Business Class Flight Deals from Chicago to Milan from $1594

Planning Your Business-Class Trip

If you’re in Chicago and Milan is your next destination, then you have many business-class flights to pick from. Chicago has two major airports, O’Hare International Airport (ORD) and Midway International Airport (MDW). However, only O’Hare has direct flights to Milan in business class. If you wish to depart from Midway, your flight will have a layover.

From Chicago O’Hare International Airport (ORD), United Airlines operates nonstop flights to Milan Malpensa Airport (MXP). This flight lasts approximately 9 hours and may cost from $4,200 to as high as $17,000 for flights during peak season and purchased at the last minute.

On this route, United also operates flights with a layover at Newark Liberty International Airport (EWR). Such a flight may take from 12 to 19 hours, depending on the layover length, and has a price that ranges from $4,000 to $10,500.

During your layover at Newark Liberty International Airport (EWR), you can relax in the United Polaris Lounge in Terminal C. Here, you will find plenty of seats, showers, work booths, a bar, a buffet, and a restaurant. The design of the lounge and its luxury is something you won’t find in many other lounges. There are also two other United Club lounges you can visit at EWR. If you have some time to spare before your flight, in Terminal C, you will find many celebrity-chef-run restaurants, like Saison by Alain Ducasse and Kaedama, a popular ramen bar. If you’re not up for a meal, you can enjoy the art exhibits displayed throughout the terminal.

If you are flying from Chicago Midway International Airport (MDW), you will have a flight with a layover. Delta Air Lines operates business-class flights on this route with layovers at Atlanta Hartsfield-Jackson International Airport (ATL) or New York John F. Kennedy International Airport (JFK). From Midway (MDW) to Milan Malpensa Airport (MXP), a flight may last from 14 to 30 hours, depending on how long your layover is. For such a flight, the price ranges from $3,700 to $9,000, depending on when you book and when you’re planning to fly.

If you have a layover at Atlanta Hartsfield-Jackson International Airport (ATL), you can rest in one of the many Delta Sky Clubs. Each lounge offers different amenities, but the main ones are the same. You will find plenty of seating options, a buffet, a bar, free Wi-Fi, and comfortable working areas. The Delta Sky Club from Concourse F, Mezzanine Level, has showers, as well as a beautiful view of the tarmac — something that the other lounges don’t have. The airport also has a Plane Train, so you can explore the airport’s terminals, shops, and restaurants before boarding your flight to Milan.

If you stop at John F. Kennedy International Airport (JFK) on your way to Milan, you can access the two Delta Sky Club lounges from Terminal 4, Concourses A and B. Both lounges offer great basic amenities such as Wi-Fi, power outlets, a buffet, and a bar. The lounge in Concourse B also has showers and a space from which you can see planes taking off and landing. At JFK, you will also find a variety of dining options, such as Deep Blue Sushi and La Vie, which is a French bistro.

If you’re thinking of departing from New York, John F. Kennedy International Airport (JFK), ITA Airways operates one-stop business-class flights via Rome Fiumicino Airport (FCO) to Milan Linate Airport (LIN). Such a flight takes between 11 and 19 hours, depending on how long your layover is, and comes with a price that ranges from $2,400 to $10,000. If you book closer to your departure date or fly during peak season, you will have to pay more for your ticket.

When you arrive in Rome at Fiumicino Airport (FCO), you can relax in the Piazza di Spagna lounge. Here, you can get a taste of Italy in terms of services, food, and hospitality. The lounge offers plenty of comfortable seating options, free Wi-Fi, and bathrooms with showers. When it comes to food, there is a self-service cold buffet and bar area with a bartender, which is available all day long. There is also a menu from which you can order warm food as well. And, of course, you can also enjoy a warm, freshly made pizza here.

Outside the lounge, you can choose from an even wider selection of Italian food. At Bufala di Fattorie Garofalo, you can purchase delicious Italian creamy cheeses. In Terminal 1, you can find Eataly — a marketplace of artisanal Italian food and beverages. Here, you can enjoy a freshly prepared meal or just purchase local products.

