Cheap Flights from Chicago, IL to Milan from $444
Return flight: Milan – Chicago
On Cheapflightsplus.com you will find 1 direct and 480 connecting flights from Chicago to Milan. You can compare airfare deals from 18 airlines and multiple travel sites from $444, 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: $444 (one-way), $761 (round-trip).
Direct flights
Check prices for return flight
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 $444. The fastest direct flight takes 8h 45m and the fastest connecting – 10h 40m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $1083 | 21:35 Chicago O'Hare International | 13:20+1 день Milan Malpensa | 8h 45m | United Airlines | UA416 |
| from $704 | 21:08 Chicago O'Hare International | 07:00+2 дня Milan Malpensa | 26h 52m layover 16h 31m - New York | Spirit Airlines | NK2542 NO789 |
| from $806 | 22:15 Chicago O'Hare International | 02:40+2 дня Milan Malpensa | 21h 25m layover 11h 5m - Reykjavik | Icelandair | FI856 U23968 |
| from $837 | 18:00 Chicago O'Hare International | 00:45+2 дня Milan Malpensa | 23h 45m layover 13h 5m - Lisbon | TAP Portugal | TP244 TP828 |
| from $444 | 05:51 Chicago O'Hare International | 10:25+2 дня Milan Milan Bergamo (Orio al Serio) | 45h 34m layover 14h 55m - New York 19h 0m - Oslo | Spirit Airlines | NK2175 N02 DY1846 |
| from $499 | 09:40 Chicago Midway | 17:55+1 день Milan Linate | 25h 15m layover 9h 53m - Toronto 4h 25m - Edinburgh | Porter Airlines | PD2388 WS16 U21988 |
| from $504 | 16:43 Chicago O'Hare International | 01:15+2 дня Milan Milan Bergamo (Orio al Serio) | 25h 32m layover 2h 33m - Toronto 11h 45m - Dublin | Air Canada | AC5014 WS34 FR9428 |
| from $504 | 10:50 Chicago O'Hare International | 01:15+2 дня Milan Milan Bergamo (Orio al Serio) | 31h 25m layover 8h 28m - Toronto 11h 45m - Dublin | Air Canada | AC4407 WS34 FR9428 |
| from $504 | 08:50 Chicago O'Hare International | 01:15+2 дня Milan Milan Bergamo (Orio al Serio) | 33h 25m layover 10h 21m - Toronto 11h 45m - Dublin | Air Canada | AC5212 WS34 FR9428 |
| from $505 | 15:50 Chicago O'Hare International | 01:15+2 дня Milan Milan Bergamo (Orio al Serio) | 26h 25m layover 3h 38m - Toronto 11h 45m - Dublin | Air Canada | AC508 WS34 FR9428 |
| from $505 | 12:00 Chicago O'Hare International | 01:15+2 дня Milan Milan Bergamo (Orio al Serio) | 30h 15m layover 7h 32m - Toronto 11h 45m - Dublin | Air Canada | AC8904 WS34 FR9428 |
| from $525 | 16:43 Chicago O'Hare International | 17:55+1 день Milan Linate | 18h 12m layover 2h 38m - Toronto 4h 25m - Edinburgh | Air Canada | AC5014 WS16 U21988 |
| from $526 | 15:50 Chicago O'Hare International | 17:55+1 день Milan Linate | 19h 5m layover 3h 43m - Toronto 4h 25m - Edinburgh | Air Canada | AC508 WS16 U21988 |
| from $548 | 19:25 Chicago O'Hare International | 21:40+1 день Milan Linate | 19h 15m layover 3h 55m - Reykjavik 3h 50m - Copenhagen | Icelandair | FI852 FI208 U21978 |
| from $548 | 19:25 Chicago O'Hare International | 21:40+1 день Milan Linate | 19h 15m layover 1h 0m - Reykjavik 6h 40m - Copenhagen | Icelandair | FI852 FI204 U21978 |
| from $561 | 14:00 Chicago O'Hare International | 17:55+1 день Milan Linate | 20h 55m layover 5h 33m - Toronto 4h 25m - Edinburgh | Air Canada | AC506 WS16 U21988 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 09, 2025
Flight Schedule Chicago (Illinois) to Milan
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$1083 |
|
|
18:00 — 00:45
+2 days
|
18:00 — 07:55
TP244
TAP Portugal
Chicago — Lisbon
13h 5m stop
21:00 — 00:45
TP828
TAP Portugal
Lisbon — Milan
|
23h 45m including layover |
Find flight
from$837 |
|
|
18:00 — 11:00
+2 days
|
18:00 — 07:55
TP244
TAP Portugal
Chicago — Lisbon
23h 20m stop
