CHI - MIL

$249 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 3/28. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$426
Overall average: $809
Scandinavian Airlines
Wed 4/15Fri 4/24
ORD - MXP • 2 stops
Cheapest non-stop
$816
United Airlines
Wed 4/15Wed 4/22
ORD - MXP • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
The Malpensa Express connects MXP to Milan in 40-50 mins.
Use the CTA Blue Line for a 45-min trip from ORD to downtown.
Expert advice
Expert advice
Expert advice
Expert advice
Video guide: How to find cheap flights to Milan
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Top airlines
Scandinavian Airlines
Cheapest • from $426 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD
-
MXP
Cheapest
ORD
-
MXP
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 24% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 32% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Milan!
Flight Deals
Booking Insights
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Flight 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

Wed, Apr 15 - Fri, Apr 24
Scandinavian Airlines Logo
7:15 pm - 7:50 pm
ORD
-
MXP
17h 35m
2 stops
Scandinavian Airlines Logo
3:55 pm - 4:10 pm
MXP
-
ORD
31h 15m
1 stop
$426Scandinavian Airlines
Wed, Feb 25 - Wed, Mar 4
Scandinavian Airlines Logo
7:20 pm - 7:10 pm
ORD
-
MXP
16h 50m
1 stop
Scandinavian Airlines Logo
8:00 pm - 4:45 pm
MXP
-
ORD
27h 45m
1 stop
$427Scandinavian Airlines
Wed, Apr 15 - Fri, Apr 24
Scandinavian Airlines Logo
7:15 pm - 7:50 pm
ORD
-
MXP
17h 35m
2 stops
Scandinavian Airlines Logo
3:55 pm - 4:10 pm
MXP
-
ORD
31h 15m
1 stop
$428Scandinavian Airlines
Wed, Apr 15 - Fri, Apr 24
Scandinavian Airlines Logo
7:15 pm - 7:50 pm
ORD
-
MXP
17h 35m
2 stops
Scandinavian Airlines Logo
11:45 am - 4:10 pm
MXP
-
ORD
35h 25m
2 stops
$429Scandinavian Airlines
Tue, Mar 3 - Mon, Mar 9
Multiple Airlines Logo
6:30 pm - 9:35 pm
ORD
-
BGY
20h 05m
2 stops
Multiple Airlines Logo
10:10 pm - 6:20 pm
BGY
-
ORD
26h 10m
2 stops
$538Multiple Airlines
Wed, Mar 4 - Mon, Mar 9
Multiple Airlines Logo
6:30 pm - 9:00 pm
ORD
-
BGY
19h 30m
2 stops
Multiple Airlines Logo
10:10 pm - 6:20 pm
BGY
-
ORD
26h 10m
2 stops
$563Multiple Airlines
Wed, Mar 18 - Tue, Mar 31
Delta Logo
12:47 pm - 8:05 am
MDW
-
MXP
13h 18m
1 stop
Delta Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$831Delta
Thu, Mar 19 - Thu, Mar 26
Delta Logo
9:35 am - 8:05 am
MDW
-
MXP
16h 30m
2 stops
Delta Logo
6:55 am - 5:54 pm
MXP
-
MDW
16h 59m
2 stops
$896Delta
Thu, Mar 19 - Tue, Mar 31
KLM Logo
10:45 am - 8:05 am
MDW
-
MXP
15h 20m
1 stop
KLM Logo
11:40 am - 10:31 pm
MXP
-
MDW
17h 51m
1 stop
$941KLM
Thu, Apr 9 - Sat, Apr 18
KLM Logo
12:47 pm - 9:25 am
MDW
-
MXP
13h 38m
1 stop
KLM Logo
11:40 am - 10:29 pm
MXP
-
MDW
17h 49m
1 stop
$1,086KLM
Booking Insights

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.

How much is a round-trip flight from Chicago to Milan?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Milan departing in April.

What is the cheapest Chicago to Milan flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Milan costs $629 on the route between Chicago O'Hare Intl Airport (ORD) and Milan Malpensa Airport (MXP). It is also the most popular route.

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 Tuesday and avoiding Mondays 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 January, where tickets cost $543 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $1,198 and $1,092 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 3 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Milan

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

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.

Duncan Madden

Duncan Madden

Expert on MXP

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.

