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

Compare Chicago to Milan flight deals

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

Book the best Milan fare with no extra fees

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 £442. Find the lowest prices on one-way and return tickets right here.

Milan.£192 per passenger.Departing Mon, 31 Aug.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Mon, 31 Aug, arriving in Milan Malpensa.Price includes taxes and charges.From £192, select.

Milan.£193 per passenger.Departing Mon, 20 Jul.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Mon, 20 Jul, arriving in Milan Bergamo.Price includes taxes and charges.From £193, select.

Milan.£196 per passenger.Departing Wed, 14 Oct.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Chicago Rockford on Wed, 14 Oct, arriving in Milan Bergamo.Price includes taxes and charges.From £196, select.

Milan.£202 per passenger.Departing Wed, 2 Sep.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Wed, 2 Sep, arriving in Milan Malpensa.Price includes taxes and charges.From £202, select.

Milan.£226 per passenger.Departing Sun, 1 Nov.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Sun, 1 Nov, arriving in Milan Malpensa.Price includes taxes and charges.From £226, select.

Milan.£226 per passenger.Departing Thu, 21 Jan.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Thu, 21 Jan, arriving in Milan Malpensa.Price includes taxes and charges.From £226, select.

Milan.£231 per passenger.Departing Tue, 1 Dec.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Tue, 1 Dec, arriving in Milan Bergamo.Price includes taxes and charges.From £231, select.

Milan.£231 per passenger.Departing Tue, 2 Mar.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Tue, 2 Mar, arriving in Milan Bergamo.Price includes taxes and charges.From £231, select.

Milan.£239 per passenger.Departing Thu, 15 Apr.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Thu, 15 Apr, arriving in Milan Bergamo.Price includes taxes and charges.From £239, select.

Milan.£253 per passenger.Departing Tue, 11 May.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Tue, 11 May, arriving in Milan Malpensa.Price includes taxes and charges.From £253, select.

Milan.£284 per passenger.Departing Sat, 20 Feb.One-way flight with Air Serbia.Outbound indirect flight with Air Serbia, departs from Chicago O'Hare International on Sat, 20 Feb, arriving in Milan Malpensa.Price includes taxes and charges.From £284, select.

Milan.£320 per passenger.Departing Mon, 7 Jun.One-way flight with Icelandair.Outbound indirect flight with Icelandair, departs from Chicago O'Hare International on Mon, 7 Jun, arriving in Milan Linate.Price includes taxes and charges.From £320, select.

Milan.£437 per passenger.Departing Tue, 28 Jul.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 28 Jul, arriving in Milan Malpensa.Price includes taxes and charges.From £437, select.

Milan.£437 per passenger.Departing Wed, 5 Aug.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 5 Aug, arriving in Milan Malpensa.Price includes taxes and charges.From £437, select.

Milan.£438 per passenger.Departing Thu, 26 Nov.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 26 Nov, arriving in Milan Malpensa.Price includes taxes and charges.From £438, select.

Milan.£438 per passenger.Departing Wed, 14 Oct.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 14 Oct, arriving in Milan Malpensa.Price includes taxes and charges.From £438, 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 August.

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

May

Jun

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	£192
Cheapest month to fly	August
Average flight time	8 hrs, 43 mins
Most popular airline	Lufthansa
Average flights per week	27

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 £423. 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 43 minutes is the average flight time from Chicago to Milan.

Which airlines fly direct from Chicago to Milan?

Lufthansa, SWISS and Brussels Airlines fly direct from Chicago to Milan.

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

As of July 2026, there are 27 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 November.

Which is the cheapest airport to fly into in Milan?

If you're flying from Chicago, the cheapest airport near Milan is Milan Malpensa – which is 25.3 miles away from the centre of Milan. We've found flights into this airport from £423.

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, 13 November 2026.

Can I get a direct flight from Chicago to Milan?

Yes – the average flight time is 8 hours and 43 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 July, the average temperature is usually around 23°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.

Travelling from Chicago to Milan: what you need to know

There are two main airports you can take off from in Chicago. Check out your options leaving from Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW) when planning your flight from Chicago to Milan.
Milan has a variety of airports you can fly into. Touch down at Milan Malpensa Airport (MXP), Milan Bergamo Airport (BGY) or Milan Linate Airport (LIN).
Around 8 hours 40 minutes is how long you can expect to be in the air on a direct Chicago to Milan flight.
Milan is seven hours ahead of Chicago and is in the UTC+1 timezone.
Chicago O'Hare International Airport (ORD) to Milan Malpensa Airport (MXP) is the most traveled route that connects these two cities. There are five departures a week to pick from. If you have things to do before heading off, the last flight from Chicago to Milan is with United Airlines at 22:30. Choose the first ORD to MXP departure with United Airlines at 21:30 to make the most of your arrival in Milan.
To ensure you don't miss your Chicago to Milan flight, allow plenty of time to check in and drop off your luggage. Turning up two hours before international departures and an hour before domestic flights is the general rule.
During popular months like 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 an international flight whenever you're travelling during peak periods in general.

How to find the cheapest flights from Chicago to Milan

Score cheap Chicago to Milan flights by booking four months ahead. Based on our research, that's the sweet spot for finding a bargain.
Plan your trip for September. That's the best month for landing a great bargain on plane tickets from Chicago to Milan. If your travel dates are flexible, use the 'Whole month' tool to see the lowest price across every month.
Locking in a cheap flight from Chicago to Milan is easy with Price Alerts. Simply create one of these automatic alerts and we'll let you know when a better deal is available.
Lock in a cheap Chicago to Milan flight with the help of our filters. Choose your preferred duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Flying from Chicago

Chicago O'Hare International Airport (ORD)

If you're looking for a direct flight from Chicago to Milan, you can depart from Chicago O'Hare International Airport (ORD). Travel from ORD to Milan Malpensa Airport (MXP) in one seamless trip.
United Airlines is a leading airline that offers direct Chicago to Milan plane tickets from ORD.
Consider adding a stopover to possibly find a cheaper Chicago to Milan flight. Just uncheck 'Direct flights only' when searching for departures from Chicago O'Hare International Airport. Break up your trip (and maybe save some cash) by stopping at one of these airports:
- Amsterdam Schiphol Airport (AMS)
- Frankfurt am Main Airport (FRA)
- Paris Charles de Gaulle Airport (CDG)
Located around 26 kms (16 miles) from the centre of Chicago, ORD can be reached in about 30 minutes by car, depending on traffic. The journey on public transport takes roughly 45 minutes.
Booked an early flight from Chicago to Milan? Avoid rushing to the airport (and get some extra shut-eye) by choosing one of these stays close to Chicago O'Hare International Airport:
When it comes to the on-time performance of Chicago O'Hare International Airport, data shows 70% of flights complete their journey on time.
ORD is located at 10000 West O'Hare.

Chicago Midway Airport (MDW)

Give yourself a moment to stretch your legs during your Chicago to Milan flight with a stopover. Atlanta Hartsfield-Jackson Airport (ATL) is a great option between Chicago Midway Airport and Milan.
On public transport, you can travel from central Chicago to MDW in around 30 minutes. The airport is roughly 14 kms (9 miles) away. Driving will take you about 25 minutes.
Start your holiday sooner with an additional night away from home. Before your flight from Chicago to Milan, unwind in one of these hotels close to Chicago Midway Airport:
76% of flights out of Chicago Midway Airport meet their expected arrival time.
You'll find MDW at 5700 South Cicero.

Arriving in Milan

Milan Malpensa Airport (MXP)

Milan Malpensa Airport (MXP) is approximately 40 kms (25 miles) from the centre of Milan. If you're catching a taxi or a ride-share, the drive will take around 50 minutes.
Getting to the centre on public transport will take you roughly 50 minutes.
If you're arriving on a late flight from Chicago to Milan, nothing beats the convenience of staying close to the terminal. Pick up your bags from the carousel and then be showered and snoozing not long after at one of these accommodation options near MXP:
Get on the fast track to adventure by picking up a Milan Malpensa Airport rental car. Grab your wheels from Surprice, RentSmart24 or Noleggiare and explore beyond Milan's usual tourist stops.
Reserving your vehicle from Milan Malpensa Airport around one week ahead can help you get the lowest rate.

Milan Bergamo Airport (BGY)

The centre of Milan is about 48 kms (30 miles) from Milan Bergamo Airport (BGY). As soon as your flight from Chicago to Milan has hit the runway and you've made your way out of the airport, expect a drive of around 50 minutes.
If you travel by public transport, you'll get to the city centre in 1 hour or so.
Place the 'Do not disturb' sign on your door and relax at a hotel near BGY. Here are a few options where you can tuck yourself in after your flight from Chicago to Milan:
Forget about inconvenient public transport timetables or slow-moving taxi lines. Pick up a Milan Bergamo Airport rental car and go in any direction that inspires you. Check out the rates and availability from Surprice, RentSmart24 and Galdieri Rent.
Lock in the best price by booking your ride from BGY two weeks in advance. You'll also have access to a wider range of vehicles.

Milan Linate Airport (LIN)

Step off your flight from Chicago to Milan and travel to your hotel or start sightseeing right away. The centre of Milan is around 8 kms (5 miles) from Milan Linate Airport (LIN) and typically takes 20 minutes to reach driving.
The journey will take about 30 minutes on public transport.
Enjoy a more relaxed start to your break by choosing a hotel near LIN after your Chicago to Milan flight. Recharge after a day of travel or simply take a moment to get your footing in a new city at:
Be in the driver's seat of the next leg of your journey by picking up a Milan Linate Airport rental car. RentSmart24, Drivalia and Noleggiare are some companies you can book with.
Enjoy a payoff when you plan ahead. Book your ride from LIN four weeks before your flight from Chicago to Milan for the most affordable rates.

Best time to go to Milan

March is the quietest month for flights from Chicago to Milan, while July is the busiest. Find the best time to visit Milan based on whether you want a bustling atmosphere or a more laid-back vibe.
Book a Chicago to Milan ticket departing in July if you're eager to experience the city during its warmest month. Expect temperatures in Milan to range from 16ºC to 35ºC.
January sees average temperatures of between -1ºC and 9ºC. Look for cheap flights from Chicago to Milan around that time if you like cooler conditions.

More about Milan

After booking your flight from Chicago to Milan, decide where you'll be dropping your bags. Make one of these accommodation options your base for exploring Milan:
There are so many things to explore in this city it can be hard to know where to begin. Leonardo's Last Supper Museum, Teatro alla Scala and Milan Cathedral are major attractions which should feature on any well-planned Milan itinerary.

Explore more of Italy

You've visited Milan, now it's time to explore other corners of Italy. Travel about 483 kms (300 miles) southeast to Rome to tick off its top attractions. From Vatican Museums to St. Peter's Basilica and Vatican Hill, there's plenty to keep you on the go.
Turin is another must-experience destination in Italy and is around 129 kms (80 miles) west of Milan. No journey is complete without visiting National Museum of Cinema, Juventus Museum and Sindone Chapel.