Cheap Flights from Chicago, IL to Milan from $225

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 $225, 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: $225 (one-way), $386 (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 $225. The fastest direct flight takes 8h 45m and the fastest connecting – 10h 35m.
Price Departure Arrival Flight Duration Airline Flight
from $608
Find flight
21:35
Chicago
O'Hare International
 13:20+1 день
Milan
Malpensa
 8h 45m United Airlines
UA416
from $225
Find flight
22:15
Chicago
O'Hare International
 22:00+1 день
Milan
Malpensa
 16h 45m
layover
6h 25m - Reykjavik
 Icelandair
FI856
FI592
from $358
Find flight
19:15
Chicago
O'Hare International
 08:35+2 дня
Milan
Malpensa
 30h 20m
layover
19h 45m - Copenhagen
 SAS
SK944
SK683
from $361
Find flight
23:20
Chicago
O'Hare International
 08:35+2 дня
Milan
Malpensa
 26h 15m
layover
14h 50m - Belgrade
 Air Serbia
JU507
JU416
from $227
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 $258
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
from $267
Find flight
20:12
Chicago
O'Hare International
 12:15+2 дня
Milan
Malpensa
 33h 3m
layover
18h 49m - New York
2h 55m - London
 Spirit Airlines
NK919
Z0702
U28303
from $267
Find flight
19:39
Chicago
O'Hare International
 16:20+2 дня
Milan
Malpensa
 37h 41m
layover
20h 58m - Orlando
3h 20m - London
 Spirit Airlines
NK507
Z0784
U28305
from $273
Find flight
20:12
Chicago
O'Hare International
 18:30+2 дня
Milan
Linate
 39h 18m
layover
18h 49m - New York
9h 15m - London
 Spirit Airlines
NK919
Z0702
U28375
from $273
Find flight
19:39
Chicago
O'Hare International
 18:30+2 дня
Milan
Linate
 39h 51m
layover
20h 58m - Orlando
5h 35m - London
 Spirit Airlines
NK507
Z0784
U28375
from $273
Find flight
20:12
Chicago
O'Hare International
 10:00+3 дня
Milan
Malpensa
 54h 48m
layover
24h 44m - New York
19h 15m - Paris
 Spirit Airlines
NK919
N0302
W46340
from $273
Find flight
19:39
Chicago
O'Hare International
 09:55+3 дня
Milan
Malpensa
 55h 16m
layover
21h 8m - Orlando
20h 45m - London
 Spirit Airlines
NK507
Z0784
U28301
from $276
Find flight
20:12
Chicago
O'Hare International
 12:30+2 дня
Milan
Linate
 33h 18m
layover
18h 49m - New York
3h 10m - London
 Spirit Airlines
NK919
Z0702
U28289
from $277
Find flight
19:39
Chicago
O'Hare International
 12:30+3 дня
Milan
Linate
 57h 51m
layover
21h 8m - Orlando
23h 20m - London
 Spirit Airlines
NK507
Z0784
U28289
from $283
Find flight
19:39
Chicago
O'Hare International
 20:10+2 дня
Milan
Malpensa
 41h 31m
layover
21h 8m - Orlando
7h 5m - London
 Spirit Airlines
NK507
Z0784
U28309
from $283
Find flight
20:12
Chicago
O'Hare International
 10:00+3 дня
Milan
Malpensa
 54h 48m
layover
23h 29m - Newark
20h 10m - Paris
 Spirit Airlines
NK919
BF721
W46340
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 03, 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
21:35 — 13:20
+1 day
21:35 — 13:20 UA416 United Airlines
Chicago — Milan
8h 45m
Find flight
from$608
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$225
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$226
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$225
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$227
09:58 — 23:20
+1 day
09:17 — 13:11 F92792 Frontier Airlines
Chicago — Orlando
6h 48m stop
20:30 — 10:00 Z0784 Z0
Orlando — London
10h 20m stop
20:20 — 23:20 W46304 Aero Services Executive
London — Milan
30h 22m
including layover
Find flight
from$295
12:52 — 22:35
+1 day
12:52 — 15:46 AC4899 Air Canada
Chicago — Toronto
6h 24m stop
22:10 — 10:00 WS34 WestJet
Toronto — Dublin
9h 5m stop
19:05 — 22:35 FR4038 Ryanair
Dublin — Milan
26h 43m
including layover
Find flight
from$297
16:42 — 22:35
+1 day
16:43 — 19:37 AC5014 Air Canada
Chicago — Toronto
2h 33m stop
22:10 — 10:00 WS34 WestJet
Toronto — Dublin
9h 5m stop
19:40 — 23:10 FR4038 Ryanair
Dublin — Milan
22h 53m
including layover
Find flight
from$297
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$227
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$267
18:00 — 01:15
+2 days
18:00 — 08:00 TP244 TAP Portugal
Chicago — Lisbon
11h stop
19:00 — 21:50 TP1038 TAP Portugal
Lisbon — Barcelona
1h 35m stop
23:25 — 01:15 W46330 Aero Services Executive
Barcelona — Milan
24h 15m
including layover
Find flight
from$301
18:00 — 01:15
+2 days
18:00 — 08:00 TP244 TAP Portugal
Chicago — Lisbon
6h 5m stop
14:05 — 16:55 TP1034 TAP Portugal
Lisbon — Barcelona
6h 30m stop
23:25 — 01:15 W46330 Aero Services Executive
Barcelona — Milan
24h 15m
including layover
Find flight
from$303
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$267
20:12 — 18:30
+2 days
20:12 — 23:31 NK919 Spirit Airlines
Chicago — New York
18h 49m stop
18:20 — 06:20 Z0702 Z0
New York — London
9h 15m stop
15:35 — 18:30 U28375 EasyJet
London — Milan
39h 18m
including layover
Find flight
from$273
21:12 — 23:20
+2 days
21:12 — 00:57 F93854 Frontier Airlines
Chicago — Orlando
19h 37m stop
20:30 — 10:00 Z0784 Z0
Orlando — London
10h 10m stop
20:20 — 23:20 W46304 Aero Services Executive
London — Milan
43h 8m
including layover
Find flight
from$299
21:28 — 10:00
+3 days
21:08 — 00:29 NK2542 Spirit Airlines
Chicago — New York
23h 29m stop
00:15 — 13:05 N0302 N0
New York — Paris
19h 15m stop
08:25 — 10:00 W46340 Aero Services Executive
Paris — Milan
53h 32m
including layover
Find flight
from$300
*Departure and arrival times - local. Updated on September 3, 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 august (from 225 $), july (from 226 $), october (from 227 $).

The most expensive months are november (from 723 $), february (from 669 $), december (from 646 $).

What is the lowest airfare Chicago to Milan?

The cheapest plane ticket found by our users is $225. 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
$225
Find
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 $ 476 . And the most expensive tickets are offered by Icelandair airline - from $ 750.

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 $608.

  • UA - United Airlines
    from $608
    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 $225.

  • KL - KLM
    from $476
    Find
  • AC - Air Canada
    from $297
    Find
  • FI - Icelandair
    from $225
    Find
  • LO - LOT
    from $575
    Find
  • OS - Austrian Airlines
    from $532
    Find
  • EI - Aer Lingus
    from $599
    Find
  • AF - Air France
    from $436
    Find
  • JU - Air Serbia
    from $361
    Find
  • LX - SWISS International Air Lines
    from $491
    Find
  • UA - United Airlines
    from $506
    Find
  • F9 - Frontier Airlines
    from $295
    Find
  • PD - Porter Airlines
    from $367
    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 $225
    Find
  • Midway-MDW
    from $299
    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.

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