MIL - CHI

$373 Find Cheap Flights from Milan to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milan to Chicago departing on 5/13. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milan to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milan to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$535
Typical prices: $982-$712
Icelandair
Tue 6/2Sun 6/7
MXP - ORD • 1 stop
Cheapest non-stop
$740
Lufthansa
Wed 10/7Wed 10/14
MXP - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
At MXP, allow an hour for check-in and security.
Take the CTA Blue Line from ORD to downtown Chicago.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $535 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with United Airlines. Average duration is 9h 40m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 79% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $516 (round-trip)
Shortest trip • 11h 30m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Milan to Chicago (MIL-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milan to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milan to Chicago

Tue, Jun 2 - Sun, Jun 7
Icelandair Logo
10:55 pm - 6:15 pm
MXP
-
ORD
26h 20m
1 stop
Icelandair Logo
7:25 pm - 3:10 pm
ORD
-
MXP
12h 45m
1 stop
$535Icelandair
Tue, Jun 9 - Mon, Jun 15
Icelandair Logo
10:55 pm - 6:15 pm
MXP
-
ORD
26h 20m
1 stop
Icelandair Logo
10:25 pm - 9:55 pm
ORD
-
MXP
16h 30m
1 stop
$536Icelandair
Tue, Jun 9 - Tue, Jun 16
Icelandair Logo
10:55 pm - 6:15 pm
MXP
-
ORD
26h 20m
1 stop
Icelandair Logo
10:25 pm - 3:10 pm
ORD
-
MXP
33h 45m
1 stop
$537Icelandair
Mon, Jun 1 - Mon, Jun 29
ITA Airways Logo
7:00 am - 1:10 pm
LIN
-
ORD
13h 10m
1 stop
ITA Airways Logo
3:00 pm - 10:10 am
ORD
-
LIN
12h 10m
1 stop
$565ITA Airways
Tue, Jun 9 - Sun, Jun 21
ITA Airways Logo
7:00 am - 1:10 pm
LIN
-
ORD
13h 10m
1 stop
ITA Airways Logo
3:00 pm - 7:40 am
ORD
-
LIN
33h 40m
1 stop
$566ITA Airways
Sun, May 10 - Tue, May 26
British Airways Logo
7:25 am - 5:35 pm
LIN
-
ORD
17h 10m
1 stop
British Airways Logo
9:15 pm - 5:15 pm
ORD
-
LIN
13h 00m
1 stop
$659British Airways
Sun, May 10 - Tue, May 26
British Airways Logo
7:25 am - 5:35 pm
LIN
-
ORD
17h 10m
1 stop
British Airways Logo
5:00 pm - 12:30 pm
ORD
-
LIN
12h 30m
1 stop
$660British Airways
Thu, May 21 - Sun, May 31
Delta Logo
11:40 am - 9:09 pm
MXP
-
MDW
16h 29m
1 stop
Delta Logo
10:59 am - 9:25 am
MDW
-
MXP
15h 26m
1 stop
$731Delta
Thu, May 21 - Sun, May 31
Delta Logo
11:40 am - 9:09 pm
MXP
-
MDW
16h 29m
1 stop
Delta Logo
10:59 am - 9:25 am
MDW
-
MXP
15h 26m
1 stop
$732Delta
Thu, Oct 8 - Mon, Oct 12
Air France Logo
6:25 am - 9:45 pm
LIN
-
MDW
22h 20m
2 stops
Air France Logo
5:59 pm - 1:55 pm
MDW
-
LIN
12h 56m
2 stops
$736Air France
Booking Insights

KAYAK's insights & trends for Milan to Chicago flights

Get data-powered insights and trends into flights from Milan to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Milan to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Milan to Chicago departing in June.

What is the cheapest Milan to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Milan to Chicago costs $612 on the route between Milan Malpensa Airport (MXP) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Milan to Chicago?

The average price of all round-trip flights from Milan to Chicago clicked on KAYAK for each day over the last 12 months.

For Milan to Chicago, Saturday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to Milan, the best deals are generally found on Tuesday, with Wednesday being the most expensive.

What is the cheapest month to fly from Milan to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milan to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Milan to Chicago is September, where tickets cost $356 (return) on average. On the other hand, the most expensive months are July and January, where the average cost of round-trip tickets is $615 and $535 respectively.

Can I save money by flying with a layover from Milan to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $749 on average.

Expert advice

Expert advice for your flight from Milan to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Duncan Madden

Duncan Madden

Expert on MXP

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Good to know

Low seasonJanuary
Cheapest flight$373
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Bergamo to Chicago

When to book flights from Milan to Chicago

Are your dates flexible? Find out the best times to travel from Milan to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Milan to Chicago

  • What amenities can I enjoy if I book a business-class ticket for my flight from Milan to Chicago?

    Booking a seat in business class has many advantages, especially on a long-haul flight from Milan to Chicago. However, business-class amenities depend on your airline. If you book with Lufthansa, you enjoy services such as priority boarding, a seat that lays down into a bed, self-service coffee, a dental hygiene kit, ear plugs, and additional legroom.

  • What airlines offer a sustainable journey for flights from Milan to Chicago?

