Skyscanner

Cheap Flights from Milan (MILA) to Chicago (CHIA)

Travellers and cabin class

Compare Milan to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from Milan to Chicago

Looking for a cheap last-minute deal or the best return flight from Milan to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.$691 per passenger.Departing Wed, 5 Nov, returning Sun, 9 Nov.Return flight with SWISS.Outbound indirect flight with SWISS, departs from Milan Malpensa on Wed, 5 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with SWISS, departs from Chicago O'Hare International on Sun, 9 Nov, arriving in Milan Malpensa.Price includes taxes and charges.From $691, select.
Chicago.$742 per passenger.Departing Thu, 5 Mar, returning Sat, 14 Mar.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Thu, 5 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sat, 14 Mar, arriving in Milan Malpensa.Price includes taxes and charges.From $742, select.
Chicago.$744 per passenger.Departing Fri, 21 Nov, returning Mon, 1 Dec.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Fri, 21 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Mon, 1 Dec, arriving in Milan Malpensa.Price includes taxes and charges.From $744, select.
Chicago.$748 per passenger.Departing Sat, 28 Feb, returning Sat, 7 Mar.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Sat, 28 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sat, 7 Mar, arriving in Milan Malpensa.Price includes taxes and charges.From $748, select.
Chicago.$749 per passenger.Departing Sat, 10 Jan, returning Sat, 17 Jan.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Sat, 10 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sat, 17 Jan, arriving in Milan Linate.Price includes taxes and charges.From $749, select.
Chicago.$798 per passenger.Departing Thu, 4 Dec, returning Sun, 7 Dec.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Thu, 4 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sun, 7 Dec, arriving in Milan Malpensa.Price includes taxes and charges.From $798, select.
Chicago.$801 per passenger.Departing Thu, 5 Feb, returning Sat, 14 Feb.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Thu, 5 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sat, 14 Feb, arriving in Milan Malpensa.Price includes taxes and charges.From $801, select.
Chicago.$804 per passenger.Departing Sat, 13 Sep, returning Wed, 24 Sep.Return flight with Icelandair.Outbound indirect flight with Icelandair, departs from Milan Malpensa on Sat, 13 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departs from Chicago O'Hare International on Wed, 24 Sep, arriving in Milan Malpensa.Price includes taxes and charges.From $804, select.

Find the cheapest month to fly from Milan to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Milan to Chicago flights are currently cheapest in November.
May
from $808
Jun
from $907
Jul
from $983
Aug
from $926
Sep
from $804
Oct
from $835
Nov
from $691
Dec
from $798
Jan
from $749
Feb
from $801
Mar
from $742
Apr
from $916

Direct flights from Milan to Chicago

Alternative Milan to Chicago routes

Looking for the cheapest, fastest or easiest route from Milan to Chicago? You could fly into the following airports instead.

Milan to Chicago: Flight information

The things to know before you go.
Cheapest flight found$691
Cheapest month to flyNovember
Average flight time9 hrs, 52 mins
Most popular airlineSWISS
Average flights per week40

Finding cheap flights from Milan to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Milan to Chicago is $691. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
9 hours and 52 minutes is the average flight time from Milan to Chicago.
SWISS, Air Canada and Lufthansa fly direct from Milan to Chicago.
As of May 2025, there are 160 flights per week flying from Milan to Chicago.
The cheapest month to fly from Milan to Chicago is usually May 2025.
If you're flying from Milan, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $691.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Milan to Chicago on Wednesday, 5 November 2025.
Yes – the average flight time is 9 hours and 52 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
The cheapest airline that flies to Chicago is SWISS. And the cheapest airline that flies to Chicago O'Hare International Airport is United.

Travelling from Milan to Chicago: what you need to know

  • You can choose from multiple airports when planning your flight from Milan to Chicago. Explore your options for jetting out of Milan from Milano Malpensa Airport (MXP), Orio al Serio International Airport (BGY) and Milano Linate Airport (LIN).

  • When it comes to choosing where to land in Chicago, O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the major entry points.

  • Around 9 hours 50 minutes is how long you'll be travelling on a direct Milan to Chicago flight.

  • Chicago is six hours behind Milan and follows the UTC-5 timezone.

  • With four weekly flights between the two airports, Milano Malpensa Airport (MXP) to O'Hare International Airport (ORD) is the most popular route. Board the earliest flight from Milan to Chicago with United Airlines at 15:05. If you prefer to make the most of your day before jetting off, the last departure from MXP to ORD is with United Airlines at 15:20.

  • For a stress-free start to your trip, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to board your Milan to Chicago flight.

  • Flying during a peak time like July? Major public holidays and other popular seasons can lead to longer queues and delays at security. Play things extra safe and arrive up to four hours before international flights and two hours before a domestic departure.

How to find the cheapest flights from Milan to Chicago

  • To snag cheap Milan to Chicago flights, reserve your journey two months ahead of your departure date.

  • Plan your trip for May. That's the best month for landing great bargains on plane tickets from Milan to Chicago. If your travel dates are flexible, use the 'Whole month' tool to find the cheapest price across each month.

  • Locking in a cheap flight from Milan to Chicago is a breeze with Price Alerts. Simply set up one of these automatic alerts and we'll get in touch when there's a better deal.