07:15 — 11:00
TP822
TAP Portugal
Lisbon — Milan
|
34h including layover |
Find flight
from$841 |
|
|
21:08 — 07:00
+2 days
|
21:08 — 00:29
NK2542
Spirit Airlines
Chicago — New York
16h 31m stop
17:00 — 07:00
NO789
Neos
New York — Milan
|
26h 52m including layover |
Find flight
from$704 |
|
|
05:51 — 10:25
+2 days
|
05:51 — 09:00
NK2175
Spirit Airlines
Chicago — New York
14h 55m stop
23:55 — 12:55
N02
N0
New York — Oslo
19h stop
07:55 — 10:25
DY1846
Norwegian
Oslo — Milan
|
45h 34m including layover |
Find flight
from$444 |
|
|
05:51 — 21:00
+1 day
|
05:51 — 09:00
NK2175
Spirit Airlines
Chicago — New York
4h 50m stop
13:50 — 05:40
H4102
Heli Securite
New York — Bucharest
13h 55m stop
19:35 — 21:00
W43135
Aero Services Executive
Bucharest — Milan
|
32h 9m including layover |
Find flight
from$586 |
|
|
08:50 — 01:15
+2 days
|
08:50 — 11:49
AC5212
Air Canada
Chicago — Toronto
10h 21m stop
22:10 — 10:00
WS34
WestJet
Toronto — Dublin
11h 45m stop
21:45 — 01:15
FR9428
Ryanair
Dublin — Milan
|
33h 25m including layover |
Find flight
from$504 |
|
|
09:40 — 17:55
+1 day
|
09:40 — 12:22
PD2388
Porter Airlines
Chicago — Toronto
9h 53m stop
22:15 — 10:05
WS16
WestJet
Toronto — Edinburgh
4h 25m stop
14:30 — 17:55
U21988
EasyJet
Edinburgh — Milan
|
25h 15m including layover |
Find flight
from$499 |
|
|
09:40 — 17:35
+1 day
|
09:40 — 12:22
PD2388
Porter Airlines
Chicago — Toronto
7h 33m stop
19:55 — 09:40
WS5943
WestJet
Toronto — Frankfurt
6h 40m stop
16:20 — 17:35
LH5668
Lufthansa
Frankfurt — Milan
|
24h 55m including layover |
Find flight
from$666 |
|
|
10:50 — 01:15
+2 days
|
10:50 — 13:42
AC4407
Air Canada
Chicago — Toronto
8h 28m stop
22:10 — 10:00
WS34
WestJet
Toronto — Dublin
11h 45m stop
21:45 — 01:15
FR9428
Ryanair
Dublin — Milan
|
31h 25m including layover |
Find flight
from$504 |
|
|
12:00 — 01:15
+2 days
|
12:00 — 14:38
AC8904
Air Canada
Chicago — Toronto
7h 32m stop
22:10 — 10:00
WS34
WestJet
Toronto — Dublin
11h 45m stop
21:45 — 01:15
FR9428
Ryanair
Dublin — Milan
|
30h 15m including layover |
Find flight
from$505 |
|
|
14:00 — 17:55
+1 day
|
14:00 — 16:42
AC506
Air Canada
Chicago — Toronto
5h 33m stop
22:15 — 10:05
WS16
WestJet
Toronto — Edinburgh
4h 25m stop
14:30 — 17:55
U21988
EasyJet
Edinburgh — Milan
|
20h 55m including layover |
Find flight
from$561 |
|
|
14:20 — 13:35
+1 day
|
14:20 — 06:10
LX7
SWISS International Air Lines
Chicago — Zurich
1h stop
07:10 — 08:45
LX2250
SWISS International Air Lines
Zurich — Budapest
3h 5m stop
11:50 — 13:35
FR8325
Ryanair
Budapest — Milan
|
16h 15m including layover |
Find flight
from$778 |
|
|
15:50 — 01:15
+2 days
|
15:50 — 18:32
AC508
Air Canada
Chicago — Toronto
3h 38m stop
22:10 — 10:00
WS34
WestJet
Toronto — Dublin
11h 45m stop
21:45 — 01:15
FR9428
Ryanair
Dublin — Milan
|
26h 25m including layover |
Find flight
from$505 |
|
|
15:50 — 17:55
+1 day
|
15:50 — 18:32
AC508
Air Canada
Chicago — Toronto
3h 43m stop
22:15 — 10:05
WS16
WestJet
Toronto — Edinburgh
4h 25m stop
14:30 — 17:55
U21988
EasyJet
Edinburgh — Milan
|
19h 5m including layover |
Find flight
from$526 |
|
|
16:43 — 01:15
+2 days
|
16:43 — 19:37
AC5014
Air Canada
Chicago — Toronto
2h 33m stop
22:10 — 10:00
WS34
WestJet
Toronto — Dublin
11h 45m stop
21:45 — 01:15
FR9428
Ryanair
Dublin — Milan
|
25h 32m including layover |
Find flight
from$504 |
|
|
16:43 — 17:55
+1 day
|
16:43 — 19:37
AC5014
Air Canada
Chicago — Toronto
2h 38m stop
22:15 — 10:05
WS16
WestJet
Toronto — Edinburgh
4h 25m stop
14:30 — 17:55
U21988
EasyJet
Edinburgh — Milan
|
18h 12m including layover |
Find flight
from$525 |
|
|
19:25 — 21:40
+1 day
|
19:25 — 06:40
FI852
Icelandair
Chicago — Reykjavik
3h 55m stop
10:35 — 15:45
FI208
Icelandair
Reykjavik — Copenhagen
