Helping travelers to find the best flight offers
Fly from Chicago to Milan with confidence—our search scans over 700 airlines, 50+ agencies and more than 5 top booking systems to uncover the best fares, schedules and booking conditions for your trip. Compare options side-by-side and lock in the ideal flight to arrive in Milan on your terms.
Fly nonstop from Chicago to Milan for the fastest, most convenient way to reach Italy’s fashion and culture hub—less time in transit means more time to explore. While connecting flights can sometimes be cheaper, a direct flight saves you layovers, reduces stress, and delivers a smoother start to your Italian adventure—book now to lock in comfort and speed.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to Milan:
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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 Chicago to Milan departs on 02/12/2026, is operated by Icelandair and costs $225
There is no information about the cheapest roundtrip flight from Chicago to Milan
Fastest flight from Chicago to Milan takes 14h 5m
There are no direct flights on this route.
The distance between Chicago and Milan is 7288km (4519 miles). There are 15 direct flights from Chicago to Milan. The time difference between Chicago and Milan is 7h. Flights from Chicago begin at 9:35 PM. The latest flight from Chicago departs at 10:35 PM
There appear to be no direct flights from Chicago to Milan at this time.... Well, or something went wrong on our side and we couldn't find anything
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The route Chicago — Milan is served by many carriers — 6 in total, including Icelandair, British Airways, Lufthansa, Aer Lingus, Frontier Airlines, and LOT Polish Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $225) 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 is served by three main airports with distinct roles. Malpensa (MXP) is the international hub typically handling long-haul and full-service carriers as well as some higher-end European connections; it sits about 50 km northwest of central Milan and can be reached by the Malpensa Express train in roughly 40–50 minutes (tickets usually in a modest fare band) or by bus and taxi in around 50–70 minutes depending on traffic. Linate (LIN) is the city’s closest airport, mainly focused on domestic and short-haul European flights operated by legacy and regional airlines; it’s about 7 km from the city center, reachable by bus or metro in roughly 20–30 minutes and by taxi in 15–25 minutes, offering convenience at a generally higher perceived price for short routes. Orio al Serio/Bergamo (BGY) functions largely as a budget and charter base used by low-cost carriers; located about 45 km northeast, transfer options include shuttle buses taking about 45–70 minutes and taxis for longer but costlier rides. Pros: Malpensa for wide connectivity, Linate for proximity and quick city access, Bergamo for lower fares; cons: Malpensa and Bergamo require longer ground transfers, while Linate can be pricier for short hops.
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Chicago has two primary airports serving different needs. O’Hare International (ORD) is the city’s main international and connecting hub, typically hosting legacy carriers like United and American along with many global airlines; it can be pricier for last-minute international flights but often offers more nonstop choices. Midway (MDW) functions more as a domestic and budget-friendly option, commonly used by low-cost carriers such as Southwest. O’Hare sits about 17–20 miles northwest of downtown — the Blue Line rail takes roughly 40–50 minutes for fares in the lower single-digit dollars, while taxis and rideshares can be 30–60 minutes depending on traffic and cost more. Midway is closer, around 8–10 miles southwest; the Orange Line reaches downtown in about 25–30 minutes for a small fare, with shorter taxi rides. Pros: O’Hare’s broad connectivity is convenient for transfers and long-haul routes; Midway’s compact layout and proximity can make domestic trips quicker and cheaper. Cons: O’Hare can be busy with longer walking and connection times, and Midway may have fewer nonstop international options.
The cheapest flight ticket from Chicago to Milan according to data for the last 48 hours costs $225
Often the best time to buy tickets from Chicago to Milan is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to Milan can be found flying in these months: May, December.
The fastest flights from Chicago to Milan start from 14 hours 5 minutes in the air.
The following airlines operate direct flights on the route Chicago — Milan:
In different months, ticket prices from Chicago to Milan vary: minimum — $411 (May 2026), maximum — $428 (December 2025). Typically, the flight costs $420–$428.
We couldn't find any special offers for flights from Chicago to Milan