MIL - CHI

$293 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 1/29. 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.
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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.
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

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Cheap Flight Deals 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.

Recent round-trip flight deals from Milan to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Milan to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
2:10 pm - 5:20 pmMXP-ORD
34h 10m1 stop
6:30 pm - 1:10 pmORD-MXP
11h 40m1 stop
$378Icelandair
Find Deal
Thu, Feb 6 - Wed, Feb 19
2:10 pm - 5:20 pmMXP-ORD
34h 10m1 stop
6:30 pm - 1:10 pmORD-MXP
11h 40m1 stop
$381Icelandair
Find Deal
Thu, Feb 6 - Wed, Feb 12
11:45 am - 6:55 pmLIN-ORD
13h 10m1 stop
4:55 pm - 11:05 amORD-LIN
12h 10m1 stop
$416Aer Lingus
Find Deal
Thu, Mar 20 - Mon, Mar 24
5:45 pm - 3:30 pmMXP-ORD
28h 45m1 stop
7:15 pm - 4:55 pmORD-MXP
14h 40m1 stop
$440TAP AIR PORTUGAL
Find Deal
Thu, Feb 6 - Wed, Feb 19
6:20 am - 3:30 pmMXP-ORD
16h 10m1 stop
8:25 pm - 11:35 pmORD-MXP
20h 10m1 stop
$449TAP AIR PORTUGAL
Find Deal
Sun, Jan 26 - Sun, Feb 2
11:20 am - 5:50 pmMXP-ORD
13h 30m1 stop
7:40 pm - 7:10 pmORD-MXP
16h 30m1 stop
$476Scandinavian Airlines
Find Deal
Thu, Feb 13 - Thu, Feb 27
8:00 pm - 5:50 pmMXP-ORD
28h 50m1 stop
7:40 pm - 6:50 pmORD-MXP
16h 10m2 stops
$477Scandinavian Airlines
Find Deal
Thu, Feb 13 - Thu, Feb 27
11:45 am - 7:15 pmLIN-ORD
14h 30m1 stop
3:55 pm - 11:05 amORD-LIN
12h 10m1 stop
$515Aer Lingus
Find Deal
Fri, Feb 14 - Sun, Mar 2
7:00 am - 2:55 pmLIN-ORD
14h 55m2 stops
10:30 pm - 5:35 pmORD-LIN
12h 05m1 stop
$610United Airlines
Find Deal
Fri, May 2 - Fri, May 16
12:15 pm - 8:00 pmMXP-ORD
14h 45m1 stop
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
$613United Airlines
Find Deal
Fri, Apr 11 - Tue, Apr 22

Flights from Milan to Chicago - Travel Insights & Trends

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 $716 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 $716.

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, Sunday is the cheapest day to fly on average and Friday is the most expensive. Flying from Chicago back to Milan, the best deals are generally found on Wednesday, 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 November, where tickets cost $439 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is $812 and $795 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 $683 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 9 weeks before departure.

Good to know

Low season

February

High season

August
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 24% increase in price.

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 $293 for a one-way ticket and $378 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: KLM, Delta, Air France, SWISS, Virgin Atlantic, American Airlines, 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?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Milan and Chicago, with Star Alliance being the most commonly used for this route.

  • 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 $814 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 $515 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.

See more FAQs

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 $615 or less one-way and $768 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.
See more tips

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 8978 reviews
8.1Crew
7.1Entertainment
6.7Food
7.7Boarding
7.3Comfort
Airline reviews

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

6.0 GoodSerena, Dec 2024DLH - ORD
Read more United Airlines reviews

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Did not even get on board. Was told I needed an esta agreement. Was not aware of this when I booked the fare and not told about them

Cramped seats. Audio jack for the in -flight entertainment was broken.

Flight was great albeit the long line before the int’l immigration given the timing of the year.

They canceled our flight and left us stranded to figure it out

We appreciated the friendly, efficient, and professional flight attendants. A wider selection of hot foods would be nice.

Did not have enough time from Venice seaport at Ravenna to get to Venice airport in order to make the scheduled flights. Need to have at least 3+ hours from ship docking to airport.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

We were sitting in SAS plus. Super friendly, service that went above and beyond on a Full Flight too! Meals were deliscious and trays were cleared promptly. Generous drinks offered throughout the flight. Would like to suggest better movies on offer to watch.... In all genres and maybe more cooking shows? There was only 1, Nadia's Everyday Baking... Thank you

The meal offered was fish. I am allergic to fish. When I told her, she just took the box of food back without offering me an alternative.... I had to ask... can I then have a bag of chips? She did give it to me. I am a Euro Bonus gold member. Please just take the time to offer something else. Easy and from a customer service point of view, .... Considerate.

compared to other business class journeys, the hard product is okay..but the service of the staff is underwhelming. They are very senior and seems only to care for the colleagues they upgraded to biz and to themselves , I was not offered food before after 1 1/2 -2 hours, and the menu had one dish and the food was not that. And i could not get the breakfast.. just coffee and a croissant. i have type 1 diabetes .. luckily i had my own food. was low in sugar after sleeping and woke up 55 minutes before landing .. not able to get food anymore !! so bad business experience!

