Cheap Flights from Chicago, IL to Milan from $262
Return flight: Milan – Chicago
On Cheapflightsplus.com you will find 370 connecting flights from Chicago to Milan. You can compare airfare deals from 18 airlines and multiple travel sites from $262, 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: $262 (one-way), $449 (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 $262. Take a look at the list of flights with layovers from Chicago to Milan from $262. There’re no direct flights. The fastest connecting flight – 10h 25m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $363 | 19:05 Chicago O'Hare International | 13:45+1 день Milan Malpensa | 11h 40m layover 2h 5m - Zurich | United Airlines | UA9727 LX1628 |
| from $382 | 19:05 Chicago O'Hare International | 13:25+1 день Milan Malpensa | 11h 20m layover 1h 45m - Zurich | SWISS International Air Lines | LX9 LX1628 |
| from $439 | 21:55 Chicago O'Hare International | 09:45+2 дня Milan Malpensa | 28h 50m layover 17h 40m - Warsaw | LOT | LO4 LO317 |
| from $262 | 05:15 Chicago O'Hare International | 08:40+2 дня Milan Malpensa | 44h 25m layover 14h 29m - Newark 19h 10m - Paris | Spirit Airlines | NK210 BF721 VY8428 |
| from $270 | 17:06 Chicago O'Hare International | 11:35+2 дня Milan Malpensa | 35h 29m layover 22h 5m - New York 2h 35m - London | Spirit Airlines | NK224 Z0702 W46302 |
| from $270 | 17:06 Chicago O'Hare International | 23:30+2 дня Milan Malpensa | 47h 24m layover 22h 5m - New York 14h 30m - London | Spirit Airlines | NK224 Z0702 W46304 |
| from $300 | 17:06 Chicago O'Hare International | 13:25+2 дня Milan Linate | 37h 19m layover 22h 5m - New York 4h 25m - London | Spirit Airlines | NK224 Z0702 U28283 |
| from $321 | 16:57 Chicago O'Hare International | 08:40+2 дня Milan Malpensa | 32h 43m layover 2h 45m - Newark 19h 10m - Paris | Spirit Airlines | NK328 BF721 VY8428 |
| from $333 | 18:30 Chicago O'Hare International | 11:35+2 дня Milan Malpensa | 34h 5m layover 1h 0m - Reykjavik 21h 40m - London | Icelandair | FI852 FI470 W46302 |
| from $338 | 18:30 Chicago O'Hare International | 23:25+1 день Milan Malpensa | 21h 55m layover 1h 0m - Reykjavik 9h 30m - London | Icelandair | FI852 FI470 W46304 |
| from $343 | 18:30 Chicago O'Hare International | 08:40+2 дня Milan Malpensa | 31h 10m layover 0h 50m - Reykjavik 19h 10m - Paris | Icelandair | FI852 FI542 VY8428 |
| from $353 | 18:30 Chicago O'Hare International | 07:55+2 дня Milan Linate | 30h 25m layover 0h 50m - Reykjavik 18h 25m - Paris | Icelandair | FI852 FI542 U24561 |
| from $356 | 18:30 Chicago O'Hare International | 20:20+1 день Milan Malpensa | 18h 50m layover 0h 55m - Reykjavik 6h 25m - Copenhagen | Icelandair | FI852 FI204 U23922 |
| from $357 | 18:30 Chicago O'Hare International | 19:15+1 день Milan Malpensa | 17h 45m layover 0h 50m - Reykjavik 5h 45m - Paris | Icelandair | FI852 FI542 U23810 |
| from $364 | 18:30 Chicago O'Hare International | 18:40+1 день Milan Linate | 17h 10m layover 0h 55m - Reykjavik 4h 50m - London | Icelandair | FI852 FI450 U26333 |
| from $364 | 18:30 Chicago O'Hare International | 18:40+1 день Milan Linate | 17h 10m layover 1h 0m - Reykjavik 4h 45m - London | Icelandair | FI852 FI470 U26333 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on January 31, 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 |
