- Must visit
Pinacoteca di Brera
One of Italy’s top art museums, featuring masterpieces by Mantegna, Bellini, Raphael, Caravaggio, and Piero della Francesca.
Flights from Chicago, IL to Milan depart on average 88 times per day, taking around 10h 13m. Cheap flight tickets for this journey start at $480 (€394) if you book in advance.
The earliest flight runs at 05:00, the last at 23:50. The fastest flight covers the 4531 miles (7293 km) distance in 11h 55m. August is the cheapest month to fly.
Distance 4531 miles (7293 km) |
Average flight duration 10h 13m |
Cheapest ticket price $480 (€394) |
Flights per day 88 |
Fastest flight 11h 55m |
First flight 5:00 AM |
Last flight 11:50 PM |
Cheapest Month Aug |
Cheapest Day Sun |
High Season Jul - Sep |
Low Season Oct - Dec |
Best time to book 42 days |
Cheapest price
$591
Average price
$709
Fastest journey
1 d 4 h 20 m
Average duration
1 d 7 h 40 m
Flights per day
2
Distance
7293 km
The best way to find a cheap flight ticket from Chicago, IL to Milan is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Milan will cost around $709 if you buy it on the day, but the cheapest tickets can be found for only $591.
Of the 2 flights that leave Chicago, IL for Milan onSun, Jul 19, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sun, Jul 19 the direct flights cover the 7293 km distance in an average of 1 d 7 h 40 m but if you time it right, some flights will get you there in just 1 d 4 h 20 m .
On Sun, Jul 19 the longest flights will take 1 d 11 h and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.




The table below shows live departures for Chicago, IL to Milan flights for today, Friday, July 17. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 9:30 PM Chicago, IL | 14h30 | 12:00 PM Milan | 0 transfersDirect | |
| Saturday, July 18 | |||||
![]() | 1:10 AM Chicago, IL | 35h00 | 12:10 PM Milan | 0 transfersDirect | |
![]() | 2:20 AM Chicago, IL | 28h20 | 6:40 AM Milan | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Milan — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Milan trip today.
One of Italy’s top art museums, featuring masterpieces by Mantegna, Bellini, Raphael, Caravaggio, and Piero della Francesca.
This contemporary art museum near Porta Romana presents rotating exhibitions in a striking former industrial distillery complex.
Italy’s leading science museum is set in a former monastery and features Leonardo galleries, trains, aircraft, and a submarine.
Milan’s central square frames the cathedral and major civic buildings, making it the city’s essential meeting point and photo stop.
This artistic district offers charming lanes, Brera atmosphere, boutiques, and easy access to galleries and evening strolls.
A large landscaped park behind the castle, perfect for walks, skyline views, and reaching landmarks like the Arch of Peace.
Saffron risotto cooked with butter, stock and cheese. It is Milan's signature dish, linked to the city's love of rich northern Italian rice cookery.
Breaded veal cutlet fried in butter until golden. A classic Milanese main, prized for its simple preparation and long-standing local tradition.
Slow-braised veal shanks with vegetables, wine and broth, often finished with gremolata. A hearty Lombard specialty commonly paired with risotto.
Three-Michelin-star fine dining by Enrico Bartolini in MUDEC. Expect refined Italian tasting menus in a polished contemporary setting.
Historic Milanese restaurant near the Duomo, famous for risotto and cotoletta. Traditional, elegant rooms and a strong local culinary identity.
Long-running local favorite for classic Milanese cuisine, especially risotto and ossobuco. Warm, old-school atmosphere in the Brera area.
Moderate for Western Europe. Hotels and central dining can be pricey, but transit is affordable and budget meals, aperitivo deals, and local cafes help keep daily costs reasonable.
Tipping is modest. Service may be included. Round up or leave €1-2 at cafes, 5-10% for good restaurant service, and round up taxi fares.
Official public transport app
Milan Malpensa Airport -> Milano Centrale
Find answers to the most common questions about traveling from Chicago, IL to Milan by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Milan, this guide helps you travel smarter and with confidence.

Most Chicago, IL to Milan flights use the O'Hare International Airport to Milan Malpensa Airport airport pair, with some services landing at Milan Linate Airport. Use this guide to compare Chicago, IL and Milan airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Lost and found is available at the station.
Available at O'Hare International Airport: Parking, Taxis, WC.
Available at O'Hare International Airport: Car Rental.
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Milan Malpensa Airport is 2 km from Milan city centre. Public transport options include:
Milan Malpensa Airport has practical services for this route, including Wifi, Shopping, Parking, ATM, Taxis, Accessibility, WC, Shower, Lounge, and Lost and Found Office.
Free Wi-Fi available throughout the airport. ATMs are located in both terminals, near check-inas and gates.
Lost and found is available at the station.
Available at Milan Malpensa Airport: Parking, Taxis, WC.
Accessibility facilities are available at Milan Malpensa Airport: Elevators, ramps.
Milan Linate Airport is 6 km from Milan city centre. Public transport options include:
Milan Linate Airport has practical services for this route, including Wifi, Shopping, Parking, ATM, Taxis, Accessibility, WC, Shower, Lounge, and Lost and Found Office.
Free Wi-Fi available throughout the airport. ATMs are located in the arrivals and departures areas.
Lost and found is available at the station.
Available at Milan Linate Airport: Parking, Taxis, WC.
Accessibility facilities are available at Milan Linate Airport: Ramps, assistance.
Here are some other resources that might have the information you need