Cheap Flights from Chicago, IL to Milan from $357
On Cheapflightsplus.com you will find 2 direct and 463 connecting flights from Chicago to Milan. You can compare airfare deals from 23 airlines and multiple travel sites from $357, 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 06:00 to 22:35 from 7 Chicago airports and arrive 06:00 to 22:35 to 4 Milan airports. Average flight time is 8h 40m.
- The fastest flight 8h 40m
- Average flight time 8h 40m
- The earliest flight 06:00
- The latest flight 22:35
- Distance 4530 ml
Best Flights from Chicago to Milan Today
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $606 | 21:40 Chicago O'Hare International | 13:20+1 день Milan Malpensa | 8h 40m | United Airlines | UA416 |
| from $3892 | 21:40 Chicago O'Hare International | 13:20+1 день Milan Malpensa | 8h 40m | Lufthansa | LH8871 |
| from $357 | 19:15 Chicago O'Hare International | 08:30+2 дня Milan Malpensa | 30h 15m layover 19h 35m - Copenhagen | SAS | SK944 SK683 |
| from $500 | 17:10 Chicago O'Hare International | 15:40+1 день Milan Malpensa | 15h 30m layover 5h 55m - Paris | Air France | AF137 U24545 |
| from $400 | 09:40 Chicago Midway | 12:45+1 день Milan Malpensa | 20h 5m layover 5h 15m - Toronto 3h 15m - Lisbon | Porter Airlines | PD2388 TP258 U23874 |
| from $496 | 21:40 Chicago O'Hare International | 20:05+1 день Milan Milan Bergamo (Orio al Serio) | 15h 25m layover 1h 35m - Munich 1h 40m - Warsaw | Lufthansa | LH435 LH1614 W61433 |
The cheapest months to travel to Milan are april (from 226 $), july (from 226 $), october (from 357 $).
The most expensive months are june (from 1 426 $), may (from 708 $), june (from 440 $).
What is the lowest airfare Chicago to Milan?
The cheapest plane ticket found by our users is $357. This airfare is for economy class on one-way SK944 flight by SAS for April 7, 2026 which leaves O'Hare International in Chicago at 19:15 am and arrives at Milan Malpensa at 08:30.
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 2 low-cost airlines. Most of the flights on this route are operated by KLM - 3 departures per week at the price of from $ 3077 . And the most expensive tickets are offered by Etihad Airways airline - from $ 28862.
Direct flights
There are 2 nonstop flights on the route. The fastest direct flight is UA416 by United Airlines takes 8h 40m and the cheapest is SK944 by SAS for $606.
- UA - United Airlinesfrom $606Find
- LH - Lufthansafrom $3892Find
Connecting Flights
There are 463 flights with layovers on the route. The fastest connecting flight is LH431 by Lufthansa takes 10h 55m and the cheapest is SK944 by SAS for $357.
- KL - KLMfrom $3077Find
- AC - Air Canadafrom $569Find
- FI - Icelandairfrom $1883Find
- LO - LOTfrom $3760Find
- EI - Aer Lingusfrom $597Find
- OS - Austrian Airlinesfrom $2598Find
- AF - Air Francefrom $496Find
- LX - SWISS International Air Linesfrom $522Find
- UA - United Airlinesfrom $631Find
- ET - Ethiopian Airlinesfrom $5721Find
- PD - Porter Airlinesfrom $400Find
- EY - Etihad Airwaysfrom $28862Find
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 $357Find
- Midway-MDWfrom $400Find
- 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
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.
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- 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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