Cheap flights from Milan to Chicago

Milan
MIL
Chicago FSS
CHI

Flight deals from Milan to Chicago

Below you can see the best deals on flights Milan — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 22 October, from $357.

Top 10 cheap flights from Milan to Chicago

FI
FI
$ 478

Milan — Chicago

16:20—21:25
5 Sep 2026
12 h 5 m
1 stop
W4
TP
TP
$ 478

Milan — Chicago

10:45—12:40
9 Sep 2026
32 h 55 m
2 stops
W4
TP
TP
$ 479

Milan — Chicago

06:40—16:00
10 Sep 2026
40 h 20 m
2 stops
FI
FI
$ 479

Milan — Chicago

22:55—18:15
8 Sep 2026
26 h 20 m
1 stop
FI
FI
$ 479

Milan — Chicago

22:55—18:15
1 Sep 2026
26 h 20 m
1 stop
FI
FI
$ 479

Milan — Chicago

22:55—18:15
4 Sep 2026
26 h 20 m
1 stop
FI
FI
$ 479

Milan — Chicago

16:20—18:15
10 Sep 2026
32 h 55 m
1 stop
FI
FI
$ 479

Milan — Chicago

22:55—18:15
15 Sep 2026
26 h 20 m
1 stop
FI
FI
$ 479

Milan — Chicago

22:55—21:25
15 Sep 2026
29 h 30 m
1 stop
FI
FI
$ 479

Milan — Chicago

16:20—18:15
24 Sep 2026
32 h 55 m
1 stop

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Milan — Chicago flight

Looking for cheap flights from Milan to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Milan — Chicago ticket online at the best price.

The route has direct flights — around 18 flights per week, flights are operated by United Airlines, Air Canada, Lufthansa, Swiss and 1 more airline, a nonstop flight takes about 9 h 38 min, the distance between the cities is around 7,308 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $348Min. price
OctoberCheapest
AugustPeak season
YesDirect flights
7,308 kmDistance
9 h 38 minTravel time
5Airlines
18 / wkFlights

Flight schedule from Milan to Chicago

The table shows direct flights from Milan to Chicago on the selected date. The flight takes approximately 9 h 38 min. Regular flights are operated by United Airlines, Air Canada, Lufthansa and Swiss. Departures from Milano Malpensa Airport, Orio al Serio International Airport and Milano Linate Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 25 Aug 2026

Flight ticket prices by day: Milan — Chicago

Below is a calendar of the lowest flight ticket prices for Milan — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $348 in October, and the most expensive are around $496 in August. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--

Prices by month

Average one-way fares from Milan to Chicago by month. Tickets are usually cheapest in January (around $484) and priciest in July (about $846) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$484lowMay$629mediumSep$604medium
Feb$496lowJun$725highOct$580medium
Mar$520lowJul$846highNov$544medium
Apr$568mediumAug$798highDec$701high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in October and most expensive in August. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

We'll let you know if you need a visa

Enter your destination or
Your nationality
Destination

How to get the best deal on a Milan — Chicago ticket

  • Book ahead: fares for Milan — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Milan is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Chicago is usually October — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Milan — Chicago route are operated by 5 airlines; United Airlines runs the most flights (around 78% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    5x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight MXP → ORD5x/week
      Duration
      9h 50m
      Days
      MTWTFSS
    77.8%Open →
  • Air CanadaAC
    1x/week
    WebsiteFleet: 20346M pax/year
    • Direct flight MXP → ORD1x/week
      Duration
      7h
      Days
      MTWTFSS
    5.6%Open →
  • LufthansaLH
    1x/week
    WebsiteFleet: 38764.5M pax/year
    • Direct flight MXP → ORD1x/week
      Duration
      7h
      Days
      MTWTFSS
    5.6%Open →
  • SwissLX
    1x/week
    WebsiteFleet: 11221.1M pax/year
    • Direct flight MXP → ORD1x/week
      Duration
      7h
      Days
      MTWTFSS
    5.6%Open →
  • AustrianOS
    1x/week
    WebsiteFleet: 6814.6M pax/year
    • Direct flight MXP → ORD1x/week
      Duration
      7h
      Days
      MTWTFSS
    5.6%Open →

Cities and airports on the Milan — Chicago route

Flights Milan — Chicago depart from Milano Malpensa Airport, Orio al Serio International Airport and Milano Linate Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Milan

MIL
Italy
About the cityHow to get thereWeatherAll about the country Italy
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

Interesting articles about Chicago

Did you know that some airports have beds?Interesting

Did you know that some airports have beds?

Did you know that some airports have beds? They are intended for passengers whose flights were canceled due to bad weather or other force majeure circumstances. These unfortunate travelers are offered…

The World’s Largest CitiesInteresting

The World’s Largest Cities

If you prefer non-stop action to quiet solitude somewhere by the sea or in the mountains—this article is for you. We’ve already told you about the oldest cities in the world, and now it’s time to delv…

Cemeteries as Museums: A Guide to the Most Beautiful NecropolisesInteresting

Cemeteries as Museums: A Guide to the Most Beautiful Necropolises

For many, a walk through a cemetery is a plot from a gothic novel or a forced necessity. But experienced travelers know: ancient burial grounds are the most honest open-air museums. There is no urban…

Tips for Travelers

5 Airports with Free City Tours

Have a long layover at the airport? Don’t rush to get upset! If you are flying through one of the cities we’ll tell you about in this article, you can count on a free tour. ISTANBUL. ATATÜRK AIRPORT I…

Looking Down: The Best Observation Decks in the WorldTips for Travelers

Looking Down: The Best Observation Decks in the World

To better understand a city or admire the surrounding nature, you need to climb higher. The ascent isn’t always easy, but it’s worth it for the experience and the view from the top. If you’re not afra…

See half the world from a portholeInteresting

See half the world from a porthole

Recently, we wrote about a Qatar Airways aircraft that completed the world’s longest commercial flight from Doha (Qatar) to Auckland (New Zealand) and how it was welcomed in the “new territory”. Today…

Frequently asked questions about the Milan — Chicago flight

How long is the flight from Milan to Chicago?

A nonstop Milan — Chicago flight takes about 9 h 38 min — the distance between the cities is around 7,308 km.

How far is it from Milan to Chicago?

The distance from Milan to Chicago is about 7,308 km, which a nonstop flight covers in around 9 h 38 min.

Are there direct flights from Milan to Chicago?

Yes, there are nonstop flights Milan — Chicago — around 18 flights per week.

Which airlines fly from Milan to Chicago?

Airlines operating Milan — Chicago include United Airlines, Air Canada, Lufthansa, Swiss, Austrian. See the full list with schedules in the "Airlines" section on this page.

Which airports do Milan — Chicago flights use?

Flights from Milan depart from Milano Malpensa Airport, Orio al Serio International Airport, Milano Linate Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Milan to Chicago?

The price of a Milan — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in October, and most expensive in August. Tickets typically cost between $348 and $496. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Milan — Chicago?

Flights Milan — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is October. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Milan to Chicago?

To catch a low fare Milan — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually October.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Milan

See all
Frankfurt am MainParisLondonOlbiaMunichRomeCagliariMadridCataniaAmsterdamBarcelonaBrusselsPalermoLisbonViennaDusseldorfNaplesBariAthensCopenhagenIstanbulIbizaZurichLuxembourg CityBrindisiTiranaCosenzaTel AvivNew York CityPalmaBucharestCairoMalagaWarsawSharm El SheikhBerlinStuttgartReykjavikManchesterHamburg

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

We use cookies and services to collect user information. This is essential for the functioning of the site and for marketing purposes. You can find out more in .