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Cheap flights from Chicago O'Hare Intl Airport to Milan from $253

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 O'Hare Intl Airport to Milan departing on 7/26. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago O'Hare Intl Airport to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:45 pm - 10:15 pm
ORD
-
BGY
23h 30m
2 stops
Multiple Airlines Logo
8:55 pm - 4:57 pm
BGY
-
ORD
27h 02m
3 stops
$609Multiple Airlines
Mon, Aug 17 - Mon, Aug 24
Scandinavian Airlines Logo
7:15 pm - 12:10 pm
ORD
-
LIN
33h 55m
2 stops
Scandinavian Airlines Logo
1:00 pm - 4:10 pm
LIN
-
ORD
34h 10m
2 stops
$670Scandinavian Airlines
Sun, Aug 23 - Wed, Aug 26
Scandinavian Airlines Logo
7:15 pm - 12:10 pm
ORD
-
LIN
33h 55m
2 stops
Scandinavian Airlines Logo
2:45 pm - 4:10 pm
LIN
-
ORD
32h 25m
1 stop
$673Scandinavian Airlines
Sat, Oct 3 - Sat, Oct 10
Multiple Airlines Logo
7:25 pm - 9:50 pm
ORD
-
BGY
19h 25m
2 stops
Multiple Airlines Logo
10:55 pm - 9:25 pm
BGY
-
ORD
29h 30m
2 stops
$674Multiple Airlines
Mon, Aug 17 - Fri, Aug 21
Multiple Airlines Logo
7:15 pm - 8:05 pm
ORD
-
BGY
17h 50m
2 stops
Multiple Airlines Logo
8:40 pm - 4:10 pm
BGY
-
ORD
26h 30m
2 stops
$685Multiple Airlines
Wed, Aug 19 - Wed, Aug 26
Multiple Airlines Logo
10:25 pm - 9:25 am
ORD
-
BGY
28h 00m
3 stops
Multiple Airlines Logo
10:00 am - 9:25 pm
BGY
-
ORD
18h 25m
2 stops
$686Multiple Airlines
Wed, Aug 19 - Wed, Aug 26
ITA Airways Logo
3:00 pm - 11:40 am
ORD
-
LIN
13h 40m
1 stop
ITA Airways Logo
7:00 pm - 1:10 pm
LIN
-
ORD
25h 10m
1 stop
$708ITA Airways
Tue, Aug 18 - Sat, Aug 22
Icelandair Logo
7:25 pm - 3:10 pm
ORD
-
MXP
12h 45m
1 stop
Icelandair Logo
4:20 pm - 9:25 pm
MXP
-
ORD
12h 05m
1 stop
$721Icelandair
Sat, Aug 15 - Sat, Aug 22
Icelandair Logo
10:25 pm - 3:10 pm
ORD
-
MXP
33h 45m
1 stop
Icelandair Logo
10:55 pm - 9:25 pm
MXP
-
ORD
29h 30m
1 stop
$727Icelandair
Fri, Aug 14 - Fri, Aug 21
ITA Airways Logo
3:00 pm - 10:10 am
ORD
-
LIN
12h 10m
1 stop
ITA Airways Logo
7:00 am - 1:10 pm
LIN
-
ORD
13h 10m
1 stop
$744ITA Airways
Sun, Sep 20 - Wed, Sep 30

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Air Canada flights from Chicago O'Hare Intl Airport to Milan

