$278 Find Cheap Flights from Chicago to Milan - Compare and Save

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.

Among airlines operating Chicago to Milan flights:

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

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

Only United Airlines operates flights between Chicago and Milan.

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).

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 Premium Economy Class

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

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

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

Prices vary by airline.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $654 round-trip via Reykjavik Keflavik Intl (KEF), compared to $1,390 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 Chicago to Milan most commonly connect through:

• Kastrup Copenhagen (CPH) - 42% of one-stop connections
• Dublin (DUB) - 14% of one-stop connections
• Lisbon Humberto Delgado (LIS) - 13% of one-stop connections
• Istanbul (IST) - 7% of one-stop connections

Kastrup Copenhagen (CPH) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 19% on the Chicago to Milan route. Wednesday is the cheapest departure day at $794 round-trip on average, while Monday is the most expensive at $975, a difference of $181. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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

Some of the most popular sights in Milan are Stazione Centrale, Milan City Centre and Duomo di Milano. These are among the most viewed places in Milan on KAYAK.

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

• Earliest: departs at 9:35 pm and lands at 6:18 am
• Latest: departs at 10:35 pm and lands at 7:18 am.

The flight takes about 8h 43m.

Last-minute fares on this route - booked within 2 weeks of departure - run 35% above the route average of $889. Book 23 weeks before departure for the lowest fares.

A nonstop flight from Chicago to Milan takes 8h 43m, 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 Chicago to Milan are currently lower than usual. Average one-way flight prices are about $493, which is 27% below the typical average for this route.

Flying via Munich Franz Josef Strauss (MUC) gives the shortest average 1-stop total travel time at 11h 29m, compared with 11h 42m via Paris Charles de Gaulle (CDG) and 12h 41m via Frankfurt am Main (FRA).

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

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 from around $1:

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

Near Milan Linate Airport (LIN) — daily rates from around $4:

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

Round-trip flights from Chicago to Milan range from $626 to $1,327, with an average of $889 over the past 12 months. Anything below $626 counts as a good deal.