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Cheap flights from Chicago to Milan from $251

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 2/11. 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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Find the cheapest flights from Chicago to Milan

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Milan that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Milan.

Cheap last minute flights

Planning a quick getaway from Chicago to Milan? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Milan, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Milan

Find recent round-trip train or bus tickets from Chicago to Milan.

All round-trip flight deals to Milan

The cheapest plane tickets to Milan found on KAYAK recently.
7:15 pm - 7:15 pmORD-MXP
17h 00m1 stop
8:05 pm - 4:10 pmMXP-ORD
27h 05m1 stop
$423Scandinavian Airlines
Find Deal
Sun, Mar 30 - Wed, Apr 16
7:15 pm - 7:55 pmORD-MXP
17h 40m2 stops
8:05 pm - 4:10 pmMXP-ORD
27h 05m1 stop
$426Scandinavian Airlines
Find Deal
Sun, Mar 30 - Wed, Apr 16
10:57 am - 9:45 amMDW-MXP
15h 48m2 stops
8:25 am - 10:27 pmMXP-MDW
20h 02m2 stops
$531Delta
Find Deal
Wed, Mar 5 - Wed, Mar 19
10:05 am - 9:45 amORD-MXP
16h 40m1 stop
12:00 pm - 9:18 amMXP-ORD
28h 18m1 stop
$532Delta
Find Deal
Sun, Feb 9 - Mon, Feb 24
6:00 pm - 4:25 pmORD-MXP
15h 25m1 stop
5:55 am - 4:10 pmMXP-ORD
17h 15m1 stop
$576TAP AIR PORTUGAL
Find Deal
Sun, Apr 27 - Fri, May 9
8:25 pm - 11:35 pmORD-MXP
20h 10m1 stop
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
$579TAP AIR PORTUGAL
Find Deal
Sun, Jan 26 - Fri, Jan 31
5:30 pm - 3:40 pmORD-LIN
15h 10m2 stops
6:55 pm - 1:55 pmLIN-ORD
26h 00m1 stop
$595British Airways
Find Deal
Wed, Jan 8 - Tue, Jan 14
4:55 pm - 1:35 pmORD-LIN
13h 40m1 stop
7:25 am - 3:55 pmLIN-ORD
15h 30m1 stop
$673British Airways
Find Deal
Sun, Mar 30 - Sun, Apr 6
4:55 pm - 11:05 amORD-LIN
12h 10m1 stop
11:20 am - 7:05 pmLIN-ORD
14h 45m1 stop
$714Aer Lingus
Find Deal
Sat, Mar 22 - Tue, Apr 1
4:55 pm - 11:05 amORD-LIN
12h 10m1 stop
11:20 am - 7:05 pmLIN-ORD
14h 45m1 stop
$743Aer Lingus
Find Deal
Fri, Mar 28 - Sun, Apr 6
6:30 pm - 4:35 pmORD-MXP
15h 05m2 stops
Tue, Feb 11
1:45 pm - 8:25 pmORD-MXP
47h 40m3 stops
Wed, Jan 29
6:30 pm - 8:40 pmORD-BGY
19h 10m2 stops
Mon, Jan 20
7:10 pm - 10:30 amORD-MXP
32h 20m1 stop
$362Scandinavian Airlines
Find Deal
Sun, Jan 19
7:15 pm - 2:45 pmORD-MXP
12h 30m1 stop
$367Scandinavian Airlines
Find Deal
Mon, Mar 31
8:55 pm - 10:40 amORD-LIN
30h 45m1 stop
$764Aer Lingus
Find Deal
Sat, May 17
8:55 pm - 10:40 amORD-LIN
30h 45m1 stop
$766Aer Lingus
Find Deal
Fri, May 16
7:10 am - 10:10 amORD-LIN
20h 00m2 stops
$858ITA Airways
Find Deal
Wed, Feb 12