If you choose to fly to Milan from San Francisco International Airport (SFO), your flight will have at least one stop. British Airways has one of the most popular and comfortable one-stop options on this route, with a layover at London Heathrow Airport (LHR) before landing at Milan Malpensa Airport (MXP). The travel time is typically 14 to 20 hours, depending on how long your layover is. For such a flight, you could pay between $3,300 and $9,500. If you book very close to your departure date, you’ll have to pay more than if you were to book at least 3 months in advance.

During your layover at LHR, you can rest in one of the four British Airways Galleries lounges. All lounges cover travelers’ basic necessities. In each of them, you’ll find plenty of seating options, free Wi-FI, a buffet and a bar, restrooms, TVs, and business centers. If you do wish for more from a lounge, then you can visit British Airways Galleries South First and Galleries Club Lounge. Here, the dining experience is even better with à la carte dining and waiter service. If you wish to freshen up before your next flight, you can use one of the well-equipped showers in the lounge. If you have time before your flight, you can do some shopping, have a meal at one of the highly rated restaurants, or relax with wellness services like spas and short-stay hotel rooms within the terminal.

When planning your trip to Milan, keep in mind that the closer to the departure date you book the ticket, the higher the cost may be. You can save money if you book your flight a few months in advance and choose one with a layover instead of a direct flight.

Choose the Best Airline for Your Flight to Milan

If you are planning to fly from Chicago to Milan, you can depart from either Chicago O’Hare International Airport (ORD) or Chicago Midway International Airport (MDW). O’Hare is the bigger airport, from which more major airlines operate flights. British Airways, Lufthansa, Delta Air Lines, United Airlines, Air France, Iberia, KLM, Emirates, Turkish Airlines, and Swiss International Air Lines are the ones that stand out when you search for flights on this route.
Delta Air Lines is the only one that flies from the Midway airport out of the major airlines, so you might want to consider this if you’re thinking of departing from there.

In this section, we will go over three major airlines that fly this route frequently: British Airways, United Airlines, and Delta Air Lines. These airlines offer consistent good services on their routes and are among the most popular choices for passengers flying transatlantic.

British Airways

Lounge Access & Perks: At Chicago O’Hare (ORD), British Airways operate the British Airways Lounge in Terminal 5, exclusively for its premium passengers. However, in April 2024, the airline moved the departing flights to Terminal 3. Since the lounge is no longer available, you can choose to relax in one of the three American Airlines Admirals Club lounges. There is also an American Airlines Flagship Lounge at ORD.

All these lounges offer the basics you would need at an airport. You will find plenty of comfortable seating options, power outlets, bathrooms, free Wi-Fi, a buffet, a bar, and working areas.

In the lounge located in Concourse G, in addition to the buffet food options, you can order something from the available menu. This place is great if you wish for a lounge full of light and a quiet room to take care of work matters.

The lounge located in Concourse H/K is the biggest out of the three and has showers, conference rooms, and a kids' room. If any of these sound like something you need before your flight, then this lounge might be perfect for you.

The lounge from Concourse L is the smallest and the least crowded one.

The American Airlines Flagship Lounge is a larger and more luxurious option. Here, the bar comes with a large selection of liquor and spirits, wines, beer, coffee, tea, and many soft drinks. The buffet also has plenty of hot and cold food options to choose from, as well as fruits and desserts. Orecchiette Porcini Bolognese, Tuscan Chicken, Roasted Yukon Gold Potatoes, and Creamy Tomato Bisque soups are just a few of the dishes you will find at the buffet. This lounge also has a nap room and a TV room.

There are multiple lounges available for you at Chicago O’Hare (ORD) if you fly with British Airways; pick the one that suits your needs the best.

Seat Type & Cabin Layout: On this route, British Airways uses Boeing 777 and 787-10 planes. These planes have a 1-2-1 configuration, with two seats in the middle and one by the windows, so you get direct aisle access no matter where you sit. The seats lie flat and have doors as well. If you're sitting in the middle, you will have a divider you can put up if you wish for more privacy. Your seat also comes with plenty of storage space, bedding, a TV, power outlets, headphones, and an amenity kit. The amenity kit will contain skincare products, socks, an eye mask, earplugs, and a dental kit — everything you need for a comfortable trip.