The food service was absolutely rubbish. Very arrogant crew. Does Scandinavian airlines think everyone eats meat??? I paid for my flight but could not eat anything because I am vegetarian!!! I was hungry for 7 hours . I demand for refund! This is absolutely unacceptable!!!! If you want more customers keep an open mind!!! Cater to all meal needs. I have flown many airlines and I never make a special request online never! They always have vegetarian options. SAS has no idea of customer service. Shitty service

Flight & service all top notch but online check-in a poor experience. Clearly a glitch on their website which prevented completion via my Android device. Also no easy way to provide this feedback to the airline so they can fix it!

Had recurring problems with the touch-screen entertainment system repeatedly making up inputs, resulting in the movies randomly jumping forward and backward. With the lack of proper controls, it was also difficult to get back to where the movie was up to. These phantom inputs were so comprehensive that the system even changed the language setting. Despite a schedule 6.25pm boarding time, it was announced in the Delta lounge at 6.15pm that boarding for the flight had started, so of course everything started to head down. While the gate continued to show a scheduled boarding of 6.25pm, it was 6.32pm before boarding actually started. No, not significantly different, and we ultimately ended up landing well before time (and landing time is arguably more important than exactly when boarding starts). Seat comfort was fine, although only a small nook for personal items, food was satisfying for me, and crew was pleasant.

Staff was fine. But plane offers very few free services.

I did not go. I rebooked my ticket. Despite that you keep sending me emails and now this survey about a trip that you should know by now did not happen. Very bad, impersonal customer service. Shows you have no idea what's going on with your customers and that you're just spamming with automated, careless communications

It was my wife and me traveling together. We purchased more expensive Economy Plus tickets, but the seat selection was not available, although this was the main reason for buying the more expensive tickets. When I called SAS, I was told that the seats could be selected once check-in is open, i.e., 30 hrs. before departure. On the inbound flight, I could check in only the first leg (Boston-Copenhagen) but the system would not allow me to check in for the connecting Copenhagen-Split flight. On the return flight, I was not able to check in and, therefore, select two seats together at all. I even received an email from the SAS stating that the check-in was open but when I attempted to do it, the system would not allow it. Trying to get help by calling SAS customer service was no help at all. Although there are signs at Boston Logan Airport implying that there is a Scandinavian Airlines lounge, there is not one. We were sent to Delta Priority Lounge where we were told that it is for business class passengers only, although the terms of Economy Plus state that the fare includes access to a lounge. The seats and the legroom were no different than standard economy cabin seats. On the flight to Copenhagen, my table was broken (not unfolding completely), so I had to hold the food tray with all the food in one hand while trying to eat with another. Overall, it was definitely not worth it paying for the Economy Plus tickets. Based on my overall experience, it is very unlikely that I will consider flying SAS in the future.

Pilot made us late 45 minutes with no explanation, missed our connection, they didn’t care

Really lovely trip and flight. The flight staff were so accommodating and warm throughout!

Friendly crew who apologised and explained reason for delay. Good on board service. Rather cramped seating. Late departure.

Very sad, couldn't stop crying. Was an hour delay in Ireland and when we got to Canada the flight was boarded and couldn't get on. Was the last flight of the day. Now in a hotel waiting on a stand by.I have to got o work, so I'll go first available while my son stays in the hotel til one's available

Was not aware that Aer Lingus was like the cut-rate services in the states, with no food or beverage (other then 3.50 Euro coffee) and no screens for entertainment. Was a great flight, but not much in the way of services.

during a very rough flight, I was forced to sit in a last row seat, fell asleep, and was forced to return to my assigned seat after the turbulence. The stewardess then used that seat to sleep.

We couldn't talk to aer lingus we had issues with the flight change and aer lingus made us talk to kayak

Very pleasant staff, there was some turbulence but the captain was very apologetic and gave notice where possible.

Flight was great. Had to wait almost 100 minutes for luggage (some problem in the delivery). This may not be an Aer Lingus problem, but an SFO problem.

Amenity kits were never handed out. There was zero friendliness and assistance by crew. Food was uneatable. One drink was offered and no wine, with dinner or before or after. Cocktails and beverages were not encouraged and when I asked for water, none was given. Poorest, most cramped business class flight I’ve ever been on.

Probably my favorite airline and way to go to Europe. Everything went smoothly! Food was tasty, crew was pleasant. Really cannot complain!

