Cheap Flights from Chicago, IL to Milan from $144
Return flight: Milan – Chicago
On Cheapflightsplus.com you will find 490 connecting flights from Chicago to Milan. You can compare airfare deals from 25 airlines and multiple travel sites from $144, 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: $144 (one-way), $247 (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 $144. Take a look at the list of flights with layovers from Chicago to Milan from $144. There’re no direct flights. The fastest connecting flight – 10h 10m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $144 | 15:55 Chicago O'Hare International | 10:55+1 день Milan Malpensa | 12h 0m layover 1h 35m - Lisbon | TAP Portugal | TP242 TP822 |
| from $144 | 15:55 Chicago O'Hare International | 17:20+1 день Milan Malpensa | 18h 25m layover 8h 0m - Lisbon | TAP Portugal | TP242 TP824 |
| from $188 | 15:55 Chicago O'Hare International | 20:05+1 день Milan Malpensa | 21h 10m layover 2h 30m - Lisbon 6h 50m - Valencia | TAP Portugal | TP242 TP1092 FR1445 |
| from $189 | 09:10 Chicago O'Hare International | 13:05+1 день Milan Malpensa | 20h 55m layover 5h 56m - Miami 1h 10m - Lisbon | United Airlines | UA582 TP224 TP822 |
| from $202 | 14:15 Chicago O'Hare International | 12:55+1 день Milan Malpensa | 15h 40m layover 2h 32m - Newark 1h 35m - Lisbon | United Airlines | UA555 TP202 TP822 |
| from $202 | 17:55 Chicago O'Hare International | 18:40+1 день Milan Malpensa | 17h 45m layover 2h 46m - Newark 2h 45m - Lisbon | United Airlines | UA2329 TP204 TP824 |
| from $202 | 08:45 Chicago O'Hare International | 13:05+1 день Milan Malpensa | 21h 20m layover 8h 5m - Newark 1h 45m - Lisbon | American Airlines | AA1211 TP202 TP822 |
| from $202 | 14:15 Chicago O'Hare International | 18:40+1 день Milan Malpensa | 21h 25m layover 2h 30m - Newark 7h 15m - Lisbon | United Airlines | UA555 TP202 TP824 |
| from $204 | 16:05 Chicago O'Hare International | 20:10+1 день Milan Malpensa | 21h 5m layover 4h 0m - Newark 5h 35m - Paris | United Airlines | UA768 BF721 VY9434 |
| from $206 | 18:40 Chicago O'Hare International | 20:10+1 день Milan Malpensa | 18h 30m layover 2h 7m - Newark 5h 35m - Paris | American Airlines | AA1247 BF721 VY9434 |
| from $216 | 18:40 Chicago O'Hare International | 21:00+1 день Milan Linate | 20h 20m layover 2h 7m - Newark 7h 30m - Paris | American Airlines | AA1247 BF721 AZ353 |
| from $216 | 16:05 Chicago O'Hare International | 20:35+1 день Milan Linate | 21h 30m layover 4h 0m - Newark 5h 50m - Paris | United Airlines | UA768 BF721 AZ353 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 08, 2024
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 |
|---|---|---|---|---|
|
15:55 — 10:55
+1 day
|
15:55 — 05:40
TP242
TAP Portugal
Chicago — Lisbon
1h 35m stop
07:15 — 10:55
TP822
TAP Portugal
Lisbon — Milan
|
12h including layover |
Find flight
from$144 |
|
|
15:55 — 17:20
+1 day
|
15:55 — 05:40
TP242
TAP Portugal
Chicago — Lisbon
8h stop
13:40 — 17:20
TP824
TAP Portugal
Lisbon — Milan
|
18h 25m including layover |
Find flight
from$144 |
|
|
05:40 — 13:05
+1 day
|
05:40 — 09:39
AA1411
American Airlines
Chicago — Miami
9h 36m stop
19:15 — 08:20
TP224
TAP Portugal
Miami — Lisbon
1h 10m stop
09:30 — 13:05
TP822
TAP Portugal
Lisbon — Milan
|
24h 25m including layover |
Find flight
from$179 |
|
|
05:40 — 18:40
+1 day
|
05:40 — 09:39
AA1411
American Airlines
Chicago — Miami
9h 36m stop
19:15 — 08:20
TP224
TAP Portugal
Miami — Lisbon
6h 40m stop
15:00 — 18:40
TP824
TAP Portugal
Lisbon — Milan
|
30h including layover |
Find flight
from$183 |
|
|
08:35 — 18:40
+1 day
|
08:35 — 11:43
AA1211
American Airlines
Chicago — Newark
8h 12m stop
19:55 — 07:45
TP202
TAP Portugal
Newark — Lisbon
7h 15m stop
15:00 — 18:40
TP824
TAP Portugal
Lisbon — Milan
|
27h 5m including layover |
Find flight
from$202 |
|
