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Cheap flights from Milan to Chicago from $277

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 4/7. 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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Find the cheapest flights from Milan to Chicago

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 - 4:25 pm
ORD
-
MXP
15h 25m
1 stop
$428TAP AIR PORTUGAL
Sun, Apr 19 - Wed, Apr 29
TAP AIR PORTUGAL Logo
5:45 pm - 2:45 pm
MXP
-
ORD
28h 00m
1 stop
TAP AIR PORTUGAL Logo
8:25 pm - 11:35 pm
ORD
-
MXP
20h 10m
1 stop
$434TAP AIR PORTUGAL
Sat, Feb 7 - Sun, Feb 15
LOT Logo
10:25 am - 8:00 pm
MXP
-
ORD
16h 35m
1 stop
LOT Logo
9:55 pm - 7:05 pm
ORD
-
MXP
14h 10m
1 stop
$498LOT
Thu, Feb 19 - Tue, Feb 24
LOT Logo
7:50 pm - 8:00 pm
MXP
-
ORD
31h 10m
1 stop
LOT Logo
10:55 pm - 7:05 pm
ORD
-
MXP
14h 10m
1 stop
$506LOT
Thu, Feb 26 - Sat, Mar 14
Scandinavian Airlines Logo
9:15 am - 4:45 pm
MXP
-
ORD
14h 30m
1 stop
Scandinavian Airlines Logo
7:20 pm - 7:10 pm
ORD
-
MXP
16h 50m
1 stop
$510Scandinavian Airlines
Mon, Feb 2 - Wed, Feb 18
Scandinavian Airlines Logo
12:55 pm - 4:45 pm
LIN
-
ORD
34h 50m
2 stops
Scandinavian Airlines Logo
7:20 pm - 12:05 pm
ORD
-
LIN
57h 45m
2 stops
$582Scandinavian Airlines
Fri, Feb 20 - Thu, Feb 26
Lufthansa Logo
6:20 am - 12:55 pm
LIN
-
ORD
13h 35m
1 stop
Lufthansa Logo
9:40 pm - 5:45 pm
ORD
-
LIN
13h 05m
1 stop
$588Lufthansa
Fri, May 1 - Tue, May 5
Lufthansa Logo
6:50 am - 12:55 pm
LIN
-
ORD
13h 05m
1 stop
Lufthansa Logo
4:05 pm - 10:00 am
ORD
-
LIN
10h 55m
1 stop
$596Lufthansa
Mon, Apr 13 - Sun, Apr 19
British Airways Logo
12:40 pm - 7:45 pm
LIN
-
ORD
13h 05m
1 stop
British Airways Logo
10:45 pm - 4:20 pm
ORD
-
LIN
11h 35m
1 stop
$608British Airways
Mon, Mar 16 - Sun, Mar 22
British Airways Logo
11:25 am - 6:45 pm
LIN
-
ORD
14h 20m
1 stop
British Airways Logo
8:35 pm - 4:20 pm
ORD
-
LIN
12h 45m
1 stop
$609British Airways
Wed, Feb 25 - Wed, Mar 4

LOT flights from Milan to Chicago

Our best LOT deals on Milan to Chicago flight tickets
LOT
Feb 19
MXP10:25 amMilan Malpensa
16h 35m
1 stop
ORD8:00 pmChicago O'Hare Intl
Feb 24
ORD9:55 pmChicago O'Hare Intl
14h 10m
1 stop
MXP7:05 pmMilan Malpensa
$498
LOT
Feb 26
MXP7:50 pmMilan Malpensa
31h 10m
1 stop
ORD8:00 pmChicago O'Hare Intl
Mar 14
ORD10:55 pmChicago O'Hare Intl
14h 10m
1 stop
MXP7:05 pmMilan Malpensa
$506
LOT
Feb 27
MXP7:50 pmMilan Malpensa
31h 10m
1 stop
ORD8:00 pmChicago O'Hare Intl
Mar 6
ORD9:55 pmChicago O'Hare Intl
14h 10m
1 stop
MXP7:05 pmMilan Malpensa
$511

Air Canada flights from Milan to Chicago

Our best Air Canada deals on Milan to Chicago flight tickets
Air Canada
Feb 19
MXP10:40 amMilan Malpensa
15h 05m
2 stops
ORD6:45 pmChicago O'Hare Intl
Feb 24
ORD10:35 amChicago O'Hare Intl
16h 20m
1 stop
MXP9:55 amMilan Malpensa
$576
Air Canada
Jan 30
MXP10:40 amMilan Malpensa
16h 30m
2 stops
ORD8:10 pmChicago O'Hare Intl
Feb 15
ORD10:35 amChicago O'Hare Intl
16h 15m
2 stops
MXP9:50 amMilan Malpensa
$585
Air Canada
Jan 25
MXP1:05 pmMilan Malpensa
14h 05m
1 stop
ORD8:10 pmChicago O'Hare Intl
Feb 7
ORD12:50 pmChicago O'Hare Intl
14h 05m
1 stop
MXP9:55 amMilan Malpensa
$589

momondo Fare Finder

 
Customize your flight search to find flights from Milan to Chicago 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 January 13, 2026.
Use the filters below to find and compare flights from Milan to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sun 4/19

