CHI - MIL

$231 Find Cheap Flights from Chicago to Milan

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Milan departing on 7/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Milan

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Milan.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Milan.
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Flights Deals

Cheap Flights from Chicago to Milan (CHI-MIL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Milan that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Milan

Tue, Oct 7 - Wed, Oct 22
Scandinavian Airlines Logo
7:15 pm - 10:30 amORD-MXP
32h 15m2 stops
Scandinavian Airlines Logo
8:05 pm - 4:10 pmMXP-ORD
27h 05m1 stop
$375Scandinavian Airlines
Find Deal
Tue, Oct 7 - Wed, Oct 22
Scandinavian Airlines Logo
7:15 pm - 7:15 pmORD-MXP
17h 00m1 stop
Scandinavian Airlines Logo
8:05 pm - 4:10 pmMXP-ORD
27h 05m1 stop
$378Scandinavian Airlines
Find Deal
Thu, Oct 9 - Wed, Oct 15
TAP AIR PORTUGAL Logo
6:00 pm - 7:15 pmORD-MXP
18h 15m1 stop
TAP AIR PORTUGAL Logo
8:15 pm - 12:35 pmMXP-ORD
23h 20m1 stop
$477TAP AIR PORTUGAL
Find Deal
Mon, Sep 15 - Thu, Sep 25
TAP AIR PORTUGAL Logo
6:10 pm - 4:25 pmORD-MXP
15h 15m1 stop
TAP AIR PORTUGAL Logo
5:25 pm - 4:30 pmMXP-ORD
30h 05m1 stop
$478TAP AIR PORTUGAL
Find Deal
Sun, Oct 26 - Thu, Nov 6
Aer Lingus Logo
4:55 pm - 11:05 amORD-LIN
12h 10m1 stop
Aer Lingus Logo
11:45 am - 5:55 pmLIN-ORD
13h 10m1 stop
$484Aer Lingus
Find Deal
Mon, Nov 24 - Tue, Dec 2
British Airways Logo
9:45 pm - 5:50 pmORD-LIN
13h 05m1 stop
British Airways Logo
6:55 pm - 1:55 pmLIN-ORD
26h 00m1 stop
$539British Airways
Find Deal
Wed, Jul 2 - Wed, Sep 10
British Airways Logo
5:45 pm - 9:45 pmORD-LIN
21h 00m1 stop
British Airways Logo
7:25 am - 5:00 pmLIN-ORD
16h 35m1 stop
$600British Airways
Find Deal
Sun, Aug 10 - Fri, Aug 22
Aer Lingus Logo
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
Aer Lingus Logo
11:20 am - 7:00 pmLIN-ORD
14h 40m1 stop
$631Aer Lingus
Find Deal
Wed, Aug 13 - Mon, Aug 25
ITA Airways Logo
3:00 pm - 3:10 pmORD-LIN
17h 10m1 stop
ITA Airways Logo
7:00 am - 1:10 pmLIN-ORD
13h 10m1 stop
$683ITA Airways
Find Deal
Sun, Aug 17 - Wed, Aug 27
ITA Airways Logo
3:00 pm - 10:10 amORD-LIN
12h 10m1 stop
ITA Airways Logo
7:00 am - 1:10 pmLIN-ORD
13h 10m1 stop
$721ITA Airways
Find Deal
Expert advice

Expert advice for your flight from Chicago to Milan

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
ORD

At ORD, consider using the CTA Blue Line for a reliable 45-minute trip to downtown Chicago, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
MXP

From MXP, the Malpensa Express offers a convenient 40-50 minute train ride to Milan city center, departing regularly from Terminal 1.

Read more about MXPby Duncan Madden
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Duncan Madden

Duncan Madden

Expert on MXP

Duncan Madden

Duncan Madden

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Read more
Useful Info

KAYAK's insights & trends for Chicago to Milan flights

Get data-powered insights and trends into flights from Chicago to Milan to help you find the cheapest flights, the best time to fly and much more.

