mon, May 25
Scandinavian Airlines
Scandinavian Airlines1 stop
CHI - MIL
Scandinavian Airlines
Scandinavian Airlines1 stop
MIL - CHI
812$
788$
Prime price per passenger
Wed, Jul 1 - Mon, Jul 6
Turkish Airlines
Turkish Airlines1 stop
CHI - MIL
Turkish Airlines
Turkish Airlines1 stop
MIL - CHI
986$
964$
Prime price per passenger
Sun, Jun 21 - Tue, Jun 23
Turkish Airlines
Turkish Airlines1 stop
CHI - MIL
Turkish Airlines
Turkish Airlines1 stop
MIL - CHI
1066$
1044$
Prime price per passenger
Sun, Jun 7 - Wed, Jun 10
TAP Portugal
TAP Portugal1 stop
CHI - MIL
TAP Portugal
TAP Portugal1 stop
MIL - CHI
1132$
1080$
Prime price per passenger
Sun, Apr 26
Air Serbia
Air Serbia1 stop
CHI - MIL
530$
494$
Prime price per passenger
Fri, May 8
Swiss International Air Lines
Swiss International Air Lines2 stops
CHI - MIL
516$
501$
Prime price per passenger
Sun, Jul 5
TAP Portugal
TAP Portugal1 stop
CHI - MIL
527$
513$
Prime price per passenger
Mon, Jun 22
TAP Portugal
TAP Portugal1 stop
CHI - MIL
779$
755$
Prime price per passenger
Mon, May 18
ITA Airways
ITA Airways1 stop
CHI - MIL
805$
768$
Prime price per passenger
Sun, Jun 7
Turkish Airlines
Turkish Airlines1 stop
CHI - MIL
801$
799$
Prime price per passenger
The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Chicago to Milan

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available at the end of June. Take advantage of this period to save on your flight tickets and make the most of your trip. Please note that prices may change after your search.
Filter by
week: Jun 29 - Jul 5
Flights from just $760
$808
$828
$869
$840
$834
$842
$887
$838
$779
$760
$778
$846
AprilMayJuneJuly
Flying Time13 h and 15 mWhen flying from Chicago to Milan, this can take around 13 h and 15 m in flying time, however this flight duration can vary due to other factors
Cheapest flight$422The best price for flights from Chicago to Milan offered by eDreams, which have been found by our customers in the last 3 days
Origin airportsO'hare International Airport, Midway International AirportFor flights from Chicago to Milan
Destination airportsMilan Malpensa Airport, Linate Airport, Orio al Serio International AirportWhen traveling from Chicago to Milan
Peak seasonMarchMarch is the busiest time to fly from Chicago to Milan according to search data results from our customers
One-way average Price$790A flight from Chicago to Milan at eDreams will cost around $790, this being based on prices of the previous 6 months of data
Best time to bookMarchAugust is one of the most frequent times to fly to Milan from Chicago according to real data from our customers
Distance: 4535 miles
Chicago airports
O'hare International Airport (ORD)How far from city center: 14 miles
Midway Airport (MDW)How far from city center: 4 miles
Milan airports
Malpensa (MXP)How far from city center: 24 miles
Linate (LIN)How far from city center: 5 miles
Orio Al Serio (BGY)How far from city center: 29 miles

Are you planning to travel to Milan for vacations, business or family visits? eDreams offers you the cheapest flights and best deals departing from Chicago. With our fast search engine you will get a large selection of airfares from standard and low cost airlines worldwide and easily book your tickets for this route. If you are flexible we help you identify the cheapest day to fly to Milan and if you need to leave soon you can check our most convenient last minute fares. Read all the useful information about your next destination and proceed to the reservation, indicating your flight dates and completing your travel booking with hotels and car rental!

Frequently asked questions about flights from Chicago to Milan

What are the benefits of booking flexible flight tickets?
Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to Italy. At eDreams have you covered!
On average, how much is the price of a flight from Chicago to Milan?
When you fly from Chicago to Milan the average price is $790. However, this price depends on many other factors such as seasonality or how far in advance the route has been booked.
For flights from Chicago to Milan, how can I find the cheapest price?
The cheapest price for a flight from Chicago to Milan is $422. At eDreams we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.
When booking, when is the best time to get the best prices for flights from Chicago to Milan?
The most popular months to book a trip from Chicago to Milan are January, October and September, based on the searches of our customers.
When is the best time to travel from Chicago to Milan?
The best time of the year to visit Milan depends on lots of personal preferences, especially the price. Regarding popularity, May is the best month to fly to Milan from Chicago in terms of searches from our customers, followed by June and October. If you prefer to avoid the busy season and get away from the crowds November, April and March are the months with fewer searches for Chicago - Milan.
How long does the flight from Chicago to Milan take?
Flight length from Chicago to Milan is around 13 h and 15 m on average, at an average distance of 4,535.18 mi, for flights for the route (which may have 1 or more stops in other cities in between).

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