5:50 am-4:00 pm

1 stop17h 10m

Chicago O'Hare Intl

Wed 4/29

6:00 pm-4:25 pm

1 stop15h 25m

$428

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Sat 2/7

5:45 pm-2:45 pm

1 stop28h 00m

Chicago O'Hare Intl

Sun 2/15

8:25 pm-11:35 pm

1 stop20h 10m

$434

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 2/19

10:25 am-8:00 pm

1 stop16h 35m

Chicago O'Hare Intl

Tue 2/24

9:55 pm-7:05 pm

1 stop14h 10m

$498

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Thu 2/26

7:50 pm-8:00 pm

1 stop31h 10m

Chicago O'Hare Intl

Sat 3/14

10:55 pm-7:05 pm

1 stop14h 10m

$506

MilanChicago

MXP - ORD

MXPORD

Milan Malpensa

Mon 2/2

9:15 am-4:45 pm

1 stop14h 30m

Chicago O'Hare Intl

Wed 2/18

7:20 pm-7:10 pm

1 stop16h 50m

$510

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 2/20

12:55 pm-4:45 pm

2 stops34h 50m

Chicago O'Hare Intl

Thu 2/26

7:20 pm-12:05 pm

2 stops57h 45m

$582

MilanChicago

LIN - ORD

LINORD

Milan Linate

Fri 5/1

6:20 am-12:55 pm

1 stop13h 35m

Chicago O'Hare Intl

Tue 5/5

9:40 pm-5:45 pm

1 stop13h 05m

$588

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 4/13

6:50 am-12:55 pm

1 stop13h 05m

Chicago O'Hare Intl

Sun 4/19

4:05 pm-10:00 am

1 stop10h 55m

$596

MilanChicago

LIN - ORD

LINORD

Milan Linate

Mon 3/16

12:40 pm-7:45 pm

1 stop13h 05m

Chicago O'Hare Intl

Sun 3/22

10:45 pm-4:20 pm

1 stop11h 35m

$608

MilanChicago

LIN - ORD

LINORD

Milan Linate

Wed 2/25

11:25 am-6:45 pm

1 stop14h 20m

Chicago O'Hare Intl

Wed 3/4

8:35 pm-4:20 pm

1 stop12h 45m

$609

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

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?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $571. If you’re not able to fly to Chicago in February, then March is your next best option. Flight prices from Milan to Chicago during March average around $591.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago 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. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Milan to Chicago for around $1,213.

What is the cheapest Milan to Chicago flight route?

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

What cabin class options are available on Milan to Chicago flights?

There are 3 cabin classes available to choose from on Milan to Chicago 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 flight prices changed over time?

As of January 2026, prices for Milan to Chicago flights are approximately 3% more expensive when compared to flights at the same time last year.

When to book flights from Milan to Chicago

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

Cheap Milan to Chicago (MIL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Milan to Chicago

Best Price Found

$771

Fastest flight time

9h 40m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Milan in the past 72 hours is $771. The best round-trip flight deal from Milan to Chicago found on momondo in the last 72 hours is $854.
The fastest flight from Milan to Chicago takes 9h 40m
Direct flights go from Milan to Chicago every day.
There are 3 airports in Chicago. From Milan there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is Milan to Chicago by plane?

    The straight-line distance from Milan to Chicago is 4526.2 mi. In terms of flight time, this usually takes a little over 9h 40m.

  • When did momondo last update prices for flights from Milan to Chicago?

    Prices for flights from Milan to Chicago are updated daily.

  • How many operators does momondo search for flights from Milan to Chicago?

  • How old do you have to be to fly from Milan to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Milan to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Milan to Chicago?

  • What is the most popular airline from Milan to Chicago?

Best airlines flying from Milan to Chicago

Compare and see reviews for airlines that fly from Milan to Chicago with momondo
Airline
Rating
Free Cancellation
Price
British AirwaysPriceFrom $525Free CancellationRating
6.7
7,665 reviews
Search British Airways flights
United AirlinesPriceFrom $672Free CancellationRating
7.4
9,148 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Milan to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo enables you to select and highlight flights to Chicago from Milan with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Milan.

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

Price alerts on flights to Chicago from Milan are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport