Cheap Flights from Chicago to Milan

Compare Chicago to Milan flight deals

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Flight deals from Chicago to Milan

Looking for a cheap last-minute deal or the best return flight from Chicago to Milan? If you want to travel next month, return fares start from $1,062. Find the lowest prices on one-way and return tickets right here.

Milan.$819 per passenger.Departing Fri, 16 Oct, returning Sun, 1 Nov.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Fri, 16 Oct, arriving in Milan Linate.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Sun, 1 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $819, select.

Milan.$852 per passenger.Departing Tue, 13 Oct, returning Sat, 17 Oct.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Tue, 13 Oct, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Sat, 17 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $852, select.

Milan.$865 per passenger.Departing Sun, 1 Nov, returning Sat, 7 Nov.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sun, 1 Nov, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Sat, 7 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From $865, select.

Milan.$904 per passenger.Departing Tue, 12 Jan, returning Tue, 26 Jan.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Tue, 12 Jan, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Tue, 26 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From $904, select.

Milan.$947 per passenger.Departing Tue, 17 Nov, returning Tue, 1 Dec.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Tue, 17 Nov, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Tue, 1 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From $947, select.

Milan.$956 per passenger.Departing Wed, 30 Sep, returning Wed, 7 Oct.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Wed, 30 Sep, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Wed, 7 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $956, select.

Milan.$973 per passenger.Departing Tue, 23 Feb, returning Tue, 9 Mar.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Tue, 23 Feb, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Tue, 9 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From $973, select.

Milan.$999 per passenger.Departing Mon, 13 Apr, returning Wed, 13 May.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Mon, 13 Apr, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Wed, 13 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $999, select.

Milan.$1,016 per passenger.Departing Sun, 23 Aug, returning Wed, 2 Sep.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Sun, 23 Aug, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Wed, 2 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,016, select.

Milan.$1,017 per passenger.Departing Thu, 3 Dec, returning Mon, 7 Dec.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Thu, 3 Dec, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Mon, 7 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,017, select.

Milan.$1,029 per passenger.Departing Tue, 25 Aug, returning Mon, 31 Aug.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Tue, 25 Aug, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Mon, 31 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,029, select.

Milan.$1,033 per passenger.Departing Mon, 11 May, returning Sat, 16 May.Return flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departs from Chicago O'Hare International on Mon, 11 May, arriving in Milan Malpensa.Inbound indirect flight with Scandinavian Airlines, departs from Milan Malpensa on Sat, 16 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,033, select.

Milan.$1,040 per passenger.Departing Tue, 8 Sep, returning Tue, 15 Sep.Return flight with Turkish Airlines.Outbound indirect flight with Turkish Airlines, departs from Chicago O'Hare International on Tue, 8 Sep, arriving in Milan Malpensa.Inbound indirect flight with Turkish Airlines, departs from Milan Malpensa on Tue, 15 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,040, select.

Milan.$1,062 per passenger.Departing Sat, 4 Apr, returning Sat, 18 Apr.Return flight with Air Serbia.Outbound indirect flight with Air Serbia, departs from Chicago O'Hare International on Sat, 4 Apr, arriving in Milan Malpensa.Inbound indirect flight with Air Serbia, departs from Milan Malpensa on Sat, 18 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,062, select.

Milan.$1,103 per passenger.Departing Wed, 29 Apr, returning Tue, 9 Jun.Return flight with Turkish Airlines.Outbound indirect flight with Turkish Airlines, departs from Chicago O'Hare International on Wed, 29 Apr, arriving in Milan Malpensa.Inbound indirect flight with Turkish Airlines, departs from Milan Malpensa on Tue, 9 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,103, select.

Milan.$1,110 per passenger.Departing Sun, 29 Mar, returning Mon, 4 May.Return flight with Turkish Airlines.Outbound indirect flight with Turkish Airlines, departs from Chicago O'Hare International on Sun, 29 Mar, arriving in Milan Malpensa.Inbound indirect flight with Turkish Airlines, departs from Milan Malpensa on Mon, 4 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $1,110, select.

Find the cheapest month to fly from Chicago to Milan

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Milan flights are currently cheapest in October.

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Direct flights from Chicago to Milan

Alternative Chicago to Milan routes

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

Chicago to Milan: Flight information

The things to know before you go.

Cheapest flight found	$819
Cheapest month to fly	October
Average flight time	8 hrs, 40 mins
Most popular airline	SWISS
Average flights per week	30

Check out these Milan hotels

Ready to plan your stay? Other travellers rate these Milan hotels for cleanliness, service and location.

