MIL - CHI

$344 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 2/23. 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
$521
Multiple Airlines
Wed 1/28Wed 2/4
BGY - ORD • 2 stops
Cheapest non-stop
$727
United Airlines
Fri 4/24Sun 4/26
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
Scandinavian Airlines
Cheapest • from $592 (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 • 19% price drop
August
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, Jan 28 - Wed, Feb 4
Multiple Airlines Logo
6:45 am - 5:20 pm
BGY
-
ORD
17h 35m2 stops
Multiple Airlines Logo
6:30 pm - 12:10 am
ORD
-
BGY
22h 40m2 stops
$521Multiple Airlines
Thu, Jan 15 - Wed, Jan 28
Scandinavian Airlines Logo
11:15 am - 4:45 pm
MXP
-
ORD
12h 30m1 stop
Scandinavian Airlines Logo
7:00 am - 10:25 am
ORD
-
MXP
20h 25m2 stops
$592Scandinavian Airlines
Sun, Jan 25 - Thu, Jan 29
Scandinavian Airlines Logo
11:15 am - 4:55 pm
MXP
-
ORD
12h 40m1 stop
Scandinavian Airlines Logo
7:10 pm - 10:25 am
ORD
-
MXP
32h 15m1 stop
$593Scandinavian Airlines
Sat, May 9 - Thu, Jun 4
Icelandair Logo
4:20 pm - 6:15 pm
MXP
-
ORD
32h 55m1 stop
Icelandair Logo
7:25 pm - 9:55 pm
ORD
-
MXP
19h 30m1 stop
$598Icelandair
Thu, Jan 15 - Wed, Jan 28
British Airways Logo
7:15 am - 1:50 pm
LIN
-
ORD
13h 35m1 stop
British Airways Logo
5:10 pm - 11:30 am
ORD
-
LIN
11h 20m1 stop
$671British Airways
Mon, Jan 26 - Mon, Feb 2
American Airlines Logo
7:35 am - 5:00 pm
LIN
-
ORD
16h 25m1 stop
American Airlines Logo
6:25 pm - 9:30 pm
ORD
-
LIN
20h 05m1 stop
$680American Airlines
Sun, Feb 1 - Sun, Feb 15
British Airways Logo
7:20 am - 3:25 pm
LIN
-
ORD
15h 05m1 stop
British Airways Logo
9:45 pm - 4:20 pm
ORD
-
LIN
11h 35m1 stop
$682British Airways
Thu, Jan 15 - Wed, Jan 28
American Airlines Logo
11:25 am - 5:00 pm
LIN
-
ORD
12h 35m1 stop
American Airlines Logo
8:45 pm - 4:20 pm
ORD
-
LIN
12h 35m1 stop
$685American Airlines
Thu, Jan 15 - Wed, Jan 28
Delta Logo
11:05 am - 10:07 pm
MXP
-
MDW
18h 02m1 stop
Delta Logo
1:26 pm - 11:40 am
MDW
-
MXP
15h 14m2 stops
$693Delta
Thu, Jan 15 - Wed, Jan 28
Delta Logo
6:30 am - 6:32 pm
LIN
-
MDW
19h 02m2 stops
Delta Logo
1:49 pm - 11:15 am
MDW
-
LIN
14h 26m2 stops
$694Delta
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 $641 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 $570 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is $902 and $825 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 $703 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.
Airports
MXP

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

ORD

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

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

Good to know

Low seasonJanuary
Cheapest flight$344
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Bergamo to Chicago

When to book flights from Milan to Chicago

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

FAQs for booking flights from Milan to Chicago

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

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

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

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

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

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

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

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

  • What is the cheapest flight from Milan to Chicago?

    In the last 3 days, the lowest price for a flight from Milan to Chicago was $344 for a one-way ticket and $521 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, SWISS, Virgin Atlantic, Air France, and Alaska Airlines 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?

    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 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 $815 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 $758 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 $816 or less one-way and $690 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 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 9092 reviews
8.1Crew
6.6Food
7.7Boarding
7.1Entertainment
7.3Comfort
Airline reviews

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

10.0 ExcellentMichele, Dec 2025
RSW - ORD
Read more United Airlines reviews

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

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.

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.

Audi visual not working for a whole group of seats in first class. How does a plane leave the main hub in such poor condition? How much that we can’t see so immediately is also compromised?

main meals are horrible but then you dont fly for the food

It was good. Couldn’t Check in online and select seats

It was great. Enough space and room for legs . Great service to.

⭐ British Airways Review — A Journey of Highs, Lows, and Lessons ⭐ I recently flew Business Class round-trip from Boston to Mumbai with British Airways, and my experience was a tale of two extremes — from disappointment to exceptional service, and then back to inconsistency. Boston → London: A Surprisingly Poor Start My journey began on a disappointing note. On a 6-hour Business Class flight, I was surprised to discover that there wasn’t a single proper vegetarian meal option available. I was offered a few bakery items only after repeatedly requesting something to eat. The flight attendant shrugged, offered no solution, and eventually — quite literally — threw some bread at me after much delay. This was not only disheartening, it was extremely surprising given my wonderful Business Class experience with BA last year. I stepped off that flight genuinely hungry and had to make a mad dash to the lounge just to get a proper meal. London → Mumbai: A Complete Turnaround The next sector restored my faith in British Airways. The entire crew was warm, welcoming, attentive, and genuinely caring. A special shoutout to Phiroze and the entire team serving the Business Class cabin — their professionalism, hospitality, and thoughtful service were extraordinary. They truly embodied what makes British Airways a global leader, and I am deeply grateful for the experience they provided. This is the BA I know and love. Mumbai → London: A Strange Meal Schedule This sector was generally fine, but the meal timing was puzzling. Lunch at 10:30 AM — for a Business cabin — felt unusual, and most passengers, including myself, barely touched it. The rest of the service was smooth, but the scheduling definitely needs a rethink. London → Boston: Mixed Experience Again The flight itself was decent, but the Business Lounge at Heathrow for this leg was a letdown. Arrived during lunch hours: no hot vegetarian options available Lounge area: dirty dishes everywhere Even after politely alerting the staff, the dishes were ignored and left uncleared For a premium cabin passenger — and at one of the world’s busiest international hubs — this was disappointing. Overall Impression My journey with British Airways felt inconsistent — two great sectors sandwiched between two that fell short of the BA standard. When BA is good, it is world-class. When it misses, the gap is noticeable. I genuinely hope the airline takes this feedback as constructive insight. I continue to believe in British Airways, and I commend the outstanding crew on the London → Mumbai sector — they were the highlight of my entire trip. With a little more focus on vegetarian meal availability, lounge service, and consistency across crews, BA can ensure every Business Class passenger experiences the premium journey they promise.

We were in business class and I had seat # 1. This was a night flight and after dinner was served, lights were dimmed and I went to sleep. The crew were loud and noisy so I didn’t get much sleep. I expect the crew to enjoy themselves but would Appreciate some decency in staying quiet while the passengers sleep

Have travelled business class with other airlines who profess to be the best in the world. They can however not beat the service and comfort that BA provide.

Well unfortunately our connecting was cancelled and next flight delayed. Was in airport 9 hours. Flight itself was good. I’m sure it was a FAA problem.

Great on board entertainment Tasty food Cattle class obviously crammed but not as bad as shorter hall flights

I was attacked in the Miami airport and the staff did nothing. On my flight from London to Miami one of the flight attendants screamed at me and demanded I keep my seat in the upright position at all times during the fight so the man behind me was comfortable for the flight. I will never in my life use British airways again

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.