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Cheap flights from Chicago to Milan from $241

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 1/27. 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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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 from Chicago to Milan

The cheapest plane tickets from Chicago to Milan found on KAYAK recently.
7:40 pm - 7:10 pmORD-MXP
16h 30m1 stop
11:20 am - 6:50 pmMXP-ORD
13h 30m1 stop
$443Scandinavian Airlines
Find Deal
Mon, Mar 3 - Mon, Mar 10
7:40 pm - 7:10 pmORD-MXP
16h 30m1 stop
11:20 am - 6:50 pmMXP-ORD
13h 30m1 stop
$446Scandinavian Airlines
Find Deal
Mon, Mar 3 - Mon, Mar 10
8:20 pm - 4:55 pmORD-MXP
13h 35m1 stop
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
$475TAP AIR PORTUGAL
Find Deal
Fri, Feb 21 - Sun, Mar 2
7:15 pm - 4:55 pmORD-MXP
14h 40m1 stop
11:55 am - 3:30 pmMXP-ORD
34h 35m1 stop
$481TAP AIR PORTUGAL
Find Deal
Wed, Feb 19 - Thu, Feb 27
3:55 pm - 11:05 amORD-LIN
12h 10m1 stop
11:45 am - 6:55 pmLIN-ORD
13h 10m1 stop
$547Aer Lingus
Find Deal
Wed, Mar 5 - Wed, Mar 12
3:55 pm - 11:05 amORD-LIN
12h 10m1 stop
11:45 am - 6:55 pmLIN-ORD
13h 10m1 stop
$555Aer Lingus
Find Deal
Wed, Mar 5 - Wed, Mar 12
7:05 am - 2:10 pmORD-LIN
24h 05m2 stops
6:30 am - 9:26 pmLIN-ORD
20h 56m2 stops
$608ITA Airways
Find Deal
Mon, Mar 3 - Mon, Mar 10
4:16 pm - 3:40 pmORD-LIN
16h 24m2 stops
7:35 am - 7:50 pmLIN-ORD
18h 15m2 stops
$650British Airways
Find Deal
Wed, Mar 5 - Wed, Mar 12
9:15 pm - 3:35 pmORD-LIN
12h 20m1 stop
7:30 pm - 12:00 pmLIN-ORD
23h 30m1 stop
$657British Airways
Find Deal
Mon, Mar 24 - Mon, Mar 31
7:05 am - 3:10 pmORD-LIN
25h 05m2 stops
7:55 pm - 9:24 pmLIN-ORD
32h 29m2 stops
$788ITA Airways
Find Deal
Wed, Feb 19 - Sun, Feb 23
7:00 am - 11:05 amORD-BGY
45h 05m2 stops
Mon, Jan 27
7:00 am - 7:30 pmORD-MXP
29h 30m2 stops
Mon, Jan 27
5:15 am - 9:40 amORD-MXP
45h 25m2 stops
Wed, Feb 26
7:40 pm - 10:30 amORD-MXP
31h 50m1 stop
$363Scandinavian Airlines
Find Deal
Mon, Mar 3
7:15 pm - 7:55 pmORD-MXP
17h 40m2 stops
$370Scandinavian Airlines
Find Deal
Mon, Mar 31
7:05 am - 11:10 amORD-LIN
21h 05m2 stops
$473ITA Airways
Find Deal
Wed, Feb 19
9:00 pm - 11:05 amORD-LIN
31h 05m1 stop
$515Aer Lingus
Find Deal
Sun, Jan 26
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
$529Aer Lingus
Find Deal
Sun, May 4
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$788United Airlines
Find Deal
Wed, Apr 9
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$848United Airlines
Find Deal
Sat, May 17
8:20 pm - 11:35 pmORD-MXP
20h 15m1 stop
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
$514TAP AIR PORTUGAL
Find Deal
Fri, Jan 24 - Sun, Feb 2
8:20 pm - 4:55 pmORD-MXP
13h 35m1 stop
5:45 pm - 3:30 pmMXP-ORD
28h 45m1 stop
$525TAP AIR PORTUGAL
Find Deal
Fri, Jan 24 - Sat, Feb 1
7:40 pm - 7:10 pmORD-MXP
16h 30m1 stop
11:20 am - 5:50 pmMXP-ORD
13h 30m1 stop
$546Scandinavian Airlines
Find Deal
Thu, Jan 23 - Mon, Feb 3
7:40 pm - 7:10 pmORD-MXP
16h 30m1 stop
11:20 am - 5:50 pmMXP-ORD
13h 30m1 stop
$596Scandinavian Airlines
Find Deal
Thu, Jan 23 - Sun, Feb 2
2:03 pm - 3:10 pmORD-LIN
18h 07m2 stops
8:00 am - 9:24 pmLIN-ORD
20h 24m2 stops
$638ITA Airways
Find Deal
Fri, Jan 24 - Tue, Feb 4
2:03 pm - 2:40 pmORD-LIN
17h 37m2 stops
7:30 am - 9:28 pmLIN-ORD
20h 58m2 stops
$706ITA Airways
Find Deal
Tue, Jan 21 - Tue, Jan 28
6:35 pm - 1:20 pmORD-LIN
11h 45m1 stop
6:55 pm - 1:55 pmLIN-ORD
26h 00m1 stop
$947British Airways
Find Deal
Fri, Jan 24 - Mon, Feb 3
9:45 pm - 6:05 pmORD-LIN
13h 20m1 stop
6:55 pm - 1:55 pmLIN-ORD
26h 00m1 stop
$964British Airways
Find Deal
Sat, Jan 25 - Mon, Feb 3
9:00 pm - 11:05 amORD-LIN
31h 05m1 stop
11:45 am - 7:15 pmLIN-ORD
14h 30m1 stop
$1,003Aer Lingus
Find Deal
Sat, Jan 25 - Sat, Feb 1
9:00 pm - 11:05 amORD-LIN
31h 05m1 stop
11:45 am - 7:15 pmLIN-ORD
14h 30m1 stop
$1,011Aer Lingus
Find Deal
Sat, Jan 25 - Sun, Feb 2
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,003United Airlines
Find Deal
Tue, Apr 8 - Tue, Apr 15
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,063United Airlines
Find Deal
Mon, Apr 7 - Sun, Apr 20
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,078United Airlines
Find Deal
Tue, Apr 8 - Fri, Apr 18
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,138United Airlines
Find Deal
Mon, Apr 7 - Sat, Apr 19
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,153United Airlines
Find Deal
Wed, Apr 16 - Thu, Apr 24
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,213United Airlines
Find Deal
Wed, Apr 23 - Mon, May 5
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,228United Airlines
Find Deal
Wed, Apr 9 - Fri, Apr 18
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,273United Airlines
Find Deal
Thu, Apr 24 - Sun, May 4
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$6,228Lufthansa
Find Deal
Tue, Apr 22 - Sat, Apr 26
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$6,568Lufthansa
Find Deal
Sat, Apr 19 - Sat, May 3