Meal & Beverage Service: With British Airways, you will get multi-course dining with menus inspired by British and international cuisine. You will be served a starter, a main course, dessert, and cheese. Lemon-grilled chicken breast, wild rice and bulgur salad, shrimp pot pie, passion fruit and blackberry panna cotta are a few of the options on the main course menu. Along with your meal, you can have a drink of your choice, be it wine, spirits, or non-alcoholic hot and cold beverages. If you want to, you can pre-order your meal at least 24 hours before your flight.

Cost Range: British Airways tickets from Chicago to Milan may cost from $3,700 to $10,600 for a round-trip flight. The price depends on when you book your ticket and in which month of the year you’re planning to travel. For example, if you book a ticket for June in April, it will be considerably cheaper than buying it at the last minute, which might cost you over $9,000.

Frequent Flyer Program: Airways Executive Club, which should be renamed The British Airways Club in 2025, is British Airways’ frequent-flyer program. After signing up for this program, you can earn miles, or Avios, based on the fare class and distance flown on your trip. You can later use these points to buy a ticket as well as other products from British Airways and its Oneworld partners, including American Airlines and Iberia. For this route, you would need at least 100,000 Avios. You will be able to see exactly how many Avios you need to get a ticket after you log into your account and choose a flight.

British Airways is ideal for you if you wish to taste British cuisine on board, have a seat with lots of privacy, and have access to many great lounges before your flight.

United Airlines

Lounge Access & Perks: At Chicago O’Hare International Airport (ORD), United Airlines operates four United Club lounges and one United Polaris lounge, which closed down in 2025 for renovations. Each lounge has a workstation area, bathrooms, a TV area, internet access, buffets with hot and cold food options, as well as a bar. The lounges are also well-designed and have plenty of seating options with power outlets close by.

The lounge located in Terminal 1, Concourse C, Near Gate C10 is one of the newest at this airport. It’s larger than the other ones and has a brighter and cozier atmosphere. While all lounges offer good food, the selection offered in this lounge is wider and better, as is the drinks selection. If you need to take a call or work in full privacy, you can use one of the enclosed working spaces. This lounge has a “wellness room” as well, available for nursing mothers. A highlight of this lounge is the brightly colored abstract murals made by local Chicago artists. These designs are meant to pay homage to the history of Chicago.

Seat Type & Cabin Layout: For this route, United operates Boeing 787-10 Dreamliner for its nonstop flights and Boeing 777-200 for flights with a layover. On both planes, you will find seats in a 1-2-1 configuration, with two seats in the middle and one by the windows. This configuration is great, as regardless of the seat you have, you will have direct aisle access. Each seat has a semi-enclosed design, lies flat, and has plenty of space to store your belongings. At your seat, you will also find Saks Fifth Avenue bedding so that you can have a comfortable sleep during the flight. You will also have a TV, an amenity kit, headphones, power outlets, and seat control buttons.

Meal & Beverage Service: United offers multi-course dining inspired by international cuisines. The menu will be slightly different depending on where you’re flying to. Colorado flat iron steak, turbot fillet, and seared chicken breast are just three out of several main course food options. You can also pre-order your meal, but make sure you do it at least 24 hours before your flight. If you need a special meal, you can also request it online. During the flight, you will also be offered a variety of snacks and drinks. You can choose to have wine with your meal, enjoy a coffee with your dessert, and have a can of soda with your snacks.

Cost Range: Business class prices from Chicago to Milan typically range from $3,600 to $10,000 for a round-trip flight. The closer you book to your departure date, the bigger the chances that your ticket will be priced higher than usual. Peak season tickets also have a higher price.

Frequent Flyer Program: MileagePlus is United’s frequent flyer program. By signing up for this program, you can earn miles when you fly with the airline or purchase different products from United’s travel partners. Later, you can use the earned miles to buy or upgrade a ticket, add more baggage to your trip, get access to certain lounges, or make purchases onboard. For a ticket on this route, you would need at least​ 200,000 miles.

If you are looking for a nonstop flight from Chicago to Milan, United is your only option. Besides getting to Milan as fast as possible, you will be able to rest comfortably during your flight, so if this is a priority for you, United is a great option.

