Cheap Flights from Chicago, IL to Milan from $406

Return flight: Milan – Chicago
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On Cheapflightsplus.com you will find 4 connecting flights from Chicago to Milan. You can compare airfare deals from 3 airlines and multiple travel sites from $406, book and save on cheap plane tickets and last minute offers. Also check out CHI-MIL flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Chicago to Milan Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $406 (one-way), $696 (round-trip).
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Best Flights from Chicago to Milan Today

Take a look at the list of non stop flights and flights with layovers from Chicago to Milan with the lowest price of $406. Take a look at the list of flights with layovers from Chicago to Milan from $406. There’re no direct flights. The fastest connecting flight – 11h 20m.
Price Departure Arrival Flight Duration Airline Flight
from $406
Find flight
19:05
Chicago
O'Hare International
 13:45+1 день
Milan
Malpensa
 11h 40m
layover
2h 5m - Zurich
 United Airlines
UA9727
LX1628
from $422
Find flight
22:35
Chicago
O'Hare International
 16:55+1 день
Milan
Linate
 11h 20m
layover
1h 30m - Frankfurt
 United Airlines
UA8835
UA9556
from $428
Find flight
19:05
Chicago
O'Hare International
 13:25+1 день
Milan
Malpensa
 11h 20m
layover
1h 45m - Zurich
 SWISS International Air Lines
LX9
LX1628
from $714
Find flight
20:30
Chicago
O'Hare International
 21:45+1 день
Milan
Malpensa
 18h 15m
layover
4h 30m - Istanbul
 Turkish Airlines
TK6
TK1877
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on March 14, 2025
Full flight schedule will help you in detecting at what time planes fly from Chicago to Milan. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
19:05 — 13:45
+1 day
19:10 — 10:50 UA9727 United Airlines
Chicago — Zurich
2h 5m stop
13:05 — 14:00 LX1628 SWISS International Air Lines
Zurich — Milan
11h 40m
including layover
Find flight
from$406
19:05 — 13:25
+1 day
19:10 — 10:50 LX9 SWISS International Air Lines
Chicago — Zurich
1h 45m stop
13:05 — 14:00 LX1628 SWISS International Air Lines
Zurich — Milan
11h 20m
including layover
Find flight
from$428
20:30 — 21:45
+1 day
21:30 — 16:10 TK6 Turkish Airlines
Chicago — Istanbul
4h 30m stop
21:55 — 23:55 TK1877 Turkish Airlines
Istanbul — Milan
18h 15m
including layover
Find flight
from$714
22:35 — 16:55
+1 day
22:00 — 13:30 UA8835 United Airlines
Chicago — Frankfurt
1h 30m stop
15:30 — 16:40 UA9556 United Airlines
Frankfurt — Milan
11h 20m
including layover
Find flight
from$422
*Departure and arrival times - local. Updated on March 14, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Chicago to Milan depends on and how to choose the most interesting flight option for you.

Distance between Chicago and Milan is 7289 miles. Time difference between the cities is 7h. Airplanes depart 19:05 to 22:35 from 7 Chicago airports and arrive 19:05 to 22:35 to 4 Milan airports. Average flight time is 11h 30m.

  • The fastest flight 11h 20m
  • Average flight time 11h 30m
  • The earliest flight 19:05
  • The latest flight 22:35
  • Distance 4530 ml

The cheapest months to travel to Milan are march (from 406 $), december (from 625 $), november (from 668 $).

The most expensive months are february (from 861 $), january (from 823 $), november (from 668 $).

What is the lowest airfare Chicago to Milan?

The cheapest plane ticket found by our users is $406. This airfare is for economy class on one-way UA9727 flight by United Airlines for March 15, 2025 which leaves O'Hare International in Chicago at 19:05 am and arrives at Milan Malpensa at 13:45.

Economy class
$406
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Business class
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First class
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Popular Airlines on the Route

The flight Chicago — Milan is served by 3 regular airlines . Most of the flights on this route are operated by Turkish Airlines - 1 departures per week at the price of from $ 714 . And the most expensive tickets are offered by Turkish Airlines airline - from $ 714.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 4 flights with layovers on the route. The fastest connecting flight is UA8835 by United Airlines takes 11h 20m and the cheapest is UA9727 by United Airlines for $406.

  • TK - Turkish Airlines
    from $714
    Find
  • UA - United Airlines
    from $406
    Find
  • LX - SWISS International Air Lines
    from $428
    Find
See more connecting flights

Airports

You can fly from Chicago to Milan from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

  • O'Hare International-ORD
    from $406
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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Milan airports

  • Linate-LIN
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  • Malpensa-MXP
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  • Milan Bergamo (Orio al Serio)-BGY
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  • Segrate-SWK
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Airplanes

There are flights to Milan from Chicago by 3 airlines that use 3 aircraft brands. They range from huge modern airplanes to small-sized.

  • Airbus A330-300
    from $406
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  • Airbus A340-600
    from $422
    Find
  • Boeing 777-300ER
    from $714
    Find

Top Domestic Destinations from Chicago

You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.

Top International Destinations from Chicago

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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