Find cheap flights to Milan
Find cheap flights to Milan

Planning a trip from Chicago to Milan? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

What is the cheapest Chicago to Milan flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to Milan.

Our data shows that the cheapest route for a return flight from Chicago to Milan cost $733 and was between Chicago O'Hare Intl Airport (ORD) and Milan Malpensa Airport (MXP). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $733.

What’s the cheapest day of the week to fly from Chicago to Milan?

The average price of all round-trip flights from Chicago to Milan clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Milan on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Chicago to Milan. For your return ticket, we recommend flying on a Saturday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Chicago to Milan?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Milan, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Milan is November, where tickets cost $617 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $1,242 and $1,147 respectively.

How far in advance should I book a flight from Chicago to Milan?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Milan, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Milan, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonJanuary
High seasonSeptember
Cheapest flight$231
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Chicago O'Hare Airport to Milan Malpensa Airport

When to book flights from Chicago to Milan

Are your dates flexible? Find out the best times to travel from Chicago to Milan based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Milan

  • What amenities do the Chicago airports have for lactating mothers?

    Both MDW and ORD have lactating pods that are secure and private places for mothers who wish to pump before takeoff. The ones at MDW can be found at Concourse A at Gate 5, while the ones in ORD are located at Terminal 1, Concourse C Gate 11 and 23, Terminal 2, Concourse F and G Gates E1 and F1, Terminal 3, Concourse G, K, L at gates G12, K5, K19, and L24.

  • Are there lounges at the Milan airports?

    Yes, there are. Both MXP and LIN have VIP lounges. At LIN, these are the Leonardo and Piranesi Lounges which are located on the mezzanine floor 1 in the boarding area, and check-in area, respectively. MXP has 5 of them found on the ground floor and first floor of Terminal 1.

  • What services are there for military personnel at ORD and MDW?

    Both of these airports have USO centers where retired and active military staff and their families can enjoy some refreshments as they wait for their flight. MDW has one at Concourse C, while ORD has one in Terminal 2, and another in Terminal 3, Concourse G.

  • Where can I get local currency at the Milan airports?

    Exchange your dollars for euros upon arrival at MXP and LIN at the Forex bureaus that are open every day. The ones at MXP can be found on the ground floor next to arrivals A and B, and on the second floor near check-in areas 5, 6, 9, 10, and 17. At LIN, the offices are on the ground floor at arrivals, and after check-in on the first floor.

  • What is the cheapest flight from Chicago to Milan?

    In the last 3 days, the lowest price for a flight from Chicago to Milan was $231 for a one-way ticket and $375 for a round-trip.

  • Do I need a passport to fly between Chicago and Milan?

    Yes

  • Which airports will I be using when flying from Chicago to Milan?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at one of these airports: Milan Linate or Milan Malpensa.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Milan?

    Iberia, British Airways, Finnair, and American Airlines offer inflight Wi-Fi service on the Chicago to Milan flight route.

  • Which aircraft models fly most regularly from Chicago to Milan?

    The Boeing 787 Dreamliner is the aircraft model that flies most regularly on the Chicago to Milan flight route.

  • Which airline alliances offer flights from Chicago to Milan?

    Star Alliance is the only airline alliance operating flights between Chicago and Milan.

  • On which days can I fly direct from Chicago to Milan?

    There are nonstop flights from Chicago to Milan on a daily basis.

  • Which is the best airline for flights from Chicago to Milan, United Airlines or Scandinavian Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Milan are United Airlines and Scandinavian Airlines. With an average price for the route of $1,368 and an overall rating of 7.4, United Airlines is the most popular choice. Scandinavian Airlines is also a great choice for the route, with an average price of $603 and an overall rating of 7.3.