3h 50m stop
19:35 — 21:40
U21978
EasyJet
Copenhagen — Milan
|
19h 15m including layover |
Find flight
from$548 |
|
|
19:25 — 21:40
+1 day
|
19:25 — 06:40
FI852
Icelandair
Chicago — Reykjavik
1h stop
07:40 — 12:55
FI204
Icelandair
Reykjavik — Copenhagen
6h 40m stop
19:35 — 21:40
U21978
EasyJet
Copenhagen — Milan
|
19h 15m including layover |
Find flight
from$548 |
|
|
21:08 — 12:05
+2 days
|
21:08 — 00:29
NK2542
Spirit Airlines
Chicago — New York
17h 51m stop
18:20 — 06:20
Z0702
Z0
New York — London
2h 45m stop
09:05 — 12:05
W46302
Aero Services Executive
London — Milan
|
31h 57m including layover |
Find flight
from$573 |
|
|
22:15 — 21:40
+1 day
|
22:15 — 09:20
FI856
Icelandair
Chicago — Reykjavik
1h 15m stop
10:35 — 15:45
FI208
Icelandair
Reykjavik — Copenhagen
3h 50m stop
19:35 — 21:40
U21978
EasyJet
Copenhagen — Milan
|
16h 25m including layover |
Find flight
from$548 |
|
|
22:15 — 12:15
+2 days
|
22:15 — 09:20
FI856
Icelandair
Chicago — Reykjavik
1h 15m stop
10:35 — 15:45
FI208
Icelandair
Reykjavik — Copenhagen
18h 30m stop
10:15 — 12:15
D83750
Djibouti Airlines
Copenhagen — Milan
|
31h including layover |
Find flight
from$599 |
|
*Departure and arrival times - local. Updated on May 9, 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 05:51 to 22:30 from 7 Chicago airports and arrive 05:51 to 22:30 to 4 Milan airports. Average flight time is 8h 45m.
- The fastest flight 8h 45m
- Average flight time 8h 45m
- The earliest flight 05:51
- The latest flight 22:30
- Distance 4530 ml
The cheapest months to travel to Milan are january (from 424 $), may (from 424 $), february (from 435 $).
The most expensive months are november (from 705 $), december (from 626 $), february (from 435 $).
What is the lowest airfare Chicago to Milan?
The cheapest plane ticket found by our users is $444. This airfare is for economy class on one-way NK2175 flight by Spirit Airlines for May 30, 2025 which leaves O'Hare International in Chicago at 05:51 am and arrives at Milan Milan Bergamo (Orio al Serio) at 10:25.
Economy class
$444
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Milan is served by 18 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Air Canada - 115 departures per week at the price of from $ 504 . And the most expensive tickets are offered by SAS airline - from $ 7929.
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 NK2175 by Spirit Airlines for $1083.
- UA - United Airlinesfrom $1083Find
See more direct flights
Connecting Flights
There are 480 flights with layovers on the route. The fastest connecting flight is BA5686 by British Airways takes 10h 40m and the cheapest is NK2175 by Spirit Airlines for $444.
- AC - Air Canadafrom $504Find
- FI - Icelandairfrom $548Find
- LO - LOTfrom $1068Find
- OS - Austrian Airlinesfrom $844Find
- EI - Aer Lingusfrom $1045Find
- LX - SWISS International Air Linesfrom $738Find
- UA - United Airlinesfrom $1095Find
- PD - Porter Airlinesfrom $499Find
- TK - Turkish Airlinesfrom $952Find
- AY - Finnairfrom $861Find
- SK - SASfrom $1377Find
- AZ - Alitaliafrom $1029Find
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-ORDfrom $444Find
- Midway-MDWfrom $499Find
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Milan airports
- Linate-LINFind
- Malpensa-MXPFind
- Milan Bergamo (Orio al Serio)-BGYFind
- Segrate-SWKFind
Airplanes
There are flights to Milan from Chicago by 18 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top Domestic Destinations from Chicago
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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.
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How to book a plane 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.