Delta Air Lines

Lounge Access & Perks: At Chicago O’Hare International Airport (ORD), Delta Air Lines operates the Delta Sky Club lounge in Terminal 5, Concourse M, between M14 & M11. The lounge recently opened. It has plenty of space, large windows with natural light, and a tarmac view. The lounge has a luxurious atmosphere with tasteful furniture and design choices. Inside the lounge, you will find two bars, both well stocked with drinks and with bartenders who can get you a drink in no time.

The buffet has a wide food selection, so you’re sure to find something to your taste. With high-backed armchairs, cafe-style seats, high-top bar stools, and more, you’re sure to find a place to comfortably relax before your flight. At each chair, you will find power outlets to keep your devices charged. The lounge also has six private phone booths, a quiet area, bathrooms, and showers.

If you fly out of Chicago Midway International Airport (MDW), you will, unfortunately have no access to airline lounges.

Seat Type & Cabin Layout: For this route, Delta uses the Airbus A330-300 and A330-900neo. Both planes have a 1-2-1 configuration, where there are two seats in the middle and one by the windows. With this configuration, no matter where you sit, you will have direct and comfortable aisle access. Compared to the A330-900neo, the A330-300 seats have no doors. However, due to the angled position of the seats, you won’t have to worry about privacy. The seats on both planes lie flat, come with comfortable bedding, and have plenty of space to store your belongings. You will also have a TV, power outlets, seat control buttons, and headphones. The amenity kit you will get during the flight will have premium skincare products from Grown Alchemist, socks, eye masks, a dental kit, and lip balm, all so you have a comfortable flight.

Meal & Beverage Service: Delta offers meals that are inspired by regional cuisine and have regionally sourced ingredients. Beef tenderloin, teriyaki chicken thigh, and taro roll are a few of the options you could find on your menu. Along with your meal, you can pick a drink from a selection of fine wines, craft beers, and premium spirits. During the flight, you will also be able to enjoy a variety of snacks. If you wish to, you can pre-order your meal at least 24 hours before your flight.

Cost Range: A round-trip Delta business-class ticket from Chicago to Milan generally ranges between $3,600 and $9,200. The price may be higher if you buy your ticket close to the departure date or if you intend to fly during peak season.

Frequent Flyer Program: SkyMiles is Delta's frequent flyer program. When you sign up for this program, you can earn and redeem miles for flights. You can earn miles by flying with Delta, using your Delta SkyMiles® American Express Card, or by purchasing from SkyMiles partners. For a round-trip business-class flight on this route, you would need to redeem 730,000 miles.

If a luxurious and comfortable lounge experience and seats with lots of privacy during the flight are what you are looking for, consider Delta as your airline for this route.

Smooth Arrival in Milan

Milan has three major airports: Milan Malpensa Airport (MXP), Milan Linate Airport (LIN), and Orio al Serio International Airport (BGY). However, only Malpensa and Linate receive international business-class flights. Malpensa (MXP) is the largest airport and is located about 50 km (31 miles) northwest of Milan’s city center. Linate (LIN) is much closer, just 8 km (5 miles) east of downtown Milan.

Priority Disembarkation & Immigration Perks

No matter if you land at Milan Malpensa Airport (MXP) or Milan Linate Airport (LIN), at both airports you will receive priority treatment. As a business-class passenger, you will be the first to leave the plane. This way, you will pass faster through immigration, baggage claim, and customs. Your baggage will also be prioritized, so it will be among the first ones to leave the plane and arrive on the carousel. You will be able to get your luggage in no time.

At both airports, you can purchase Fast-Track ahead of time to pass security screening and passport control even faster. This service is very useful during peak times. Make sure you have the confirmation on your phone or printed out so you can show it at the airport.

Navigating the Arrival Terminal

At Milan Malpensa Airport (MXP), you will arrive at Terminal 1 since your flight is an international one. The terminal is very easy to navigate, so you won’t have to worry about finding your way around. You will see lots of clear signs that direct you to baggage claim, customs, and ground transportation. You will also find restaurants, shops, and information desks for assistance. Just outside the arrivals area, you can find your way into the city using a taxi, train, or rental car.