Baggage check in was very slow. No sign that the check in was TAP until the station opened. Understaffed and overworked team.

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

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

When I tried to enter my identity details, your app told me information was missing but did not highlight the missing data. This was frustrating. Also, there was an unexplained delay of about 2 hours in taking off. This was also frustrating. Otherwise the experience was good.

The flight was delayed without any type of notice. After passing through the gate, people were lined up at the passages boarding bridge standing for about half hour with no clue when they can board after ‘boarding’. No explanation or indication of the new departure time. All you can do is standing up and waiting.

First, I was moved from my scheduled flight at 10:45 to 6:30. Bad form as I had a scheduled lesson in the morning that I couldn't get a refund for. Second, we were bused out to the plane and bused back to the terminal and sat and sat all with NO explanation until the end of the long wait. Third, once we boarded the plane, we again sat for at least an hour WITH NO EXPLANATORY ANNOUNCEMENT. Plane left and arrived 2 hours late. I missed a train connection adding hours to my trip home. Lastly, it's time the airport is upgraded or TAP gets priority for walk-on gates. As a 74 year old, carrying my carry on luggage up and down stairs between the terminal and the plane is a pain. Might be the last time I fly TAP.

The flight was cancelled. the staff did not know how to arrange overnight, food and transportation accommodations required by law, causing long lines lasting several hours. the rebooked flight was then delayed 5 times from 9am to 4:45pm

Flight delays. Mad rush with no help from staff. Staff for TAP is elusive like the Tasmanian devil... you hear about it but never seen it. Seats were the only thing that was ok as its lie flat, but trying to sleep was like being at a concert as the crew were chit chatting non stop while you are trying to sleep. Food was seriously better in Premium EY on other airlines like Singapore Airlines, Lufthansa, United. We traveled Business Class on TAP. Crew were friendly enough but not very present at lull period of flight.

The flight staff was nice enough but the seats were not up to business class standards. The food was also not something I would get on any day. The seats we had were right up to the galley and the crew were very noisy with their chatting the entire flight which woke us up after we fell asleep and we could not get back to sleep due to all the chit chat! The flight was delayed and we were in transit for less than an hour in Lisbon yet there were no TAP staff anywhere to be found to assist pax who were worried about catching our connecting flight. Another thing that was poor in service was that, if TAP flies out of Rome at 5.55am, TAP should have a lounge open for your Business Class pax. We were told that the lounge opens at 5.30am yet TAP's flight is scheduled to leave at 5.55am. Why offer a departure that early when you don't have lounge open by at least 4.30am? It's been a very disappointing experience with TAP and we paid for Business Class. It is at best a Premium Ey class on better known airlines like Lufthansa, British Airways, United. It's at best sort of comparable to Economy class on Singapore Airlines but I still think Singapore Airlines Economy class service is better apart from the seats.

Crew woke me up to see if I wanted food - NEVER want food on a 12 hour flight more than I want to sleep. Sleep was not easy, as a child screamed and threw fits 70%of the flight. That same child kicked my seat most of the flight. BUT, despite the child and a poor boarding effort, the rest was solid. The crew worked hard otherwise - just don’t wake me up IF I actually get to sleep.

It is the worst ever airline. All employees I spoke with over the phone were pompous asses.

Not online or self check in, sent emails in Italian language ,not recommended.

No online or self check in. Sent emails in Italian language. In general, not recommended airline company.

Premium Economy was average for class. Seat comfort was just okay. Crew was attentive. Checkin was fine and moved quickly. Boarding process in Rome was not well organized.

It was horrible the woman next to me was sick and I asked if they would change my seat and they said that they didn’t have any available. I sat next to this women for 9 hour and now I am sick .

We booked and purchase our seats in February for a September flight. We choose seats then also, did the online check in on the app the day before and all was fine. At the airline check in they charged our seats and we were not even sitting together after paying for business class seats. They separated us with no explanation and would not change them back. I was very upset. On the return flight, they tried to put us on standby! When again, we purchased seats in February for this flight. The plane was old and smaller and the business class seats were not comfortable like the flight from NYC. Flight attendants were hard to find once the first meal was served, luckily the flights were smooth.

Crew was good. Very nice staff. Wine was good. Problems- no AC while waiting for takeoff. Long wait so we should have been more comfortable. No water for quite awhile. Food should have been better for an Italian airline. Chicken was pressed rounds of processed meat- not tasty. We had only one hour for our connection- ran through airport- plane waited for us and staff was helpful.

Poor , i missed the next flight to new york . We stayed inside the plane for almost 30 or 40min

Very frustrating trip. From Rome to boston , and i missed the next flight to new york

Everything was fine except the food. They really need to work on the quality of the food.

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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