|---|---|---|---|---|
|
05:15 — 07:00
+1 day
|
05:15 — 08:31
NK210
Spirit Airlines
Chicago — New York
8h 29m stop
17:00 — 07:00
NO789
Neos
New York — Milan
|
18h 45m including layover |
Find flight
from$486 |
|
|
06:00 — 07:30
+1 day
|
06:00 — 09:11
UA2343
United Airlines
Chicago — Newark
8h 29m stop
17:40 — 07:30
UA19
United Airlines
Newark — Milan
|
18h 30m including layover |
Find flight
from$580 |
|
|
07:20 — 10:20
+1 day
|
07:20 — 10:32
AC8958
Air Canada
Chicago — Montreal
9h 53m stop
20:25 — 10:20
AC894
Air Canada
Montreal — Milan
|
20h including layover |
Find flight
from$539 |
|
|
07:20 — 10:20
+1 day
|
07:20 — 10:32
UA8452
United Airlines
Chicago — Montreal
9h 53m stop
20:25 — 10:20
UA8060
United Airlines
Montreal — Milan
|
20h including layover |
Find flight
from$575 |
|
|
09:10 — 07:30
+1 day
|
09:10 — 12:28
UA2462
United Airlines
Chicago — Newark
5h 12m stop
17:40 — 07:30
UA19
United Airlines
Newark — Milan
|
15h 20m including layover |
Find flight
from$586 |
|
|
10:50 — 07:30
+1 day
|
10:50 — 14:06
UA2091
United Airlines
Chicago — Newark
3h 34m stop
17:40 — 07:30
UA19
United Airlines
Newark — Milan
|
13h 40m including layover |
Find flight
from$586 |
|
|
11:35 — 10:20
+1 day
|
11:35 — 14:47
AC8960
Air Canada
Chicago — Montreal
5h 38m stop
20:25 — 10:20
AC894
Air Canada
Montreal — Milan
|
15h 45m including layover |
Find flight
from$539 |
|
|
11:35 — 10:20
+1 day
|
11:35 — 14:47
UA8344
United Airlines
Chicago — Montreal
5h 38m stop
20:25 — 10:20
UA8060
United Airlines
Montreal — Milan
|
15h 45m including layover |
Find flight
from$586 |
|
|
15:35 — 10:20
+1 day
|
15:35 — 18:47
AC8962
Air Canada
Chicago — Montreal
1h 38m stop
20:25 — 10:20
AC894
Air Canada
Montreal — Milan
|
11h 45m including layover |
Find flight
from$539 |
|
|
15:55 — 10:00
+1 day
|
15:55 — 07:25
LH431
Lufthansa
Chicago — Frankfurt
1h 20m stop
08:45 — 10:00
LH6904
Lufthansa
Frankfurt — Milan
|
11h 5m including layover |
Find flight
from$533 |
|
|
16:08 — 07:30
+2 days
|
16:08 — 19:23
UA795
United Airlines
Chicago — Newark
22h 17m stop
17:40 — 07:30
UA19
United Airlines
Newark — Milan
|
32h 22m including layover |
Find flight
from$541 |
|
|
16:45 — 12:45
+1 day
|
16:45 — 07:55
IB342
Iberia
Chicago — Madrid
2h 35m stop
10:30 — 12:45
W46312
Aero Services Executive
Madrid — Milan
|
13h including layover |
Find flight
from$514 |
|
|
17:00 — 11:15
+1 day
|
17:00 — 06:50
BA294
British Airways
Chicago — London
1h 25m stop
08:15 — 11:15
BA586
British Airways
London — Milan
|
11h 15m including layover |
Find flight
from$541 |
|
|
17:30 — 19:05
+1 day
|
12:30 — 05:00
JU507
Air Serbia
Chicago — Belgrade
7h 20m stop
17:20 — 19:05
JU418
Air Serbia
Belgrade — Milan
|
18h 35m including layover |
Find flight
from$515 |
|
|
18:20 — 07:30
+2 days
|
18:20 — 21:41
UA534
United Airlines
Chicago — Newark
19h 59m stop
17:40 — 07:30
UA19
United Airlines
Newark — Milan
|
30h 10m including layover |
Find flight
from$538 |
|
|
18:35 — 15:35
+1 day
|
18:30 — 08:15
BA1543
British Airways
Chicago — London
4h 25m stop
12:40 — 15:35
BA7301
British Airways
London — Milan
|
14h including layover |
Find flight
from$564 |
|
|
19:05 — 13:45
+1 day
|
19:10 — 10:50
UA9727
United Airlines
Chicago — Zurich
2h 5m stop
13:05 — 14:00
LX1628
SWISS International Air Lines
Zurich — Milan
|
11h 40m including layover |
Find flight