Milan Linate Airport (LIN) is a smaller, easy-to-navigate airport. The airport has only one terminal, which has a straightforward layout, and you can easily find what you need there. Inside the terminal, you will find several shops, restaurants, and cafes, and outside the terminal, you will find transportation to the city center.

Getting to Milan City Center

From Milan Malpensa Airport (MXP)

There are several ways to get from Milan Malpensa Airport (MXP) to the city center.

Malpensa Express Train:

• Route: The train arrives at Terminal 1, then passes through Terminal 2. After that, it departs to Milano Centrale or Milano Cadorna.
• Frequency: The train leaves every 30 minutes from 5:37 am to 00:20 am every day.
• Duration: It takes 51 minutes to reach Milano Centrale and 37 minutes to reach Milano Cadorna.
• Cost: €13 ($14) per person.
• Insider Tip: After purchasing your ticket, make sure to validate it at the nearby validation machine; otherwise, you may get fined by the train conductor.

The Malpensa Express Train is the best choice if you want the fastest and most reliable public transport option.

Bus Services:

• Operators: Several companies operate buses that will take you from the airport to the city center: Terravision, Malpensa Shuttle, and others. You can find the buses outside of both terminal buildings. Follow the signs to “buses” if you can’t see them.
• Frequency: The buses usually run every 20-30 minutes from 12:20 am to 11:50 pm every day.
• Duration: It takes about 50 minutes to reach Milano Centrale.
• Cost: €10 ($11) one-way per person.
• Insider Tip: Purchase your bus tickets online in advance so you don’t waste your time waiting in line.

If you don’t mind crowded spaces, then the bus is a good option, as you get to enjoy the scenery on your way to the center of Milan.

Taxi:

• Availability: 24/7. There are designated taxi stands outside of each of the Arrival Halls, so you will easily find them.
• Duration: It takes about 50 minutes to reach Milan’s city center, depending on traffic.
• Cost: Fixed rate of €104 ($110) to Milan’s city center.
• Insider Tip: Board only taxis that are licensed by the City of Milan — they should be white. Official taxis charge a fixed rate to the city center, so you won’t have any unpleasant surprises upon arriving at your destination.

Taxis are wonderful if you don’t want the struggle of carrying your luggage on public transport.

Private Transfer:

• Availability: 24/7. To get a private transfer, you have to book the service in advance. There are many companies that offer this service.
• Duration: It takes about 50 minutes to get to the center of Milan.
• Cost: It depends on the company that you pick, but it usually starts at €95 ($99).
• Insider Tip: If you’re traveling in a group, book your private transfer in advance to ensure you get a spacious enough vehicle for all travelers and their luggage.

If you are looking for a luxurious, comfortable, and efficient transfer to Milan’s center, then a private transfer is ideal for you.

Uber:

• Availability: 24/7. Download the app or visit the Uber website to request a car to your destination.
• Duration: Similar to taxis, it takes about 50 minutes to get to the center of the city.
• Cost: Starts at approximately €115 ($120) for Uber Black, depending on demand and vehicle type.
• Insider Tip: Check the pickup locations in the app, as there are designated places outside the arrival terminals for Uber cars.

If you’re already familiar with Uber, then this might be the best choice for your ride to the city center.

From Milan Linate Airport (LIN):

Metro (M4 Line)

• Route: Direct connection from the airport’s station to San Babila station in central Milan. The metro station is located outside the terminal, within walking distance from the airport.
• Frequency: Every 30 minutes, daily from 6:00 am to 12:30 am.
• Duration: About 12 minutes to reach the center of Milan.
• Cost: €2.20 ($2.50) per person.
• Insider Tip: Before boarding, validate your ticket at the machines located in the station before the platform. If you’re using a contactless card or mobile ticket, scan it at the ticket gates when you enter the station; otherwise, you risk getting fined.

If you wish to get to the center as fast as possible and avoid traffic, then the metro is the ideal choice.

