Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Milan to Chicago from $369

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 2/16. 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
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Milan to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Milan to Chicago 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 Milan to Chicago.

Cheap last minute flights

Planning a quick getaway from Milan to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Milan to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:45 am - 6:55 pmLIN-ORD
13h 10m1 stop
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
$425Aer Lingus
Find Deal
Wed, Mar 26 - Sun, Mar 30
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
8:20 pm - 11:05 amORD-MXP
31h 45m1 stop
$427TAP AIR PORTUGAL
Find Deal
Wed, Jan 15 - Fri, Jan 24
8:00 pm - 3:50 pmMXP-ORD
26h 50m1 stop
7:10 pm - 7:10 pmORD-MXP
17h 00m1 stop
$496Scandinavian Airlines
Find Deal
Wed, Dec 11 - Thu, Jan 9
8:00 pm - 3:50 pmMXP-ORD
26h 50m1 stop
7:10 pm - 7:10 pmORD-MXP
17h 00m1 stop
$501Scandinavian Airlines
Find Deal
Thu, Jan 9 - Thu, Jan 23
6:55 pm - 1:55 pmLIN-ORD
26h 00m1 stop
9:45 pm - 5:50 pmORD-LIN
13h 05m1 stop
$554British Airways
Find Deal
Fri, Dec 6 - Sun, Dec 8
11:20 am - 5:00 pmMXP-ORD
12h 40m1 stop
6:30 pm - 2:25 pmORD-MXP
12h 55m1 stop
$556British Airways
Find Deal
Wed, Dec 4 - Sun, Dec 8
4:00 pm - 1:10 pmLIN-ORD
28h 10m1 stop
3:00 pm - 3:00 pmORD-LIN
17h 00m2 stops
$567ITA Airways
Find Deal
Thu, May 8 - Mon, May 12
6:25 am - 2:45 pmLIN-ORD
15h 20m2 stops
1:19 pm - 4:55 pmORD-LIN
20h 36m2 stops
$601United Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
6:25 am - 10:54 amLIN-ORD
35h 29m2 stops
5:55 pm - 11:20 amORD-LIN
10h 25m1 stop
$605United Airlines
Find Deal
Fri, Jan 10 - Fri, Jan 17
12:00 pm - 9:55 amLIN-ORD
28h 55m2 stops
7:00 am - 10:10 amORD-LIN
20h 10m2 stops
$784ITA Airways
Find Deal
Thu, Jan 9 - Thu, Jan 23
2:10 pm - 5:20 pmMXP-ORD
34h 10m1 stop
$369Icelandair
Find Deal
Sun, Feb 16
9:30 am - 4:30 pmMXP-ORD
14h 00m1 stop
$387Air Serbia
Find Deal
Mon, May 19
9:30 am - 4:30 pmMXP-ORD
14h 00m1 stop
$388Air Serbia
Find Deal
Mon, May 19
5:45 pm - 3:30 pmMXP-ORD
28h 45m1 stop
$408TAP AIR PORTUGAL
Find Deal
Sat, Feb 15
5:45 pm - 4:30 pmMXP-ORD
28h 45m1 stop
$523TAP AIR PORTUGAL
Find Deal
Sat, Mar 22
4:35 pm - 2:45 pmLIN-ORD
29h 10m1 stop
$619British Airways
Find Deal
Mon, Dec 23
7:35 am - 1:55 pmLIN-ORD
13h 20m1 stop
$663British Airways
Find Deal
Mon, Mar 3
3:05 pm - 6:10 pmMXP-ORD
10h 05mnonstop
$1,368United Airlines
Find Deal
Thu, Nov 28
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
$1,378United Airlines
Find Deal
Mon, May 19
12:55 pm - 3:50 pmLIN-ORD
33h 55m2 stops
$1,833Scandinavian Airlines
Find Deal
Sat, Jan 4
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
8:20 pm - 4:55 pmORD-MXP
13h 35m1 stop
$507TAP AIR PORTUGAL
Find Deal
Fri, Nov 22 - Fri, Dec 6
1:10 pm - 6:45 pmMXP-ORD
12h 35m1 stop
10:05 pm - 4:20 pmORD-MXP
11h 15m1 stop
$609American Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 2
3:05 pm - 6:10 pmMXP-ORD
10h 05mnonstop
9:30 pm - 12:50 pmORD-MXP
8h 20mnonstop
$613United Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 2
10:15 am - 10:05 pmMXP-ORD
18h 50m2 stops
10:05 pm - 7:50 pmORD-MXP
14h 45m1 stop
$615American Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 2
3:05 pm - 6:10 pmMXP-ORD
10h 05mnonstop
12:45 pm - 7:30 amORD-MXP
11h 45m1 stop
$617United Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 2
11:30 am - 6:45 pmLIN-ORD
14h 15m1 stop
6:30 pm - 3:00 pmORD-LIN
13h 30m1 stop
$670British Airways
Find Deal
Fri, Nov 22 - Fri, Dec 6
10:15 am - 5:37 pmMXP-ORD
14h 22m1 stop
5:00 pm - 12:15 pmORD-MXP
12h 15m1 stop
$694British Airways
Find Deal
Sun, Nov 24 - Mon, Dec 9
8:00 pm - 9:36 pmMXP-ORD
32h 36m2 stops
7:10 pm - 7:10 pmORD-MXP
17h 00m1 stop
$823Scandinavian Airlines
Find Deal
Sun, Nov 24 - Mon, Dec 9
8:00 pm - 9:36 pmMXP-ORD
32h 36m2 stops
7:10 pm - 7:10 pmORD-MXP
17h 00m1 stop
$849Scandinavian Airlines
Find Deal
Sun, Nov 24 - Sat, Dec 7
8:00 am - 9:36 pmLIN-ORD
20h 36m2 stops
1:59 pm - 2:10 pmORD-LIN
17h 11m2 stops
$1,378ITA Airways
Find Deal
Fri, Nov 22 - Fri, Dec 6
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
$683United Airlines
Find Deal
Tue, Apr 15 - Thu, Apr 24
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
$873United Airlines
Find Deal
Thu, Apr 17 - Thu, Apr 24
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
$884United Airlines
Find Deal
Tue, Apr 15 - Sat, Apr 26
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
$963United Airlines
Find Deal
Thu, Apr 24 - Fri, May 2
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
$1,048United Airlines
Find Deal
Tue, Apr 15 - Fri, Apr 25
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
$1,074United Airlines
Find Deal
Thu, Apr 17 - Sat, Apr 26
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
$1,107Lufthansa
Find Deal
Thu, Apr 24 - Sat, May 3
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
$1,196United Airlines
Find Deal
Sat, Apr 19 - Sun, May 4
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
9:25 pm - 1:20 pmORD-MXP
8h 55mnonstop
$1,238United Airlines
Find Deal
Thu, Apr 17 - Fri, Apr 25

