$418 Cheap Flights from Milan (LIN) to Chicago (ORD)

View $418 flight on Thu, Jan 15, 2026Opens in a new window

Popular airlines from Linate Airport (LIN) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Milan to Chicago (LIN-ORD)

Prices were available within the past 7 days and start at $418 for one-way flights and $547 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Aer Lingus
Fri, Nov 14 - Wed, Nov 26
LIN
Milan
ORD
Chicago
$547 Roundtrip, found 13 hours ago
$547
Roundtrip
found 13 hours ago
Select Aer Lingus flight, departing Fri, Nov 14 from Milan to Chicago, returning Wed, Nov 26, priced at $547 found 13 hours ago
Aer Lingus
Wed, Nov 26 - Sat, Dec 6
LIN
Milan
ORD
Chicago
$561 Roundtrip, found 6 days ago
$561
Roundtrip
found 6 days ago
Select Aer Lingus flight, departing Wed, Nov 26 from Milan to Chicago, returning Sat, Dec 6, priced at $561 found 6 days ago
Aer Lingus
Tue, Nov 25 - Sun, Nov 30
LIN
Milan
ORD
Chicago
$563 Roundtrip, found 1 day ago
$563
Roundtrip
found 1 day ago
Select Aer Lingus flight, departing Tue, Nov 25 from Milan to Chicago, returning Sun, Nov 30, priced at $563 found 1 day ago
Aer Lingus
Tue, Nov 11 - Sun, Nov 16
LIN
Milan
ORD
Chicago
$565 Roundtrip, found 4 days ago
$565
Roundtrip
found 4 days ago
Select Aer Lingus flight, departing Tue, Nov 11 from Milan to Chicago, returning Sun, Nov 16, priced at $565 found 4 days ago
Aer Lingus
Wed, Dec 3 - Sun, Dec 14
LIN
Milan
ORD
Chicago
$565 Roundtrip, found 4 days ago
$565
Roundtrip
found 4 days ago
Select Aer Lingus flight, departing Wed, Dec 3 from Milan to Chicago, returning Sun, Dec 14, priced at $565 found 4 days ago
Aer Lingus
Fri, Nov 14 - Tue, Nov 18
LIN
Milan
ORD
Chicago
$587 Roundtrip, found 22 hours ago
$587
Roundtrip
found 22 hours ago
Select Aer Lingus flight, departing Fri, Nov 14 from Milan to Chicago, returning Tue, Nov 18, priced at $587 found 22 hours ago
ITA Airways
Wed, Apr 1 - Fri, Apr 17
LIN
Milan
ORD
Chicago
$636 Roundtrip, found 5 days ago
$636
Roundtrip
found 5 days ago
Select ITA Airways flight, departing Wed, Apr 1 from Milan to Chicago, returning Fri, Apr 17, priced at $636 found 5 days ago
Lufthansa
Sat, Nov 1 - Wed, Nov 5
LIN
Milan
ORD
Chicago
$641 Roundtrip, found 5 days ago
$641
Roundtrip
found 5 days ago
Select Lufthansa flight, departing Sat, Nov 1 from Milan to Chicago, returning Wed, Nov 5, priced at $641 found 5 days ago
American Airlines
Fri, Nov 14 - Fri, Nov 28
LIN
Milan
ORD
Chicago
$643 Roundtrip, found 5 days ago
$643
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Nov 14 from Milan to Chicago, returning Fri, Nov 28, priced at $643 found 5 days ago
British Airways
Tue, Nov 25 - Tue, Dec 2
LIN
Milan
ORD
Chicago
$646 Roundtrip, found 5 days ago
$646
Roundtrip
found 5 days ago
Select British Airways flight, departing Tue, Nov 25 from Milan to Chicago, returning Tue, Dec 2, priced at $646 found 5 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $645
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $645

Frequently asked questions

How much does a flight from Linate Airport (LIN) to O'Hare Intl. Airport (ORD) cost?
Snag a cheap one-way flight from $418 or cheap return flight from $547 from Linate Airport (LIN) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Linate Airport (LIN) to O'Hare Intl. Airport (ORD)?
Planning your trip for November may help you find better deals, as it's the cheapest month for flights between LIN and ORD. You'll usually find the lowest fares during off-peak months.
What is the cheapest airline that flies from Linate Airport (LIN) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll fly you from LIN to ORD. Then, sort your results by "Price (lowest to highest)" to snag a great deal.
How many flights per day from Linate Airport (LIN) to O'Hare Intl. Airport (ORD)?
Direct flights from Linate Airport (LIN) to O'Hare Intl. Airport (ORD) aren't available daily, so you'll need to take a flight with a layover. Explore your options with our filter tool. Enter your travel dates and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from LIN to ORD?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change based on a number of factors, such as the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Linate Airport (LIN) to O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) without delays, select a flight that leaves from Linate Airport (LIN) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Linate Airport (LIN) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book your flight from LIN to ORD generally means paying more. While you may come across some last-minute deals, there's no guarantee. Be flexible with your travel plans for the best chance of snagging a bargain.
Is it cheaper to book a LIN to ORD flight and hotel package?
You can save money by booking a LIN to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. After choosing your preferred flights and accommodations, you can add extras like car rentals, activities and tours.
Can I cancel or change the date of my flight from Linate Airport (LIN) to O'Hare Intl. Airport (ORD)?
If you reserved your LIN to ORD flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the fare type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Linate
Destination airport
O'Hare Intl.
Airlines serving
Aer Lingus, Air Canada, Air France, American Airlines, Austrian Airlines, British Airways, Brussels Airlines, Delta, ITA Airways, Iberia, KLM, Lufthansa, United
Roundtrip price
$546
Distance
4539 mi

Book with confidence

Milan to Chicago Flights

The cheapest times to fly from Milan to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Milan to Chicago are during the month of November. You can find some of the cheapest flights from Milan to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Milan to Chicago

Sunday is one of the best days to book for cheap flights from Milan to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Milan to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Milan to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $418 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Milan to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Milan to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Milan to Chicago Flights

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*Available to One Key members.