MIL - CHI

$354 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 5/18. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$537
Typical prices: $729-$890
Icelandair
Wed 4/22Tue 4/28
MXP - ORD • 1 stop
Cheapest non-stop
$753
Lufthansa
Thu 4/9Wed 4/22
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 $537 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
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 • 16% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Wed, Apr 22 - Tue, Apr 28
Icelandair Logo
4:20 pm - 6:15 pm
MXP
-
ORD
32h 55m
1 stop
Icelandair Logo
7:25 pm - 3:10 pm
ORD
-
MXP
12h 45m
1 stop
$537Icelandair
Tue, Sep 8 - Fri, Sep 18
Icelandair Logo
10:55 pm - 9:25 pm
MXP
-
ORD
29h 30m
1 stop
Icelandair Logo
10:25 pm - 3:10 pm
ORD
-
MXP
33h 45m
1 stop
$548Icelandair
Sun, May 24 - Sat, May 30
Icelandair Logo
4:20 pm - 6:15 pm
MXP
-
ORD
32h 55m
1 stop
Icelandair Logo
10:25 pm - 3:10 pm
ORD
-
MXP
33h 45m
1 stop
$573Icelandair
Mon, Apr 27 - Mon, May 4
ITA Airways Logo
7:00 pm - 6:44 pm
LIN
-
ORD
30h 44m
2 stops
ITA Airways Logo
3:00 pm - 7:10 pm
ORD
-
LIN
21h 10m
1 stop
$606ITA Airways
Mon, Apr 27 - Tue, May 5
ITA Airways Logo
9:00 pm - 6:44 pm
LIN
-
ORD
28h 44m
2 stops
ITA Airways Logo
11:00 am - 11:40 am
ORD
-
LIN
17h 40m
2 stops
$611ITA Airways
Wed, Sep 9 - Fri, Sep 18
British Airways Logo
11:10 am - 6:15 pm
LIN
-
ORD
14h 05m
1 stop
British Airways Logo
9:15 pm - 4:40 pm
ORD
-
LIN
12h 25m
1 stop
$634British Airways
Mon, Apr 27 - Mon, May 4
British Airways Logo
7:30 pm - 12:20 pm
LIN
-
ORD
23h 50m
1 stop
British Airways Logo
5:00 pm - 12:30 pm
ORD
-
LIN
12h 30m
1 stop
$635British Airways
Thu, Apr 16 - Wed, Apr 29
American Airlines Logo
11:05 am - 5:35 pm
LIN
-
ORD
13h 30m
1 stop
American Airlines Logo
5:55 pm - 1:25 pm
ORD
-
LIN
12h 30m
1 stop
$646American Airlines
Thu, Apr 9 - Mon, Apr 20
Delta Logo
6:40 am - 5:54 pm
LIN
-
MDW
18h 14m
2 stops
Delta Logo
1:24 pm - 11:20 am
MDW
-
LIN
14h 56m
2 stops
$659Delta
Thu, Apr 9 - Wed, Apr 22
Delta Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
Delta Logo
9:29 am - 10:25 am
MDW
-
MXP
17h 56m
2 stops
$659Delta
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.

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 $626 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 Sunday, with Thursday 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 February, where tickets cost $614 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is $911 and $827 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$357
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Milan Malpensa Airport 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.

  • How many flights are there between Milan and Chicago per day?

    There is a maximum of 1 nonstop flight a day that takes off from Milan and lands in Chicago, with an average flight time of 9h 40m. The most common departure time is 3:00 pm and most flights take off in the afternoon. Each week, there are 7 flights.

  • 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 $357 for a one-way ticket and $537 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 $909 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 $711 or less one-way and $788 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 3 airlines serving 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 9431 reviews
6.6Food
7.3Comfort
8.1Crew
7.7Boarding
7.1Entertainment
Airline reviews

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

6.0 GoodAnonymous, Mar 2026
FRA - ORD
Read more United Airlines reviews

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

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.

We paid for Business Class seats, but system did not have us and they were not available.

the service on Business class should be improved to be at par with industry leaders like Cathay Pacific and Singapore AIrlines. A lot of room for improvement.

I paid for a very expensive Business Class seat to and from Cairo Egypt from Charleston SC. There was partnership from states to London using American Airlines. That leg was amazing. The British Airlines leg was a joke. They used the standard no leg room 3 by 3 seats. A tray was put on the middle seat. The trip was 5 hours, from London to Cairo, thus my BC purchase. There was no screen proving tv/movie options, only a small device plug. The fold down tray and the bag of peanuts were typical of normal short run flying. The one toilet was located in the galley. We all got to know each other well. This was my first and last trip with British Airlines. I now understand why they would NEVER give me a seat chart so that I could make a selection.prior to departure. It honestly would not have made a difference, there were less than 50% of occupied seats. Apparently everyone got the memo but me. I have never felt so cheated as with that trip, got to so another going back to London, yeah. I will be sending a letter to customer service and asking for a refund. I will be photos comparing the two BC legs. OH, one more thing. The FC ticket holders got bulkhead and exit row seats. I know they had to be thrilled

Late takeoff, but on time landing. Lost bags, 3 days to find them, still in transit to my location. Power outlets broken, Wi-Fi not working, so much for working on the long flight.

Delays on take off, delays at gate on landing, lugging lost to the ether. power on seats not working, couldn't work due to that and no WiFi. The crew was great and boarding was orderly if confused and rushed.

Late! Late and late! More than 1hr 30mn. This sucks when it is the last of a 4 flight journey. I missed my dinner! Which is not nice on Valentine’s Day!!! But better than the gate next to us, the poor Chinese people were rebooked to the next day flight. AA had to call security as it became very heated with the passengers! It was a mess at DFW that afternoon/evening. I wish they had some food for the people who travel as part of international journey. Indigo does it in India and it is fantastic.

Good. For a long flight. The comfort of the seat could be better. Also, the food was « normal » plane food. Not indian plane food unfortunately! Everything else was smooth and great.

The seats were comfortable. So many empty seats allowed for stretching out and sleeping. The onboard entertainment was pretty good. The cabin crew were so kind and kept the passengers well- hydrated, and well fed.

We had American Airlines on our return and it was confusing if we were going with Aa or BA I had 2 different flight numbers and didn’t get our gate until it was boarding. So we were a bit nervous as the which it was

Our Jackson, Mississippi to Dallas Fort Worth flight was delayed on 1/19/26.. This was changed to Jackson to Charlotte in the last minute because of this delay. This started some kind of disconnect between American Airlines and British Airways bookings. We could not go past the passport control in London Heathrow. I had to go to the counter and waited for more than 30 minutes to get a new boarding pass. Problems did not end there. Somehow our entire return flight was canceled by someone. I had to make several phone calls over several days to fix the problem – this was not easy from India. Looks like there was some kind of disconnect between two airlines or some agent did not do it right. I’m anxious to know what went wrong.

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.