One Way

Popular Filters

One Way Price

CAD 1,097 CAD 2,500

Duration

11 h 35 m 38 h 0 m

Stops From Milan

Departure From Milan

Before 6 AM

CAD 1,097

6 AM - 12 PM

CAD 1,554

12 PM - 6 PM

CAD 1,406

After 6 PM

CAD 1,308

Arrival at Chicago

6 AM - 12 PM

CAD 1,690

12 PM - 6 PM

CAD 1,097

After 6 PM

CAD 1,406

Alliances & Airlines

Oneworld

()

SkyTeam

(4)

Star Alliance

(19)

+ 2 more

Layover Airports

+ 3 more

Layover Duration

55 m 25 h 0 m

Milan To Chicago Flights

Book Milan to Chicago flight tickets at lowest price. Get best deals on your upcoming Milan to Chicago flights only on MakeMyTrip. Also Book Chicago to Milan Flights. Currently 20 flights flying from Milan to Chicago. To save maximum on flight booking click on below Fare Calendar button and choose your dates.Avail Zero Cancellation for flight bookings.


Sorted By:
Departure
Duration
Arrival
Price
TAP Portugal

CAD 1,097

Milan to Chicago , 3 Apr

TAP Portugal TP | 829

05:50

Fri, 3 Apr 26

Terminal T1

Milan, Italy

03 h

07:50

Fri, 3 Apr 26

Terminal T1

Lisbon, Portugal

BAGGAGE : CHECK INCABIN

Information not available

TAP Portugal TP | 243

12:35

Fri, 3 Apr 26

Terminal T1

Lisbon, Portugal

09 h 25 m

16:00

Fri, 3 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

TAP Portugal

CAD 1,308

Milan to Chicago , 3 Apr

TAP Portugal TP | 827

20:00

Fri, 3 Apr 26

Terminal T1

Milan, Italy

03 h

22:00

Fri, 3 Apr 26

Terminal T1

Lisbon, Portugal

BAGGAGE : CHECK INCABIN

Information not available

TAP Portugal TP | 243

12:40

Sat, 4 Apr 26

Terminal T1

Lisbon, Portugal

09 h 25 m

16:05

Sat, 4 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

ITA Airways

CAD 1,406

Milan-Linate Airport to Chicago , 3 Apr

ITA Airways AZ | 2061

16:30

Fri, 3 Apr 26

Milan-Linate Airport, Italy

01 h 10 m

17:40

Fri, 3 Apr 26

Terminal T1

Rome - Fiumicino Apt, Italy

BAGGAGE : CHECK INCABIN

Information not available

ITA Airways AZ | 614

10:25

Sat, 4 Apr 26

Terminal T1

Rome - Fiumicino Apt, Italy

09 h 15 m

13:40

Sat, 4 Apr 26

Terminal E

Boston, United States

BAGGAGE : CHECK INCABIN

Information not available

ITA Airways AZ | 4384 | Operated By United Airlines

16:28

Sat, 4 Apr 26

Terminal B

Boston, United States

03 h

18:28

Sat, 4 Apr 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

LOT Polish Airlines

CAD 1,498

Milan to Chicago , 3 Apr

LOT Polish Airlines LO | 320

19:40

Fri, 3 Apr 26

Terminal T1

Milan, Italy

02 h 10 m

21:50

Fri, 3 Apr 26

Warsaw, Poland

BAGGAGE : CHECK INCABIN

Information not available

LOT Polish Airlines LO | 3

16:40

Sat, 4 Apr 26

Warsaw, Poland

10 h 10 m

19:50

Sat, 4 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

ITA Airways

CAD 1,535

Milan-Linate Airport to Chicago , 3 Apr

ITA Airways AZ | 2059

16:00

Fri, 3 Apr 26

Milan-Linate Airport, Italy

01 h 10 m

17:10

Fri, 3 Apr 26

Terminal T1

Rome - Fiumicino Apt, Italy

BAGGAGE : CHECK INCABIN

Information not available

ITA Airways AZ | 614

10:25

Sat, 4 Apr 26

Terminal T1

Rome - Fiumicino Apt, Italy

09 h 15 m

13:40

Sat, 4 Apr 26

Terminal E

Boston, United States

BAGGAGE : CHECK INCABIN

Information not available

ITA Airways AZ | 4384 | Operated By United Airlines

