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Cheap flights from Chicago to Milan from $299

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 8/12. 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 to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:40 pm - 4:40 pm
ORD
-
MXP
18h 00m
2 stops
Multiple Airlines Logo
6:30 am - 2:44 pm
MXP
-
ORD
15h 14m
2 stops
$775Multiple Airlines
Mon, Aug 3 - Wed, Aug 19
United Airlines Logo
9:40 pm - 1:20 pm
ORD
-
MXP
8h 40mnonstop
United Airlines Logo
3:20 pm - 6:10 pm
MXP
-
ORD
9h 50mnonstop
$776United Airlines
Mon, Aug 3 - Wed, Aug 19
Delta Logo
10:54 am - 9:25 am
MDW
-
MXP
15h 31m
1 stop
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$777Delta
Mon, Aug 3 - Wed, Aug 19
United Airlines Logo
9:40 pm - 1:20 pm
ORD
-
MXP
8h 40mnonstop
United Airlines Logo
3:20 pm - 6:10 pm
MXP
-
ORD
9h 50mnonstop
$777United Airlines
Wed, Aug 12 - Wed, Aug 19
United Airlines Logo
9:40 pm - 1:20 pm
ORD
-
MXP
8h 40mnonstop
United Airlines Logo
9:00 am - 2:55 pm
MXP
-
ORD
12h 55m
1 stop
$778United Airlines
Mon, Aug 3 - Wed, Aug 19
Air France Logo
10:54 am - 9:25 am
MDW
-
MXP
15h 31m
1 stop
Air France Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$781Air France
Mon, Aug 3 - Wed, Aug 19
Scandinavian Airlines Logo
7:15 pm - 7:10 pm
ORD
-
MXP
16h 55m
1 stop
Scandinavian Airlines Logo
8:00 pm - 4:10 pm
MXP
-
ORD
27h 10m
1 stop
$782Scandinavian Airlines
Thu, Sep 3 - Tue, Sep 8
Delta Logo
5:10 pm - 9:25 am
MDW
-
MXP
33h 15m
1 stop
Delta Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$782Delta
Mon, Aug 3 - Wed, Aug 19
Air France Logo
10:54 am - 9:25 am
MDW
-
MXP
15h 31m
1 stop
Air France Logo
11:40 am - 10:36 pm
MXP
-
MDW
17h 56m
1 stop
$783Air France
Mon, Aug 3 - Wed, Aug 19
KLM Logo
5:10 pm - 9:25 am
MDW
-
MXP
33h 15m
1 stop
KLM Logo
11:40 am - 4:15 pm
MXP
-
MDW
35h 35m
1 stop
$823KLM
Tue, Aug 18 - Tue, Aug 25

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Delta flights from Chicago to Milan Malpensa Airport

Our best Delta deals on Chicago to Milan Malpensa Airport flight tickets
Delta
Aug 3
MDW10:54 amChicago Midway
15h 31m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$777
Delta
Aug 3
MDW5:10 pmChicago Midway
33h 15m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$782
Delta
Aug 3
ORD6:40 amChicago O'Hare Intl
19h 45m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP11:40 amMilan Malpensa
16h 15m
1 stop
ORD8:55 pmChicago O'Hare Intl
$783

KLM flights from Chicago to Milan Malpensa Airport

Our best KLM deals on Chicago to Milan Malpensa Airport flight tickets
KLM
Aug 18
MDW5:10 pmChicago Midway
33h 15m
1 stop
MXP9:25 amMilan Malpensa
Aug 25
MXP11:40 amMilan Malpensa
35h 35m
1 stop
MDW4:15 pmChicago Midway
$823
KLM
Aug 19
MDW10:54 amChicago Midway
15h 31m
1 stop
MXP9:25 amMilan Malpensa
Aug 23
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$842
KLM
Aug 24
MDW6:05 amChicago Midway
20h 20m
1 stop
MXP9:25 amMilan Malpensa
Aug 31
MXP11:40 amMilan Malpensa
17h 56m
1 stop
MDW10:36 pmChicago Midway
$950

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Milan Malpensa 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 June 23, 2026.
Use the filters below to find and compare flights from Chicago to Milan Malpensa Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 8/3

