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Cheap flights from Milan to Chicago from $322

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 10/27. 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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Cheap round-trip flights

TAP AIR PORTUGAL Logo
5:30 pm - 10:55 amMXP-ORD
24h 25m1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 7:15 pmORD-MXP
18h 15m1 stop
$437TAP AIR PORTUGAL
Find Deal
Wed, Sep 17 - Sun, Sep 21
TAP AIR PORTUGAL Logo
11:50 am - 10:55 amMXP-ORD
30h 05m1 stop
TAP AIR PORTUGAL Logo
6:10 pm - 12:45 amORD-MXP
23h 35m1 stop
$440TAP AIR PORTUGAL
Find Deal
Wed, Sep 10 - Mon, Sep 22
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
Scandinavian Airlines Logo
7:20 pm - 8:25 amORD-MXP
30h 05m1 stop
$486Scandinavian Airlines
Find Deal
Mon, Nov 10 - Thu, Nov 13
Scandinavian Airlines Logo
11:15 am - 4:45 pmMXP-ORD
12h 30m1 stop
Scandinavian Airlines Logo
7:20 pm - 7:10 pmORD-MXP
16h 50m1 stop
$534Scandinavian Airlines
Find Deal
Thu, Nov 13 - Thu, Nov 20
United Airlines Logo
9:10 am - 2:55 pmMXP-ORD
12h 45m1 stop
United Airlines Logo
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$547United Airlines
Find Deal
Thu, Sep 11 - Sat, Sep 27
United Airlines Logo
9:10 am - 2:55 pmMXP-ORD
12h 45m1 stop
United Airlines Logo
2:08 pm - 10:00 amORD-MXP
12h 52m1 stop
$550United Airlines
Find Deal
Mon, Aug 25 - Sun, Sep 7
Aer Lingus Logo
11:20 am - 7:00 pmLIN-ORD
14h 40m1 stop
Aer Lingus Logo
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
$566Aer Lingus
Find Deal
Tue, Sep 16 - Tue, Sep 23
Aer Lingus Logo
11:20 am - 7:00 pmLIN-ORD
14h 40m1 stop
Aer Lingus Logo
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
$586Aer Lingus
Find Deal
Thu, Sep 11 - Sat, Sep 27
Lufthansa Logo
7:00 am - 12:55 pmLIN-ORD
12h 55m1 stop
Lufthansa Logo
3:35 pm - 9:20 amORD-LIN
10h 45m1 stop
$596Lufthansa
Find Deal
Wed, Sep 17 - Sun, Sep 21
Lufthansa Logo
7:00 am - 2:55 pmLIN-ORD
14h 55m1 stop
Lufthansa Logo
9:40 pm - 5:50 pmORD-LIN
13h 10m1 stop
$597Lufthansa
Find Deal
Mon, Aug 25 - Sun, Sep 7

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
Sep 17
MXP5:30 pmMilan Malpensa
24h 25m
1 stop
ORD10:55 amChicago O'Hare Intl
Sep 21
ORD6:00 pmChicago O'Hare Intl
18h 15m
1 stop
MXP7:15 pmMilan Malpensa
$437
Find similar
TAP AIR PORTUGAL
Sep 10
MXP11:50 amMilan Malpensa
30h 05m
1 stop
ORD10:55 amChicago O'Hare Intl
Sep 22
ORD6:10 pmChicago O'Hare Intl
23h 35m
1 stop
MXP12:45 amMilan Malpensa
$440
Find similar
TAP AIR PORTUGAL
Sep 17
MXP5:30 pmMilan Malpensa
24h 25m
1 stop
ORD10:55 amChicago O'Hare Intl
Sep 21
ORD6:00 pmChicago O'Hare Intl
23h 45m
1 stop
MXP12:45 amMilan Malpensa
$461
Find similar

