Cheap Flights from Milan to Chicago

Compare Milan to Chicago flight deals

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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 $972. Find the lowest prices on one-way and return tickets right here.

Chicago.$946 per passenger.Departing Thu, 1 Oct, returning Wed, 7 Oct.Return flight with Icelandair.Outbound indirect flight with Icelandair, departs from Milan Malpensa on Thu, 1 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departs from Chicago O'Hare International on Wed, 7 Oct, arriving in Milan Malpensa.Price includes taxes and charges.From $946, select.

Chicago.$948 per passenger.Departing Wed, 31 Mar, returning Tue, 6 Apr.Return flight with Icelandair.Outbound indirect flight with Icelandair, departs from Milan Malpensa on Wed, 31 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departs from Chicago O'Hare International on Tue, 6 Apr, arriving in Milan Malpensa.Price includes taxes and charges.From $948, select.

Chicago.$951 per passenger.Departing Sat, 17 Apr, returning Tue, 27 Apr.Return flight with Icelandair.Outbound indirect flight with Icelandair, departs from Milan Malpensa on Sat, 17 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departs from Chicago O'Hare International on Tue, 27 Apr, arriving in Milan Malpensa.Price includes taxes and charges.From $951, select.

Chicago.$959 per passenger.Departing Mon, 31 Aug, returning Sat, 24 Oct.Return flight with Icelandair.Outbound indirect flight with Icelandair, departs from Milan Malpensa on Mon, 31 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Milan Malpensa.Price includes taxes and charges.From $959, select.

Chicago.$961 per passenger.Departing Sat, 5 Sep, returning Sat, 3 Oct.Return flight with Icelandair.Outbound indirect flight with Icelandair, departs from Milan Malpensa on Sat, 5 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departs from Chicago O'Hare International on Sat, 3 Oct, arriving in Milan Malpensa.Price includes taxes and charges.From $961, select.

Chicago.$968 per passenger.Departing Mon, 7 Sep, returning Mon, 21 Sep.Return flight with Icelandair.Outbound indirect flight with Icelandair, departs from Milan Malpensa on Mon, 7 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departs from Chicago O'Hare International on Mon, 21 Sep, arriving in Milan Malpensa.Price includes taxes and charges.From $968, select.

Chicago.$972 per passenger.Departing Sun, 22 Nov, returning Mon, 30 Nov.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Sun, 22 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Mon, 30 Nov, arriving in Milan Malpensa.Price includes taxes and charges.From $972, select.

Chicago.$972 per passenger.Departing Thu, 27 Aug, returning Mon, 31 Aug.Return flight with Icelandair.Outbound indirect flight with Icelandair, departs from Milan Malpensa on Thu, 27 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departs from Chicago O'Hare International on Mon, 31 Aug, arriving in Milan Malpensa.Price includes taxes and charges.From $972, select.

Chicago.$972 per passenger.Departing Fri, 28 Aug, returning Mon, 7 Sep.Return flight with Icelandair.Outbound indirect flight with Icelandair, departs from Milan Malpensa on Fri, 28 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departs from Chicago O'Hare International on Mon, 7 Sep, arriving in Milan Malpensa.Price includes taxes and charges.From $972, select.

Chicago.$973 per passenger.Departing Wed, 9 Dec, returning Thu, 31 Dec.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Wed, 9 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Thu, 31 Dec, arriving in Milan Malpensa.Price includes taxes and charges.From $973, select.

Chicago.$974 per passenger.Departing Mon, 8 Feb, returning Sun, 21 Feb.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Mon, 8 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sun, 21 Feb, arriving in Milan Malpensa.Price includes taxes and charges.From $974, select.

Chicago.$974 per passenger.Departing Wed, 18 Nov, returning Tue, 1 Dec.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Wed, 18 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Tue, 1 Dec, arriving in Milan Malpensa.Price includes taxes and charges.From $974, select.

Chicago.$974 per passenger.Departing Tue, 2 Mar, returning Fri, 5 Mar.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Tue, 2 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Fri, 5 Mar, arriving in Milan Malpensa.Price includes taxes and charges.From $974, select.

Chicago.$980 per passenger.Departing Sat, 30 Jan, returning Sat, 6 Feb.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Sat, 30 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sat, 6 Feb, arriving in Milan Malpensa.Price includes taxes and charges.From $980, select.

Chicago.$980 per passenger.Departing Thu, 24 Dec, returning Mon, 11 Jan.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Thu, 24 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Mon, 11 Jan, arriving in Milan Malpensa.Price includes taxes and charges.From $980, select.

