$217 Find Cheap Flights from Chicago to Milan - Compare and Save

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

• Earliest: departs at 9:35 pm and lands at 6:15 am
• Latest: departs at 10:35 pm and lands at 7:15 am.

The flight takes about 8h 40m.

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

• Economy Class
• Premium Economy Class
• Business Class
• First Class

Prices vary by airline.

A nonstop flight from Chicago to Milan takes 8h 40m, 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.

Round-trip flights from Chicago to Milan range from $662 to $1,365, with an average of $958 over the past 12 months. Anything below $662 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 32% above the $958 route average. Book 23 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $676 round-trip via Reykjavik Keflavik Intl (KEF), compared to $1,382 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-way fares from Chicago to Milan are currently lower than usual. Average one-way flight prices are about $408, which is 42% below the typical average for this route.

Since Milan is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Milan Malpensa Airport (MXP) — daily rates averaging $36:

• Felirent
• Goldcar Rental SP
• Rent Smart 24
• Europcar
• SURPRICE CAR RENTAL

Near Milan Linate Airport (LIN) — daily rates averaging $45:

• NOLEGGIARE
• DRIVALIA
• Rent Smart 24
• Budget
• Europcar

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

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

• Kastrup Copenhagen (CPH) - 41% of one-stop connections
• Dublin (DUB) - 16% of one-stop connections
• Lisbon Humberto Delgado (LIS) - 12% of one-stop connections
• Istanbul (IST) - 7% of one-stop connections

Yes. Flexible dates can save you up to 17% on flights from Chicago to Milan. Thursday is the cheapest departure day at $891 round-trip on average, while Monday is the most expensive at $1,073, a difference of $182.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Only United Airlines operates flights between Chicago and Milan.

Flying via Munich Franz Josef Strauss (MUC) gives the shortest average 1-stop total travel time at 11h 29m, compared with 11h 39m via Paris Charles de Gaulle (CDG) and 12h 29m via New York John F Kennedy Intl (JFK).

Milan is 6 hours ahead of Chicago (Central European Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Some of the most popular sights in Milan are Duomo di Milano, Piazza del Duomo and Galleria Vittorio Emanuele II. These are among the most viewed places in Milan on KAYAK.

Among airlines operating Chicago to Milan flights:

• United Airlines: offers extra legroom; offers free seat selection
• Lufthansa: offers extra legroom

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

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 always check the fare details before booking.

Both MDW and ORD have lactating pods that are secure and private places for mothers who wish to pump before takeoff. The ones at MDW can be found at Concourse A at Gate 5, while the ones in ORD are located at Terminal 1, Concourse C Gate 11 and 23, Terminal 2, Concourse F and G Gates E1 and F1, Terminal 3, Concourse G, K, L at gates G12, K5, K19, and L24.

Yes, there are. Both MXP and LIN have VIP lounges. At LIN, these are the Leonardo and Piranesi Lounges which are located on the mezzanine floor 1 in the boarding area, and check-in area, respectively. MXP has 5 of them found on the ground floor and first floor of Terminal 1.

Both of these airports have USO centers where retired and active military staff and their families can enjoy some refreshments as they wait for their flight. MDW has one at Concourse C, while ORD has one in Terminal 2, and another in Terminal 3, Concourse G.

Exchange your dollars for euros upon arrival at MXP and LIN at the Forex bureaus that are open every day. The ones at MXP can be found on the ground floor next to arrivals A and B, and on the second floor near check-in areas 5, 6, 9, 10, and 17. At LIN, the offices are on the ground floor at arrivals, and after check-in on the first floor.