    Book with Delta Air Lines if you prefer more sustainable travel from Milan to Chicago. Delta embraces eco-friendly food packaging to reduce landfill waste by 90%. The company also ensures a greener environment by using sustainable aviation fuel (SAF) in its fleet. Another airline offering an environmentally friendly journey is KLM. This company avoids fossil fuels by using SAF from recycling feedstock and residues. These airlines are committed to achieving zero carbon emissions by 2050.

  • Are there allowances to upgrade to first class from Milan to Chicago?

    Opportunities to upgrade to first class depend on the airline on which you travel. Most airlines email passengers about available first-class seats a few days before flight departure. This way, you have an opportunity to upgrade. However, you need to do so at least 24 hours before departure. Flying as a first-class passenger means enjoying exclusive services, including a blanket, complimentary snacks and drinks, a pillow, and a lie-flat bed. However, amenities vary from one airline to another.

  • What other cities does Chicago O’Hare International Airport serve?

    Chicago O'Hare serves a few nearby cities. After arriving at the airport, you can go to Bensenville and Wood Dale to the southwest, Schiller Park to the southeast, Park Ridge to the northeast, and Des Plaines to the north. You can connect to these cities using buses and trains or rent a car at the airport.

  • What is the cheapest flight from Milan to Chicago?

    In the last 3 days, the lowest price for a flight from Milan to Chicago was $373 for a one-way ticket and $535 for a round-trip.

  • Do I need a passport to fly between Milan and Chicago?

    Yes

  • Which airlines offer Wi-Fi service onboard planes from Milan to Chicago?

    KLM, American Airlines, Air France, and Delta offer inflight Wi-Fi service on the Milan to Chicago flight route.

  • Which aircraft models fly most regularly from Milan to Chicago?

    The Boeing 787 Dreamliner is the aircraft model that flies most regularly on the Milan to Chicago flight route.

  • Which airline alliances offer flights from Milan to Chicago?

    Star Alliance is the only airline alliance operating flights between Milan and Chicago.

  • On which days can I fly direct from Milan to Chicago?

    There are nonstop flights from Milan to Chicago on a daily basis.

  • Which is the best airline for flights from Milan to Chicago, United Airlines or Lufthansa?

    The two airlines most popular with KAYAK users for flights from Milan to Chicago are United Airlines and Lufthansa. With an average price for the route of $895 and an overall rating of 7.4, United Airlines is the most popular choice. Lufthansa is also a great choice for the route, with an average price of $854 and an overall rating of 6.8.

  • How does KAYAK find such low prices on flights from Milan to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Milan to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milan to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Milan is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Milan to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Milan with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milan to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Milan up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Milan to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $990 or less one-way and $655 or less round-trip.
  • Common layovers for flights from Milan to Chicago are in major cities such as London and Amsterdam. However, the layover city and duration depend on your airline. For this reason, check the flight route before booking to avoid a longer journey.
  • Milan Malpensa Airport (MXP) is the largest and offers VIP services to passengers needing smooth travel experiences. You enjoy services such as meet and greet, fast-track check-in through security, luggage assistance, and luxury transportation.
  • Your airline determines the carry-on and checked luggage allowance for the cheap flights from Milan to Chicago. If you book with Turkish Airlines, the maximum carry-on luggage weight is 17 lbs. and not exceeding 21.6 x 15.7 x 7.9 inches.
  • When flying from Milan to Chicago, an alternative airport is Milan Linate Airport (LIN). Though it's further from downtown Milan, this airport is less busy than MXP airport. Therefore, you don't have to worry about long queues.
  • MXP airport is a hub for Lufthansa, Blue Panorama Airlines, and easyJet, serving as a gateway to major cities worldwide. At the same time, Chicago O’Hare International Airport (ORD) is a hub for American Airlines and United Airlines. It links major cities in the U.S. and other European countries.

Prefer to fly direct from Milan to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Milan to Chicago.
Find which airlines fly direct from Milan to Chicago, which days they fly and book direct flights.

Direct departures

Milan to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Milan

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Reviews of the top airlines flying from Milan to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Milan to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Milan to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9680 reviews
7.7Boarding
7.1Entertainment
8.1Crew
7.3Comfort
6.6Food
Airline reviews

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

8.0 ExcellentAnonymous, Apr 2026
ZRH - ORD
Read more United Airlines reviews

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Everything could have been better. What needed to be wrong with United went wrong

It was good. The seats in economy weren’t bad

Very good. Comfortable and I felt well taken care of from start to finish

We were in premium economy seats that appeared to be locked in plae, No reclining. My aching back.

I don’t understand how they charge as much as they do for such a poor experience

I wish the plane had pod seating for business class. I had a window seat (8K) and I had to climb over the person sitting on the aisle when I needed to get up. Also there is no partition between the seats for privacy when sleeping. The Asian airlines have much nicer business class seating. Their seats are wider for better comfort when sleeping.

The seat space seemed small especially when the person ahead reclined but other than that, very good.

Luggage transfer in Chicago was not performed in time. I received my luggage at my destination two days later.

Food was poor quality and the screens for entertainment didn’t work properly

It was a short flight, everything was good with it.

Everything you need to know for your flight from Milan to Chicago

Cabin class types available on flights from Milan to Chicago

Cabin classes available on flights from Milan to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.