Moscova Luxury B&B

1.46 km from city centre

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Per night

Hotel Calimala Milano

1.97 km from city centre

$457

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Aparthotel Meneghino

1.42 km from city centre

$280

Per night

Moscova Luxury B&B

1.46 km from city centre

$368

Per night

Hotel Calimala Milano

1.97 km from city centre

$457

Per night

Aparthotel Meneghino

1.42 km from city centre

$280

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Finding cheap flights from Chicago to Milan: Frequently asked questions

How many airports are there in Milan?

There are 4 airports in Milan: Milan Linate, Milan Malpensa, Milan Bergamo, and Verona Brescia.

How much are return flights from Chicago to Milan?

The best price we found for a return flight from Chicago to Milan is $819. 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 Chicago to Milan?

8 hours and 40 minutes is the average flight time from Chicago to Milan.

Which airlines fly direct from Chicago to Milan?

SWISS, Lufthansa and United fly direct from Chicago to Milan.

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

As of March 2026, there are 30 flights per week flying from Chicago to Milan.

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

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

Which is the cheapest airport to fly into in Milan?

If you're flying from Chicago, the cheapest airport near Milan is Milan Linate – which is 7.4 km away from the centre of Milan. We've found flights into this airport from $819.

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Milan on Friday, 16 October 2026.

Can I get a direct flight from Chicago to Milan?

Yes – the average flight time is 8 hours and 40 minutes.

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

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 Milan 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 Milan?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Milan is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Milan?

In March, the average temperature is usually around 8°C. August is typically the warmest month in Milan, when it usually averages around 28°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -1°C. The rainiest month is November.

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

The cheapest airline that flies to Milan is Scandinavian Airlines. And the cheapest airline that flies to Milan Malpensa Airport is United.

Flying from Chicago to Milan: what you need to know

There are a couple of main airports you can fly out of in Chicago. Explore your options leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW) when searching for a flight from Chicago to Milan.
Disembark at one of Milan's major gateways like Milano Malpensa Airport (MXP). You can also come in for landing at Orio al Serio International Airport (BGY) or Milano Linate Airport (LIN).
Hop on a direct Chicago to Milan flight and you'll be in the air for an average of 8 hours 40 minutes.
Milan is six hours ahead of Chicago and is in the UTC+1 timezone.
With four weekly flights between the two airports, O'Hare International Airport (ORD) to Milano Malpensa Airport (MXP) is the most popular route. Board the first flight from Chicago to Milan with United Airlines at 21:30. If you prefer to make the most of your day before leaving, the latest flight from ORD to MXP is with United Airlines at 22:30.
To ensure you board your Chicago to Milan flight, leave plenty of time for things like check-in and baggage drop. 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 August, it's best to get to the airport well in advance. Plan to arrive two hours before a domestic departure and four hours ahead for an international flight whenever you're travelling during a peak period in general.

How to find the cheapest flights from Chicago to Milan

Lock in cheap Chicago to Milan flights by booking six months ahead. According to our research, that's the ideal time frame for finding a bargain.
The best month for scoring cheap plane tickets from Chicago to Milan is September. Use the 'Whole month' tool to compare prices, then choose the dates offering the lowest fares.
Locking in a cheap flight from Chicago to Milan is easy with Price Alerts. All you need to do is create one of these automatic alerts and we'll get in touch as soon as a better deal is available.
Select your preferred arrival and departure times, airlines and number of stops by using the filters. Alternatively, sort your Chicago to Milan flight results by 'Best,' 'Fastest' or 'Cheapest.'

Flying from Chicago

O'Hare International Airport (ORD)