  • Find an affordable Milan to Chicago flight with the help of our filters. Select your ideal duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Flying from Milan

Milano Malpensa Airport (MXP)

  • You can get a direct flight from Milan to Chicago leaving from Milano Malpensa Airport (MXP). Start your trip at MXP and land at O'Hare International Airport (ORD).

  • Keep an eye out for promotions with United Airlines. This airline offers direct Milan to Chicago plane tickets out of MXP.

  • Think about adding a stopover to potentially find a cheaper Milan to Chicago flight. Just deselect 'Direct flights only' when browsing departures from Milano Malpensa Airport. Take a pause at one of these popular airports:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • Charles de Gaulle Airport (CDG)

    • Frankfurt Airport (FRA)

  • Located around 40 kilometres from central Milan, MXP can be reached in about 45 minutes by car, depending on traffic. The journey on public transport is roughly 55 minutes.

  • After a leisurely start to your holiday? Stay near Milano Malpensa Airport. Whether you're taking an early flight from Milan to Chicago or just don't like being rushed, these hotels are perfect:

  • 68.23% of flights departing from Milano Malpensa Airport touch down at their destination on time.

Orio al Serio International Airport (BGY)

  • Get the most out of your holiday with a stopover on your Milan to Chicago flight. Visit family or friends or tick a new city off your list. Whatever you choose to do, check out these options between Orio al Serio International Airport and Chicago:

    • Amsterdam Airport Schiphol (AMS)

    • Vienna International Airport (VIE)

    • Barcelona-El Prat Airport (BCN)

  • BGY is about 48 kilometres from central Milan. It'll take 1 hour or so to get to the airport driving from the city centre. Public transport takes roughly 2 hours 20 minutes.

  • It's your holiday, so why not book an extra night away from home? Think about kicking back in one of these accommodation options near Orio al Serio International Airport the day before your flight from Milan to Chicago:

  • Orio al Serio International Airport has an on-time performance of 67.49%. This figure reflects how frequently flights departing from this airport arrive on schedule.

Milano Linate Airport (LIN)

  • You can lock in a ticket from Milan to Chicago with a stop or two out of Milano Linate Airport (LIN). Here are some of the most popular stopovers between LIN and Chicago:

    • Charles de Gaulle Airport (CDG)

    • Brussels Airport (BRU)

    • Amsterdam Airport Schiphol (AMS)

  • The journey to LIN from central Milan is around 45 minutes on public transport. If you prefer to travel by car, it'll take you roughly 30 minutes to cover the 8 kilometres or so.

  • Set yourself up for a smooth departure — stay close to Milano Linate Airport and know you'll get to your boarding gate with time to spare. Get comfy at one of these hotels the day before if you have an early Milan to Chicago flight:

  • Airports have an on-time performance rating that tracks how often flights arrive without delays. At LIN, that rate is 79.56%.

Arriving in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is approximately 26 kilometres from central Chicago. If you're catching a cab or a ride-share, the drive takes roughly 35 minutes.

  • Travelling to the centre by public transport takes roughly 55 minutes.

  • The last thing you want is a long journey to your hotel if you're getting in late on a flight from Milan to Chicago. Reserve one of these accommodation options near ORD instead:

  • Follow your own route with an O'Hare International Airport rental car. Pick up your wheels from Routes Car Rentals, Dollar or Budget and venture far and wide through Chicago and beyond.

  • Secure the lowest price by reserving your ride from O'Hare International Airport around four weeks before your departure date.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is around 14 kilometres from central Chicago. After your flight from Milan to Chicago, it takes approximately 20 minutes to reach the heart of the city in a cab or ride-share.

  • Public transport will get you there in about 45 minutes.

  • You'll find some comfortable places to lay your head close to MDW. Unwind after your Milan to Chicago flight at any of these perfectly located options:

  • The quickest way to get to where you're going is with a Chicago Midway International Airport rental car. Collect a set of wheels from Dollar, Hertz or Budget and make a speedy getaway.

  • Avoid last-minute price surges. Securing your ride four weeks ahead of your arrival at MDW can land you a better rate.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Set off for the city centre after your flight from Milan to Chicago has landed. Central Chicago is around 129 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by car.

  • The journey takes around 4 hours 15 minutes when travelling on public transport.

  • Take control of the next part of your journey by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National make getting on the road smooth sailing.

  • Rental agencies sometimes offer deals on early bookings, so reserve your vehicle from RFD in advance of your flight from Milan to Chicago. A bit of planning goes a long way in savings.

  • Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • August is the most popular month for flights from Milan to Chicago. To avoid the crowds, head to Chicago in January.

  • Before locking in your Milan to Chicago tickets, consider what kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap flights from Milan to Chicago around that time if you want to travel in cooler conditions.

More about Chicago

  • When it comes to looking for somewhere to lay your head, you'll find the top stays in Chicago right here. Explore these hotels as soon as you've booked your flight from Milan to Chicago:

  • There are so many things to explore in this city it can be hard to know where to begin. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are highlights which should be on every Chicago itinerary.

Explore more of United States

  • Columbus is just one of the many cities in United States waiting to be discovered once you've taken in the sights of Chicago. Around 451 kilometres to the south-east, check out popular attractions including Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another favourite destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Milan to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.