Cheap Flights from Milan to Chicago — $428

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.

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.

In different months, ticket prices from Milan to Chicago vary: minimum — $350 (December 2025), maximum — $385 (June 2026). Typically, the flight costs $372–$767.