If you're after a direct flight from Chicago to Milan, you can leave from O'Hare International Airport (ORD). Travel from ORD to Milano Malpensa Airport (MXP) in one seamless trip.
Look out for deals with United Airlines. This carrier offers direct Chicago to Milan plane tickets from ORD.
Consider adding a stopover to potentially save money on your Chicago to Milan flight. Simply deselect 'Direct flights only' when searching for departures from O'Hare International Airport. Break up your trip (and maybe save some cash) by stopping at one of these airports:
- Amsterdam Airport Schiphol (AMS)
- Frankfurt Airport (FRA)
- Charles de Gaulle Airport (CDG)
Travelling from central Chicago to ORD takes around 55 minutes on public transport. If you drive, ride-share or grab a cab, you'll cover the 26 kilometres in 35 minutes or so, depending on traffic.
Want a leisurely start to your travels? Stay near O'Hare International Airport. Whether you're catching an early flight from Chicago to Milan or want to avoid feeling rushed, these hotels are just the thing:
74.85% of flights that take off from O'Hare International Airport land at their destination on time.
The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Think about adding a stop at Hartsfield-Jackson Atlanta International Airport (ATL). It's a key stopover on a Chicago to Milan flight leaving Chicago Midway International Airport. Use a long layover to get out and explore, or take advantage of a short break to visit an airport cafe.
On public transport, you can travel from central Chicago to MDW in around 45 minutes. The airport is roughly 14 kilometres away. Driving will take you about 20 minutes.
It's your holiday, so why not book an extra night away? Think about kicking back in one of these accommodation options near Chicago Midway International Airport the day before your flight from Chicago to Milan:
Chicago Midway International Airport has an on-time performance rate of 78%. This figure provides insight into how frequently flights that leave from this airport make it to their destination on time.
The address for MDW is 5700 South Cicero.

Arriving in Milan

Milano Malpensa Airport (MXP)

The distance from Milano Malpensa Airport (MXP) to central Milan is roughly 40 kilometres. It'll take you around 45 minutes to get to the centre driving.
Getting to the centre by public transport takes about 55 minutes.
If you're arriving on a late flight from Chicago to Milan, few things beat the convenience of staying near the terminal. Grab your suitcases from the carousel and then be showered and relaxing not long after at one of these accommodation options near MXP:
Go wherever you want, whenever you want with a Milano Malpensa Airport rental car. Pick up a set of wheels from Surprice, RentSmart24 or Noleggiare and chase adventure across Milan and beyond.
Lock in the lowest price by reserving your vehicle from Milano Malpensa Airport about one week before your travel date.

Orio al Serio International Airport (BGY)

After your flight from Chicago to Milan has touched down, you can get to the city centre in around 1 hour by car. Central Milan is approximately 48 kilometres from Orio al Serio International Airport (BGY).
You can expect the trip to take approximately 2 hours 20 minutes on public transport.
After your flight from Chicago to Milan, settle in at a hotel near BGY. These are some comfortable options that'll help you switch to relaxation mode:
Surprice, RentSmart24 and Galdieri Rent make collecting an Orio al Serio International Airport rental car easy and quick. These trusted companies are located in or around the terminal and will have you behind the wheel before you know it.
Snap up the best price by booking your ride from BGY two weeks ahead of time. You can also expect to have a bigger selection of vehicles.

Milano Linate Airport (LIN)

Step off your flight from Chicago to Milan and go directly to your hotel or start taking in the sights right away. Central Milan is around 8 kilometres from Milano Linate Airport (LIN) and usually takes 30 minutes to drive there.
Public transport can take you there in around 45 minutes.
Enjoy a restful, unhurried start to your trip by choosing a hotel near LIN after your Chicago to Milan flight. Rest up after a long day of travel or just take a moment to settle into a new destination at:
Take control of the next chapter of your journey with a Milano Linate Airport rental car. RentSmart24, Drivalia and Noleggiare will get you on the road.
Plan ahead and enjoy the payoff. Book your vehicle from LIN four weeks before your flight from Chicago to Milan for the most affordable rates.

Best time to go to Milan

July is the busiest month for flights from Chicago to Milan. To escape the crowds, go to Milan in January.
When booking your Chicago to Milan tickets, think about the type of weather you enjoy. July is the warmest month in Milan, with temperatures ranging from 16ºC to 35ºC.
Look for cheap flights from Chicago to Milan in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -1ºC and 9ºC on average.

More about Milan

After booking your flight from Chicago to Milan, decide where you'll be dropping your bags. Make one of these options your base for exploring Milan:
All great adventures should include some sightseeing. Grande Museo del Duomo di Milano, Milan Cathedral and The Last Supper Museum are must-visits when exploring Milan.

Explore more of Italy

You've seen Milan, now it's time to discover other parts of Italy. Journey about 483 kilometres south-east to Rome to check off its leading sights. From Colosseum to Trevi Fountain and Roman Forum, you'll have a full itinerary ahead.
Turin is another must-experience destination in Italy and is around 129 kilometres west of Milan. No journey is complete without seeing Galleria Sabauda (Palazzo Reale), Egyptian Museum and Royal Palace of Turin.