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$878United Airlines
Find Deal
Wed, Apr 9
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$2,383United Airlines
Find Deal
Wed, Apr 9
4:45 pm - 2:05 pmORD-MXP
14h 20m1 stop
12:15 pm - 2:45 pmMXP-ORD
33h 30m1 stop
$1,082American Airlines
Find Deal
Mon, Dec 23 - Sun, Jan 12
4:45 pm - 2:05 pmORD-MXP
14h 20m1 stop
11:30 am - 12:27 amMXP-ORD
19h 57m2 stops
$1,220American Airlines
Find Deal
Mon, Dec 23 - Sun, Jan 12
5:07 pm - 9:50 amORD-MXP
33h 43m2 stops
8:00 pm - 3:50 pmMXP-ORD
26h 50m1 stop
$1,515
Find Deal
Sat, Dec 21 - Sun, Dec 29
3:55 pm - 4:55 pmORD-LIN
18h 00m1 stop
6:25 am - 7:32 pmLIN-ORD
20h 07m2 stops
$1,959United Airlines
Find Deal
Sun, Dec 22 - Tue, Dec 31
3:15 pm - 4:55 pmORD-LIN
18h 40m1 stop
6:25 am - 10:10 amLIN-ORD
34h 45m2 stops
$2,060United Airlines
Find Deal
Sun, Dec 22 - Fri, Jan 3
7:10 pm - 1:05 pmORD-MXP
34h 55m2 stops
1:55 pm - 3:50 pmMXP-ORD
32h 55m2 stops
$2,653Scandinavian Airlines
Find Deal
Fri, Dec 20 - Sun, Jan 5
7:10 pm - 10:05 amORD-MXP
31h 55m2 stops
4:05 pm - 3:50 pmMXP-ORD
30h 45m1 stop
$2,668Scandinavian Airlines
Find Deal
Fri, Dec 20 - Sat, Jan 4
8:15 am - 1:10 pmORD-LIN
21h 55m2 stops
6:30 am - 9:30 pmLIN-ORD
22h 00m2 stops
$3,098ITA Airways
Find Deal
Mon, Dec 23 - Wed, Jan 1
1:59 pm - 5:10 pmORD-LIN
20h 11m2 stops
7:55 pm - 9:28 pmLIN-ORD
32h 33m2 stops
$3,556ITA Airways
Find Deal
Thu, Dec 19 - Sun, Jan 5
3:55 pm - 11:05 amORD-LIN
12h 10m1 stop
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$6,596Aer Lingus
Find Deal
Mon, Dec 23 - Fri, Jan 3
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,361United Airlines
Find Deal
Tue, Apr 8 - Thu, Apr 17
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,421United Airlines
Find Deal
Wed, Apr 23 - Sat, May 10
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:10 pmMXP-ORD
9h 50mnonstop
$1,456United Airlines
Find Deal
Tue, Apr 29 - Wed, Jun 11
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,481United Airlines
Find Deal
Sat, Apr 26 - Sat, May 10
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,494United Airlines
Find Deal
Fri, Apr 25 - Mon, May 12
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,506United Airlines
Find Deal
Fri, Apr 25 - Sun, May 11
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:10 pmMXP-ORD
9h 50mnonstop
$1,516United Airlines
Find Deal
Thu, May 8 - Tue, May 27
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:10 pmMXP-ORD
9h 50mnonstop
$1,526United Airlines
Find Deal
Sun, Apr 27 - Sun, May 25
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$5,841Lufthansa
Find Deal
Sat, Apr 19 - Sat, May 3
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$5,992Lufthansa
Find Deal
Tue, Apr 22 - Sat, Apr 26

KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets
KLM
Mar 4
ORD10:05 amChicago O'Hare Intl
16h 40m
1 stop
MXP9:45 amMilan Malpensa
Mar 19
MXP10:05 amMilan Malpensa
14h 48m
1 stop
ORD6:53 pmChicago O'Hare Intl
KLM
Jan 31
ORD2:03 pmChicago O'Hare Intl
12h 42m
1 stop
MXP9:45 amMilan Malpensa
Feb 7
MXP12:00 pmMilan Malpensa
18h 49m
2 stops
ORD11:49 pmChicago O'Hare Intl
KLM
Jan 20
ORD11:05 amChicago O'Hare Intl
15h 40m
2 stops
MXP9:45 amMilan Malpensa
Jan 27
MXP12:00 pmMilan Malpensa
18h 59m
2 stops
ORD11:59 pmChicago O'Hare Intl

Delta flights from Chicago to Milan

Our best Delta deals on Chicago to Milan flight tickets
Delta
Mar 5
MDW10:57 amChicago Midway
15h 48m
2 stops
MXP9:45 amMilan Malpensa
Mar 19
MXP8:25 amMilan Malpensa
20h 02m
2 stops
MDW10:27 pmChicago Midway
Delta
Feb 9
ORD10:05 amChicago O'Hare Intl
16h 40m
1 stop
MXP9:45 amMilan Malpensa
Feb 24
MXP12:00 pmMilan Malpensa
28h 18m
1 stop
ORD9:18 amChicago O'Hare Intl
Delta
Jan 20
ORD10:05 amChicago O'Hare Intl
16h 40m
1 stop
MXP9:45 amMilan Malpensa
Jan 30
MXP12:00 pmMilan Malpensa
16h 28m
1 stop
ORD9:28 pmChicago O'Hare Intl

See travel insights to Milan from

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

What is the cheapest month to fly to Milan?

The month of February is, on average, the cheapest month to fly to Milan from Chicago, with most prices found around $537. The month of November is another great option to travel to Milan, with average flight prices from Chicago averaging around $608.

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

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $826. The most expensive day to fly to Milan is Friday, with ticket prices averaging around $945.

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

In the morning is the cheapest time of day to fly from Chicago to Milan when you can find flight prices for as low as $703. Flying to Milan in the morning is an ideal time because this is during off-peak travel hours. Flights to Milan are more costly in the evening, with an average ticket price of $949. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Milan flight route?

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

How far in advance should I book a flight to Milan?

The best time to book a flight to Milan from Chicago is 60 days out, which is when prices tend to be around $1,002. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan from Chicago for as low as $357 on momondo.

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

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

You could potentially save up to 71% on your flight if you consider stops on a Chicago to Milan flight.

How have Chicago to Milan flight prices changed over time?

As of December 2024, prices for Chicago to Milan flights are approximately 39% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Milan

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

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

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

Best Price Found

$251

Fastest flight time

8h 45m

Direct flights

Every day

Airports in Milan

3 airports
The best one-way flight to Milan from Chicago in the past 72 hours is $251. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $423.
The fastest flight from Chicago to Milan takes 8h 45m
Direct flights go from Chicago to Milan every day.
There are 3 airports near Milan: Milan Linate (LIN), Milan Malpensa (MXP), Bergamo Orio Al Serio (BGY)

  • How far is Chicago to Milan by plane?

    There are 4526.2 mi between Chicago and Milan. By plane, this route typically takes 11h 05m.

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

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

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

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

    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.

  • 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 to Milan?

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


Best airlines flying from Chicago to Milan

Compare and see reviews for airlines that fly from Chicago to Milan with momondo
Airline
Rating
Free Cancellation
Price
IcelandairPriceFrom $382Free CancellationRating
7.1
510 reviews
Search Icelandair flights
Scandinavian AirlinesPriceFrom $447Free CancellationRating
7.3
1,309 reviews
Search Scandinavian Airlines flights
TAP AIR PORTUGALPriceFrom $454Free CancellationRating
7.1
1,877 reviews
Search TAP AIR PORTUGAL flights
Aer LingusPriceFrom $509Free CancellationRating
7.1
1,073 reviews
Search Aer Lingus flights
Turkish AirlinesPriceFrom $525Free CancellationRating
7.3
3,907 reviews
Search Turkish Airlines flights
LufthansaPriceFrom $536Free CancellationRating
6.8
7,091 reviews
Search Lufthansa flights
American AirlinesPriceFrom $550Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
British AirwaysPriceFrom $656Free CancellationRating
6.6
6,820 reviews
Search British Airways flights
ITA AirwaysPriceFrom $715Free CancellationRating
6.7
907 reviews
Search ITA Airways flights
United AirlinesPriceFrom $774Free CancellationRating
7.4
9,059 reviews
Search United Airlines flights

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

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Milan.

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

Yes momondo offers price alerts on flights to Milan from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan