$208 Find Cheap Flights from Chicago Midway Airport to Italy

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Italy departing on 10/30. 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

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Cheap Flights from Midway to Italy

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milan
Milan1 stop$830
Florence
Florence2 stops$933
Naples
Naples1 stop$521
Palermo
Palermo2 stops$771
Bologna
Bologna2 stops$988
Turin
Turin2 stops$1,085
Milan
Milan1 stop$830
Florence
Florence2 stops$933
Naples
Naples1 stop$521
Palermo
Palermo2 stops$771
Bologna
Bologna2 stops$988
Turin
Turin2 stops$1,085

Book Cheap Midway to Italy Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Italy 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 Midway to Italy

Mon, Nov 17 - Wed, Nov 26
Delta Logo
1:05 pm - 7:55 amMDW-FCO
11h 50m1 stop
Delta Logo
12:40 pm - 9:44 pmFCO-MDW
16h 04m1 stop
$399Delta
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Wed, Nov 12 - Tue, Nov 18
Delta Logo
1:05 pm - 10:30 amMDW-FCO
14h 25m1 stop
Delta Logo
9:20 am - 9:44 pmFCO-MDW
19h 24m2 stops
$403Delta
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Sun, Oct 19 - Wed, Nov 19
Delta Logo
9:35 am - 9:20 amMDW-FCO
16h 45m1 stop
Delta Logo
9:20 am - 9:44 pmFCO-MDW
19h 24m2 stops
$404Delta
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Wed, Oct 29 - Fri, Nov 7
Delta Logo
1:48 pm - 11:45 amMDW-FCO
15h 57m2 stops
Delta Logo
12:40 pm - 10:14 pmFCO-MDW
16h 34m1 stop
$418Delta
Find Deal
Sun, Oct 19 - Wed, Nov 19
 Logo
5:56 pm - 2:30 pmMDW-FCO
13h 34m1 stop
 Logo
7:10 pm - 11:25 pmFCO-MDW
35h 15m1 stop
Tue, Nov 18 - Wed, Dec 3
KLM Logo
1:00 pm - 7:55 amMDW-FCO
11h 55m1 stop
KLM Logo
12:40 pm - 9:44 pmFCO-MDW
16h 04m1 stop
$502KLM
Find Deal
Sun, Nov 16 - Sun, Nov 23
 Logo
1:05 pm - 7:55 amMDW-FCO
11h 50m1 stop
 Logo
12:40 pm - 9:44 pmFCO-MDW
16h 04m1 stop
Mon, Dec 1 - Sun, Dec 14
KLM Logo
1:05 pm - 10:30 amMDW-FCO
14h 25m1 stop
KLM Logo
12:40 pm - 9:44 pmFCO-MDW
16h 04m1 stop
$540KLM
Find Deal
Mon, Oct 20 - Thu, Oct 30
Air France Logo
12:48 pm - 9:25 amMDW-MXP
13h 37m1 stop
Air France Logo
6:55 am - 5:43 pmMXP-MDW
16h 48m2 stops
$999Air France
Find Deal
Mon, Oct 20 - Tue, Oct 28
Air France Logo
10:35 am - 9:25 amMDW-MXP
15h 50m1 stop
Air France Logo
6:55 am - 5:43 pmMXP-MDW
16h 48m2 stops
$1,074Air France
Find Deal
Booking Insights

KAYAK's insights & trends for Midway to Italy flights

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

What is the cheapest month to fly from Chicago Midway Airport to Italy?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Italy, 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 Midway Airport to Italy is February, when tickets cost $586 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $1,997 and $1,234 respectively.


Good to know

Cheapest flight$208
Flight from Chicago Midway Airport to Milan Malpensa Airport

FAQs - booking Italy flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Italy?

    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 Midway Airport to Italy.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Italy 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 Midway Airport to Italy?

    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 from Chicago Midway Airport to Italy with an airline and back with another airline.

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

    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 from Chicago Midway Airport to Italy up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Italy?

    The cheapest time of day to fly to Italy is generally at night, when round-trip flights cost $835 on average. Morning departures are around 60% more expensive than evening flights, on average. The most expensive time of day to fly to Italy is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,512.

Reviews of the top airline flying from Midway to Italy

 
Need help choosing which airline to fly with from Midway to Italy? 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.
8.0
DeltaOverall score based on 7980 reviews
7.9Comfort
8.2Boarding
8.5Crew
7.9Entertainment
7.3Food
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Everything you need to know for your flight from Midway to Italy

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