Our best Air Canada deals on Chicago O'Hare Intl Airport to Milan flight tickets
Air Canada
Aug 3
ORD11:05 amChicago O'Hare Intl
16h 15m
1 stop
MXP10:20 amMilan Malpensa
Aug 19
MXP12:20 pmMilan Malpensa
14h 45m
1 stop
ORD8:05 pmChicago O'Hare Intl
$727
Air Canada
Aug 3
ORD9:50 amChicago O'Hare Intl
17h 30m
2 stops
MXP10:20 amMilan Malpensa
Aug 19
MXP12:20 pmMilan Malpensa
14h 45m
1 stop
ORD8:05 pmChicago O'Hare Intl
$731
Air Canada
Aug 3
ORD11:05 amChicago O'Hare Intl
16h 15m
1 stop
MXP10:20 amMilan Malpensa
Aug 19
MXP12:20 pmMilan Malpensa
14h 45m
1 stop
ORD8:05 pmChicago O'Hare Intl
$732

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

Our best TAP AIR PORTUGAL deals on Chicago O'Hare Intl Airport to Milan flight tickets
TAP AIR PORTUGAL
Jul 11
ORD6:05 pmChicago O'Hare Intl
15h 20m
1 stop
MXP4:25 pmMilan Malpensa
Sep 6
MXP5:50 amMilan Malpensa
17h 10m
1 stop
ORD4:00 pmChicago O'Hare Intl
$825
TAP AIR PORTUGAL
Jul 8
ORD4:40 pmChicago O'Hare Intl
16h 45m
1 stop
MXP4:25 pmMilan Malpensa
Jul 15
MXP8:00 pmMilan Malpensa
23h 40m
1 stop
ORD12:40 pmChicago O'Hare Intl
$830
TAP AIR PORTUGAL
Jul 11
ORD6:05 pmChicago O'Hare Intl
15h 20m
1 stop
MXP4:25 pmMilan Malpensa
Sep 6
MXP5:50 amMilan Malpensa
17h 10m
1 stop
ORD4:00 pmChicago O'Hare Intl
$855

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Milan 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 July 2, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 8/17

3:45 pm-10:15 pm

2 stops23h 30m

Bergamo Orio Al Serio

Mon 8/24

8:55 pm-4:57 pm

3 stops27h 02m

$609

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 8/23

7:15 pm-12:10 pm

2 stops33h 55m

Milan Linate

Wed 8/26

1:00 pm-4:10 pm

2 stops34h 10m

$670

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sat 10/3

7:15 pm-12:10 pm

2 stops33h 55m

Milan Linate

Sat 10/10

2:45 pm-4:10 pm

1 stop32h 25m

$673

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Mon 8/17

7:25 pm-9:50 pm

2 stops19h 25m

Bergamo Orio Al Serio

Fri 8/21

10:55 pm-9:25 pm

2 stops29h 30m

$674

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 8/19

7:15 pm-8:05 pm

2 stops17h 50m

Bergamo Orio Al Serio

Wed 8/26

8:40 pm-4:10 pm

2 stops26h 30m

$685

ChicagoBergamo

ORD - BGY

ORDBGY

Chicago O'Hare Intl

Wed 8/19

10:25 pm-9:25 am

3 stops28h 00m

Bergamo Orio Al Serio

Wed 8/26

10:00 am-9:25 pm

2 stops18h 25m

$686

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Tue 8/18

3:00 pm-11:40 am

1 stop13h 40m

Milan Linate

Sat 8/22

7:00 pm-1:10 pm

1 stop25h 10m

$708
Quickest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Sat 8/15

7:25 pm-3:10 pm

1 stop12h 45m

Milan Malpensa

Sat 8/22

4:20 pm-9:25 pm

1 stop12h 05m

$721

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Fri 8/14

10:25 pm-3:10 pm

1 stop33h 45m

Milan Malpensa

Fri 8/21

10:55 pm-9:25 pm

1 stop29h 30m

$727

ChicagoMilan

ORD - LIN

ORDLIN

Chicago O'Hare Intl

Sun 9/20

3:00 pm-10:10 am

1 stop12h 10m

Milan Linate

Wed 9/30

7:00 am-1:10 pm

1 stop13h 10m

$744

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Milan from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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 typical price of a round-trip flight between Chicago O'Hare Intl Airport and Milan?

