Cheap Flights from Chicago, IL to Milan from $171
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 $171, 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
Best Flights from Chicago to Milan Today
Price | Departure | Arrival | Flight Duration | Airline | Flight |
---|---|---|---|---|---|
from $381 | 21:35 Chicago O'Hare International | 13:20+1 день Milan Malpensa | 8h 45m | United Airlines | UA416 |
from $171 | 19:25 Chicago O'Hare International | 14:10+1 день Milan Malpensa | 11h 45m layover 1h 20m - Reykjavik | Icelandair | FI852 FI590 |
from $171 | 22:15 Chicago O'Hare International | 22:00+1 день Milan Malpensa | 16h 45m layover 6h 25m - Reykjavik | Icelandair | FI856 FI592 |
from $172 | 22:15 Chicago O'Hare International | 14:10+2 дня Milan Malpensa | 32h 55m layover 22h 40m - Reykjavik | Icelandair | FI856 FI590 |
from $211 | 18:15 Chicago O'Hare International | 00:50+2 дня Milan Malpensa | 23h 35m layover 12h 50m - Lisbon | TAP Portugal | TP244 TP828 |
from $272 | 19:15 Chicago O'Hare International | 08:35+2 дня Milan Malpensa | 30h 20m layover 19h 45m - Copenhagen | SAS | SK944 SK683 |
from $172 | 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 $196 | 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 $202 | 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 $202 | 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 $207 | 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 $207 | 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 $207 | 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 $207 | 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 $209 | 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 $210 | 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 |
Flight Schedule Chicago (Illinois) to Milan
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$381 |
|
18:15 — 00:50
+2 days
|
18:00 — 07:55
TP244
TAP Portugal
Chicago — Lisbon
12h 50m stop
21:00 — 00:45
TP828
TAP Portugal
Lisbon — Milan
|
23h 35m including layover |
Find flight
from$211 |
|
18:15 — 11:00
+2 days
|
18:00 — 07:55
TP244
TAP Portugal
Chicago — Lisbon
23h stop
07:15 — 11:00
TP822
TAP Portugal
Lisbon — Milan
|
33h 45m including layover |
Find flight
from$213 |
|
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$171 |
|
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$171 |
|
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$171 |
|
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$172 |
|
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$224 |
|
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$225 |
|
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$225 |
|
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$172 |
|
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$202 |
|
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$202 |
|
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$207 |
|
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$227 |
|
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$228 |
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 228 $), august (from 228 $), october (from 230 $).
The most expensive months are november (from 732 $), february (from 677 $), december (from 654 $).
What is the lowest airfare Chicago to Milan?
The cheapest plane ticket found by our users is $171. 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.
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 $ 361 . And the most expensive tickets are offered by SWISS International Air Lines airline - from $ 441.
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 $381.
- UA - United Airlinesfrom $381Find
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 $171.
- KL - KLMfrom $361Find
- AC - Air Canadafrom $225Find
- FI - Icelandairfrom $171Find
- LO - LOTfrom $437Find
- OS - Austrian Airlinesfrom $404Find
- EI - Aer Lingusfrom $415Find
- AF - Air Francefrom $331Find
- JU - Air Serbiafrom $273Find
- LX - SWISS International Air Linesfrom $360Find
- UA - United Airlinesfrom $383Find
- F9 - Frontier Airlinesfrom $224Find
- PD - Porter Airlinesfrom $279Find
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 $171Find
- Midway-MDWfrom $227Find
- 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 23 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?

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