16:28

Sat, 4 Apr 26

Terminal B

Boston, United States

03 h

18:28

Sat, 4 Apr 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

ITA Airways

CAD 1,554

Milan-Linate Airport to Chicago , 3 Apr

ITA Airways AZ | 2045

11:30

Fri, 3 Apr 26

Milan-Linate Airport, Italy

01 h 10 m

12:40

Fri, 3 Apr 26

Terminal T1

Rome - Fiumicino Apt, Italy

BAGGAGE : CHECK INCABIN

Information not available

ITA Airways AZ | 614

10:25

Sat, 4 Apr 26

Terminal T1

Rome - Fiumicino Apt, Italy

09 h 15 m

13:40

Sat, 4 Apr 26

Terminal E

Boston, United States

BAGGAGE : CHECK INCABIN

Information not available

ITA Airways AZ | 4384 | Operated By United Airlines

16:28

Sat, 4 Apr 26

Terminal B

Boston, United States

03 h

18:28

Sat, 4 Apr 26

Terminal T1

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

LOT Polish Airlines

CAD 1,599

Milan to Chicago , 3 Apr

LOT Polish Airlines LO | 320

19:40

Fri, 3 Apr 26

Terminal T1

Milan, Italy

02 h 10 m

21:50

Fri, 3 Apr 26

Warsaw, Poland

BAGGAGE : CHECK INCABIN

Information not available

LOT Polish Airlines LO | 1

12:00

Sat, 4 Apr 26

Warsaw, Poland

10 h 10 m

15:10

Sat, 4 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

TAP Portugal

CAD 1,617

Milan to Chicago , 3 Apr

TAP Portugal TP | 825

17:25

Fri, 3 Apr 26

Terminal T1

Milan, Italy

03 h

19:25

Fri, 3 Apr 26

Terminal T1

Lisbon, Portugal

BAGGAGE : CHECK INCABIN

Information not available

TAP Portugal TP | 243

12:40

Sat, 4 Apr 26

Terminal T1

Lisbon, Portugal

09 h 25 m

16:05

Sat, 4 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Turkish Airlines

CAD 1,690

Transit Visa may be required

Milan to Chicago , 3 Apr

Turkish Airlines TK | 1900

20:10

Fri, 3 Apr 26

Terminal T1

Milan, Italy

02 h 55 m

00:05

Sat, 4 Apr 26

Istanbul, Turkey

BAGGAGE : CHECK INCABIN

Information not available

Turkish Airlines TK | 185

06:30

Sat, 4 Apr 26

Istanbul, Turkey

11 h 10 m

09:40

Sat, 4 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Lufthansa, United Airlines

CAD 2,271

Milan-Linate Airport to Chicago , 3 Apr

Lufthansa LH | 1853 | Operated By Air Dolomiti

13:40

Fri, 3 Apr 26

Milan-Linate Airport, Italy

01 h 05 m

14:45

Fri, 3 Apr 26

Terminal T2

Munich, Germany

BAGGAGE : CHECK INCABIN

Information not available

United Airlines UA | 8855 | Operated By Lufthansa

15:40

Fri, 3 Apr 26

Terminal T2

Munich, Germany

09 h 35 m

18:15

Fri, 3 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Chicago Address

Milan Address

Milan to Chicago Flights Information:-

Looking for Milan to Chicago Flight? Here’s all you need to know! For convenience and to save time, pick the airport that is closest to your destination. The nearest airport to Chicago is Chicago Midway Intl and the IATA code for the same is CHI.
Currently, there are 8 airlines operating flights between the two destinations and approximately 20 flights take off from Milan to Chicago every week.

Need information on Milan to Chicago airfare?

The minimum airfare for a Milan to Chicago flight would be 1097, which may go up to 2451 depending on the route, booking time and availability.
It is recommended that you book a round-trip, since it always works out to be more economical.