Good to know

Low seasonJanuary
Cheapest flight$249
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 49% increase in price.
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 $249 for a one-way ticket and $426 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?

    American Airlines, and Finnair 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?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago and Milan, with oneworld being the most commonly used for this route.

  • What is the most popular layover when flying to Milan from Chicago?

    Copenhagen is the most popular layover city among KAYAK users traveling from Chicago to Milan.

  • 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 $1,301 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 $584 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 $764 or less one-way and $1,070 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.

Reviews of the 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 9201 reviews
7.3Comfort
8.1Crew
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

6.0 GoodPatricia, Jan 2026
ORD - LAS
Read more United Airlines reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Fantastic. The only thing - out of my six luggage one was lost in Copenhagen, however it was delivered Home 3 Days later so all great..

The crew was friendly, the flight was pleasant. Thank you for your service!

Our trip plan from Kayak stated we were flying SAS. That was not true. The first leg was a Delta flight. We wasted 25 minutes before finding out to check in with the correct airline. Then our SAS flight for the second leg arrived 25 minutes late, and our third leg flight with SAS closed the gate knowing the flight delay was SAS’s fault, and that this flight would only be backed up 5 minutes. The final kicker was that between Delta and SAS, they lost all our checked luggage.

Flight was completely full January 9th? I problem i had the stewardess was bumping into me constantly walking by? very annoying.. on Austrian air I dint have this issue at all...

Amazing! Everyone was so nice and the food was so good!!

Terrible customer service. The flight attendants were rude. We experienced significant turbulence for a large portion of the flight and there was very little check in from the flight deck. The space was extremely limited to the point where it felt like torture. Never again

I was surprised how good an American airline can be - I was really impressed.

Excellent service throughout. Airport process is quick and easy. Very courteous staff. Great service in the plane! Just outstanding punctuality and service overall!!

I have paid for extra legroom on my flight. My seat was broken and did not recline. The crew could not fix it and refused to provide me with another seat

Over all experience was good. However the connection time was too short at CPG. We missed our connecting flight to AMS as the passport control line was too long and by the time we got our passport control done it was too late I wish there were some SAS staff to help us out at the passport control center Though they put us in a KLM flight from CPG to AMS, That flight was also delayed by over two hours

The trip was mostly nice, till the last moment when they had some issue with opening the flight door. The flight arrived late by 10 minutes, which was ok-ish, but then we got stuck on the plane for 35 minutes at the bridge and that costed our connection flight to LAX which left with 12+ passengers still on our flight. It added 2 days to our trip home, and we had to make lots of rearrangements to deal with the ripple effects. Don't book a 1+ stop trip with a layover time less than 2 hours.

Very nice experience. Flight had good entertainment system and good food options. Customer service was very friendly and nice as well.

Canceled my flight couple hours before takeoff. They could not find a decent re-routing and refused to pay for when i subjected alternative with Lufthansa.

Seats a little to soft on the SFO DUB flight

Well, I think we left close to on time. Crew was “eh”.

Flight takeoff was delayed an hour, but arrival time was not updated at the same time as departure time, so those picking me up at the other end were not alerted to the change in my arrival.

Seats are terribly cramped. I’m only 5’2” and my knees were practically in my face. No room to put a normal size bag under the seat and when the person in front of you reclined their seat your tray table was in your lap. This is the airline’s way of cramming more seats into the plane to make more money. I’ll think twice about taking Aer Lingus again since there are a few other options from Boston to the Emerald Isle.

Couldn’t check In online, message was couldn’t check in until Sunday morning though plane left Saturday night. Checked in okay at airport but caused slot if stress.

It all went very well, except for the ramp coordination upon landing in Boston. That, however, was resolved in fairly short order.

The biking process was confusing and I was called for a seat assignment from I number I repeatedly though was spam, but the flight itself was great

Bad. They gave me a voucher for food to use at the airport but didn’t have time since I had to catch the other plane. No refunds and lack of communication

Late. Lack of updates. Rude hostesses. Terrible food. Lack of headphones.

