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Fly from Milan to Chicago with confidence — our search scans over 700 airlines, 50+ travel agencies and more than 5 top booking systems to uncover the best fares, schedules and ticket conditions for your trip. Compare nonstop and connecting options in seconds and lock in the deal that suits your budget and timing.
Fly direct from Milan to Chicago for the fastest, most convenient way to bridge Italy and the Windy City—less time in transit means more time exploring Chicago’s neighborhoods and business districts. While connecting routes can sometimes offer lower fares, a nonstop flight saves time, reduces hassle, and keeps your journey comfortable and straightforward.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Milan to Chicago:
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We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
The cheapest one-way flight from Milan to Chicago departs on 04/25/2026, is operated by TAP Portugal and costs $428
There is no information about the cheapest roundtrip flight from Milan to Chicago
Fastest flight from Milan to Chicago takes 17h 25m
There are no direct flights on this route.
The distance between Milan and Chicago is 7288km (4519 miles). There are 12 direct flights from Milan to Chicago. The time difference between Milan and Chicago is 7h. Flights from Milan begin at 3:05 PM. The latest flight from Milan departs at 3:05 PM
The route Milan — Chicago is served by many carriers — 4 in total, including United Airlines, TAP Portugal, Air Serbia, and Condor. This gives passengers wide opportunities: from finding the lowest fare (from $428) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
starting at $858
starting at $428
starting at $461
starting at $553
Milan — Chicago
04/25/2026
Departure
Direct flight
UA415
starting at $858
Milan — Chicago
07/15/2026
Departure
Direct flight
UA7812
starting at $1,316
Milan — Chicago
07/16/2026
Departure
Direct flight
UA7812
starting at $1,032
Milan — Chicago
07/17/2026
Departure
Direct flight
UA7812
starting at $1,463
Milan — Chicago
07/19/2026
Departure
Direct flight
UA7812
starting at $1,412
Unable to find information about the schedule of direct flights from
Milan Malpensa (MXP) is the city’s main international gateway and typically handles long-haul and many scheduled carrier flights, so it often serves as the premium hub for intercontinental travel. Located about 50 km northwest of central Milan, transfer options include the Malpensa Express train (around 40–50 minutes), regional trains or buses (45–60 minutes), and taxis or private transfers (roughly 50–70 minutes), with fares varying by service and time of day. Pros: good frequency of international connections and full-service facilities; cons: longer transfer times and additional travel costs compared with city airports. It can be pricier to reach central Milan than closer alternatives. Milan Linate (LIN) functions as the city’s near-urban airport and is typically oriented toward domestic and short-haul European flights, with many business travellers using it for convenience. It lies approximately 7 km east of the city centre, so transfers are usually quick—by bus or taxi about 15–30 minutes, and by local tram/metro connections with similar journey times; fares are generally modest. Pros: very convenient for downtown access and business routes; cons: fewer long-haul options and sometimes higher ticket rates on limited routes. Expect fast city transfers but a smaller route network than the main international airport. Orio al Serio / Bergamo (BGY) often operates as Milan’s budget and low-cost carrier airport, serving many inexpensive European routes and charter services. It’s situated roughly 45 km northeast of Milan, with shuttle buses and regional coaches typically taking 45–70 minutes to reach central Milan; taxi or private transfers can be quicker but cost more. Pros: strong low-cost carrier presence and competitive fares; cons: longer transfer times to downtown and fewer full-service amenities. For price-sensitive travellers it can be a cheaper option, though the total journey time to the city can be noticeably longer than from Linate.
Chicago is served mainly by two airports with different roles. O’Hare International (ORD) is the city’s primary international and connecting hub, used heavily by legacy carriers and major international airlines; fares can be competitive for long-haul and connecting itineraries. It sits about 17–20 miles Northwest of downtown with transit options including the CTA Blue Line (roughly 45–60 minutes, low-cost fare), taxis and ride-shares (30–50 minutes, variable fares), and express shuttles. Pros: extensive flight choice and frequent schedules; cons: can be busy and spread out, with longer intra-airport transfers. Midway (MDW) is Chicago’s smaller, more budget-leaning airport, favored by low-cost and domestic carriers and typically offering lower fares on short-haul routes. Located some 10–13 miles Southwest of the Loop, it’s connected by the CTA Orange Line (about 25–35 minutes, budget-friendly), buses, and taxis/ride-shares (20–40 minutes, price varies). Pros: easier navigation and quicker check-ins; cons: fewer international options and less frequent late-night connections.
We couldn't find any special offers for flights from Milan to Chicago
The cheapest flight ticket from Milan to Chicago according to data for the last 48 hours costs $428
Often the best time to buy tickets from Milan to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Milan to Chicago can be found flying in these months: December, January, June.
The fastest flights from Milan to Chicago start from 17 hours 25 minutes in the air.
The following airlines operate direct flights on the route Milan — Chicago: United Airlines
In different months, ticket prices from Milan to Chicago vary: minimum — $350 (December 2025), maximum — $385 (June 2026). Typically, the flight costs $372–$767.