$293 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 10/20. 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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Best Italy Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milan
Milan1 stop$515
Florence
Florence2 stops$632
Naples
Naples1 stop$616
Palermo
Palermo2 stops$1,004
Bologna
Bologna2 stops$846
Turin
Turin2 stops$882
Milan
Milan1 stop$515
Florence
Florence2 stops$632
Naples
Naples1 stop$616
Palermo
Palermo2 stops$1,004
Bologna
Bologna2 stops$846
Turin
Turin2 stops$882

Cheap Flights from Midway to Italy

 
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, Oct 13 - Wed, Oct 22
Delta Logo
10:35 am - 9:25 amMDW-MXP
15h 50m1 stop
Delta Logo
6:50 am - 4:23 pmMXP-MDW
16h 33m2 stops
$515Delta
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Tue, Nov 11 - Fri, Nov 21
KLM Logo
1:00 pm - 7:55 amMDW-FCO
11h 55m1 stop
KLM Logo
10:15 am - 9:44 pmFCO-MDW
18h 29m1 stop
$518KLM
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Mon, Oct 13 - Wed, Oct 22
Delta Logo
9:30 am - 9:25 amMDW-MXP
16h 55m2 stops
Delta Logo
6:50 am - 4:23 pmMXP-MDW
16h 33m2 stops
$519Delta
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Mon, Nov 10 - Wed, Nov 19
Delta Logo
6:00 am - 9:45 amMDW-FCO
20h 45m2 stops
Delta Logo
9:20 am - 9:44 pmFCO-MDW
19h 24m2 stops
$523Delta
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Tue, Nov 11 - Tue, Nov 18
KLM Logo
1:05 pm - 10:30 amMDW-FCO
14h 25m1 stop
KLM Logo
10:05 am - 6:36 pmFCO-MDW
15h 31m1 stop
$529KLM
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Wed, Oct 22 - Wed, Nov 12
Delta Logo
10:35 am - 7:35 amMDW-FCO
14h 00m1 stop
Delta Logo
12:00 pm - 9:51 amFCO-MDW
28h 51m2 stops
$534Delta
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Mon, Oct 13 - Wed, Oct 22
Delta Logo
1:00 pm - 11:20 amMDW-LIN
15h 20m2 stops
Delta Logo
6:30 am - 4:23 pmLIN-MDW
16h 53m2 stops
$537Delta
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Tue, Oct 14 - Wed, Nov 5
Delta Logo
9:30 am - 9:20 amMDW-FCO
16h 50m1 stop
Delta Logo
6:00 am - 6:36 pmFCO-MDW
19h 36m2 stops
$550Delta
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Sun, Aug 3 - Sun, Aug 24
Air France Logo
1:09 pm - 10:25 amMDW-MXP
14h 16m2 stops
Air France Logo
6:50 am - 5:47 pmMXP-MDW
17h 57m2 stops
$852Air France
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Wed, Jul 23 - Wed, Jul 30
Air France Logo
10:30 am - 9:25 amMDW-MXP
15h 55m1 stop
Air France Logo
11:40 am - 9:42 pmMXP-MDW
17h 02m1 stop
$1,056Air France
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Useful Info

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 January and May, when the average cost of round-trip tickets is $1,234 and $1,192 respectively.

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Good to know

Cheapest flight$293
Flight from Chicago Midway Airport to Naples

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.

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 7950 reviews
7.3Food
8.2Boarding
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

10.0 ExcellentHartaj, Jun 2025EWR - RDU
Read more Delta reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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