|
08:45 — 13:05
+1 day
|
08:45 — 11:50
AA1211
American Airlines
Chicago — Newark
8h 5m stop
19:55 — 07:45
TP202
TAP Portugal
Newark — Lisbon
1h 45m stop
09:30 — 13:05
TP822
TAP Portugal
Lisbon — Milan
|
21h 20m including layover |
Find flight
from$202 |
|
|
09:10 — 13:05
+1 day
|
09:10 — 13:19
UA582
United Airlines
Chicago — Miami
5h 56m stop
19:15 — 08:20
TP224
TAP Portugal
Miami — Lisbon
1h 10m stop
09:30 — 13:05
TP822
TAP Portugal
Lisbon — Milan
|
20h 55m including layover |
Find flight
from$189 |
|
|
09:10 — 18:40
+1 day
|
09:10 — 13:19
UA582
United Airlines
Chicago — Miami
5h 56m stop
19:15 — 08:20
TP224
TAP Portugal
Miami — Lisbon
6h 40m stop
15:00 — 18:40
TP824
TAP Portugal
Lisbon — Milan
|
26h 30m including layover |
Find flight
from$191 |
|
|
11:05 — 18:40
+1 day
|
11:05 — 14:19
B61712
JetBlue
Chicago — Boston
9h 11m stop
23:30 — 12:45
TP214
TAP Portugal
Boston — Lisbon
2h 15m stop
15:00 — 18:40
TP824
TAP Portugal
Lisbon — Milan
|
24h 35m including layover |
Find flight
from$235 |
|
|
11:22 — 13:05
+1 day
|
11:22 — 14:52
B6312
JetBlue
Chicago — Boston
3h 28m stop
18:20 — 05:45
TP218
TAP Portugal
Boston — Lisbon
3h 45m stop
09:30 — 13:05
TP822
TAP Portugal
Lisbon — Milan
|
18h 43m including layover |
Find flight
from$234 |
|
|
12:00 — 10:55
+1 day
|
12:00 — 15:17
AA832
American Airlines
Chicago — Boston
3h 28m stop
18:45 — 06:00
TP218
TAP Portugal
Boston — Lisbon
1h 15m stop
07:15 — 10:55
TP822
TAP Portugal
Lisbon — Milan
|
15h 55m including layover |
Find flight
from$241 |
|
|
13:02 — 17:20
+1 day
|
13:02 — 16:29
AA496
American Airlines
Chicago — New York
5h 31m stop
22:00 — 09:30
TP210
TAP Portugal
New York — Lisbon
4h 10m stop
13:40 — 17:20
TP824
TAP Portugal
Lisbon — Milan
|
21h 18m including layover |
Find flight
from$242 |
|
|
14:00 — 12:55
+2 days
|
14:00 — 18:17
AA791
American Airlines
Chicago — Miami
24h 58m stop
19:15 — 08:20
TP224
TAP Portugal
Miami — Lisbon
1h stop
09:20 — 12:55
TP822
TAP Portugal
Lisbon — Milan
|
39h 55m including layover |
Find flight
from$179 |
|
|
14:25 — 12:55
+2 days
|
14:25 — 18:48
UA3404
United Airlines
Chicago — Miami
24h 27m stop
19:15 — 08:20
TP224
TAP Portugal
Miami — Lisbon
1h stop
09:20 — 12:55
TP822
TAP Portugal
Lisbon — Milan
|
39h 30m including layover |
Find flight
from$189 |
|
|
16:50 — 12:55
+2 days
|
16:50 — 20:55
AA2323
American Airlines
Chicago — Miami
22h 20m stop
19:15 — 08:20
TP224
TAP Portugal
Miami — Lisbon
1h stop
09:20 — 12:55
TP822
TAP Portugal
Lisbon — Milan
|
37h 5m including layover |
Find flight
from$179 |
|
|
16:50 — 18:40
+2 days
|
16:50 — 20:55
AA2323
American Airlines
Chicago — Miami
22h 20m stop
19:15 — 08:20
TP224
TAP Portugal
Miami — Lisbon
6h 40m stop
15:00 — 18:40
TP824
TAP Portugal
Lisbon — Milan
|
42h 50m including layover |
Find flight
from$185 |
|
|
17:00 — 14:45
+2 days
|
17:00 — 20:06
AA2382
American Airlines
Chicago — Newark
3h 39m stop
23:45 — 11:40
TP212
TAP Portugal
Newark — Porto
23h 40m stop
11:20 — 14:45
TP816
TAP Portugal
Porto — Milan
|
38h 45m including layover |
Find flight
from$203 |
|
|
17:55 — 18:40
+1 day
|
17:55 — 21:09
UA2329
United Airlines
Chicago — Newark
2h 46m stop
23:55 — 12:15
TP204
TAP Portugal
Newark — Lisbon
2h 45m stop
15:00 — 18:40
TP824
TAP Portugal
Lisbon — Milan
|
17h 45m including layover |
Find flight
from$202 |
|
|
18:40 — 08:00
+2 days
|
18:40 — 21:48
AA1247
American Airlines
Chicago — Newark
2h 7m stop
23:55 — 13:05
BF721
Bluebird Cargo
Newark — Paris
17h 25m stop
06:30 — 08:00
VY9432
Vueling
Paris — Milan
|
30h 20m including layover |
Find flight
from$196 |
|
|
18:40 — 20:10
+1 day
|
18:40 — 21:48
AA1247
American Airlines
Chicago — Newark
2h 7m stop
23:55 — 13:05
BF721
Bluebird Cargo
Newark — Paris
5h 35m stop
18:40 — 20:10
VY9434
Vueling
Paris — Milan
|
18h 30m including layover |
Find flight
from$206 |
|
|
19:45 — 20:10
+2 days
|
