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Cheap flights from Milan to Chicago from $306

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 5/8. 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

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Find the cheapest flights from Milan to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Milan to Chicago.
Icelandair Logo
3:30 pm - 9:15 pmMXP-ORD
12h 45m1 stop
Icelandair Logo
7:25 pm - 2:30 pmORD-MXP
12h 05m1 stop
$456Icelandair
Find Deal
Sun, Sep 21 - Sat, Oct 4
Scandinavian Airlines Logo
3:30 pm - 4:10 pmMXP-ORD
31h 40m1 stop
Scandinavian Airlines Logo
7:15 pm - 8:35 amORD-MXP
30h 20m1 stop
$475Scandinavian Airlines
Find Deal
Fri, Aug 29 - Thu, Sep 18
Scandinavian Airlines Logo
3:30 pm - 4:10 pmMXP-ORD
31h 40m1 stop
Scandinavian Airlines Logo
7:15 pm - 7:55 pmORD-MXP
17h 40m2 stops
$476Scandinavian Airlines
Find Deal
Fri, Aug 29 - Thu, Sep 18
Scandinavian Airlines Logo
8:45 pm - 4:10 pmMXP-ORD
50h 25m2 stops
Scandinavian Airlines Logo
7:15 pm - 10:30 amORD-MXP
32h 15m1 stop
$495Scandinavian Airlines
Find Deal
Thu, Sep 18 - Sun, Sep 21
TAP AIR PORTUGAL Logo
8:15 pm - 4:30 pmMXP-ORD
27h 15m1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 7:15 pmORD-MXP
18h 15m1 stop
$584TAP AIR PORTUGAL
Find Deal
Fri, Sep 12 - Fri, Sep 26
United Airlines Logo
7:00 am - 2:50 pmLIN-ORD
14h 50m2 stops
United Airlines Logo
12:50 pm - 12:00 pmORD-LIN
16h 10m2 stops
$631United Airlines
Find Deal
Wed, Sep 17 - Sun, Sep 21
United Airlines Logo
7:00 am - 2:50 pmLIN-ORD
14h 50m2 stops
United Airlines Logo
12:50 pm - 12:00 pmORD-LIN
16h 10m2 stops
$632United Airlines
Find Deal
Wed, Sep 17 - Sun, Sep 21
Lufthansa Logo
3:20 pm - 6:00 pmMXP-ORD
9h 40mnonstop
Lufthansa Logo
5:50 pm - 12:05 pmORD-MXP
11h 15m1 stop
$656Lufthansa
Find Deal
Wed, Apr 30 - Wed, May 7
Lufthansa Logo
7:00 am - 12:55 pmLIN-ORD
12h 55m1 stop
Lufthansa Logo
3:35 pm - 9:20 amORD-LIN
10h 45m1 stop
$658Lufthansa
Find Deal
Thu, Apr 24 - Sun, May 4
Aer Lingus Logo
11:20 am - 7:00 pmLIN-ORD
14h 40m1 stop
Aer Lingus Logo
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
$931Aer Lingus
Find Deal
Fri, Apr 11 - Wed, Apr 30

Icelandair flights from Milan to Chicago

Our best Icelandair deals on Milan to Chicago flight tickets
Icelandair
Sep 21
MXP3:30 pmMilan Malpensa
12h 45m
1 stop
ORD9:15 pmChicago O'Hare Intl
Oct 4
ORD7:25 pmChicago O'Hare Intl
12h 05m
1 stop
MXP2:30 pmMilan Malpensa
Icelandair
May 4
MXP3:10 pmMilan Malpensa
13h 05m
1 stop
ORD9:15 pmChicago O'Hare Intl
May 7
ORD7:25 pmChicago O'Hare Intl
11h 45m
1 stop
MXP2:10 pmMilan Malpensa
Icelandair
May 4
MXP3:10 pmMilan Malpensa
13h 05m
1 stop
ORD9:15 pmChicago O'Hare Intl
May 7
ORD7:25 pmChicago O'Hare Intl
11h 45m
1 stop
MXP2:10 pmMilan Malpensa

ITA Airways flights from Milan to Chicago

Our best ITA Airways deals on Milan to Chicago flight tickets
ITA Airways
Sep 17
LIN7:00 amMilan Linate
13h 10m
1 stop
ORD1:10 pmChicago O'Hare Intl
Sep 21
ORD3:00 pmChicago O'Hare Intl
13h 40m
1 stop
LIN11:40 amMilan Linate
ITA Airways
Sep 15
LIN7:00 amMilan Linate
13h 10m
1 stop
ORD1:10 pmChicago O'Hare Intl
Sep 28
ORD3:00 pmChicago O'Hare Intl
22h 10m
1 stop
LIN8:10 pmMilan Linate
ITA Airways
Jul 19
LIN7:00 amMilan Linate
13h 10m
1 stop
ORD1:10 pmChicago O'Hare Intl
Aug 1
ORD3:00 pmChicago O'Hare Intl
20h 10m
1 stop
LIN6:10 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 typical price of a round-trip flight between Milan and Chicago?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Milan, with most prices found around $443. If you’re not able to fly to Chicago in November, then February is your next best option. Flight prices from Milan to Chicago during February average around $570.

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

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $881. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Milan to Chicago for around $963.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Milan to Chicago during this time can be as low as $561. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $911.

What is the cheapest Milan to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Milan when booking 24 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $716 when searching 24 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Milan for as low as $525 on momondo.

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

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

How have Milan to Chicago flight prices changed over time?

As of April 2025, prices for Milan to Chicago flights are approximately 4% 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

$306

Fastest flight time

9h 40m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Milan in the past 72 hours is $306. The best round-trip flight deal from Milan to Chicago found on momondo in the last 72 hours is $456.
The fastest flight from Milan to Chicago takes 9h 40m
Direct flights go from Milan to Chicago every day.
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
TAP AIR PORTUGALPriceFrom $537Free CancellationRating
7.1
1,831 reviews
Search TAP AIR PORTUGAL flights
United AirlinesPriceFrom $625Free CancellationRating
7.4
8,615 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
Saint John

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.


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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