MIL - CHI

$269 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 3/4. 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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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$427
Typical prices: $590-$879
TAP AIR PORTUGAL
Tue 4/21Wed 5/6
MXP - ORD • 1 stop
Cheapest non-stop
$632
Lufthansa
Wed 4/29Wed 5/6
MXP - ORD • Non-stop
Our travelers' advice
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
TAP AIR PORTUGAL
Cheapest • from $427 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MXP
-
ORD
Cheapest
MXP
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 20% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, Apr 21 - Wed, May 6
TAP AIR PORTUGAL Logo
8:00 pm - 4:00 pm
MXP
-
ORD
27h 00m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 12:45 am
ORD
-
MXP
23h 45m
1 stop
$427TAP AIR PORTUGAL
Tue, Apr 21 - Wed, May 6
TAP AIR PORTUGAL Logo
5:25 pm - 4:00 pm
MXP
-
ORD
29h 35m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 12:45 am
ORD
-
MXP
23h 45m
1 stop
$429TAP AIR PORTUGAL
Wed, Mar 18 - Wed, Mar 25
Multiple Airlines Logo
6:45 am - 6:20 pm
BGY
-
ORD
17h 35m
2 stops
Multiple Airlines Logo
7:30 pm - 12:10 am
ORD
-
BGY
22h 40m
2 stops
$504Multiple Airlines
Thu, May 21 - Sun, May 31
Multiple Airlines Logo
9:45 pm - 3:00 pm
MXP
-
ORD
24h 15m
1 stop
Multiple Airlines Logo
5:00 pm - 1:20 pm
ORD
-
MXP
13h 20m
1 stop
$531Multiple Airlines
Thu, May 7 - Thu, May 14
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
$566ITA Airways
Wed, Apr 22 - Thu, May 7
Air Canada Logo
6:50 am - 6:47 pm
LIN
-
ORD
18h 57m
2 stops
Air Canada Logo
3:50 pm - 2:40 pm
ORD
-
LIN
15h 50m
2 stops
$590Air Canada
Thu, May 7 - Mon, May 11
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
$593ITA Airways
Fri, Feb 13 - Fri, Feb 20
Air Canada Logo
6:10 am - 3:10 pm
LIN
-
ORD
16h 00m
2 stops
Air Canada Logo
12:50 pm - 11:55 am
ORD
-
LIN
16h 05m
2 stops
$600Air Canada
Sun, Apr 19 - Sat, May 2
British Airways Logo
7:25 am - 3:00 pm
LIN
-
ORD
14h 35m
1 stop
British Airways Logo
9:15 pm - 10:10 am
ORD
-
LIN
29h 55m
1 stop
$601British Airways
Sun, Apr 19 - Sat, May 2
British Airways Logo
11:00 am - 5:35 pm
LIN
-
ORD
13h 35m
1 stop
British Airways Logo
9:15 pm - 10:10 am
ORD
-
LIN
29h 55m
1 stop
$609British Airways
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 $623 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, Tuesday 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 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 February, where tickets cost $571 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is $938 and $828 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
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 9% 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 $269 for a one-way ticket and $427 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, SWISS, Virgin Atlantic, Air France, American Airlines, and Delta.

  • 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?

    oneworld, and Star Alliance are the airline alliances operating flights between Milan and Chicago, with oneworld 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 $875 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 $550 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 $998 or less one-way and $884 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.

Reviews of the top 4 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 9215 reviews
8.1Crew
7.1Entertainment
7.3Comfort
7.7Boarding
6.6Food
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
NRT - ORD
Read more United Airlines reviews

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.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

Our trip plan from Kayak stated we were flying SAS. That was not true. The first leg was a Delta flight. We wasted 25 minutes before finding out to check in with the correct airline. Then our SAS flight for the second leg arrived 25 minutes late, and our third leg flight with SAS closed the gate knowing the flight delay was SAS’s fault, and that this flight would only be backed up 5 minutes. The final kicker was that between Delta and SAS, they lost all our checked luggage.

Since our earlier flight was delayed, we missed this flight and were rerouted on Lufthansa 2 days later.

Scandinavian Airlines is terrible. Flight was late. Lost luggage. Rude flight attendants. Terrible experience.

The flight was very cold, and the seats were rather uncomfortable. The food has been better on our other SAS experiences. Most significantly, the luggage with most of my wife's personal items and clothes didn't make the flight. Hoping for a quick resolution, but no real opportunity to speak with a Human has us concerned.

Ancient aircraft (busted armrests, poor cabin temperature with no option for passenger control). Garbage everywhere. Risible checking of safely conditions on landing. Also, late.

Feels like economy sits are getting smaller especially while eating food

I was surprised how good an American airline can be - I was really impressed.

Cut out the nickel and dime pricing for "seat selection" and baggage, To do this on an international flight is just mind boggling. Seriously, why treat customers this way??? Nobody wants these hidden extra fees and everybody hates them. Also plane was too warm and no air vent, and water dripped from the ceiling at one point,

It was so hot on the plane. No air jets above the seats

Scandinavian was perfect. Nice A350 with an on time departure and an an experienced crew. What a difference from TAP.

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.

I darted through the Frankfurt airport to make my connecting flight. I asked if it was a possibility to upgrade and the agent did. This was the kindest gesture and it made up for the previous delayed flight and distress/anxiety of anticipating that Zi was going to miss my Frankfurt-Chicago connection. I cannot express my gratitude for the upgrade.. I am 5feet 10 inches do the leg space was amazing.

I meant this flight was not good, the one from Tirana to Frankfurt was better!

I was very grateful for Lufthansa's role in organizing mobility support. The touchscreen on my seat was faulty: slow, stained (I couldn't get it clean), and glitchy. This made selecting movies extremely time consuming, and twice I had to start all over from the beginning.

My touch screen at my seat wasn't working, the films BA advertised on the website for this flight were not available, and the plane was a little dated, food was good and the staff were good, just let down by the aircraft facilities.

Did not like the seating configuration at all with 2+3+2 in business class. Lacking total privacy and comfort

The flight crew was kind, flexible, and accommodating. The seats on the plane were extremely uncomfortable.

Check-in experience, for business call please provide a premium experience

Lost my luggage, ran out of food choices in business class, ground crew was completely unapologetic.

Excellent. The crew and flight were great. Checking in was easy and everyone was very helpful.

Entertainment devices on A380 need to be fixed, the seats might do with updates.

Gate agents were late…flight was late and air attendants unhelpful.

Everything. Employees offered to help me because I had to use a cane.

Check-in and boarding were great. On flight staff were rude and disrespectful. Paid for extra room and found it incredibly cramped. Bathrooms kept in poor condition. Overall negative experience.

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.