19:45 — 23:13
F91482
Frontier Airlines
Chicago — Newark
24h 42m stop
23:55 — 13:05
BF721
Bluebird Cargo
Newark — Paris
5h 35m stop
18:40 — 20:10
VY9434
Vueling
Paris — Milan
|
41h 25m including layover |
Find flight
from$194 |
|
|
19:45 — 14:45
+3 days
|
19:45 — 23:13
F91482
Frontier Airlines
Chicago — Newark
24h 32m stop
23:45 — 11:40
TP212
TAP Portugal
Newark — Porto
23h 40m stop
11:20 — 14:45
TP816
TAP Portugal
Porto — Milan
|
60h including layover |
Find flight
from$196 |
|
|
20:50 — 14:45
+3 days
|
20:50 — 23:58
AA2918
American Airlines
Chicago — Newark
23h 47m stop
23:45 — 11:40
TP212
TAP Portugal
Newark — Porto
23h 40m stop
11:20 — 14:45
TP816
TAP Portugal
Porto — Milan
|
58h 55m including layover |
Find flight
from$203 |
|
|
20:50 — 08:00
+3 days
|
20:50 — 23:58
AA968
American Airlines
Chicago — Newark
23h 57m stop
23:55 — 13:05
BF721
Bluebird Cargo
Newark — Paris
17h 25m stop
06:30 — 08:00
VY9432
Vueling
Paris — Milan
|
52h 10m including layover |
Find flight
from$227 |
|
|
21:30 — 19:55
+2 days
|
21:30 — 00:59
UA1774
United Airlines
Chicago — Newark
22h 56m stop
23:55 — 13:20
BF721
Bluebird Cargo
Newark — Paris
5h 10m stop
18:30 — 19:55
VY9434
Vueling
Paris — Milan
|
39h 25m including layover |
Find flight
from$201 |
|
|
21:30 — 14:45
+3 days
|
21:30 — 00:59
UA1774
United Airlines
Chicago — Newark
22h 46m stop
23:45 — 11:40
TP212
TAP Portugal
Newark — Porto
23h 40m stop
11:20 — 14:45
TP816
TAP Portugal
Porto — Milan
|
58h 15m including layover |
Find flight
from$203 |
|
*Departure and arrival times - local. Updated on May 8, 2024
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 23:30 from 7 Chicago airports and arrive 05:15 to 23:30 to 4 Milan airports. Average flight time is 18h 5m.
- The fastest flight 10h 10m
- Average flight time 18h 5m
- The earliest flight 05:15
- The latest flight 23:30
- Distance 4530 ml
What is the lowest airfare Chicago to Milan?
The cheapest plane ticket found by our users is $144. This airfare is for economy class on one-way TP242 flight by TAP Portugal for November 29, 2020 which leaves O'Hare International in Chicago at 15:55 am and arrives at Milan Malpensa at 23:30.
Economy class
$144
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Milan is served by 25 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Delta Air Lines Inc. - 76 departures per week at the price of from $ 241 . And the most expensive tickets are offered by Finnair airline - from $ 1492.
Direct flights
There’re no direct flights on this route. Try flights with stops.
Connecting Flights
There are 490 flights with layovers on the route. The fastest connecting flight is UA972 by United Airlines takes 10h 10m and the cheapest is TP242 by TAP Portugal for $144.
- from $241Find
- from $189Find
- from $291Find
- from $364Find
- LO - LOTfrom $491Find
- LX - SWISS International Air Linesfrom $408Find
- WN - Southwest Airlinesfrom $248Find
- SK - SASfrom $745Find
- IB - Iberiafrom $435Find
- SN - Brussels Airlinesfrom $407Find
- AA - American Airlinesfrom $179Find
- KL - KLMfrom $402Find
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 $144Find
- Midway-MDWfrom $248Find
- 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 25 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.
- Airbus A330-900 NEOfrom $144Find
- Airbus A320-100/200from $196Find
- Boeing 737-900from $202Find
- Airbus A320from $217Find
- Embraer Lineage 1000from $221Find
- Embraer 175from $241Find
- Embraer 175 (short wing)from $257Find
- Embraer 190from $284Find
- Canadair CRJ900from $362Find
- Bombardier CRJ 900from $371Find
Top Domestic Destinations from Chicago
You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.
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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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