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Cheap flights from Chicago to Milan from $209

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 10/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags
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Sun 6/23
Sun 6/30

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Easily compare round-trip flights from Chicago to Milan

Below you can see the best fares for your round-trip flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Milan by changing tabs
Aer Lingus
Jul 21
ORD3:45 pmChicago O'Hare Intl
11h 55m
1 stop
LIN10:40 amMilan Linate
Nov 6
LIN11:45 amMilan Linate
13h 10m
1 stop
ORD5:55 pmChicago O'Hare Intl
Scandinavian Airlines
Nov 18
ORD7:10 pmChicago O'Hare Intl
33h 55m
2 stops
LIN12:05 pmMilan Linate
Nov 26
LIN12:55 pmMilan Linate
33h 55m
2 stops
ORD3:50 pmChicago O'Hare Intl
Multiple Airlines
Nov 24
ORD6:35 pmChicago O'Hare Intl
11h 45m
1 stop
LIN1:20 pmMilan Linate
Nov 26
LIN7:50 amMilan Linate
13h 40m
1 stop
ORD2:30 pmChicago O'Hare Intl
American Airlines
Nov 6
ORD5:00 pmChicago O'Hare Intl
15h 45m
1 stop
LIN3:45 pmMilan Linate
Dec 4
LIN7:50 amMilan Linate
13h 40m
1 stop
ORD2:30 pmChicago O'Hare Intl
Air Canada
Nov 19
ORD7:20 amChicago O'Hare Intl
22h 40m
2 stops
LIN1:00 pmMilan Linate
Nov 26
LIN6:20 amMilan Linate
15h 27m
2 stops
ORD2:47 pmChicago O'Hare Intl
ITA Airways
Aug 6
ORD3:00 pmChicago O'Hare Intl
17h 10m
1 stop
LIN3:10 pmMilan Linate
Aug 20
LIN4:00 pmMilan Linate
28h 10m
1 stop
ORD1:10 pmChicago O'Hare Intl

Find the cheapest one-way flights from Chicago to Milan

If you're looking for one-way flights from Chicago to Milan, view some of our deals below provided by Lufthansa, TAP AIR PORTUGAL and United Airlines
Multiple Airlines
Oct 29
ORD11:14 amChicago O'Hare Intl
30h 41m
2 stops
BGY11:55 pmBergamo Orio Al Serio
Multiple Airlines
Sep 9
ORD4:57 pmChicago O'Hare Intl
33h 58m
2 stops
BGY9:55 amBergamo Orio Al Serio
TAP AIR PORTUGAL
Sep 4
ORD6:00 pmChicago O'Hare Intl
23h 35m
1 stop
MXP12:35 amMilan Malpensa

Find the cheapest direct flights from Chicago to Milan

United Airlines
Jul 21
ORD9:35 pmChicago O'Hare Intl
8h 45m
MXP1:20 pmMilan Malpensa
Nov 8
MXP3:05 pmMilan Malpensa
10h 05m
ORD6:10 pmChicago O'Hare Intl
United Airlines
Jul 21
ORD9:35 pmChicago O'Hare Intl
8h 45m
MXP1:20 pmMilan Malpensa
Nov 4
MXP3:05 pmMilan Malpensa
10h 05m
ORD6:10 pmChicago O'Hare Intl
United Airlines
Aug 14
ORD9:35 pmChicago O'Hare Intl
8h 45m
MXP1:20 pmMilan Malpensa
Aug 27
MXP3:20 pmMilan Malpensa
9h 45m
ORD6:05 pmChicago O'Hare Intl
United Airlines
Aug 4
ORD9:35 pmChicago O'Hare Intl
8h 45m
MXP1:20 pmMilan Malpensa
Aug 20
MXP3:20 pmMilan Malpensa
9h 45m
ORD6:05 pmChicago O'Hare Intl
United Airlines
Aug 4
ORD9:35 pmChicago O'Hare Intl
8h 45m
MXP1:20 pmMilan Malpensa
Aug 20
MXP3:20 pmMilan Malpensa
9h 45m
ORD6:05 pmChicago O'Hare Intl
United Airlines
Aug 8
ORD9:35 pmChicago O'Hare Intl
8h 45m
MXP1:20 pmMilan Malpensa
Aug 23
MXP3:20 pmMilan Malpensa
9h 45m
ORD6:05 pmChicago O'Hare Intl

Search last-minute flights to Milan from Chicago

Find and compare round-trip flight prices for your last-minute flight from Chicago to Milan
Multiple Airlines
Jun 26
ORD6:00 amChicago O'Hare Intl
28h 00m
2 stops
MXP5:00 pmMilan Malpensa
Jul 2
MXP11:00 pmMilan Malpensa
22h 54m
2 stops
ORD2:54 pmChicago O'Hare Intl
Scandinavian Airlines
Jun 26
ORD7:45 pmChicago O'Hare Intl
11h 55m
1 stop
MXP2:40 pmMilan Malpensa
Jul 2
MXP10:10 pmMilan Malpensa
26h 45m
1 stop
ORD5:55 pmChicago O'Hare Intl
ITA Airways
Jun 25
ORD3:00 pmChicago O'Hare Intl
20h 10m
1 stop
LIN6:10 pmMilan Linate
Jul 10
LIN10:25 pmMilan Linate
21h 45m
2 stops
ORD1:10 pmChicago O'Hare Intl
Turkish Airlines
Jun 25
ORD11:25 amChicago O'Hare Intl
15h 00m
1 stop
MXP9:25 amMilan Malpensa
Jul 10
MXP7:40 pmMilan Malpensa
21h 00m
1 stop
ORD9:40 amChicago O'Hare Intl
Icelandair
Jun 26
ORD10:15 pmChicago O'Hare Intl
14h 00m
2 stops
MXP7:15 pmMilan Malpensa
Jul 17
MXP11:00 pmMilan Malpensa
26h 15m
1 stop
ORD6:15 pmChicago O'Hare Intl
LOT
Jun 27
ORD5:10 pmChicago O'Hare Intl
42h 55m
2 stops
MXP7:05 pmMilan Malpensa
Jul 14
MXP10:30 amMilan Malpensa
16h 10m
1 stop
ORD7:40 pmChicago O'Hare Intl

