Cheap Flights from Chicago, IL to Milan from $220
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 $220, 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.
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
Best Flights from Chicago to Milan Today
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $491 | 21:35 Chicago O'Hare International | 13:20+1 день Milan Malpensa | 8h 45m | United Airlines | UA416 |
| from $220 | 22:15 Chicago O'Hare International | 22:00+1 день Milan Malpensa | 16h 45m layover 6h 25m - Reykjavik | Icelandair | FI856 FI592 |
| from $272 | 18:15 Chicago O'Hare International | 00:50+2 дня Milan Malpensa | 23h 35m layover 12h 50m - Lisbon | TAP Portugal | TP244 TP828 |
| from $222 | 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 $253 | 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 |
The cheapest months to travel to Milan are august (from 220 $), july (from 221 $), october (from 222 $).
The most expensive months are november (from 707 $), february (from 654 $), december (from 631 $).
What is the lowest airfare Chicago to Milan?
The cheapest plane ticket found by our users is $220. 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.
Flight Schedule Chicago (Illinois) to Milan
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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 $ 465 . And the most expensive tickets are offered by Lufthansa airline - from $ 568.
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 $491.
- UA - United Airlinesfrom $491Find
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 $220.
- KL - KLMfrom $465Find
- AC - Air Canadafrom $290Find
- FI - Icelandairfrom $220Find
- LO - LOTfrom $563Find
- OS - Austrian Airlinesfrom $521Find
- EI - Aer Lingusfrom $535Find
- AF - Air Francefrom $426Find
- JU - Air Serbiafrom $352Find
- LX - SWISS International Air Linesfrom $464Find
- UA - United Airlinesfrom $493Find
- F9 - Frontier Airlinesfrom $289Find
- PD - Porter Airlinesfrom $359Find
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 $220Find
- Midway-MDWfrom $292Find
- 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?
- 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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