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Cheap flights from Milan to Chicago

One-way from €361, found by travellers in the last 7 days. The live price is checked when you book.

Departure
Return
Prices for nearby dates
Thu, Dec 17Any priceFri, Dec 18Any priceSat, Dec 19Any priceSun, Dec 20€361Mon, Dec 21Any priceTue, Dec 22Any priceWed, Dec 23Any priceThu, Dec 24Any price

Cheapest one-way tickets

Recent finds on different dates, for 1 adult. Booking opens on Aviasales, which shows baggage, fare rules and the live price.

Cheapest
€361
Ryanair, flight FR 8121Found 5 days ago, 1 adult
Check live price
20:35MilanSun, Dec 20
Travel time 15h, 3 stopsBGYORD
04:35ChicagoMon, Dec 21
€380
ALPAVIA, flight AL 2990Found today, 1 adult
Check live price
22:00MilanMon, Dec 7
Travel time 12h 30m, 2 stopsBGYORD
03:30ChicagoTue, Dec 8
€414
Vueling, flight VY 6043Found yesterday, 1 adult
Check live price
13:10MilanTue, Nov 3
Travel time 13h 35m, 2 stopsMXPORD
19:45ChicagoTue, Nov 3
€425
TAP Air Portugal, flight TP 829Found 4 days ago, 1 adult
Check live price
06:20MilanFri, Nov 20
Travel time 12h 35m, 1 stopMXPORD
11:55ChicagoFri, Nov 20
€549
Air Cairo, flight SM 806Found 2 days ago, 1 adult
Check live price
08:05MilanThu, Oct 29
Travel time 16h 10m, 1 stopMXPORD
18:15ChicagoThu, Oct 29

Round trips

The cheapest return tickets found recently, price for the whole trip.

Plan the rest of the trip

  • Mobile data in United StatesTravel eSIM from $4, installed before you fly.
    Compare plans
  • Getting from the airportTransfers and car hire in Chicago, booked ahead at a fixed price.
    See options
  • Things to do in ChicagoPopular tours from $27.95 per person.
    See ideas
  • Travel insuranceTravel insurance quotes for United States from EKTA; check what each policy covers.
    Get a quote
  • Flight delayed?Arrived 3+ hours late, cancelled at short notice or bumped? Up to €600 per person under EU261.
    Check

Price calendar

The lowest one-way fare found for each day over the next 60 days. A dash means no recent fare; you can still pick that day.

October 2026

MoTuWeThFrSaSu12345678910111213141516171819202122232425–26–27–28€56829€54930€55431€681

November 2026

MoTuWeThFrSaSu1€5692–3€4144–5–6–7–8–9–10–11–12–13–14–15–16–17–18–19–20€42521–22–23–24–25–26–27–28–29–30–

December 2026

MoTuWeThFrSaSu1–2–3–4–5–6–7€3808–9–10–11–12–13–14–15–16–17–18–19–20€36121–22–23–2425262728293031
€380 or lessGreen: the cheapest fifth of fares on this route. Lowest in these 60 days: Dec 20, €361.

Lowest fares by month

In the fares found this week, December has the lowest: from €361 one-way, against €549 in October. Pick a month to see its cheapest date.

  1. Oct€549
  2. Nov€414
  3. Dec€361
  4. Janno fares yet
  5. Febno fares yet
  6. Marno fares yet
  7. Aprno fares yet
  8. Mayno fares yet
  9. Junno fares yet
  10. Julno fares yet
  11. Augno fares yet
  12. Sepno fares yet
€0€200€400€600OctNov€361DecJanFebMarAprMayJunJulAugSep
Show as a table
MonthCheapest one-wayDateStops
October€549Thu, Oct 291 stop
November€414Tue, Nov 32 stops
December€361Sun, Dec 203 stops
January 2027—
February 2027—
March 2027—
April 2027—
May 2027—
June 2027—
July 2027—
August 2027—
September 2027—

Fares and weather by month

The lowest one-way fare found for each month, next to the weather in Chicago. Average daily high and low and monthly precipitation, 1991–2020 normals.

Oct2026NovDecJan2027FebMarAprMayJunJulAugSep
Lowest fare€549€414€361–––––––––
High °C18°10°3°0°3°9°16°22°27°30°28°25°
Low °C8°2°-4°-7°-5°0°5°11°17°20°19°15°
Precipitation mm98695958546810512111510210485

Source: Chicago on Wikipedia, CC BY-SA 4.0.

Questions travellers ask

What is the cheapest month to fly from Milan to Chicago?

In the fares found this week, December has the lowest: from €361 one-way, against €549 in October.

What is the weather in Chicago in December?

In December, the cheapest month to fly, the average daily high in Chicago is 3 °C and the low -4 °C.

Are there direct flights from Milan to Chicago?

None of the fares found recently are nonstop. The cheapest options have at least one stop.

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