American Airlines flights from Milan to Chicago

Our best American Airlines deals on Milan to Chicago flight tickets
American Airlines
Dec 5
MXP10:15 amMilan Malpensa
28h 31m
1 stop
ORD7:46 amChicago O'Hare Intl
Dec 9
ORD9:45 pmChicago O'Hare Intl
15h 05m
1 stop
MXP7:50 pmMilan Malpensa
American Airlines
Dec 5
MXP10:15 amMilan Malpensa
28h 31m
1 stop
ORD7:46 amChicago O'Hare Intl
Dec 11
ORD8:43 amChicago O'Hare Intl
16h 27m
1 stop
MXP8:10 amMilan Malpensa
American Airlines
Jan 10
LIN6:55 pmMilan Linate
26h 50m
1 stop
ORD2:45 pmChicago O'Hare Intl
Jan 17
ORD9:45 pmChicago O'Hare Intl
16h 50m
1 stop
LIN9:35 pmMilan Linate

Brussels Airlines flights from Milan to Chicago

Our best Brussels Airlines deals on Milan to Chicago flight tickets
Brussels Airlines
Dec 5
LIN6:55 amMilan Linate
12h 20m
1 stop
ORD12:15 pmChicago O'Hare Intl
Dec 9
ORD5:50 pmChicago O'Hare Intl
17h 00m
2 stops
LIN5:50 pmMilan Linate
Brussels Airlines
Mar 24
LIN6:55 amMilan Linate
12h 20m
1 stop
ORD1:15 pmChicago O'Hare Intl
Apr 8
ORD5:50 pmChicago O'Hare Intl
17h 10m
1 stop
LIN6:00 pmMilan Linate
Brussels Airlines
Mar 24
LIN6:55 amMilan Linate
12h 20m
1 stop
ORD1:15 pmChicago O'Hare Intl
Apr 8
ORD4:05 pmChicago O'Hare Intl
18h 55m
2 stops
LIN6:00 pmMilan Linate

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 cheapest month to fly from Milan to Chicago?

November. The cheapest time of year to fly to Chicago from Milan is November. Most expensive is July

What is the cheapest day to depart Milan for Chicago?

Friday. The cheapest day of the week is typically Friday. The most expensive is typically Monday

When is the cheapest time to fly from Milan to Chicago?

In the evening. Milan to Chicago flights are approximately 30% more expensive at noon than in the evening

What is the cheapest Milan to Chicago flight route?

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

How far in advance should you book Milan to Chicago flights?

57 days before. The cheapest time to buy a flight from Milan to Chicago is approximately 57 days to departure

Can stopping save me money on Milan to Chicago flights?

You could potentially save up to 39% on your flight if you consider stops on a Milan to Chicago flight.

How have Milan to Chicago flight prices changed over time?

As of November 2024, prices for Milan to Chicago flights are approximately 22% cheaper 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

$369

Fastest flight time

9h 40m

Direct flights

Mon, Tue, Wed, Fri and Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Milan in the past 72 hours is $369. The best round-trip flight deal from Milan to Chicago found on momondo in the last 72 hours is $425.
The fastest flight from Milan to Chicago takes 9h 40m
Direct flights go from Milan to Chicago on Monday, Tuesday, Wednesday, Friday and Sunday. Airlines offering direct flights are: United Airlines, Lufthansa and SWISS.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • 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
Scandinavian AirlinesPriceFrom $350Free CancellationRating
7.3
1,301 reviews
Search Scandinavian Airlines flights
TAP AIR PORTUGALPriceFrom $560Free CancellationRating
7.1
1,892 reviews
Search TAP AIR PORTUGAL flights
United AirlinesPriceFrom $624Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
  • United Airlines Flights From Milan to Chicago

    Across 6 United Airlines flights from Milan to Chicago this week, the average price was $870, with the best United Airlines deals starting from $624 round-trip. 9,171 users have rated United Airlines on momondo, with an average score of 7.4/10.


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.


An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 11/25
Mon 12/2
Email me momondo's favorite deals

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