Delta flights from Chicago to Milan

Our best Delta deals on Chicago to Milan flight tickets
Delta
Mar 19
ORD8:25 amChicago O'Hare Intl
18h 20m
1 stop
MXP8:45 amMilan Malpensa
Mar 26
MXP8:25 amMilan Malpensa
15h 18m
1 stop
ORD5:43 pmChicago O'Hare Intl
Delta
Mar 10
ORD2:30 pmChicago O'Hare Intl
11h 35m
1 stop
MXP8:05 amMilan Malpensa
Mar 25
MXP11:00 amMilan Malpensa
16h 26m
1 stop
ORD9:26 pmChicago O'Hare Intl
Delta
Mar 5
ORD4:58 pmChicago O'Hare Intl
15h 17m
2 stops
MXP3:15 pmMilan Malpensa
Mar 12
MXP10:05 amMilan Malpensa
16h 53m
1 stop
ORD8:58 pmChicago O'Hare Intl

KLM flights from Chicago to Milan

Our best KLM deals on Chicago to Milan flight tickets
KLM
Mar 10
MDW12:51 pmChicago Midway
13h 14m
1 stop
MXP8:05 amMilan Malpensa
Mar 25
MXP11:00 amMilan Malpensa
28h 09m
2 stops
MDW9:09 amChicago Midway
KLM
Mar 12
ORD5:25 pmChicago O'Hare Intl
23h 30m
1 stop
LIN10:55 pmMilan Linate
Mar 19
LIN6:30 amMilan Linate
15h 00m
1 stop
ORD3:30 pmChicago O'Hare Intl
KLM
Mar 2
ORD4:25 pmChicago O'Hare Intl
11h 05m
1 stop
LIN10:30 amMilan Linate
Mar 10
LIN11:25 amMilan Linate
15h 19m
2 stops
ORD8:44 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 $538. 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?

You are more likely to see cheaper flights to Milan from Chicago when booking 2 weeks ahead of your departure date. In general, you can expect to find flights to Milan for around $995 when searching 2 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milan from Chicago for as low as $798 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.

How have Chicago to Milan flight prices changed over time?

As of January 2025, prices for Chicago to Milan flights are approximately 14% more expensive 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

$241

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 $241. The best round-trip flight deal from Chicago to Milan found on momondo in the last 72 hours is $443.
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 10h 45m.

  • 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
Scandinavian AirlinesPriceFrom $443Free CancellationRating
7.3
1,320 reviews
Search Scandinavian Airlines flights
TAP AIR PORTUGALPriceFrom $454Free CancellationRating
7.1
1,867 reviews
Search TAP AIR PORTUGAL flights
Aer LingusPriceFrom $509Free CancellationRating
7.1
1,079 reviews
Search Aer Lingus flights
Turkish AirlinesPriceFrom $525Free CancellationRating
7.3
3,931 reviews
Search Turkish Airlines flights
LufthansaPriceFrom $536Free CancellationRating
6.7
7,106 reviews
Search Lufthansa flights
American AirlinesPriceFrom $550Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $555Free CancellationRating
8.0
8,521 reviews
Search Delta flights
IcelandairPriceFrom $597Free CancellationRating
7.1
501 reviews
Search Icelandair flights
British AirwaysPriceFrom $615Free CancellationRating
6.6
6,834 reviews
Search British Airways flights
Air FrancePriceFrom $625Free CancellationRating
7.4
1,490 reviews
Search Air France flights

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Livigno
Bellagio
Varenna
Stresa
Brescia
Menaggio
Bormio
Assago
Rho
Novara
Saronno
Monza
Crema
Lecco
Domodossola
Lainate
Cernobbio
Mandello del Lario
Levanto
Bellano

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