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Cheap flights from Milan to Chicago from $318

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Milan to Chicago departing on 3/5. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
TAP AIR PORTUGAL Logo
5:50 am - 4:00 pm
MXP
-
ORD
17h 10m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 7:00 pm
ORD
-
MXP
18h 00m
1 stop
$492TAP AIR PORTUGAL
Wed, Apr 15 - Wed, Apr 22
TAP AIR PORTUGAL Logo
8:00 pm - 4:00 pm
MXP
-
ORD
27h 00m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 7:00 pm
ORD
-
MXP
18h 00m
1 stop
$497TAP AIR PORTUGAL
Tue, Apr 21 - Wed, May 6
TAP AIR PORTUGAL Logo
5:25 pm - 4:00 pm
MXP
-
ORD
29h 35m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 12:45 am
ORD
-
MXP
23h 45m
1 stop
$498TAP AIR PORTUGAL
Tue, Apr 21 - Wed, May 6
Icelandair Logo
4:20 pm - 6:15 pm
MXP
-
ORD
32h 55m
1 stop
Icelandair Logo
7:25 pm - 3:10 pm
ORD
-
MXP
12h 45m
1 stop
$530Icelandair
Sat, Apr 25 - Tue, May 5
ITA Airways Logo
7:00 am - 1:10 pm
LIN
-
ORD
13h 10m
1 stop
ITA Airways Logo
3:00 pm - 10:10 am
ORD
-
LIN
12h 10m
1 stop
$544ITA Airways
Thu, May 7 - Mon, May 11
ITA Airways Logo
7:00 am - 1:10 pm
LIN
-
ORD
13h 10m
1 stop
ITA Airways Logo
3:00 pm - 10:10 am
ORD
-
LIN
12h 10m
1 stop
$566ITA Airways
Thu, May 7 - Thu, May 14
Multiple Airlines Logo
7:25 am - 6:15 pm
LIN
-
ORD
17h 50m
1 stop
Multiple Airlines Logo
5:00 pm - 12:30 pm
ORD
-
LIN
12h 30m
1 stop
$584Multiple Airlines
Thu, May 21 - Sun, May 31
Air Canada Logo
6:50 am - 2:55 pm
LIN
-
ORD
15h 05m
2 stops
Air Canada Logo
3:50 pm - 2:40 pm
ORD
-
LIN
15h 50m
2 stops
$590Air Canada
Sun, Apr 26 - Sun, May 3
Air Canada Logo
6:10 am - 2:55 pm
LIN
-
ORD
15h 45m
2 stops
Air Canada Logo
6:25 pm - 2:10 pm
ORD
-
LIN
13h 45m
2 stops
$599Air Canada
Wed, Feb 25 - Sun, Mar 8
Multiple Airlines Logo
8:30 pm - 4:55 pm
BGY
-
ORD
27h 25m
2 stops
Multiple Airlines Logo
8:20 pm - 7:55 pm
ORD
-
BGY
17h 35m
2 stops
$647Multiple Airlines
Thu, Mar 5 - Mon, Mar 9

Austrian Airlines flights from Milan to Chicago O'Hare Intl Airport

Our best Austrian Airlines deals on Milan to Chicago O'Hare Intl Airport flight tickets
Austrian Airlines
Mar 30
LIN8:00 pmMilan Linate
24h 20m
1 stop
ORD1:20 pmChicago O'Hare Intl
Apr 13
ORD1:00 pmChicago O'Hare Intl
18h 10m
2 stops
LIN2:10 pmMilan Linate
$643
Austrian Airlines
Apr 21
LIN7:00 amMilan Linate
13h 20m
1 stop
ORD1:20 pmChicago O'Hare Intl
May 5
ORD12:55 pmChicago O'Hare Intl
18h 15m
2 stops
LIN2:10 pmMilan Linate
$684
Austrian Airlines
Feb 25
LIN7:20 amMilan Linate
13h 40m
1 stop
ORD2:00 pmChicago O'Hare Intl
Mar 6
ORD4:20 pmChicago O'Hare Intl
33h 55m
1 stop
LIN9:15 amMilan Linate
$727

TAP AIR PORTUGAL flights from Milan to Chicago O'Hare Intl Airport

Our best TAP AIR PORTUGAL deals on Milan to Chicago O'Hare Intl Airport flight tickets
TAP AIR PORTUGAL
Apr 15
MXP5:50 amMilan Malpensa
17h 10m
1 stop
ORD4:00 pmChicago O'Hare Intl
Apr 22
ORD6:00 pmChicago O'Hare Intl
18h 00m
1 stop
MXP7:00 pmMilan Malpensa
$492
TAP AIR PORTUGAL
Apr 21
MXP8:00 pmMilan Malpensa
27h 00m
1 stop
ORD4:00 pmChicago O'Hare Intl
May 6
ORD6:00 pmChicago O'Hare Intl
18h 00m
1 stop
MXP7:00 pmMilan Malpensa
$497
TAP AIR PORTUGAL
Apr 21
MXP5:25 pmMilan Malpensa
29h 35m
1 stop
ORD4:00 pmChicago O'Hare Intl
May 6
ORD6:00 pmChicago O'Hare Intl
23h 45m
1 stop
MXP12:45 amMilan Malpensa
$498

momondo Fare Finder

 
Customize your flight search to find flights from Milan to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Milan to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 4/15

5:50 am-4:00 pm

1 stop17h 10m

Chicago O'Hare Intl

Wed 4/22

6:00 pm-7:00 pm

1 stop18h 00m

$492

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 4/21

8:00 pm-4:00 pm

1 stop27h 00m

Chicago O'Hare Intl

Wed 5/6

6:00 pm-7:00 pm

1 stop18h 00m

$497

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Tue 4/21

5:25 pm-4:00 pm

1 stop29h 35m

Chicago O'Hare Intl

Wed 5/6

6:00 pm-12:45 am

1 stop23h 45m

$498

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 4/25

4:20 pm-6:15 pm

1 stop32h 55m

Chicago O'Hare Intl

Tue 5/5

7:25 pm-3:10 pm

1 stop12h 45m

$530

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 5/7

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Mon 5/11

3:00 pm-10:10 am

1 stop12h 10m

$544

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 5/7

7:00 am-1:10 pm

1 stop13h 10m

Chicago O'Hare Intl

Thu 5/14

3:00 pm-10:10 am

1 stop12h 10m

$566

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 5/21

7:25 am-6:15 pm

1 stop17h 50m

Chicago O'Hare Intl

Sun 5/31

5:00 pm-12:30 pm

1 stop12h 30m

$584

MilanChicago

LIN - ORD

LINORD

Milan Linate

Sun 4/26

6:50 am-2:55 pm

2 stops15h 05m

Chicago O'Hare Intl

Sun 5/3

3:50 pm-2:40 pm

2 stops15h 50m

$590

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 2/25

6:10 am-2:55 pm

2 stops15h 45m

Chicago O'Hare Intl

Sun 3/8

6:25 pm-2:10 pm

2 stops13h 45m

$599

BergamoChicago

BGY - ORD

BGYORD

Bergamo Orio Al Serio

Thu 3/5

8:30 pm-4:55 pm

2 stops27h 25m

Chicago O'Hare Intl

Mon 3/9

8:20 pm-7:55 pm

2 stops17h 35m

$647

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Milan to Chicago O'Hare Intl Airport

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 Milan and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Milan averaging around $557.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Tuesday when prices can be found for as low as $789. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Milan because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,213.

What is the cheapest Milan to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Milan when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $877 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Milan for as low as $531 on momondo.

What cabin class options are available on Milan to Chicago O'Hare Intl flights?

There are 3 cabin classes available to choose from on Milan to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Milan to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Milan to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Milan to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Milan to Chicago O'Hare Intl Airport (MIL to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milan to Chicago O'Hare Intl Airport

Best Price Found

$801

Fastest flight time

9h 40m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Milan in the past 72 hours is $801. The best round-trip flight deal from Milan to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $875.
The fastest flight from Milan to Chicago O'Hare Intl Airport takes 9h 40m
Direct flights go from Milan to Chicago O'Hare Intl Airport every day.
Search flight deals

  • How far is Milan to Chicago O'Hare Intl by plane?

    Milan and Chicago O'Hare Intl are 4532.4 mi apart from one another. Flights usually cover this in 9h 40m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Milan to Chicago O'Hare Intl Airport?

    Prices for flights from Milan to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Milan to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Milan to Chicago O'Hare Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Milan to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Milan to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Milan to Chicago O'Hare Intl Airport?

Best airlines flying from Milan to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Milan to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
British AirwaysPriceFrom $525Free CancellationRating
6.7
7,715 reviews
Search British Airways flights
United AirlinesPriceFrom $695Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
New Buffalo
Kenosha
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Milan to Chicago?

Finding the right flight to Chicago from Milan is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Milan to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Milan on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Milan to Chicago?

momondo helps you find the best flight between Milan and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Milan to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Milan to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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