MIL - CHI

$374 Find Cheap Flights from Milan to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milan to Chicago departing on 10/1. 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

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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milan to Chicago.
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Flights 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, Oct 1 - Thu, Oct 9
TAP AIR PORTUGAL Logo
5:55 am - 4:10 pmMXP-ORD
17h 15m1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 4:25 pmORD-MXP
15h 25m1 stop
$374TAP AIR PORTUGAL
Find Deal
Wed, Sep 17 - Sun, Sep 21
TAP AIR PORTUGAL Logo
8:15 pm - 10:55 amMXP-ORD
21h 40m1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 7:15 pmORD-MXP
18h 15m1 stop
$375TAP AIR PORTUGAL
Find Deal
Mon, Sep 22 - Mon, Sep 29
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
$543Aer Lingus
Find Deal
Sat, Nov 15 - Mon, Nov 24
Aer Lingus Logo
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
Aer Lingus Logo
3:55 pm - 11:05 amORD-LIN
12h 10m1 stop
$550Aer Lingus
Find Deal
Sun, Sep 21 - Sun, Oct 19
British Airways Logo
7:25 am - 1:50 pmLIN-ORD
13h 25m1 stop
British Airways Logo
4:55 pm - 12:30 pmORD-LIN
12h 35m1 stop
$596British Airways
Find Deal
Wed, Oct 1 - Thu, Oct 9
British Airways Logo
7:30 pm - 1:55 pmLIN-ORD
25h 25m1 stop
British Airways Logo
10:35 pm - 6:55 pmORD-LIN
13h 20m1 stop
$606British Airways
Find Deal
Mon, Sep 15 - Wed, Oct 1
United Airlines Logo
11:15 am - 1:14 pmMXP-ORD
32h 59m2 stops
United Airlines Logo
8:40 am - 10:00 amORD-MXP
18h 20m1 stop
$647United Airlines
Find Deal
Wed, Oct 1 - Thu, Oct 9
United Airlines Logo
3:20 pm - 6:10 pmMXP-ORD
9h 50mnonstop
United Airlines Logo
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$651United Airlines
Find Deal
Tue, Nov 4 - Thu, Mar 5
Lufthansa Logo
6:15 am - 1:10 pmLIN-ORD
13h 55m1 stop
Lufthansa Logo
9:50 pm - 7:00 pmORD-LIN
14h 10m1 stop
$661Lufthansa
Find Deal
Thu, Aug 21 - Sat, Aug 30
Lufthansa Logo
6:20 am - 11:00 amMXP-ORD
11h 40m1 stop
Lufthansa Logo
10:30 pm - 6:00 pmORD-MXP
12h 30m1 stop
$745Lufthansa
Find Deal
Expert advice

Expert advice for your flight from Milan to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MXP

At MXP, allow an hour for check-in and security during peak times, as queues can be long and chaotic.

Read more about MXPby Duncan Madden
ORD

Take the CTA Blue Line from ORD to downtown Chicago for a reliable 45-minute journey, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek

Stefanie Waldek

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.

Read more
Duncan Madden

Duncan Madden

Expert on MXP

Duncan Madden

Duncan Madden

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.

Read more
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Milan to Chicago.

Our data shows that the cheapest route for a return flight from Milan to Chicago cost $650 and was between Milan Malpensa Airport (MXP) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $650.

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 Sunday is the most expensive. Flying from Chicago back to Milan, the best deals are generally found on Tuesday, with Saturday 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 November, where tickets cost $471 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is $886 and $858 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 1 stop layover the cheapest option at $1,240 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Milan to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$374
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 27% 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.

  • 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 $376 for a one-way ticket and $374 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?

    All the following airlines offer inflight Wi-Fi service on the Milan to Chicago flight route: Air France, KLM, Delta, SWISS, Virgin Atlantic, United Airlines, and Alaska Airlines.

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

    The Boeing 787-8 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 Scandinavian Airlines?

    The two airlines most popular with KAYAK users for flights from Milan to Chicago are United Airlines and Scandinavian Airlines. With an average price for the route of $800 and an overall rating of 7.4, United Airlines is the most popular choice. Scandinavian Airlines is also a great choice for the route, with an average price of $521 and an overall rating of 7.3.

  • 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 $787 or less one-way and $664 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?

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
See more direct flights

Top 5 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 8790 reviews
6.6Food
7.7Boarding
7.3Comfort
7.0Entertainment
8.1Crew
Airline reviews

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

6.0 GoodAnonymous, Jun 2025MLI - ORD
Read more United Airlines reviews

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

I would definitely use a Linus again, the price was right, the service is excellent. No delays. Wish I had a direct flight from my hometown Detroit.

i used to fly aer Lingus regularly but due to price - poor seating etc i have been using other carriers - i now have aer lingus in my state and the price is always the highest - i have flown to Ireland 11 times in last 24 months and have not used Hartford because of price

Nicest staff I’ve experienced on a plane! Good food, great entertainment, and they gave out little blankets that my kids loved. All in all, great experience.

I dont fly them much anymore. Other carries offere better pricing and better seating options

Seats weren't very comfortable for a long haul flight but the service made up for it.

Unfortunately the flight was delayed for 50 min. Just as we were about to board so that was a drag. The boarding was average. The bag check in process was new to us and efficient. And the flight itself was smooth- basically no turbulence.

I liked how they looked after couples by providing a row of 4 seats if available.

It was ok not that much because I always travel with Emirates airlines, Etihad, airlines, Qatar airlines compare to them food and comfortable was too low . Staff was good . Helpful

Noted in last review. Good to know, though air Lingus on European flights does not offer any food or drink, even though we were on the plane for 3 1/2 hours from Naples to Dublin everything you had to purchase even water.