Chicago.$986 per passenger.Departing Tue, 20 Oct, returning Thu, 5 Nov.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Tue, 20 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Thu, 5 Nov, arriving in Milan Malpensa.Price includes taxes and charges.From $986, 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 October.

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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	$946
Cheapest month to fly	October
Average flight time	9 hrs, 51 mins
Most popular airline	Lufthansa
Average flights per week	28

Finding cheap flights from Milan to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are return flights from Milan to Chicago?

The best price we found for a return flight from Milan to Chicago is $946. 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.

How long does it take to fly from Milan to Chicago?

9 hours and 51 minutes is the average flight time from Milan to Chicago.

Which airlines fly direct from Milan to Chicago?

Lufthansa, SWISS and Air Canada fly direct from Milan to Chicago.

How many flights are there a week from Milan to Chicago?

As of July 2026, there are 28 flights per week flying from Milan to Chicago.

When is the cheapest time to fly from Milan to Chicago?

The cheapest month to fly from Milan to Chicago is usually October.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Milan, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the centre of Chicago. We've found flights into this airport from $946.

Which upcoming date is cheapest to fly from Milan to Chicago on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Milan to Chicago on Thursday, 1 October 2026.

Can I get a direct flight from Milan to Chicago?

Yes – the average flight time is 9 hours and 51 minutes.

How can I get the best flight deal from Milan to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In July, the average temperature is usually around 22°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.

Which is the cheapest airline to fly from Milan to Chicago with?

The cheapest airline that flies to Chicago is Icelandair. And the cheapest airline that flies to Chicago O'Hare International Airport is United.

Flying from Milan to Chicago: what you need to know

When searching for your flight from Milan to Chicago, there's a nice selection of airports you can take off from. Milan Malpensa Airport (MXP), Milan Bergamo Airport (BGY) and Milan Linate Airport (LIN) are some of Milan's main terminals.
When it comes to landing in Chicago, Chicago O'Hare International Airport (ORD) and Chicago Midway Airport (MDW) are the primary gateways.
The average time for a direct Milan to Chicago flight is 9 hours 50 minutes.
Chicago is seven hours behind Milan and observes the UTC-6 timezone.
With five flights a week between the two airports, Milan Malpensa Airport (MXP) to Chicago O'Hare International Airport (ORD) is the busiest 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 taking off, the latest departure from MXP to ORD is with United Airlines at 15:20.
For stress-free travel, turn up at the airport two hours ahead of international flights and an hour before domestic departures. That way, you won't have to rush to board your Milan to Chicago flight.
During popular months such as July, it's a good idea to get to the airport earlier than usual. Plan to arrive two hours before a domestic departure and four hours ahead for international flights whenever you're travelling during high season in general.

How to find the cheapest flights from Milan to Chicago

Don't wait until the last moment. You're more likely to find cheap Milan to Chicago flights if you book in advance. Airlines often have some fantastic early bird deals.
Finding cheap plane tickets from Milan to Chicago is more likely if you can be flexible with your travel dates. Try using the 'Whole month' function to see the lowest fares across every month and bag a fantastic deal.
You don't need to check every day to find out if prices have dropped when you set up a Price Alert. We'll notify you when a better deal comes up on cheap flights from Milan to Chicago.
Select your ideal arrival and departure times, number of stops and airlines with the filters. Or sort your Milan to Chicago flight results by 'Cheapest,' 'Fastest' or 'Best.'

Flying from Milan

Milan Malpensa Airport (MXP)

Depart from Milan Malpensa Airport (MXP) on a nonstop flight from Milan to Chicago. From MXP, you can fly directly into Chicago O'Hare International Airport (ORD).
Look out for deals with United Airlines. This airline offers direct Milan to Chicago plane tickets from MXP.
Stopovers are the perfect opportunity to break up your trip — and possibly even tour another city. When searching for Milan to Chicago flights leaving from Milan Malpensa Airport, uncheck the 'Direct flights only' box to see where you can visit along the way. Some popular options include:
- Atlanta Hartsfield-Jackson Airport (ATL)
- London Heathrow Airport (LHR)
- Frankfurt am Main Airport (FRA)
MXP is about 40 kilometres from central Milan. If you're ride-sharing, catching a taxi or driving from the centre, it'll take you 50 minutes or so to get there, depending on traffic conditions. If you're planning to take public transport, expect the journey time to be around 50 minutes.
In search of a convenient hotel close to Milan Malpensa Airport? If you're catching an early flight from Milan to Chicago, these stays will have you sleeping moments from check-in:
Of all flights departing from Milan Malpensa Airport, 76% touch down on time at their destination.