3:40 pm-4:40 pm

2 stops18h 00m

Milan Malpensa

Wed 8/19

6:30 am-2:44 pm

2 stops15h 14m

$775
Quickest round-trip

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 8/3

9:40 pm-1:20 pm

Nonstop8h 40m

Milan Malpensa

Wed 8/19

3:20 pm-6:10 pm

Nonstop9h 50m

$776

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$777

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Wed 8/12

9:40 pm-1:20 pm

Nonstop8h 40m

Milan Malpensa

Wed 8/19

3:20 pm-6:10 pm

Nonstop9h 50m

$777

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Mon 8/3

9:40 pm-1:20 pm

Nonstop8h 40m

Milan Malpensa

Wed 8/19

9:00 am-2:55 pm

1 stop12h 55m

$778

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$781

ChicagoMilan

ORD - MXP

ORDMXP

Chicago O'Hare Intl

Thu 9/3

7:15 pm-7:10 pm

1 stop16h 55m

Milan Malpensa

Tue 9/8

8:00 pm-4:10 pm

1 stop27h 10m

$782

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

5:10 pm-9:25 am

1 stop33h 15m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$782

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 8/3

10:54 am-9:25 am

1 stop15h 31m

Milan Malpensa

Wed 8/19

11:40 am-10:36 pm

1 stop17h 56m

$783

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 8/18

5:10 pm-9:25 am

1 stop33h 15m

Milan Malpensa

Tue 8/25

11:40 am-4:15 pm

1 stop35h 35m

$823

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 Milan from

How to get the cheapest flight ticket from Chicago to Milan Malpensa 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 Chicago and Milan Malpensa Airport?

What is the cheapest month to fly to Milan Malpensa Airport?

In general, July is the cheapest month to fly from Chicago to Milan Malpensa Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $187. If you don’t want to visit Milan Malpensa Airport in July, then you should wait until November to fly from Chicago, when ticket prices are also cheap, with an average price of $373.

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

Our data shows that Monday is the least expensive day to fly to Milan Malpensa Airport. Tickets to fly out on this day can be as low as $1,339. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,574.

What is the cheapest Chicago to Milan Malpensa flight route?

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

How far in advance should I book a flight from Chicago to Milan Malpensa Airport?

You are more likely to see cheaper flights to Milan Malpensa Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Milan Malpensa Airport for around $860 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan Malpensa Airport from Chicago for as low as $555 on momondo.

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

There are 3 cabin classes available to choose from on Chicago to Milan Malpensa Airport 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 to Milan Malpensa Airport flights?

You could potentially save up to 19% on your flight if you consider stops on a Chicago to Milan Malpensa Airport flight.

When to book flights from Chicago to Milan Malpensa Airport

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

Cheap Chicago to Milan Malpensa Airport (CHI to MXP) flight deals and tips

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

Best Price Found

$874

Fastest flight time

8h 40m

Direct flights

Every day
The best one-way flight to Milan Malpensa Airport from Chicago in the past 72 hours is $874. The best round-trip flight deal from Chicago to Milan Malpensa Airport found on momondo in the last 72 hours is $1,060.
The fastest flight from Chicago to Milan Malpensa Airport takes 8h 40m
Direct flights go from Chicago to Milan Malpensa Airport every day.
Search flight deals

Frequently asked questions about flying from Chicago to Milan Malpensa Airport

  • How far is Chicago to Milan Malpensa by plane?

    There are 4501.5 mi between Chicago and Milan Malpensa. By plane, this route typically takes 8h 40m.

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

    Prices for flights from Chicago to Milan Malpensa Airport are refreshed on a daily basis.

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

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

    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 Malpensa Airport.

  • What documentation or ID do you need to fly to Milan Malpensa Airport?

    The required travel and health documents for your Milan Malpensa Airport 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 Malpensa Airport. 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 to Milan Malpensa Airport?

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

Best airlines flying from Chicago to Milan Malpensa Airport

Compare and see reviews for airlines that fly from Chicago to Milan Malpensa Airport with momondo
Airline
Rating
Free Cancellation
Price
TAP AIR PORTUGALPriceFrom $401Free CancellationRating
7.2
2,294 reviews
Search TAP AIR PORTUGAL flights
Scandinavian AirlinesPriceFrom $420Free CancellationRating
7.4
1,848 reviews
Search Scandinavian Airlines flights
Turkish AirlinesPriceFrom $534Free CancellationRating
7.4
4,414 reviews
Search Turkish Airlines flights
British AirwaysPriceFrom $644Free CancellationRating
6.7
8,067 reviews
Search British Airways flights
United AirlinesPriceFrom $774Free CancellationRating
7.4
9,878 reviews
Search United Airlines flights
LufthansaPriceFrom $840Free CancellationRating
6.8
8,090 reviews
Search Lufthansa flights

  • United Airlines Flights From Chicago to Milan Malpensa Airport

    United Airlines flies from Chicago to Milan Malpensa Airport around 7 times per week, with 9,878 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Chicago to Milan Malpensa Airport in the last 72 hours was $774 (round-trip), much lower than the average airfare cost of $1,243 for United Airlines flights on this route.

  • Lufthansa Flights From Chicago to Milan Malpensa Airport

    The best Lufthansa deal for Chicago to Milan Malpensa Airport flight tickets found on momondo in the last 72 hours was $840, round-trip. It should be noted that an average Lufthansa flight deal for this route in this time was higher, at $1,193 round-trip. Lufthansa operates 7 flights out of Chicago into Milan Malpensa Airport in an average week, so prices vary by time and availability. 8,090 Lufthansa reviews by users on momondo have scored the airline at 6.8/10.

Traveling to a place near Milan?

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

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Milan for you.

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 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 Milan from Chicago.

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

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

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