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
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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 28, 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
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Business class
?
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First class
?
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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 $241
    Find
  • from $189
    Find
  • from $291
    Find
  • from $364
    Find
  • LO - LOT
    from $491
    Find
  • LX - SWISS International Air Lines
    from $408
    Find
  • WN - Southwest Airlines
    from $248
    Find
  • SK - SAS
    from $745
    Find
  • IB - Iberia
    from $435
    Find
  • SN - Brussels Airlines
    from $407
    Find
  • AA - American Airlines
    from $179
    Find
  • KL - KLM
    from $402
    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 $144
    Find
  • Midway-MDW
    from $248
    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

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.

    To find a plane ticket, please select dates.

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