Milan Bergamo Airport (BGY)

Visit family or friends or just take a moment to stretch your legs with a stopover. If you'd like to break up your Milan to Chicago flight, check out these options when departing from Milan Bergamo Airport:
- Amsterdam Schiphol Airport (AMS)
- Barcelona Airport (BCN)
- Vienna Airport (VIE)
BGY is around 48 kilometres from central Milan. It takes 50 minutes or so to get to the airport in a car from the city centre. Public transport takes roughly 1 hour.
Want to treat yourself to an extra night away before catching your flight from Milan to Chicago? Check in to a hotel near Milan Bergamo Airport before your trip officially starts. These stays are calling your name:
As far as flight punctuality goes, Milan Bergamo Airport has an on-time arrival performance of 75%.

Milan Linate Airport (LIN)

Booking a ticket from Milan to Chicago with a stop or two can offer you a bigger choice of departure times along with better fares. When flying from Milan Linate Airport (LIN), here's where you can detour to on your way to Chicago:
- Amsterdam Schiphol Airport (AMS)
- Paris Charles de Gaulle Airport (CDG)
- Brussels International Airport (BRU)
LIN is around 8 kilometres from central Milan. Driving from the city centre to the airport takes about 20 minutes. If you're considering public transport, you can expect a journey of around 30 minutes.
Relax in bed for a little longer and still make your Milan to Chicago flight without having to rush. These accommodation options near Milan Linate Airport make getting to the terminal a breeze if you're flying out first thing:
LIN has a solid on-time arrivals rating of 83%, so there's a high chance your flight will stay on track and land as expected.

Arriving in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) is approximately 26 kilometres from the centre of Chicago. If you're catching a taxi or a ride-share, the drive takes around 30 minutes.
When travelling by public transport, expect a journey time of about 45 minutes.
If you have a late flight from Milan to Chicago, few things beat the convenience of staying near the terminal. Grab your bags from the carousel and then be showered and snoozing not long after at one of these hotels near ORD:
Pick up a Chicago O'Hare International Airport rental car and explore Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are popular providers you can book with here.
Lock in the best possible rate by reserving your vehicle from Chicago O'Hare International Airport about four weeks before your departure date.
You'll find ORD at 10000 West O'Hare.

Chicago Midway Airport (MDW)

Chicago Midway Airport (MDW) is around 14 kilometres from central Chicago. Following your flight from Milan to Chicago, it'll take you approximately 25 minutes to reach the heart of the city in a taxi or ride-share.
You can expect the journey to take roughly 30 minutes on public transport.
Hang the 'Do not disturb' sign on your door and relax at a hotel near MDW. Here are a few options where you can settle in after your flight from Milan to Chicago:
The quickest way to get to where you're going is with a Chicago Midway Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and be on your way in a flash.
Score the best price by securing your ride from MDW four weeks ahead of time. You'll also have access to a wider range of vehicles.
You can find Chicago Midway Airport at 5700 South Cicero.

Chicago Rockford Airport (RFD)

Chicago Rockford Airport (RFD) is roughly 129 kilometres from central Chicago. It takes about 1 hour 40 minutes to get to the city centre by car after your flight from Milan to Chicago.
If you go by public transport, the journey takes about 2 hours.
Start your trip without worrying about how to get to your destination with a Chicago Rockford Airport rental car. You can book your wheels with reliable companies here like Budget, Alamo and National.
Rental agencies sometimes offer discounts for early bookings, so secure your vehicle from RFD well ahead of your flight from Milan to Chicago. A little prep today saves cash tomorrow.
The street address for Chicago Rockford Airport is 2 Airport Cir.

Best time to go to Chicago

March is the quietest month for flights from Milan to Chicago, while July is the most popular. Work out the ideal time to go to Chicago based on whether you prefer a laid-back vibe or a more bustling atmosphere.
When booking your Milan to Chicago tickets, consider the weather you're most comfortable in. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.
If you want cooler conditions, look for a cheap flight from Milan to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

When it comes to searching for somewhere to lay your head, you'll find the most popular stays in Chicago right here. Explore these hotels once you've booked your flight from Milan to Chicago:
There are so many things to discover in this city it can be hard to know where to start. Millennium Park, The Art Institute of Chicago and Willis Tower are leading attractions which should feature on any good Chicago itinerary.

Explore more of the United States

Chicago will leave a lasting impression, but there are so many other corners of the United States waiting to be explored. Around 451 kilometres southeast of Chicago, a visit to Columbus will keep you on the go. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Columbus Park of Roses and Ohio Theatre.
Around 257 kilometres southeast of Chicago, Indianapolis is another essential stop in the United States. Experience this destination's highlights firsthand at Lucas Oil Stadium, Eiteljorg Museum of American Indians and Western Art and The Children's Museum of Indianapolis.