Flight was delayed but crew gave little to no communication, then “began boarding” but really just had everyone stand up and wait for an hour without any news or updates, as if we were going to start boarding at any second. Total chaos. Seemed like this was their first time boarding a plane. When we arrived at our destination, we waited for over an hour for the baggage claim belt to even turn on. Probably waited at baggage claim for our luggage for close to two hours. Everyone was very confused and of course we all worried that the luggage was lost. Again, zero communication and everyone we asked just said “I don’t know.” So we were left wondering whether to wait, or file a missing baggage claim, or check the other baggage claim belts (which we did every fifteen-twenty minutes because we were just confused). Lack of communication throughout the experience was a huge issue.

From Casablanca to Lisbon our baggage 2 pound over they want me to pay $120 for 2 pound which unexpected we are two family 8 of us they counters lady her customer service is not good I fly frequently for my business next time fly with TAP Air I will think twice

Booked business with TAP from LAX to Cabo Verde - overall ok, but just doesn’t feel like business class. More of a budget airline

Poor. Our flight was delayed and they told me I would be fine to make my connection in Lisbon, I missed it. Then they told me my bag would be automatically loaded onto my new flight to rome. It wasn’t. It’s been 4 days and I still don’t have it.

Flew Business class and did not like anything, flight attendants were rude and not helpful. Food was of poor quality and I did not eat meals.

Plane was delayed, reading the gates on their screens was horrible. They posted it a half an hour before the plane boarded. By the time I got there with my premier boarding they have filled the plane because it was over booked. Gate closed at 12:03 I was there at 11:54 plane took over around 12:20. I was told they would put me on the next flight. I had to go to TAP information desk. They didn’t give me a voucher they just said they would put me on the next flight. At the desk I was told I had to punches a ticket. The woman said buy it online because it’s cheaper. It in fact was not cheaper. But I had gotten out of the long line that formed so I paid 200$ for a new ticket. At a later flight, not the next flight. I had checked my bag and was told it would be on my new flight. I was then bumped to an earlier flight and was told my bag would also be on my flight. After landing in Madrid loosing a day in my hotel i landed without my bag. They didn’t load it on any flight that day. It arrived in madrid the next day. Essentially ruining the first two days of my vacation. I’m now seeking compensation.

The business class seats were smaller and closer together than other airlines.

Didn't like much. Wheelchair assistance was almost nonexistent. No one at TAP check in process helpful. On the plane, stewards were not friendly and disorganized. Food was terrible for 8 hr flight. We were skipped at snack time and even though we tried to get attention using overhead call system no one even looked up at us to acknowledge. Being at the back of first section and by the lavatory we only were able to request when they came to pick up everyone else's garbage and they were nonchalant...no apology or even choice. The 1/2 half bread with slice of cheese was a waste. Deplaning was horrible but I'll blame lisbon airport for that. Plane left late at made good time still arrived about 15 behind schedule and for using remote deplaning and bus to terminal took another 20 min to gate. Those with connections were highly stressed. Took us 2 hrs from landing to get to ground transportation and exit airport. And that was with wheelchair assistance.

I was unable to board this flight because of visa changes that I was not alerted about and I’ve been unable to contact Kayak to obtain a refund / credit anything.

The issue was not with BA it was with the link yoiu sent fopr booking the flight

Loved the boarding option from Business class lounge, experience on flight was excellent, plenty of good food choices

Getting the boarding passes between the BA and AA apps was very clunky.

The airline was not clear about a new departure time so we got to the airport early anyway. The flight left early which was great because of weather. The check in process was very easy and staff were friendly and helpful. The crew was great and our flight was very good.

Awful it always is unfortunately is the only way to fly direct to london

Boarding was efficient and quick, crew was very attentive, seats were comfortable.

The space is tight. Either you sit straight up the whole time, but the minute you relax, your knees hit the back of the seat in front of you. My seat would not recline so I was quite uncomfortable. Didn’t use my tray table bc it was stained and sticky and nasty. I was also seating in one of the last rows and one crew member and people going to the bathroom kept hitting my elbow resting on the armrest.

Had a nice little suite although I couldn’t close the door (but I didn’t ask anyone to help). 5K is a nice seat and very private (you look in on first class). Enjoyable flight and nice crew.

The plane was known to be late in advance of takeoff. My guess is that it was known to be late at 11am or 5 hours before scheduled takeoff time. We were late to leave and with a wheelchair and the a cart, we only made it to gate. We raced! Inside plane, all was great

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.