  • How does KAYAK find such low prices on flights from Chicago to Milan?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Milan.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Milan?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Milan from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Milan?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Milan with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Milan?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Milan from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Milan

  • Looking for a cheap flight? 25% of our users found flights on this route for $578 or less one-way and $923 or less round-trip.
  • When flying from Chicago (CHI) to Milan (MIL), you will most likely depart from either Chicago Midway Airport (MDW) or Chicago O’Hare International Airport (ORD). Even though MDW is much smaller than ORD, most travelers choose to fly from MDW because it is much closer to the city center and less busy. Upon arrival in Milan, you will most likely land at Milan Malpensa Airport (MXP), located to the northwest of the city, or Milano Linate Airport (LIN), which is towards the east and the closest to the city center.
  • Chicago O’Hare (ORD) has a fun and colorful area set aside for children to play. This is set up in the Family Lounge which is located at Terminal 2’s main hall, adjacent to Gate F1.
  • If you need to carry out business upon arrival, Milano Linate (LIN) offers the Linate Centre. This is a meeting room which is equipped with free Wi-Fi, a table fitted with microphones and ports to charge your laptops, a photocopier, and much more. You can find it on the second floor of the airport.
  • If you are looking to hire a car to use as you are in Milan, Milan Malpensa (MXP) provides car hire services. This can be done at the rental car offices located at Terminal 1 and Terminal 2.
  • Take a moment away from the hustle of the airport at Chicago Midway (MDW) and relax in the Yoga room before your flight. It is open every day from 6am to 10pm and is situated at Concourse c.

Prefer to fly direct from Chicago to Milan?

Find which airlines fly direct from Chicago to Milan, which days they fly and book direct flights.

Direct departures

Chicago to Milan

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Milan to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to Milan

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Milan. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Milan? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8790 reviews
6.6Food
7.7Boarding
7.3Comfort
7.0Entertainment
8.1Crew
Airline reviews

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

4.0 OkayJ, May 2025ORD - EDI
Read more United Airlines reviews

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

Standard short hop flight. No food, no entertainment. Just get in, get something to drink, and try to be as comfortable as you can for an hour.

Cancelled my flight. Only option had a layover in Italy. No compensation for the 4 extra hours of travel time. The travel agency, cheapflightfares, blamed Scandinavian airlines and said there was nothing they could do. Scandinavian airlines said since it was booked through a travel agency there was nothing they could do. The entire thing was incredibly frustrating. Never booking through kayak or with Scandinavian again.

Name change on tickets for a misspelled name was very hard to change

They cancelled our flight home less than 24 hours before it was supposed to leave. It partially ruined our last day because I was on the phone trying to get 5 people home and the stress that it causes. We still arrived at the airport with no definite flight plans. The actual flight was good but my kids really misses the kids meals I had ordered for them which obviously didn’t make it to the new flight.

Very unfriendly approach to me when you rescheduled my return flight due to your delay. No help to address my health concerns because I am diabetics and had orthopedic problems. No clear explanation where to clear customs. I had poor customer service

The seats were really cramped. The high backs on the chairs made you feel claustrophobic.

Boarding was chaotic and the flight left late but arrived at a decent time. This may have been because of the sxsw festival that was going on.

The flight got canceled and you just send an email in the middle of the night and no solution to how to get on the next flight or provide other solutions.

You cost me my time and did not compensate properly. Gfy.

Missed a connecting flight and SAS was at fault. I was awarded a $20 voucher in exchange for 8 hours of my time? Gfy.

I would definitely use a Linus again, the price was right, the service is excellent. No delays. Wish I had a direct flight from my hometown Detroit.

There was no room in the seats, smallest room we've ever had and the food was awful.

I dont fly them much anymore. Other carries offere better pricing and better seating options

Seats weren't very comfortable for a long haul flight but the service made up for it.

Unfortunately the flight was delayed for 50 min. Just as we were about to board so that was a drag. The boarding was average. The bag check in process was new to us and efficient. And the flight itself was smooth- basically no turbulence.

I liked how they looked after couples by providing a row of 4 seats if available.

