Flights from Chicago to Milan, Italy

Did you mean flights from Milan to Chicago?

Chicago to Milan Last modified: Sep 19, 2023 12:10 -04:00

We've scanned 109,155,000 round trip itineraries and found the cheapest flights to Milan. Tap Portugal & United frequently offer the best deals to Milan flights, or select your preferred carrier below to see the cheapest days to fly.

Tap Portugal
Fri 11/10
1 stop
Thu 11/16
1 stop
Tue 10/3
Tue 10/10
Multiple Airlines
Wed 10/18
1 stop
Tue 10/24
1 stop
Wed 10/11
Wed 10/18
Multiple Airlines
Thu 12/7
2 stops
Thu 12/14
2 stops
Major Airlines
Sun 10/1
1 stop
Wed 10/18
1 stop

How Much is a Flight from Chicago to Milan?

We have collected flight cost data from across the web for travel from Chicago to Milan, and have found the average flight price for this trip to be $572.

Where To Buy Cheap Flights from Chicago to Milan?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Chicago to Milan based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Chicago to Milan?

The chart below shows up-to-date information regarding how far in advance to book your flight from Chicago to Milan.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $1,666 $670
7-14 days $609 $605
14-21 days $605 $605
21-30 days $605 $605
30-60 days $659 $497
60-90 days $1,245 $497
90+ days $1,249 $497

Cheapest Day To Fly from Chicago to Milan

We've examined 218,310,000 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to Milan is Saturday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday

Compare Flight Prices from Chicago to Milan by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Chicago to Milan flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
September Chicago Milan Tap Portugal 9/27/23 10/4/23 1 $605
October Chicago Milan United 10/3/23 10/10/23 0 $605
November Chicago Milan Tap Portugal 11/10/23 11/16/23 1 $497
December Chicago Milan Tap Portugal 12/3/23 12/12/23 1 $579
January Chicago Milan Tap Portugal 1/19/24 1/26/24 1 $497
February Chicago Milan Tap Portugal 2/4/24 2/10/24 1 $497
March Chicago Milan Tap Portugal 3/3/24 3/12/24 1 $497
April Chicago Milan Tap Portugal 4/19/24 4/26/24 1 $497

Cheap Last Minute Flights from Chicago to Milan

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Milan. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

17 18 19 20 21 22 23
24 25 26 27 28 29 30
$1,157 $868
1 2 3 4 5 6 7
$868 $692
8 9 10 11 12 13 14
$692 $659
15 16 17 18 19 20 21
$659 $659
22 23 24 25 26 27 28

Connecting Flights vs Direct Flights from Chicago to Milan

Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Chicago to Milan is $669.

The average price for direct flights from Chicago to Milan is $1,497.

One Way Flights vs Round Trip Flights from Chicago to Milan

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Milan. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to Milan is $372.

The average price for round trip flights from Chicago to Milan is $669.

Chicago to Milan Flight Questions

Airlines in Chicago flying to Milan Last modified: Sep 19, 2023 12:10 -04:00Number of routes searched: 0Number of itineraries searched: 0

Wondering which airlines fly out of Chicago to Milan? We've gathered the average price of Chicago airlines with flights to Milan. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Chicago to Milan Airports

These are the major commercial airports we're currently monitoring in Chicago and Milan. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Domestic Flights from Chicago - CHI Last modified: Sep 19, 2023 12:10 -04:00

Cheap Flights from Chicago to Milan