$375 Find Cheap Flights from Milan to Chicago - Compare and Save

Booking a seat in business class has many advantages, especially on a long-haul flight from Milan to Chicago. However, business-class amenities depend on your airline. If you book with Lufthansa, you enjoy services such as priority boarding, a seat that lays down into a bed, self-service coffee, a dental hygiene kit, ear plugs, and additional legroom.

Book with Delta Air Lines if you prefer more sustainable travel from Milan to Chicago. Delta embraces eco-friendly food packaging to reduce landfill waste by 90%. The company also ensures a greener environment by using sustainable aviation fuel (SAF) in its fleet. Another airline offering an environmentally friendly journey is KLM. This company avoids fossil fuels by using SAF from recycling feedstock and residues. These airlines are committed to achieving zero carbon emissions by 2050.

Opportunities to upgrade to first class depend on the airline on which you travel. Most airlines email passengers about available first-class seats a few days before flight departure. This way, you have an opportunity to upgrade. However, you need to do so at least 24 hours before departure. Flying as a first-class passenger means enjoying exclusive services, including a blanket, complimentary snacks and drinks, a pillow, and a lie-flat bed. However, amenities vary from one airline to another.

Chicago O'Hare serves a few nearby cities. After arriving at the airport, you can go to Bensenville and Wood Dale to the southwest, Schiller Park to the southeast, Park Ridge to the northeast, and Des Plaines to the north. You can connect to these cities using buses and trains or rent a car at the airport.

Among airlines operating Milan to Chicago flights:

• United Airlines: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only United Airlines operates flights between Milan and Chicago.

Flights from Milan to Chicago may depart from several airports in Milan area, including Milan Linate (LIN) and Milan Malpensa (MXP), with arrivals available at Chicago area airports such as Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Here are some options for this route, based on selected ticket types and cabin classes:

• United Airlines: a cabin bag and a checked bag in Economy Class
• Lufthansa: a cabin bag and a checked bag in Economy Class
• SWISS: a cabin bag and a checked bag in Economy Class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Three cabin classes are available on flights from Milan to Chicago:

• Economy Class
• Premium Economy Class
• Business Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $611 round-trip via Boston Logan Intl (BOS), compared to $856 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $75–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

One-stop flights from Milan to Chicago most commonly connect through:

• Rome Fiumicino (FCO) - 18% of one-stop connections
• London Heathrow (LHR) - 14% of one-stop connections
• Lisbon Humberto Delgado (LIS) - 14% of one-stop connections
• Kastrup Copenhagen (CPH) - 12% of one-stop connections

Rome Fiumicino (FCO) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 13% on the Milan to Chicago route. Thursday is the cheapest departure day at $755 round-trip on average, while Tuesday is the most expensive at $861, a difference of $106. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Milan to Chicago route, 17% of flights were delayed in the past 3 months, with delays averaging 4 hours 14 minutes.

Afternoon is the busiest departure period on Milan to Chicago flights, with 100% of flights leaving in that window. Morning departures account for 0%, evening flights for 0%, and night flights for 0%.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

These are the earliest and latest flight times available from Milan to Chicago:

• Earliest: departs at 3:15 pm and lands at 1:08 am
• Latest: departs at 3:20 pm and lands at 1:13 am.

The flight takes about 9h 53m.

Last-minute fares on this route - booked within 2 weeks of departure - run 23% above the route average of $790. Book 5 weeks before departure for the lowest fares.

A nonstop flight from Milan to Chicago takes 9h 53m, covering 4,526 miles.

Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

One-way fares from Milan to Chicago are currently lower than usual. Average one-way flight prices are about $400, which is 36% below the typical average for this route.

United Airlines is the only airline operating Milan to Chicago flights. 83% of its flights are on time.

Afternoon flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Munich Franz Josef Strauss (MUC) gives the shortest average 1-stop total travel time at 11h 19m, compared with 12h 08m via Paris Charles de Gaulle (CDG) and 12h 25m via Frankfurt am Main (FRA).

Chicago is 7 hours behind Milan (Central Time vs Central European Time). Plan for the time shift when scheduling connections or first-day activities.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

• Routes Car & Truck Rentals
• Europcar
• Hertz
• Dollar
• Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

• Alamo
• Enterprise Rent-A-Car
• Budget
• Avis
• National

Round-trip flights from Milan to Chicago range from $668 to $976, with an average of $790 over the past 12 months. Anything below $668 counts as a good deal.