Food was very bad. Boarding was disorganized and messy. Crew was friendly

It was ok not that much because I always travel with Emirates airlines, Etihad, airlines, Qatar airlines compare to them food and comfortable was too low . Staff was good . Helpful

Boarding seemed a bit chaotic and we had to walk outside across the tarmac. Passengers of all ages had to drag carry on luggage up the outside stairway into the aircraft. There was no WiFi. Very uncomfortable crammed seats. Glad in-air time was only an hour!

Booked through Kayak, couldnt take flight, Kayak punted to Orbiz, Orbiz punted to Aer Lingus, Aer Lingus said sorry about your luck, try Kayak/Orbiz. Terrible customer service collecting air fares and not even offering a voucher when customers cant take flight

Terrible flight attendant attitude. Average 3-star hotel employee has better hospitality skills. Business class seats are literally a joke. TAP executives should ride business class in other airlines to develop some rudimentary sense of what business class is.

I’ve never had worse food in business class ever!

Checked bG chstgr was extremely high. Over $120. It was s bsit and switch knowing an international passenger would have t9 check a bag.

On time, politeness, food okay but entertneiment mediocre with only old movie and the so called new we’re 2 or 3…

Awful. I told them to cancel my return flight and they didn’t then charged me +$800 days before the flight for a biz class upgrade bid. When I called to confirm cancellation and get refund on buz class upgrade they said I had to go thru orbitz and it was too late. Scammers. Beware.

Flight was packed. This was a very uncomfortable experience. Boarding process could be explained better. Despite recommending a window seat when travelling with a pet in the cabin, the seat in front of me had less space than the center and aisle seats. For Premium Economy, the seats were crammed with minimal legroom. I hate to think what Regular Economy was like. The cabin crew missed me at first when handing out meals. When my meal eventually came, there were no utensils. I'd originally booked to fly Business Class; those seats didn't look that great either.

Flight was packed. This was a very uncomfortable experience. Boarding process could be explained better. Despite recommending a window seat when travelling with a pet in the cabin, the seat in front of me had less space than the center and aisle seats. For Premium Economy, the seats were crammed with minimal legroom. I hate to think what Regular Economy was like. The cabin crew missed me at first when handing out meals. When my meal eventually came, there were no utensils.

First time and I enjoyed the trip…. Will fly again soon 🔜

Delayed flight because other plane was occupying the gate for longer than expected. Once we boarded the plane had to wait 1 hour before taking off. We. Almost lost our connection flight and the baggage didn’t make it. We had to wait two days to receive our luggage. Hope they improve the timing or work with the airport to get better service.

I’m still missing my bags. I’m soo frustrated

The payment system was not working so was unable to connect wifi the entire flight

everything to do with KAYAK was terrible. Your customer facing departments are utterly useless, timewasting and unhelpful.

I ordered short ribs for main course. It tasted sweet, really sweet. Horrible.

charging port did not work, no entertainment system. Other than that the flight was good and safe.

Our luggage didn’t arrive with us, that puts a damper on the whole trip.

The screen didn’t work and I didn’t get the seat upgrade I paid $300 for. They were no help with that,

Paid $180 for seat selection, and selection essnt honored. Have to call for a refund.

Was 3 hrs delayed and my poor friend I met in Barcelona was waiting at airport for 3 hrs. Dallas airport was awful

The internet was horrible. Plus they charged me $25 for service that didn't work which should have been free since I'm Concierge Key. The flight attendant Rick Young was excellent. Greeted me by name and very attentive.

Not good. First time flying AA in years and won’t be doing so again. We departed late and missed our connecting flight to Barcelona. As a result we missed the first two days of a Mediterranean cruise. No reason given for the delay. Got rerouted from JFK to Heathrow and then to Barcelona. Flight to Heathrow was delayed causing us to miss the flight to Barcelona again. Routed then to Palmero where we had to purchase transportation and a 2 night hotel stay to pick up the cruise there. Probably cost us $2k plus.

Everything you need to know for your flight from Chicago to Milan

Cabin class types available on flights from Chicago to Milan

Cabin classes available on flights from Chicago to Milan. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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