S$ 357 Cheap Flights from Chicago to Milan (CHI-MIL)

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Cheap Flights from Chicago to Milan starting at S$ 357

Book one-way or return flights from Chicago to Milan from as little as S$ 357. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Chicago to Milan? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to Milan. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Cheapest Airlines flying from Chicago to Milan

View airlines operating flights from Chicago to Milan. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

American Airlines

From S$ 357

Frontier Airlines

From S$ 408

Spirit Airlines

From S$ 412

Icelandair

From S$ 435

United Airlines

From S$ 572

Scandinavian Airlines

From S$ 593

IBERIA

From S$ 635

Jetblue Airways

From S$ 635

Southwest Airlines

From S$ 670

British Airways

From S$ 678

ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Milan

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Milan.

Cheapest
ORD
22:45
30h 5m
1 transfer
MXP
11:50
O'Hare International Airport - Milan Malpensa Airport
Mon, Jul 8American Airlines
S$ 357
ORD
09:45
19h 40m
2 transfer
LIN
12:25
O'Hare International Airport - Linate Airport
Sun, Jul 21American Airlines
S$ 375
ORD
22:45
27h 50m
1 transfer
BGY
09:35
O'Hare International Airport - Orio al Serio International Airport
Mon, Jul 8American Airlines
S$ 389
ORD
22:45
27h 50m
1 transfer
BGY
09:35
O'Hare International Airport - Orio al Serio International Airport
Mon, Jul 8American Airlines
S$ 389
Find More Flights

Frequently Asked Questions

When to buy flight tickets from Chicago (CHI) to Milan (MIL) the cheapest?
Airlines adjust prices for flights from Chicago to Milan based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much is a flight from Chicago (CHI) to Milan (MIL) cost?
According to Trip.com's data, the lowest price is around S$ 2,091.
How long is a flight from Chicago (CHI) to Milan (MIL)?
It takes about 8 hours 45 minutes to fly from Chicago (CHI) to Milan (MIL).
What is the transportation method from the main airport to downtown in Milan?
- The distance from Milan Malpensa Airport to downtown is about 40km, by taxi about 1 hour.
- The distance from Linate Airport to downtown is about 7km, by taxi about 20 minutes.
- The distance from Orio al Serio International Airport to downtown is about 46km, by taxi about 1 hour.
What are the most popular airlines that fly from Chicago (CHI) to Milan (MIL)?
Airlines with flights from Chicago (CHI) to Milan (MIL): Air Canada, United Airlines, Austrian Airlines, Brussels Airlines and Swiss Airlines.
What's the most popular airline for direct flights from Chicago (CHI) to Milan (MIL)?
United Airlines operates 2 direct flights from Chicago (CHI) to Milan (MIL).
How many airports in Milan?
There are 4 airports near Milan: Milan Malpensa Airport, Linate Airport, Orio al Serio International Airport and Parma Giuseppe Verdi Airport.

How to find a cheap flight from Chicago to Milan

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Milan. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

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Flight Information from Chicago to Milan

Cheapest direct flight price	S$ 356
Cheapest return ticket price	S$ 891
Cheapest month	April
Peak season for travel	June
Flight distance	7,290.86km
Average flight time	8 hours 45 minutes
Popular airline	British Airways