Flight tickets from Milan to Chicago from ₹ 28,111

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? If you want to travel next month, return fares start from ₹ 50,030. Find the lowest prices on one-way and return tickets right here.

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 April.

Direct flights from Milan to Chicago

Milan to Chicago: Flight information

The things to know before you go.
Cheapest flight found₹ 28,111
Cheapest month to flyApril
Average flight time9 hrs, 50 mins
Most popular airlineSWISS
Average flights per week30

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 ₹ 43,464. 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 50 minutes is the average flight time from Milan to Chicago.
SWISS, Air Canada and Lufthansa fly direct from Milan to Chicago.
As of March 2026, there are 30 flights per week flying from Milan to Chicago.
The cheapest month to fly from Milan to Chicago is usually September.
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 ₹ 43,464.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Milan to Chicago on Friday, 4 September 2026.
Yes – the average flight time is 9 hours and 50 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 March, the average temperature is usually around 3°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 British Airways. 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 organising your flight from Milan to Chicago. Explore your options for departing Milan from Milano Malpensa Airport (MXP), Orio al Serio International Airport (BGY) and Milano Linate Airport (LIN).

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

  • Take a direct Milan to Chicago flight and you'll be in transit for an average of 9 hours 50 minutes.

  • Chicago's timezone is UTC-5, making Chicago six hours behind Milan.

  • With four flights a week 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 get more out of your day before you fly, the latest flight from MXP to ORD is with United Airlines at 15:20.

  • To ensure you get on your Milan to Chicago flight, leave plenty of time to check in and drop off your luggage. Turning up two hours ahead of international departures and one hour before domestic flights is a good rule of thumb.

  • During popular months such as July, it's best to get to the airport even earlier. Plan to arrive two hours before domestic departures and four hours ahead of international flights whenever you're flying during a peak period in general.

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)

  • If you're looking for a direct flight from Milan to Chicago, you can depart from Milano Malpensa Airport (MXP). Get from MXP to O'Hare International Airport (ORD) without any stops.

  • Reserve your Milan to Chicago plane tickets with United Airlines. This airline is a top pick for direct flights from MXP.

  • A stopover is the perfect opportunity to break up your trip — and possibly even tour another city. When browsing Milan to Chicago flights leaving from Milano Malpensa Airport, deselect the 'Direct flights only' box to see where you can stop along the way. Consider one of these popular options:

    • Hartsfield-Jackson Atlanta International Airport (ATL)

    • London Heathrow Airport (LHR)

    • Frankfurt Airport (FRA)

  • MXP is around 40 kilometres from central Milan. If you're ride-sharing, catching a cab or driving from the centre, it'll take you 45 minutes or so to get there, depending on traffic conditions. If you're using public transport, expect the journey time to be around 55 minutes.

  • After a leisurely start to your trip? Stay near Milano Malpensa Airport. Whether you have an early flight from Milan to Chicago or want to avoid feeling rushed, these hotels are perfect:

  • When it comes to the on-time performance of Milano Malpensa Airport, data shows 68.23% of flights stick to their scheduled arrival time.

Orio al Serio International Airport (BGY)

  • Get more out of your holiday with a stopover on your Milan to Chicago flight. Visit friends or family or cross another city off your list. Whatever you'd like to do, check out these options between Orio al Serio International Airport and Chicago:

    • Amsterdam Airport Schiphol (AMS)

    • Barcelona-El Prat Airport (BCN)

    • Vienna International Airport (VIE)

  • BGY is around 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.

  • Kick off your holiday early with an extra night away from home. Before catching your flight from Milan to Chicago, take it easy in one of these hotels close to Orio al Serio International Airport:

  • Orio al Serio International Airport has an on-time performance rate of 68%. This figure sheds light on how often flights that depart from this airport land at their destination on schedule.

Milano Linate Airport (LIN)

  • You can reserve a ticket from Milan to Chicago with one or more stops departing from Milano Linate Airport (LIN). These are some of the most popular stopovers between LIN and Chicago:

    • Amsterdam Airport Schiphol (AMS)

    • Charles de Gaulle Airport (CDG)

    • Brussels Airport (BRU)

  • LIN is roughly 8 kilometres from central Milan. The drive from the city centre to the terminal takes about 30 minutes. If you're thinking about taking public transport, expect a journey time of around 45 minutes.

  • Take the uncertainty out of departure day — stay near Milano Linate Airport and know you'll reach your boarding gate with time to spare. Check in to one of these hotels the day before if you're catching an early Milan to Chicago flight:

  • Flights departing from LIN land at their destination on schedule 79.56% of the time.

Arriving in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago takes around 35 minutes to reach by car. The centre is roughly 26 kilometres away.

  • Travelling to the centre on public transport typically takes 55 minutes.

  • Book a hotel near ORD if you're coming in on a late flight from Milan to Chicago. Check in to one of these accommodation options and avoid the hassle of a long transfer:

  • Go where the road takes you with an O'Hare International Airport rental car. Book your wheels from Routes Car Rentals, Dollar or Budget and experience more of Chicago and beyond.

  • Get the best deal by booking your ride from O'Hare International Airport around four weeks before your trip.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Milan to Chicago has touched down, you can reach the city centre in about 20 minutes by car. Central Chicago is roughly 14 kilometres from Chicago Midway International Airport (MDW).

  • Travelling by public transport will take approximately 45 minutes.

  • You'll find some great places to call home for the night near MDW. Settle in and get cosy after your Milan to Chicago flight at one of these perfectly located options:

  • No need to worry about public transport schedules or long cab queues. Pick up a Chicago Midway International Airport rental car and take your journey in whatever direction you like. Check out the rates and availability from Dollar, Hertz and Budget.

  • Snap up a deal by securing your ride from MDW four weeks in advance. You'll also have access to a greater selection of vehicles.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 129 kilometres from central Chicago. It'll take you about 1 hour 25 minutes to reach the city centre by cab or ride-share once you've stepped off your flight from Milan to Chicago.

  • The journey takes roughly 4 hours 15 minutes using public transport.

  • Whether you're after a zippy mini for solo travel or a roomy SUV to fit the whole crew comfortably, you'll find the right Chicago Rockford International Airport rental car for you. Explore the range of wheels available here from providers such as Budget, Alamo and National.

  • If you're hoping for a specific make or model, booking early increases your chances of getting your first choice. Book your ride from RFD at least a few weeks ahead of your flight from Milan to Chicago.

  • Chicago Rockford International Airport's street address is 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 to 29ºC.

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

More about Chicago

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.

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