Cheap Flights from Chicago, IL to Milan from $220

Return flight: Milan – Chicago

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 $220, 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.

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 august (from 220 $), july (from 221 $), october (from 222 $).

The most expensive months are november (from 707 $), february (from 654 $), december (from 631 $).

What is the lowest airfare Chicago to Milan?

The cheapest plane ticket found by our users is $220. 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
$220
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Business class
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First class
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Flight Schedule Chicago (Illinois) to Milan

17:10 — 10:00+2days
33h 50m flight time
Find flight
from$222
17:10 — 20:28 Chicago — New York
NK328 Spirit Airlines
3h 47m stop
00:15 — 13:10 New York — Paris
N0302 N0
19h 15m stop
08:25 — 10:00 Paris — Milan
W46340 Aero Services Executive
17:10 — 22:35+1day
22h 25m flight time
Find flight
from$261
17:10 — 20:28 Chicago — New York
NK328 Spirit Airlines
3h 47m stop
00:15 — 13:10 New York — Paris
N0302 N0
7h 50m stop
21:00 — 22:35 Paris — Milan
TO3930 Transavia France
17:10 — 18:55+1day
18h 45m flight time
Find flight
from$262
17:10 — 20:28 Chicago — New York
NK328 Spirit Airlines
3h 47m stop
00:15 — 13:10 New York — Paris
N0302 N0
4h 15m stop
17:25 — 18:55 Paris — Milan
U24563 EasyJet
17:10 — 07:50+2days
31h 40m flight time
Find flight
from$265
17:10 — 20:28 Chicago — New York
NK328 Spirit Airlines
3h 47m stop
00:15 — 13:05 New York — Paris
N0302 N0
17h 20m stop
06:25 — 07:50 Paris — Milan
U24889 EasyJet
17:10 — 23:15+1day
23h 5m flight time
Find flight
from$266
17:10 — 20:28 Chicago — New York
NK328 Spirit Airlines
3h 47m stop
00:15 — 13:10 New York — Paris
N0302 N0
8h 35m stop
21:45 — 23:15 Paris — Milan
U23814 EasyJet
19:25 — 22:00+1day
19h 35m flight time
Find flight
from$220
19:25 — 06:40 Chicago — Reykjavik
FI852 Icelandair
9h 5m stop
15:45 — 22:00 Reykjavik — Milan
FI592 Icelandair
19:25 — 14:10+1day
11h 45m flight time
Find flight
from$221
19:25 — 06:40 Chicago — Reykjavik
FI852 Icelandair
1h 20m stop
08:00 — 14:10 Reykjavik — Milan
FI590 Icelandair
19:25 — 17:20+1day
14h 55m flight time
Find flight
from$253
19:25 — 06:40 Chicago — Reykjavik
FI852 Icelandair
1h 10m stop
07:50 — 12:35 Reykjavik — Oslo
FI318 Icelandair
2h 5m stop
14:40 — 17:20 Oslo — Milan
U21990 EasyJet
19:25 — 20:15+1day
17h 50m flight time
Find flight
from$258
19:25 — 06:40 Chicago — Reykjavik
FI852 Icelandair
55m stop
07:35 — 13:10 Reykjavik — Berlin
FI528 Icelandair
5h 25m stop
18:35 — 20:15 Berlin — Milan
U21998 EasyJet
19:25 — 16:10+1day
13h 45m flight time
Find flight
from$262
19:25 — 06:40 Chicago — Reykjavik
FI852 Icelandair
55m stop
07:35 — 13:10 Reykjavik — Berlin
FI528 Icelandair
1h 20m stop
14:30 — 16:10 Berlin — Milan
U25071 EasyJet
19:39 — 16:20+2days
37h 41m flight time
Find flight
from$261
19:39 — 23:32 Chicago — Orlando
NK507 Spirit Airlines
20h 58m stop
20:30 — 10:00 Orlando — London
Z0784 Z0
3h 20m stop
13:20 — 16:20 London — Milan
U28305 EasyJet
20:12 — 12:15+2days
33h 3m flight time
Find flight
from$261
20:12 — 23:31 Chicago — New York
NK919 Spirit Airlines
18h 49m stop
18:20 — 06:20 New York — London
Z0702 Z0
2h 55m stop
09:15 — 12:15 London — Milan
U28303 EasyJet
21:35 — 13:20+1day
8h 45m flight time
Find flight
from$491
Chicago — Milan
UA416 United Airlines
22:15 — 22:00+1day
16h 45m flight time
Find flight
from$220
22:15 — 09:20 Chicago — Reykjavik
FI856 Icelandair
6h 25m stop
15:45 — 22:00 Reykjavik — Milan
FI592 Icelandair
22:15 — 14:10+2days
32h 55m flight time
Find flight
from$222
22:15 — 09:20 Chicago — Reykjavik
FI856 Icelandair
22h 40m stop
08:20 — 14:30 Reykjavik — Milan
FI590 Icelandair
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 and arrival times - local. Updated on October 14, 2025.

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 $ 465 . And the most expensive tickets are offered by Lufthansa airline - from $ 568.

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 $491.

  • UA - United Airlines
    from $491
    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 $220.

  • KL - KLM
    from $465
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  • AC - Air Canada
    from $290
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  • FI - Icelandair
    from $220
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  • LO - LOT
    from $563
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  • OS - Austrian Airlines
    from $521
    Find
  • EI - Aer Lingus
    from $535
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  • AF - Air France
    from $426
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  • JU - Air Serbia
    from $352
    Find
  • LX - SWISS International Air Lines
    from $464
    Find
  • UA - United Airlines
    from $493
    Find
  • F9 - Frontier Airlines
    from $289
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  • PD - Porter Airlines
    from $359
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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 $220
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  • Midway-MDW
    from $292
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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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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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