Flight Details for Milan to Chicago

If you are looking for Milan to Chicago flights, there is no dearth of options to choose from. Several reputed airlines currently offer both direct and indirect flights between the two destinations. Some of these are Air Dolomiti, Brussels Airlines, ITA Airways, LOT Polish Airlines, Lufthansa, TAP Portugal, Turkish Airlines, United Airlines. Out of these, only 0 airlines operate direct flights. Indirect flights may involve more travel time, but they usually cost lesser than direct flights.

The number of flights operated by each airline is as follows:Air Dolomiti : 2, Brussels Airlines : 2, ITA Airways : 2, LOT Polish Airlines : 2, Lufthansa : 2, TAP Portugal : 2, Turkish Airlines : 2, United Airlines : 2

To board the first Milan to Chicago flight, choose TAP Portugal, which departs at 05:50 The last flight for this route is Turkish Airlines, departing at 20:10

Chicago Airport Information

Chicago Midway Intl

About Milan (MIL)

Famously known for its historic richness and modernised sights, Milan, stands firm as the financial hub of Italy. The city has fetched the second most populous city tag and still manages to be the urban area of the country. Milan has re-formed itself after the destructive war, and now it appears no less than a striking cosmopolitan location. What makes Milan an interesting location for the tourists is the zest to live life with all its diverse colours and shades. The city enjoys every moment from shopping, playing, singing, theatres, to the exuberant night-life. It is considered as the fashion capital of Italy, fashionistas, media and socialites from all over the world gather at the place to capture the true essence of fashion. Some of the scenic locations of the city includes, 'The Duomo', which is by far the biggest Gothic Cathedrals in the whole world, 'The Brera art gallery', 'La Scala, one of the famous opera houses, 'The Pirelli Tower', a great example of the modern Italian architecture, 'The Castello Sforzesco', and 'The San Siro'. The cherry on the cake is the famous painting “Leonardo Da Vinci”, which has time and again earned laurels for the city. The tourists can comfortably plan a trip to Milan at any time of the year, as the city observes a considerate weather throughout the year. The best way to get in to the city is to travel by air. One can land at the Malpensa Airport, Orlo Al Serio Airport, or Linate Airport, or can opt for the other mediums, like trains, buses and cars, depending on their suitability and comfort. With numerous scenic museums, palaces, building, monuments, and streets, Milan forms itself into an exquisite bouquet of beautiful surroundings. The culture of serving 'Aperitivo' is well established in Milan. In this meal, many bars offers drinks and cocktails at a fixed price, and the drinks are well complemented with snacks and small appetizers. There are other restaurants as well who serve delectable cuisines to the visitors. The night-life of the city is happening and vibrant with places to go and mingle with your dear ones. MakeMyTrip offers plans and deals to help their customers enjoy several benefits through their trip. The online booking facility, cheap offers and economical deals makes the process a mere cakewalk for yearning customers.

About Chicago (CHI)

Chicago is a dazzling city that captivates visitors with its vibrant atmosphere and stunning architecture. For travelers from Canada, Chicago offers an array of experiences, from world-class museums to picturesque waterfront parks. The city's rich cultural heritage and dynamic arts scene make it a must-visit destination.

Best Time to Visit

The ideal time to visit Chicago is during the spring (April to June) and fall (September to November) when the weather is pleasant, and the city is alive with festivals. Summers can be warm and bustling, while winters are cold and snowy, perfect for those who enjoy winter sports.

Getting There

Chicago is served by two major airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). There are numerous flights to Chicago from Canada, including direct flights from Toronto, Vancouver, and Montreal. Ensure you have a valid passport and check visa requirements before booking your flight. Airlines such as Air Canada and United Airlines offer cheap flights to Chicago, making it accessible for Canadian travelers.

Where to Stay

Chicago boasts a wide range of accommodation options to suit all budgets. For luxury, consider staying in the Magnificent Mile area, home to upscale hotels and designer boutiques. Budget travelers can find affordable options in neighborhoods like Lincoln Park and Wicker Park. The Loop, Chicago's downtown area, is ideal for tourists wanting to be close to major attractions.

