Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

CHI - MIL

$202 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 6/25. 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
0 bags
Thu 6/6
Thu 6/13

Search 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.
In the last 7 days travelers have searched 42,573,820 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
7:45 pm - 7:15 pmORD-MXP
16h 30m1 stop
11:20 am - 5:55 pmMXP-ORD
13h 35m1 stop
$559Scandinavian Airlines
Find Deal
Sun, Sep 29 - Thu, Oct 17
7:45 pm - 7:55 pmORD-MXP
41h 10m2 stops
11:20 am - 5:55 pmMXP-ORD
13h 35m1 stop
$563Scandinavian Airlines
Find Deal
Sun, Sep 29 - Thu, Oct 17
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
11:20 am - 7:05 pmLIN-ORD
14h 45m1 stop
$576Aer Lingus
Find Deal
Sun, Sep 29 - Thu, Oct 17
3:45 pm - 10:40 amORD-LIN
11h 55m1 stop
11:20 am - 7:05 pmLIN-ORD
14h 45m1 stop
$577Aer Lingus
Find Deal
Mon, Sep 9 - Fri, Sep 20
6:00 pm - 12:35 amORD-MXP
23h 35m1 stop
5:55 am - 4:10 pmMXP-ORD
17h 15m1 stop
$580TAP AIR PORTUGAL
Find Deal
Wed, Oct 2 - Wed, Oct 16
6:00 pm - 4:25 pmORD-MXP
15h 25m1 stop
6:20 am - 4:30 pmMXP-ORD
16h 10m1 stop
$609TAP AIR PORTUGAL
Find Deal
Sun, Sep 29 - Wed, Oct 30
9:35 pm - 1:20 pmORD-MXP
8h 45mnonstop
10:40 am - 5:10 pmMXP-ORD
12h 30m1 stop
$761United Airlines
Find Deal
Mon, Sep 23 - Fri, Nov 1
6:00 pm - 11:20 amORD-LIN
10h 20m1 stop
2:55 pm - 9:05 pmLIN-ORD
12h 10m1 stop
$789United Airlines
Find Deal
Mon, Sep 23 - Fri, Nov 1
9:25 pm - 7:35 pmORD-MXP
15h 10m1 stop
3:20 pm - 6:05 pmMXP-ORD
9h 45mnonstop
$858Lufthansa
Find Deal
Wed, Jul 17 - Wed, Aug 21
9:25 pm - 5:50 pmORD-LIN
13h 25m1 stop
6:25 pm - 12:15 pmLIN-ORD
24h 50m1 stop
$1,037Lufthansa
Find Deal
Tue, Jul 16 - Tue, Jul 23

Flights from Chicago to Milan - Travel Insights & Trends

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.

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 one-way flights from Chicago to Milan.
Our data shows that the cheapest route for a one-way flight from Chicago to Milan cost $1,042 and was between Chicago O'Hare Intl Airport and Milan Malpensa Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $1,213.

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

The average price of all flights from Chicago to Milan clicked on KAYAK for each day over the last 12 months.
When flying from Chicago to Milan, you should consider leaving on a Tuesday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Tuesdays.

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 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 February, where tickets cost $533 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $1,290 and $1,201 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Chicago to Milan, you should book around 2 days before departure. For the absolute cheapest price, our data suggests you should book 7 days before departure.

Which airlines provide the cheapest flights from Chicago to Milan?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, TAP AIR PORTUGAL offered the best one-way deal for that route, at $511. KAYAK users also found Chicago to Milan round-trip flights on Scandinavian Airlines from $559 and on Aer Lingus from $576.

Which airlines fly non-stop between Chicago and Milan?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Milan.
There is just one airline that flies from Chicago to Milan direct and that is United Airlines. The best one-way deal found from United Airlines for the route is $794.

How many flights are there between Chicago and Milan per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago and lands in Milan, with an average flight time of 8h 50m. The most common departure time is 9:00 pm and most flights take off in the evening. Each week, there are 7 flights.

Which cabin class options are there for flights between Chicago and Milan?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to Milan take?

A direct flight to Milan will take on average 8h 45m to travel the 4,526 miles flying distance from Chicago.

What’s the earliest departure time from Chicago to Milan?

Early birds can take the earliest flight from Chicago at 9:30 pm and will be landing in Milan at 1:20 pm.

What’s the latest departure time from Chicago to Milan?

If you prefer to fly at night, the latest flight from Chicago to Milan jets off at 9:35 pm and lands at 1:20 pm.

Good to know

Low season

February

High season

September

Cheapest flight

$202
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago Midway 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 $202 for a one-way ticket and $559 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, Delta or Scandinavian Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Milan are Delta and Scandinavian Airlines. With an average price for the route of $945 and an overall rating of 8.0, Delta is the most popular choice. Scandinavian Airlines is also a great choice for the route, with an average price of $676 and an overall rating of 7.4.

  • 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.

See more FAQs

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 $1,209 or less one-way and $1,311 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.
See more tips

Prefer to fly non-stop from Chicago to Milan?

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

Nonstop departures

Chicago to Milan

Monday

Air Canada, Austrian Airlines, Brussels Airlines, +2 more

Air Canada, Austrian Airlines, +3 more

Tuesday

Air Canada, Austrian Airlines, Brussels Airlines, +2 more

Air Canada, Austrian Airlines, +3 more

Wednesday

Air Canada, Austrian Airlines, Brussels Airlines, +2 more

Air Canada, Austrian Airlines, +3 more

Thursday

Air Canada, Austrian Airlines, Brussels Airlines, +2 more

Air Canada, Austrian Airlines, +3 more

Friday

Air Canada, Austrian Airlines, Brussels Airlines, +2 more

Air Canada, Austrian Airlines, +3 more

Saturday

Air Canada, Austrian Airlines, Brussels Airlines, +2 more

Air Canada, Austrian Airlines, +3 more

Sunday

Air Canada, Austrian Airlines, Brussels Airlines, +2 more

Air Canada, Austrian Airlines, +3 more

See more direct flights

Nonstop returns

Milan to Chicago

Monday

Air Canada, Austrian Airlines, Brussels Airlines, +3 more

Air Canada, Austrian Airlines, +4 more

Tuesday

Air Canada, Austrian Airlines, Brussels Airlines, +3 more

Air Canada, Austrian Airlines, +4 more

Wednesday

Air Canada, Austrian Airlines, Brussels Airlines, +3 more

Air Canada, Austrian Airlines, +4 more

Thursday

Air Canada, Austrian Airlines, Brussels Airlines, +3 more

Air Canada, Austrian Airlines, +4 more

Friday

Air Canada, Austrian Airlines, Brussels Airlines, +3 more

Air Canada, Austrian Airlines, +4 more

Saturday

Air Canada, Austrian Airlines, Brussels Airlines, +3 more

Air Canada, Austrian Airlines, +4 more

Sunday

Air Canada, Austrian Airlines, Brussels Airlines, +3 more

Air Canada, Austrian Airlines, +4 more

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
Scandinavian AirlinesOverall score based on 1432 reviews
8.1Crew
7.3Comfort
6.8Food
7.7Boarding
6.7Entertainment
Airline reviews

Bathrooms weren’t too clean. Onboard entertainment was light. Other than that everything was great. Food, service, comfort and crew. Although it was hard to understand the crew announcements.

10.0 ExcellentAna, May 2024CPH - LAX
Read more about Scandinavian Airlines reviews

Bathrooms weren’t too clean. Onboard entertainment was light. Other than that everything was great. Food, service, comfort and crew. Although it was hard to understand the crew announcements.

TERRIBLE! Staff was unfriendly, rude, and demeaning. One flight attendant touched me to grab the complimentary blanket off my neck because I couldn't take it home, while a bunch of other people took theirs home. I have never been so ill treated. I am not happy at all. And flight was delayed, no information until short notice for everything. Lost an entire day at my destination. I expect a full refund for that experience. Never will fly with them EVER again

My return flight has been changed to JFK from EWR without any notice or reason

Flight was delayed 3 hours. Pilot cancelled flight under 4 people volunteered to change their seats to economy from business class.

I couldn’t make it to the airport for my original flight due to bad weather; roads were shut down, buses and trains were closed. Since the plane wasn’t cancelled, I still had to pay $720 to change my ticket.

Good friendly service and food - The seats in business class are old, too hard and not very comfortable.

My seat was not the one I paid for, the crew was very curt, and the cabin was extremely warm.

Old plane with terrible business class seats - good food and service. Boarding was a joke with business class boarding last.

Best airline to travel on a budget- really like their reasonably priced access to the SAS lounges where available.

The flight was cancelled early on and messed up the whole vacation and hard to get a refund from Kayak as they owned the ticket and of course they did not believe that SAS cancelled the ticket. Definite bad side to third party. SAS had rescheduled but overlapped the connecting flights. That did not work. Flight was cancelled long ago but Kayak still has it. Like it was taken? Bad IT ? Or all assumptions and no follow up which is the whole IT world. It needs to wake up and be more efficient. Especially as the world is going, there will be no freedom to do anything. And we will be living like the Middle Ages. Yeah, go read up on that while you still can.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The flight was half full and I presume that the next few days are even less busy not sure why they are still charging a premium to change a flight.

Are Longus was fine. I booked thru Kayak and was unable to get my business class seat early. Sat next to galley. Crew forgot to wake me for breakfast.

I loved how they arrange boarding (starting with people seated in back and moving to the front). Flight crew was very polite and welcoming. Seating was ok, I felt like there was enough leg space however it is noticeable when the passenger in front of you sets their seat back.

Nice to be on a flight that wasn't fully booked so there were only two of us in the three seat row.

The only problem was there are games on the entertaiment system. The guy behind me played poker the entire time and poking the back of my seat. I hope they remove these.

Great travel. Wonderful experience. Hope to do it again in the near future. God willing

Aer Lingus doesn't have plug ins for devices at each seat. They also did not give me a dairy free meal as requested and confirmed by staff. It was as if I had not requested anything. Otherwise, they were great!

The transatlantic flight was wonderful. The regional reminded me of jet blue. Crazy and packed. Not enough overhead space and tough on elderly.

They lost my baggage on my connecting flight and we’re an hour late so I nearly missed it

All OK. Food, best bring your own. Even a BigMac will be better.

I thought Miami's airport was very disorganized during the Boarding.

Very efficient boarding - other airlines could learn from them. Friendly, efficient crew. Red eye flight, so dinner meal was irrelevant. Breakfast could have been more substantial. Seats reasonably comfy.

Perfect although it took an hour to board the plane but other than that it was great

Everything was nearly perfect, and TAP staff were especially helpful when we missed our connecting flights and had to get on the next flight to Rome. The only aspect that could have been better was boarding: it was somewhat disorganized, which created a bit of stress. But in the end, everyone got on the plane, so the less-then-perfect boarding process did not take away from the overall excellent experience.

The quality of the aircraft and the professionalism of TAP's staff were perfect. The quality of vegan meals can be hit or miss depending on the airline and the city of departure; on this flight, our vegan meals were quite good. The boarding process for the connecting flight in Lisbon could have been organized a bit better, but it did not spoil our overall experience with TAP, which was excellent. I'd definitely recommend TAP to others.

We liked the crew. They were competent, professional and friendly. The only big negative was our departure was delayed several times and the airport staff did not communicate what the problems were and what we should expect.

Two of three flight attendants were not super kind as I would expect. The very kind young lady in my section was wonderful but then lady and man up front were not. Sorry but it makes a difference !

Airline attendant never walks along the isle to check if everyone is ok. The food is worst I’ve experienced. Chicken pasta is very salty while the fish is bland and over-cooked. Only two toilets for the entire economy section.

This was a full flight in an ancient plane. The seats were tight and uncomfortable.

Pros: "Food service was very good - and the crew kept going even after we hit turbulence. I'd already been served, but I know from past experience with other airlines that there's nothing worse than smelling the hot food and being told that service is being discontinued,,,,while you're now hungry"
Cons: "Lisbon airport was stressful, perhaps more guidance before releasing us into the melee. I found an Air Portugal email about Lisbon Airport just now"

Bordón could be bettet if the company say before boarding the order of the different groups.

Disappointed everytime. The app doesn't load the boarding passes. They have lots of agent that seem to be busy doing nothing with a long line waiting to get paper boarding passes. Food choices are poor. Entertainment is less than entertaining.

Horrible experience. Nothing to give to kids to keep them entertained.

Trouble keeps changing the time and I was booked different flight without knowing it was bad experience

Hated every minute of it. Delayed for over 10 hours only to have to cancel rental car, car insurance and hotel. Its taken me 3days to get to my final destination when it should have only taken 12-14 hours. Very unhappy with Lufthansa.