from$363 |
|
|
19:05 — 13:25
+1 day
|
19:10 — 10:50
LX9
SWISS International Air Lines
Chicago — Zurich
1h 45m stop
13:05 — 14:00
LX1628
SWISS International Air Lines
Zurich — Milan
|
11h 20m including layover |
Find flight
from$382 |
|
|
20:20 — 18:10
+1 day
|
19:15 — 09:05
TP244
TAP Portugal
Chicago — Lisbon
4h 15m stop
17:10 — 20:55
U27697
EasyJet
Lisbon — Milan
|
14h 50m including layover |
Find flight
from$532 |
|
|
20:40 — 08:10
+2 days
|
20:25 — 23:33
BA5240
British Airways
Chicago — New York
18h 21m stop
18:20 — 08:10
BA1582
British Airways
New York — Milan
|
28h 30m including layover |
Find flight
from$506 |
|
|
21:45 — 23:25
+1 day
|
21:45 — 11:30
IB3635
Iberia
Chicago — London
8h 55m stop
20:25 — 23:25
W46304
Aero Services Executive
London — Milan
|
18h 40m including layover |
Find flight
from$533 |
|
|
21:55 — 09:45
+2 days
|
21:55 — 13:50
LO4
LOT
Chicago — Warsaw
17h 40m stop
07:30 — 09:45
LO317
LOT
Warsaw — Milan
|
28h 50m including layover |
Find flight
from$439 |
|
|
22:35 — 16:55
+1 day
|
22:00 — 13:30
UA8835
United Airlines
Chicago — Frankfurt
1h 30m stop
15:30 — 16:40
UA9556
United Airlines
Frankfurt — Milan
|
11h 20m including layover |
Find flight
from$377 |
|
*Departure and arrival times - local. Updated on January 31, 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 05:15 to 22:35 from 7 Chicago airports and arrive 05:15 to 22:35 to 4 Milan airports. Average flight time is 18h 10m.
- The fastest flight 10h 25m
- Average flight time 18h 10m
- The earliest flight 05:15
- The latest flight 22:35
- Distance 4530 ml
The cheapest months to travel to Milan are february (from 262 $), november (from 277 $), january (from 298 $).
The most expensive months are december (from 392 $), january (from 298 $), november (from 277 $).
What is the lowest airfare Chicago to Milan?
The cheapest plane ticket found by our users is $262. This airfare is for economy class on one-way NK210 flight by Spirit Airlines for February 1, 2025 which leaves O'Hare International in Chicago at 05:15 am and arrives at Milan Malpensa at 08:40.
Economy class
$262
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 - 78 departures per week at the price of from $ 499 . And the most expensive tickets are offered by Air Canada airline - from $ 4410.
Direct flights
There’re no direct flights on this route. Try flights with stops.
Connecting Flights
There are 370 flights with layovers on the route. The fastest connecting flight is SN8804 by Brussels Airlines takes 10h 25m and the cheapest is NK210 by Spirit Airlines for $262.
- from $499Find
- from $363Find
- FI - Icelandairfrom $333Find
- LO - LOTfrom $439Find
- OS - Austrian Airlinesfrom $544Find
- EI - Aer Lingusfrom $724Find
- JU - Air Serbiafrom $515Find
- LX - SWISS International Air Linesfrom $382Find
- F9 - Frontier Airlinesfrom $536Find
- TK - Turkish Airlinesfrom $497Find
- AY - Finnairfrom $564Find
- SK - SASfrom $593Find
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 $262Find
- Midway-MDWFind
- 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 3 aircraft brands. They range from huge modern airplanes to small-sized.
- Airbus A330-300from $363Find
- Airbus A340-600from $377Find
- Boeing 777-300ERfrom $768Find
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.
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