Must-See Places & Experiences

Chicago is renowned for its iconic landmarks and cultural institutions. Don't miss:
• The Art Institute of Chicago
• Millennium Park and the famous Cloud Gate sculpture
• Navy Pier, offering entertainment and stunning lake views
• Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium
• The Magnificent Mile for shopping
• Willis Tower Skydeck for breathtaking city views

Local Transportation

Chicago's public transportation system is efficient and easy to navigate. The Chicago Transit Authority (CTA) operates buses and trains that connect the city and suburbs. Taxis and ride-sharing services like Uber and Lyft are readily available. For a scenic option, consider renting a bike and exploring the city's extensive bike paths.

Food & Dining

Chicago's culinary scene is diverse and delicious. Be sure to try local specialties such as deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. The city offers a variety of dining options, from Michelin-starred restaurants to casual eateries. Recommended spots include:
• Lou Malnati's Pizzeria for deep-dish pizza
• Portillo's for Chicago-style hot dogs
• Alinea for an upscale dining experience

Practical Travel Tips

• Currency: The US Dollar (USD)
• Language: English
• Safety: Chicago is generally safe, but be aware of your surroundings and avoid less populated areas at night
• Useful Apps: Download the CTA Transit app for public transport information and OpenTable for restaurant reservations

Start planning your trip and book your Chicago flight today. With so much to offer, Chicago is a city that promises unforgettable experiences for Canadian travelers.

Frequently Asked Questions - Milan to Chicago Flights

Can I find cheap accommodation near to airport when travelling from Milan to Chicago?

There are several accommodation options available near the Chicago Midway Intl. You can check for both budget friendly and well as five star accommodation near the airport depending on your requirement and budget. These hotels are mostly suitable for business travellers.

Is passport mandatory to travel from Milan to Chicago?

When making an international trip, passport is mandatory as it defines your identity to the other nation officials. The VISA norms may differ from country to country, which means some would allow Visa on arrival and others may require you to obtain visa in advance. But the availability of passport is mandatory at the time of departure and arrival as well.

How do MakeMyTrip finds the lowest available dare for flights from Milan to Chicago?

MakeMyTrip is a popular travel portal that also works as a travel search engine that allows you to see best available results for your flight search. Every time you make search for flights to any destination, the MMT algorithm picks all the available air carriers for the route and filter rates basis on the cheapest fare available in their system. At MMT, you can not only search flights on the basis of the fare, but you can also see which flight offers direct route, which has multiple stop-overs, baggage allowance, in-flight meal options, cancellation policy, etc. You can also check available discounts offered by payments partners and air carriers when booking the flight.

Which airlines offer cheapest airfare from Milan to Chicago?

There is no set pricing for airlines to offer cheap flight fare from Milan to Chicago. These fares are mostly decided on the basis of algorithms followed by air carriers to final the prizing based on demand. However, some multiple route flights with stop-overs offer cheap flights as compared to direct flight departing from Milan to Chicago.

Can I cancel my ticket from Milan to Chicago without cancellation charges?

To avoid cancellation charges on your air tickets, you need to make a selection at the time of booking for ZERO cancellation. Please note, the zero cancellation facility is chargeable with minimum amount and can help you save a lot at the time sudden cancellations.

Is there a way to make flexible departure date bookings for your Milan to Chicago flight tickets?

Some travel portals like MakeMyTrip offer flexible departure and arrival booking option with certain air carrier when booking from Milan to Chicago. You can check the flexible booking flight options once you get the results filters based on your search and make the booking accordingly. Please note, some airlines make charge extra for flexible travel dates.

What is the best time to book cheap flight tickets from Milan to Chicago?

To get cheap flight tickets from Milan to Chicago, the best time would be to plan your trip during the off season. At that time the flight tickets are usually cheaper than the peak season and the accommodation booking is also available at the affordable price. The other way of booking cheap flight tickets from Milan (MIL) to Chicago (CHI) is to book atleast 4 weeks in advance before your departure date to get competitive pricing on your tickets even during the peak season.