International route
Cheap flights from Chicago to Milan
O'Hare International Airport (ORD) to Milan Malpensa Airport (MXP). 4,511 miles, connecting flights only.
ORD to MXP at a glance
Computed from airline schedules and the fares we track for this route. Refreshed several times a day.
- Distance
- 4,511 milesgreat-circle
- Typical flight time
- 8h 40mif flown nonstop
- Nonstop airlines
- None (connecting only)
- Nonstop flights per day
- 0connections available
- Cheapest month
- January 2027over the next six months
- Best day to fly
- Tuesday19% less than Friday
- Time difference
- 7h aheadMilan vs Chicago
Chicago to Milan
Round trips from $401
Per traveler, taxes and fees included. Lowest fare we found departs Tue, Jan 19.
Cheapest month: January 2027
See fares on these datesLock any fare free — pay only when you accept your last-minute deal
Or ask an agent on WhatsAppChicago to Milan fares by month
Lowest round-trip economy fare per traveler in each of the next six months, taxes and fees included. Select a month to search that date.
Airlines flying Chicago to Milan
No nonstop service: 21 airlines offer one-stop itineraries.
- EIAer LingusConnecting via SNN · first checked bag from $70
- ACAir CanadaStar AllianceConnecting via YUL · first checked bag from $35
- AFAir FranceSkyTeamConnecting via CDG, ORY · first checked bag from $75
- ASAlaska AirlinesoneworldConnecting via PDX · first checked bag from $35
- AAAmerican AirlinesoneworldConnecting via DFW, MIA, PHL, DCA · first checked bag from $40
- OSAustrian AirlinesStar AllianceConnecting via VIE · first checked bag from $75
- BABritish AirwaysoneworldConnecting via LHR · first checked bag from $75
- DLDelta Air LinesSkyTeamConnecting via ATL, SLC, JFK · first checked bag from $35
- AYFinnaironeworldConnecting via HEL · first checked bag from $70
- FIIcelandairConnecting via KEF · first checked bag from $70
- AZITA AirwaysConnecting via FCO · first checked bag from $70
- B6JetBlueConnecting via JFK, BOS · first checked bag from $40
- LHLufthansaStar AllianceConnecting via FRA, MUC · first checked bag from $75
- NONorse Atlantic AirwaysLow-costConnecting via OSL · first checked bag from $80
- SKSAS Scandinavian AirlinesSkyTeamConnecting via ARN, OSL · first checked bag from $70
- LXSWISSStar AllianceConnecting via ZRH, GVA · first checked bag from $75
- TPTAP Air PortugalStar AllianceConnecting via OPO · first checked bag from $70
- TKTurkish AirlinesStar AllianceConnecting via IST · first checked bag from $70
- UAUnited AirlinesStar AllianceConnecting via DEN, IAD · first checked bag from $40
- VSVirgin AtlanticSkyTeamConnecting via LHR · first checked bag from $75
- WSWestJetConnecting via YYZ · first checked bag from $35
Connecting options
Hubs where one airline can carry you on both legs, most choices first.
- New York (JFK)DLB62 airlines
- London (LHR)BAVS2 airlines
- Oslo (OSL)SKNO2 airlines
- Dallas (DFW)AA1 airline
- Miami (MIA)AA1 airline
Which airport should I use?
Chicago has 2 airports and Milan has 2 airports. Fares can differ by $50 to $150 round trip between them, so check the alternatives before you book.
Other departure airports near Chicago
Other arrival airports near Milan
Tips for this route
- There is no scheduled nonstop between ORD and MXP. Every itinerary connects, most often through JFK, LHR or OSL, so sort results by total travel time rather than price alone.
- January 2027 is the cheapest month to fly over the next six months, with round trips from $401; September 2026 is the most expensive at $517 and up, a difference of $116 per traveler.
- Departing on a Tuesday averages 19% less than a Friday on this route. If your dates are flexible, shift the outbound by a day or two and check the calendar view before you book.
- Book 2 to 5 months ahead for the best fares; long-haul seats sell out earliest for summer and holiday travel.
- Milan is 7 hours ahead of Chicago. Expect to lose 7 hours on the clock heading east, so an overnight or late-afternoon departure tends to arrive at a more usable hour.
Ready to compare live fares?
See every airline on ORD–MXP side by side with bags and seat rules spelled out.
Search Chicago to MilanChicago to Milan: common questions
How long is the flight from Chicago to Milan?
There are no nonstop flights, so the trip from Chicago (ORD) to Milan (MXP) takes 8h 40m of flying plus a layover, usually 11h 40m or more door to door across 4,511 miles.
Which airlines fly nonstop from ORD to MXP?
No airline currently flies nonstop between Chicago (ORD) and Milan (MXP). The most common connections are through JFK, LHR and OSL.
What is the cheapest month to fly from Chicago to Milan?
Over the next six months, January 2027 has the lowest round-trip fares from Chicago (ORD) to Milan (MXP), starting at $401 per traveler including taxes and fees. Within any month, Tuesday departures average the lowest prices.
How far in advance should I book Chicago to Milan flights?
Book 2 to 5 months ahead for the best fares; long-haul seats sell out earliest for summer and holiday travel. Air1 Tickets includes free cancellation within 24 hours of booking on every fare, so you can lock in a good price and keep looking.
What is the time difference between Chicago and Milan?
Milan is 7 hours ahead of Chicago. ORD is on America/Chicago time and MXP on Europe/Rome time. Departure and arrival times in search results are always shown in local time at each airport.
Related routes
Other popular city pairs from the same departure city and to the same destination, with the lowest round-trip fares we found.