Icelandair flights from Chicago to Milan

Our best Icelandair deals on Chicago to Milan flight tickets
Icelandair
Aug 30
ORD7:25 pmChicago O'Hare Intl
11h 45m
1 stop
MXP2:10 pmMilan Malpensa
Sep 2
MXP3:10 pmMilan Malpensa
50h 04m
2 stops
ORD10:14 amChicago O'Hare Intl
Icelandair
Jul 16
ORD8:40 amChicago O'Hare Intl
30h 20m
2 stops
MXP10:00 pmMilan Malpensa
Jul 23
MXP11:00 pmMilan Malpensa
26h 15m
1 stop
ORD6:15 pmChicago O'Hare Intl
Icelandair
Jun 26
ORD10:15 pmChicago O'Hare Intl
14h 00m
2 stops
MXP7:15 pmMilan Malpensa
Jul 17
MXP11:00 pmMilan Malpensa
26h 15m
1 stop
ORD6:15 pmChicago O'Hare Intl

Air Canada flights from Chicago to Milan

Our best Air Canada deals on Chicago to Milan flight tickets
Air Canada
Nov 19
ORD7:20 amChicago O'Hare Intl
22h 40m
2 stops
LIN1:00 pmMilan Linate
Nov 26
LIN6:20 amMilan Linate
15h 27m
2 stops
ORD2:47 pmChicago O'Hare Intl
Air Canada
Oct 30
ORD4:35 pmChicago O'Hare Intl
15h 30m
2 stops
LIN2:05 pmMilan Linate
Nov 6
LIN6:20 amMilan Linate
15h 27m
2 stops
ORD2:47 pmChicago O'Hare Intl
Air Canada
Nov 20
ORD4:35 pmChicago O'Hare Intl
14h 30m
2 stops
LIN2:05 pmMilan Linate
Nov 29
LIN6:20 amMilan Linate
16h 17m
2 stops
ORD3:37 pmChicago O'Hare Intl

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 cheapest month to fly from Chicago to Milan?

February. The cheapest time of year to fly to Milan from Chicago is February. Most expensive is June

What is the cheapest day to depart Chicago for Milan?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Friday

When is the cheapest time to fly from Chicago to Milan?

In the morning. Chicago to Milan flights are approximately 26% more expensive at noon than in the morning

What is the cheapest airline that flies to Milan from Chicago?

Scandinavian Airlines. Aer Lingus, American Airlines, and Delta are the most popular carriers operating from Chicago to Milan

What is the cheapest Chicago to Milan flight route?

Chicago O'Hare Intl - Milan Malpensa. Fly from Chicago O'Hare Intl to Milan Malpensa for the best Chicago - Milan flight prices

How far in advance should you book Chicago to Milan flights?

15 days before. The cheapest time to buy a flight from Chicago to Milan is approximately 15 days to departure

Can stopping save me money on Chicago to Milan flights?

You could potentially save up to 37% on your flight if you consider stops on a Chicago to Milan flight.

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

Best Price Found

$209

Fastest flight time

8h 45m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Milan

3 airports
The best one-way flight to Milan from Chicago in the past 72 hours is $209. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $542.
The fastest flight from Chicago to Milan takes 8h 45m
Direct flights go from Chicago to Milan on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines and Lufthansa.
There are 3 airports near Milan: Milan Linate (LIN), Milan Malpensa (MXP), Bergamo Orio Al Serio (BGY)

  • How far is Chicago to Milan by plane?

    There are 4526.2 mi between Chicago and Milan. By plane, this route typically takes 8h 45m.

  • 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?

  • 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.


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
Scandinavian AirlinesPriceFrom $403Free CancellationRating
7.4
1,365 reviews
Search Scandinavian Airlines flights
TAP AIR PORTUGALPriceFrom $467Free CancellationRating
7.1
2,063 reviews
Search TAP AIR PORTUGAL flights
Aer LingusPriceFrom $495Free CancellationRating
7.2
1,259 reviews
Search Aer Lingus flights
American AirlinesPriceFrom $527Free CancellationRating
7.3
10,000 reviews
Search American Airlines flights
British AirwaysPriceFrom $532Free CancellationRating
6.7
6,714 reviews
Search British Airways flights
Turkish AirlinesPriceFrom $589Free CancellationRating
7.4
3,730 reviews
Search Turkish Airlines flights
DeltaPriceFrom $642Free CancellationRating
8.0
10,000 reviews
Search Delta flights
SWISSPriceFrom $669Free CancellationRating
7.7
1,882 reviews
Search SWISS flights
LufthansaPriceFrom $684Free CancellationRating
6.9
7,441 reviews
Search Lufthansa flights
United AirlinesPriceFrom $794Free CancellationRating
7.4
10,000 reviews
Search United Airlines flights

Why 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.


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Airports listed have a maximum distance of 25.0 mi from Milan