Seats were alarming close to the row in front of you. I didn’t do the measurements online, which I’m sure they’re available, but it seemed much tighter than other planes, but the airplane itself was well maintained and looked fairly new. My only complaint on the staff was that we’re on an international flight. Normally they give you wine with dinner and the flight attendant decided to pull some strict restrictions and wouldn’t give more than one glass of wine per person, and you could not share with your spouse, which seemed ridiculous when we have four people on the plane with us and only one person ordered wine asked for a second one and she said oh absolutely not. It’s only one per person Which on a transcontinental usually is not the case. They’re very attentive on making sure everyone is as comfortable as possible.

Terrible flight attendant attitude. Average 3-star hotel employee has better hospitality skills. Business class seats are literally a joke. TAP executives should ride business class in other airlines to develop some rudimentary sense of what business class is.

I’ve never had worse food in business class ever!

Checkin was very slow, we had checked in online and hoping we could do a bag drop at the airport. However everyone with checked bags had to queue up and it took over 40mins. Our advice arrive extra early or you will be rushing to the gate.

Very pleasant flight, crew was very nice. The flight was really smooth, big plane. The seats are kind of close together, so comfort was just OK. The boarding process on the way back to New York was a little chaotic. It took a long time.There were no announcements, no loudspeaker just one staff yelling out of instructions and a lot of people crowding in before their term to board. So that could really be improved a lot.

The crew was very nice. The food was good. The entertainment on the way back to Miami wasn’t as good as the flight over. I wanted to watch Wicked but on the way over from Miami to Lisbon but the screen didn’t work. On the way from Lisbon to Miami Wicked wasn’t an option. Liked the option to check out overhead carry on with our checked luggage Overall the flights were very good. I would fly TaP again

Awful. I told them to cancel my return flight and they didn’t then charged me +$800 days before the flight for a biz class upgrade bid. When I called to confirm cancellation and get refund on buz class upgrade they said I had to go thru orbitz and it was too late. Scammers. Beware.

Got in on time. Food was the worst ever. Comfort was terrible. Check in was incredibly bad.

The flight schedules are better than some airlines. Their website is terrible, it doesn’t store any information so every time you fly you have to re-enter the data. The flight was late taking off but we still got to our destination on time.

Great overall experience with TAP - would not hesitate to recommend for your next trip to or from Portugal

Flight delayed by >1 hour. Long boarding involving riding a shuttle to the plane.

The crew was the best I’ve ever encountered. Business class was spacious, immaculate, and very modern.

I wish seats were not reclinable. It's so claustrophobic when the person in front of you spends most of a nine hour flight leaned all the way back. The crew was really nice though and the dinner (red Thai curry) was pretty compelling.

Our flights were severely delayed, then canceled and we had to fly out next day with no sleep accommodation help. This led to our baggage being lost and the service reps after baggage couldn’t be bothered to help. They kept sending us to different counters when we were at the right counter to begin with. The only saving grace was the angel woman supervisor with blond hair who helped us put in a missing baggage claim.

The boarding system was all bogus - employees at the boarding gate were not sound like proffesional or may be possibly rational

I got an email in the morning of the flight 1/7, from Kayak, that I was rebooked from UA 906 to LH 430. Nobody at Lufthansa ot United knew about this. I went to both counters. at the airport. Also, Cheap Flights, who I booked the ticket through, did not know. I ended up staying on the United flight. But this was very disturbing, since I got a very late notice that I was rebooked to an earlier flight, I hurried to the airport to find out after a lot of inquiring that this was a mistake. Not a good Kayak experience.

After living in Europe for five years and flying with Lufthansa and KLM airlines, I’ve realized that United Airlines is now a budget carrier. The flight attendant are not friendly. The seats are not comfortable. And everything comes at a cost. I will be flying with KLM and Skyteam like Delta to the US going forward no doubt. United Airlines is not what it once was:

Delayed take off but I think they waited for passengers.

I had to fly United where the flight crew was atrocious

Flight was delayed for no reason and I missed my connection. This added another day of travel and I missed an event I was traveling home for.

I traveled with my sister, however ,we booked a flight separately, and we don't sitting next to each other. The staff on the board where on the top of this unit they find us sitting together. Ty lufthansa team. U are the best

Better synchronizing the boarding processes. The audio announcements, the personnel and the digital signage were not saying the same thing. All confusion.

The first class seats were unusable, mine at the end of the flight, my husband's in the middle of the flight, and the one next to me was unusable either, they had to move the person to another seat.

Last minute gate change. Didn’t put our TSA global on our trip even though we asked multiple times to confirm. Did not help with food when could not eat what was served.

Our luggage didn’t arrive with us, that puts a damper on the whole trip.

The cabin was bit colder than I like but the crew members looked after us very well. They did even offer hot water bottle and hot chocolate. I cannot rate the crew enough excellent is not good enough. They really were wonderful.

Boarding is always a challenge as folks in al groups crowd around for no reason, but crew handled it well. I once again applaud the LHR ground baggage staff as they got our bags from a flight at Terminal 5A to a flight in Terminal 5C within 40 minutes...amazing!

This flight from London to Chicago was actually on an AA airline. I did book through BA but the flight was AA. Great flight, hectic in Chicago, I wouldn't choose to fly through Chicago again, but that's not the airlines fault. The flight itself was great.

Push back is not working when I complaint a male staff he told me that most of the seats are like that so we can’t do anything

Seats were way too small. I got claustrophobic waiting for trash from meal to be taken away. I couldn't move to even close my tray until trash was taken.

Was 3 hrs delayed and my poor friend I met in Barcelona was waiting at airport for 3 hrs. Dallas airport was awful

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.

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