Cheap Flights from Chicago, IL to Milan from $219

Return flight: Milan – Chicago
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On Cheapflightsplus.com you will find 1 direct and 999 connecting flights from Chicago to Milan. You can compare airfare deals from 23 airlines and multiple travel sites from $219, 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: $219 (one-way), $376 (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 $219. The fastest direct flight takes 8h 45m and the fastest connecting – 10h 35m.
Price Departure Arrival Flight Duration Airline Flight
from $591
Find flight
21:35
Chicago
O'Hare International
 13:20+1 день
Milan
Malpensa
 8h 45m United Airlines
UA416
from $219
Find flight
19:25
Chicago
O'Hare International
 14:10+1 день
Milan
Malpensa
 11h 45m
layover
1h 20m - Reykjavik
 Icelandair
FI852
FI590
from $348
Find flight
19:15
Chicago
O'Hare International
 08:35+2 дня
Milan
Malpensa
 30h 20m
layover
19h 45m - Copenhagen
 SAS
SK944
SK683
from $221
Find flight
17:10
Chicago
O'Hare International
 10:00+2 дня
Milan
Malpensa
 33h 50m
layover
3h 47m - New York
19h 15m - Paris
 Spirit Airlines
NK328
N0302
W46340
from $251
Find flight
19:25
Chicago
O'Hare International
 17:20+1 день
Milan
Linate
 14h 55m
layover
1h 10m - Reykjavik
2h 5m - Oslo
 Icelandair
FI852
FI318
U21990
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 18, 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
17:10 — 10:00
+2 days
17:10 — 20:28 NK328 Spirit Airlines
Chicago — New York
3h 47m stop
00:15 — 13:10 N0302 N0
New York — Paris
19h 15m stop
08:25 — 10:00 W46340 Aero Services Executive
Paris — Milan
33h 50m
including layover
Find flight
from$221
17:10 — 22:35
+1 day
17:10 — 20:28 NK328 Spirit Airlines
Chicago — New York
3h 47m stop
00:15 — 13:10 N0302 N0
New York — Paris
7h 50m stop
21:00 — 22:35 TO3930 Transavia France
Paris — Milan
22h 25m
including layover
Find flight
from$260
17:10 — 18:55
+1 day
17:10 — 20:28 NK328 Spirit Airlines
Chicago — New York
3h 47m stop
00:15 — 13:10 N0302 N0
New York — Paris
4h 15m stop
17:25 — 18:55 U24563 EasyJet
Paris — Milan
18h 45m
including layover
Find flight
from$261
17:10 — 07:50
+2 days
17:10 — 20:28 NK328 Spirit Airlines
Chicago — New York
3h 47m stop
00:15 — 13:05 N0302 N0
New York — Paris
17h 20m stop
06:25 — 07:50 U24889 EasyJet
Paris — Milan
31h 40m
including layover
Find flight
from$263
19:25 — 14:10
+1 day
19:25 — 06:40 FI852 Icelandair
Chicago — Reykjavik
1h 20m stop
08:00 — 14:10 FI590 Icelandair
Reykjavik — Milan
11h 45m
including layover
Find flight
from$219
19:25 — 22:00
+1 day
19:25 — 06:40 FI852 Icelandair
Chicago — Reykjavik
9h 5m stop
15:45 — 22:00 FI592 Icelandair
Reykjavik — Milan
19h 35m
including layover
Find flight
from$219
19:25 — 17:20
+1 day
19:25 — 06:40 FI852 Icelandair
Chicago — Reykjavik
1h 10m stop
07:50 — 12:35 FI318 Icelandair
Reykjavik — Oslo
2h 5m stop
14:40 — 17:20 U21990 EasyJet
Oslo — Milan
14h 55m
including layover
Find flight
from$251
19:25 — 20:15
+1 day
19:25 — 06:40 FI852 Icelandair
Chicago — Reykjavik
55m stop
07:35 — 13:10 FI528 Icelandair
Reykjavik — Berlin
5h 25m stop
18:35 — 20:15 U21998 EasyJet
Berlin — Milan
17h 50m
including layover
Find flight
from$257
19:25 — 16:10
+1 day
19:25 — 06:40 FI852 Icelandair
Chicago — Reykjavik
55m stop
07:35 — 13:10 FI528 Icelandair
Reykjavik — Berlin
1h 20m stop
14:30 — 16:10 U25071 EasyJet
Berlin — Milan
13h 45m
including layover
Find flight
from$261
19:25 — 20:00
+1 day
19:25 — 06:40 FI852 Icelandair
Chicago — Reykjavik
55m stop
07:35 — 13:00 FI542 Icelandair
Reykjavik — Paris
5h 25m stop
18:25 — 20:00 FR3500 Ryanair
Paris — Milan
17h 35m
including layover
Find flight
from$264
19:39 — 16:20
+2 days
19:39 — 23:32 NK507 Spirit Airlines
Chicago — Orlando
20h 58m stop
20:30 — 10:00 Z0784 Z0
Orlando — London
3h 20m stop
13:20 — 16:20 U28305 EasyJet
London — Milan
37h 41m
including layover
Find flight
from$259
20:12 — 12:15
+2 days
20:12 — 23:31 NK919 Spirit Airlines
Chicago — New York
18h 49m stop
18:20 — 06:20 Z0702 Z0
New York — London
2h 55m stop
09:15 — 12:15 U28303 EasyJet
London — Milan
33h 3m
including layover
Find flight
from$259
21:35 — 13:20
+1 day
21:35 — 13:20 UA416 United Airlines
Chicago — Milan
8h 45m
Find flight
from$591
22:15 — 22:00
+1 day
22:15 — 09:20 FI856 Icelandair
Chicago — Reykjavik
6h 25m stop
15:45 — 22:00 FI592 Icelandair
Reykjavik — Milan
16h 45m
including layover
Find flight
from$219
22:15 — 14:10
+2 days
22:15 — 09:20 FI856 Icelandair
Chicago — Reykjavik
22h 40m stop
08:20 — 14:30 FI590 Icelandair
Reykjavik — Milan
32h 55m
including layover
Find flight
from$221
*Departure and arrival times - local. Updated on September 18, 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 05:01 to 23:45 from 7 Chicago airports and arrive 05:01 to 23:45 to 4 Milan airports. Average flight time is 8h 45m.