What is the cheapest month to fly to Milan?

The month of July is, on average, the cheapest month to fly to Milan from Chicago O'Hare Intl Airport, with most prices found around $187. The month of October is another great option to travel to Milan, with average flight prices from Chicago O'Hare Intl Airport averaging around $266.

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

Our data shows that Friday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,344. The most expensive day to fly to Milan is Sunday, with ticket prices averaging around $1,574.

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

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

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

You are more likely to see cheaper flights to Milan from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Milan for around $856 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan from Chicago O'Hare Intl Airport for as low as $555 on momondo.

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

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

Can stopping save me money on Chicago O'Hare Intl Airport to Milan flights?

You could potentially save up to 39% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Milan flight.

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

As of July 2026, prices for Chicago O'Hare Intl Airport to Milan flights are approximately 31% more expensive when compared to flights at the same time last year.

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

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

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

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

Best Price Found

$874

Fastest flight time

8h 40m

Direct flights

Every day

Airports in Milan

2 airports
The best one-way flight to Milan from Chicago O'Hare Intl Airport in the past 72 hours is $874. The best round-trip flight deal from Chicago O'Hare Intl Airport to Milan found on momondo in the last 72 hours is $985.
The fastest flight from Chicago O'Hare Intl Airport to Milan takes 8h 40m
Direct flights go from Chicago O'Hare Intl Airport to Milan every day.
There are 2 airports in Milan. From Chicago O'Hare Intl Airport there are direct flights to Milan Malpensa (MXP).
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Milan

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

    The distance between Chicago O'Hare Intl and Milan is about 4532.4 mi. In terms of flight time, this usually takes a little over 8h 40m.

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

    Prices for flights from Chicago O'Hare Intl Airport to Milan are updated daily.

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

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

    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 Chicago O'Hare Intl Airport 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.

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

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

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

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Milan with momondo
Airline
Rating
Free Cancellation
Price
TAP AIR PORTUGALPriceFrom $401Free CancellationRating
7.2
2,311 reviews
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesPriceFrom $420Free CancellationRating
7.4
1,862 reviews
Search Scandinavian Airlines flights
Turkish AirlinesPriceFrom $534Free CancellationRating
7.4
4,438 reviews
Search Turkish Airlines flights
Aer LingusPriceFrom $627Free CancellationRating
7.3
1,638 reviews
Search Aer Lingus flights
British AirwaysPriceFrom $644Free CancellationRating
6.7
8,091 reviews
Search British Airways flights
ITA AirwaysPriceFrom $644Free CancellationRating
6.7
1,271 reviews
Search ITA Airways flights
United AirlinesPriceFrom $774Free CancellationRating
7.4
9,927 reviews
Search United Airlines flights
LufthansaPriceFrom $840Free CancellationRating
6.8
8,108 reviews
Search Lufthansa flights

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

    United Airlines flies from Chicago O'Hare Intl Airport to Milan around 7 times per week, with 9,925 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago O'Hare Intl Airport to Milan in the last 72 hours was $774 (round-trip), much lower than the average airfare cost of $1,238 for United Airlines flights on this route.

  • Lufthansa Flights From Chicago O'Hare Intl Airport to Milan

    Across 8,108 Lufthansa reviews on momondo, the average score is 6.8/10. Lufthansa flies from Chicago O'Hare Intl Airport to Milan about 7 times each week, with ticket deals ranging from $840 to $1,193. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Bellagio
Varenna
Stresa
Brescia
Livigno
Lecco
Monza
Domodossola
Menaggio
Bellano
Assago
Crema
Cernobbio
Levanto
Moltrasio
Baveno
Bormio
Rho
Novara
Iseo

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 allows you to filter the results for Chicago to Milan flights to just show those with flexible booking policies.

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

Once you have performed a search for Chicago to Milan flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Milan from Chicago 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 Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan
Milan Linate Airport
Milan Malpensa Airport