Bus Services

• Operators: Milan’s local urban buses, 73 and X73. The bus stop is located just outside the Arrivals area of the airport terminal.
• Route: Connects Linate Airport to San Babila metro station.
• Frequency: from 6:05 am until 12:40 am. Bus 73 operates daily, departing every 10 minutes, while Bus X73 departs every 20 minutes and operates from Monday to Friday.
• Duration: About 25 minutes to the city center, depending on traffic.
• Cost: €2.20 ($2.50) per person.
• Insider Tip: Buy your ticket online on the ATM Milano app, ticket machines, or newsstands at the airport. If you buy a ticket on the bus, you will have to pay more for it. Don’t forget to validate your ticket upon boarding.

If you’re looking for a budget-friendly option to get to the city center, then the bus is a great choice.

Taxi

• Availability: Readily available 24/7 outside the arrivals terminal.
• Duration: About 25 minutes to the city center, depending on traffic.
• Cost: Starting at €40 ($43). The price is not set and will be charged based on the taximeter.
• Insider Tip: Official Milan taxis are white and display their license visibly, so make sure you’re taking an official taxi for your ride.

Taxis are a perfect choice if you wish to get to the center in privacy and comfort.

Private Transfer

• Availability: Operates 24/7 but must be booked in advance.
• Duration: About 20 minutes to central Milan.
• Cost: Starting at €60 ($65), depending on the type of vehicle you request and how many people will travel.
• Insider Tip: The arrival process can get quite lengthy, so schedule your pick-up time at least 30 minutes after your arrival time.

If you want to skip the line for a taxi or have special requirements, such as a baby seat, then a private transfer is exactly what you need.

Uber

• Availability: Uber is available at Linate 24/7, mainly offering Uber Black, Uber Van, and Uber Lux.
• Duration: Approximately 20 minutes to the city center.
• Cost: Starting at €34 ($37), depending on the time of day and the vehicle you need.
• Insider Tip: UberX is not available in Milan. Check the app for the exact pickup point; you will also see it marked outside the terminal.

Uber is the way to go if you’re already familiar with it and wish to have as seamless an arrival as possible.

Travel Tips for Business-Class Fliers

Business class flights are perfect if you like the idea of arriving rested and ready for what’s outside the airport. Enjoying these perks, however, doesn't mean you have to empty your pockets. We compiled a list of tips that can get you a good deal on business-class tickets so you get to enjoy the experience at a reasonable price.

Book in advance: Ticket prices fluctuate, and they are usually the highest closer to the departure date. If you wish to buy a ticket at a lower price, book it in advance if you can. By booking 3–6 months in advance, you can save up to 30% compared to buying a last-minute ticket.

Opt for flights with layovers: Flights with layovers often have a better price than direct flights. While for this route, your flight options are mostly the ones with layovers, you can consider this tip for your next trip.

Fly midweek: Many people are flying during the weekends, either for vacations or work trips. If you’re flexible with your dates, we recommend that you book tickets for Tuesday and Wednesday when the demand is lower and airlines sell tickets at a lower price.

Use booking platforms: Researching and gathering information for your next flight can be too much to deal with when you have other important matters needing your attention. To make the process easier, you can get the help of online travel agencies (OTAs) like Priceline. OTAs have expert travel agents who can help you find the perfect ticket. Something that you can’t get without OTAs is the unpublished discounted fares for business-class tickets that they have access to. With the help of an OTA, you can find a ticket for your trip much faster and even get a better price for it.

While you’re in Milan, consider getting a Milan pass. Passes are access tickets that usually include free public transport, guided tours, free or discounted passes to Milan’s most iconic attractions, and many other perks. You can get a pass for 1 or more days, depending on how long your stay is. Prices for these tickets start at €14 ($15) per person.

Final Insights

Flying in business class is sure to make your journey to Milan memorable, from the moment you set foot inside the airport to the moment you leave to explore the city.

To enjoy the luxurious experience of business class and save money on your flight, use the tips we provided. Your journey to finding a ticket can be as smooth as flying in business class, and if you need help with this process, you can always rely on us. On our website, you can find and explore business-class fares or sign up for exclusive deals. If you need help with anything else, you can always contact our team for expert booking assistance.
Enjoy your trip!