This flight is always a cramped bus. The gate area was inadequate and announcements were hard to hear. The flight was delayed 45 minutes to an hour by a broken aircraft door, making our total delay from Vilnius 5 hours.

didn’t even get to go one of my returning flights cancelled and I wasn’t even in their system, vacation ruined thanks for nothing

You need to reimburse me for my seats purchased and luggage.

Flight delay wasn’t managed well. I was booked for the next flight for 2 days later!

My baggage has been lost for the last 6 days! The problem originated at LAX with Lufthansa, which was a very big disappointment from LAX to Munich. The flight was delayed over an hour, the overhead bins on the window side are too small for most carryon's, the in-seat video screen were very poor as they would not respond to your touch quickly and would stop and start all over again, the earphone jacks are not like most standard ones, the seats still has wrappers and trash in pockets and on the seats. and there was no USB outlet to charge your phone or other devices. The German reputation for quality is bogus with this airline. BUT the responsibility for delivering my luggage became Air Dolomiti's as they were the last leg of the trip. The baggage area was chaos because several flights arrived at once. I took me over an hour to file a claim, the agent entered my info incorrectly, and the contact numbers for Lost and Found at the airport was never answered. I have never been called by Air Dolomiti or the baggage delivery company. I had to do all the calling. AD's live agents gave me two wrong phone numbers for the baggage company. When I finally got the right one on my third call, OF COURSE, no one answers and I still do not have any information on when my bags should arrive. VERY UNPROFESSIONAL operations by Lufthansa and Air Dolomiti. I will make sure I book any other air carriers on the rest of my flights to Italy this year.

Book cheap flights from Chicago to Milan

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Milan found on KAYAK in the last 72 hours.
6/25Tue
2 stops
44h 59mMDW-MXP
$202
6/25Tue
2 stops
32h 24mORD-MXP
$227
9/11Wed
1 stopTAP AIR PORTUGAL
18h 30mORD-MXP
$511
7/31Wed
1 stopTAP AIR PORTUGAL
18h 30mORD-MXP
$569
9/19Thu
1 stopScandinavian Airlines
16h 30mORD-MXP
$631
7/8Mon
1 stopAer Lingus
30h 45mORD-LIN
$631
7/29Mon
1 stopAer Lingus
30h 45mORD-LIN
$685
7/29Mon
2 stopsScandinavian Airlines
33h 20mORD-LIN
$751
6/16Sun
nonstopUnited Airlines
8h 45mORD-MXP
$1,028
9/19Thu
nonstopUnited Airlines
8h 45mORD-MXP
$1,057

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to Milan

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Milan that are departing in the next 10 days.
5/9Thu
multi-stopScandinavian Airlines
16h 30mORD-MXP
5/23Thu
multi-stopScandinavian Airlines
15h 40mMXP-ORD
$806
5/9Thu
multi-stopScandinavian Airlines
16h 30mORD-MXP
12/17Tue
multi-stopScandinavian Airlines
29h 05mMXP-ORD
$882
5/9Thu
multi-stop
25h 45mORD-MXP
5/23Thu
multi-stop
45h 32mMXP-ORD
$886
5/9Thu
multi-stopScandinavian Airlines
17h 10mORD-MXP
12/17Tue
multi-stopScandinavian Airlines
29h 05mMXP-ORD
$888
5/12Sun
multi-stopLufthansa
12h 10mORD-MXP
5/21Tue
nonstopLufthansa
9h 35mMXP-ORD
$1,903
5/7Tue
multi-stopAer Lingus
11h 55mORD-LIN
5/10Fri
multi-stopAer Lingus
14h 45mLIN-ORD
$1,987
5/10Fri
multi-stopUnited Airlines
26h 55mORD-MXP
5/12Sun
nonstopUnited Airlines
9h 35mMXP-ORD
$2,063
5/9Thu
multi-stopLufthansa
12h 05mORD-MXP
5/23Thu
nonstopLufthansa
9h 45mMXP-ORD
$2,130
5/12Sun
nonstopUnited Airlines
8h 50mORD-MXP
5/21Tue
nonstopUnited Airlines
9h 35mMXP-ORD
$2,172
5/9Thu
multi-stopTAP AIR PORTUGAL
21h 35mORD-MXP
5/19Sun
multi-stopTAP AIR PORTUGAL
29h 06mMXP-ORD
$2,931

Search by stops

Search by airline

Search by price

Flights to Milan

Return flight deals:

Milan - Chicago

Cabin classes:

$3,520
$2,141
$1,124