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

Our best Scandinavian Airlines deals on Milan to Chicago O'Hare Intl Airport flight tickets
Scandinavian Airlines
Nov 10
MXP11:15 amMilan Malpensa
12h 30m
1 stop
ORD4:45 pmChicago O'Hare Intl
Nov 13
ORD7:20 pmChicago O'Hare Intl
30h 05m
1 stop
MXP8:25 amMilan Malpensa
$486
Find similar
Scandinavian Airlines
Nov 13
MXP11:15 amMilan Malpensa
12h 30m
1 stop
ORD4:45 pmChicago O'Hare Intl
Nov 20
ORD7:20 pmChicago O'Hare Intl
16h 50m
1 stop
MXP7:10 pmMilan Malpensa
$534
Find similar
Scandinavian Airlines
Nov 14
MXP9:15 amMilan Malpensa
14h 30m
1 stop
ORD4:45 pmChicago O'Hare Intl
Nov 20
ORD7:20 pmChicago O'Hare Intl
30h 05m
1 stop
MXP8:25 amMilan Malpensa
$540
Find similar

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 August 3, 2025.
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 9/17

5:30 pm-10:55 am

1 stop24h 25m

Chicago O'Hare Intl

Sun 9/21

6:00 pm-7:15 pm

1 stop18h 15m

$437

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Wed 9/10

11:50 am-10:55 am

1 stop30h 05m

Chicago O'Hare Intl

Mon 9/22

6:10 pm-12:45 am

1 stop23h 35m

$440

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 11/10

11:15 am-4:45 pm

1 stop12h 30m

Chicago O'Hare Intl

Thu 11/13

7:20 pm-8:25 am

1 stop30h 05m

$486

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 11/13

11:15 am-4:45 pm

1 stop12h 30m

Chicago O'Hare Intl

Thu 11/20

7:20 pm-7:10 pm

1 stop16h 50m

$534

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 9/11

9:10 am-2:55 pm

1 stop12h 45m

Chicago O'Hare Intl

Sat 9/27

9:35 pm-1:20 pm

Nonstop8h 45m

$547

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 8/25

9:10 am-2:55 pm

1 stop12h 45m

Chicago O'Hare Intl

Sun 9/7

2:08 pm-10:00 am

1 stop12h 52m

$550

MilanChicago

LIN - ORD

LINORD

Milan Linate

Tue 9/16

11:20 am-7:00 pm

1 stop14h 40m

Chicago O'Hare Intl

Tue 9/23

3:45 pm-10:40 am

1 stop11h 55m

$566

MilanChicago

LIN - ORD

LINORD

Milan Linate

Thu 9/11

11:20 am-7:00 pm

1 stop14h 40m

Chicago O'Hare Intl

Sat 9/27

3:45 pm-10:40 am

1 stop11h 55m

$586

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 9/17

7:00 am-12:55 pm

1 stop12h 55m

Chicago O'Hare Intl

Sun 9/21

3:35 pm-9:20 am

1 stop10h 45m

$596

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 8/25

7:00 am-2:55 pm

1 stop14h 55m

Chicago O'Hare Intl

Sun 9/7

9:40 pm-5:50 pm

1 stop13h 10m

$597

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Milan averaging around $511.

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 $824. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday 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 $1,009.

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

Flying to Chicago O'Hare Intl Airport from Milan in the morning is the least expensive time of day to depart. momondo users have found prices as low as $586 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $878. Of course, these prices can vary depending on the time of year and what airport you fly to.

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 $728 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 $556 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?

As of August 2025, prices for Milan to Chicago O'Hare Intl Airport flights are approximately 74% more expensive when compared to flights at the same time last year.

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

$322

Fastest flight time

9h 50m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Milan in the past 72 hours is $322. The best round-trip flight deal from Milan to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $437.
The fastest flight from Milan to Chicago O'Hare Intl Airport takes 9h 50m
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 50m, 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
6.6
7,230 reviews
Search British Airways flights
United AirlinesPriceFrom $626Free CancellationRating
7.4
8,905 reviews
Search United Airlines flights

  • United Airlines Flights From Milan to Chicago O'Hare Intl Airport

    United Airlines flies from Milan to Chicago O'Hare Intl Airport around 7 times per week, with 8,905 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Milan to Chicago O'Hare Intl Airport in the last 72 hours was $626 (round-trip), much lower than the average airfare cost of $943 for United Airlines flights on this route.

Traveling to a place near Chicago?

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

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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