  • The fastest flight 8h 45m
  • Average flight time 8h 45m
  • The earliest flight 05:01
  • The latest flight 23:45
  • Distance 4530 ml

The cheapest months to travel to Milan are july (from 219 $), august (from 219 $), october (from 221 $).

The most expensive months are november (from 703 $), february (from 650 $), december (from 628 $).

What is the lowest airfare Chicago to Milan?

The cheapest plane ticket found by our users is $219. This airfare is for economy class on one-way FI856 flight by Icelandair for August 7, 2025 which leaves O'Hare International in Chicago at 22:15 am and arrives at Milan Malpensa at 22:00.

Economy class
$219
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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 23 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by KLM - 16 departures per week at the price of from $ 463 . And the most expensive tickets are offered by Icelandair airline - from $ 729.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA416 by United Airlines takes 8h 45m and the cheapest is FI856 by Icelandair for $591.

  • UA - United Airlines
    from $591
    Find
See more direct flights

Connecting Flights

There are 999 flights with layovers on the route. The fastest connecting flight is LH437 by Lufthansa takes 10h 35m and the cheapest is FI856 by Icelandair for $219.

  • KL - KLM
    from $463
    Find
  • AC - Air Canada
    from $289
    Find
  • FI - Icelandair
    from $219
    Find
  • LO - LOT
    from $559
    Find
  • OS - Austrian Airlines
    from $518
    Find
  • EI - Aer Lingus
    from $583
    Find
  • AF - Air France
    from $424
    Find
  • JU - Air Serbia
    from $351
    Find
  • LX - SWISS International Air Lines
    from $477
    Find
  • UA - United Airlines
    from $492
    Find
  • F9 - Frontier Airlines
    from $287
    Find
  • PD - Porter Airlines
    from $357
    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 $219
    Find
  • Midway-MDW
    from $290
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

Milan airports

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

Airplanes

There are flights to Milan from Chicago by 23 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

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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