$233 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 11/18. 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$823
Florence
Florence2 stops$693
Naples
Naples1 stop$582
Palermo
Palermo2 stops$973
Bologna
Bologna2 stops$598
Turin
Turin2 stops$1,214
Milan
Milan1 stop$823
Florence
Florence2 stops$693
Naples
Naples1 stop$582
Palermo
Palermo2 stops$973
Bologna
Bologna2 stops$598
Turin
Turin2 stops$1,214

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

Tue, Dec 2 - Thu, Dec 11
Delta Logo
10:49 am - 9:45 amMDW-FCO
15h 56m2 stops
Delta Logo
10:05 am - 6:00 pmFCO-MDW
14h 55m1 stop
$495Delta
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Wed, Jan 7 - Thu, Jan 15
Delta Logo
5:59 pm - 3:20 pmMDW-FCO
14h 21m2 stops
Delta Logo
12:40 pm - 9:46 pmFCO-MDW
16h 06m1 stop
$509Delta
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Tue, Oct 21 - Tue, Nov 4
Delta Logo
12:48 pm - 11:05 amMDW-FCO
15h 17m1 stop
Delta Logo
6:00 am - 6:25 pmFCO-MDW
19h 25m2 stops
$511Delta
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Mon, Oct 27 - Wed, Nov 5
Delta Logo
10:35 am - 9:30 amMDW-FCO
16h 55m1 stop
Delta Logo
6:10 am - 4:15 pmFCO-MDW
17h 05m2 stops
$513Delta
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Tue, Oct 28 - Tue, Nov 4
Air France Logo
1:08 pm - 6:55 amMDW-FCO
11h 47m1 stop
Air France Logo
9:20 am - 10:14 pmFCO-MDW
19h 54m2 stops
$602Air France
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Sun, Jan 18 - Fri, Feb 13
KLM Logo
6:00 am - 10:30 amMDW-FCO
21h 30m1 stop
KLM Logo
12:40 pm - 9:46 pmFCO-MDW
16h 06m1 stop
$614KLM
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Sun, Sep 28 - Tue, Oct 14
Logo
6:30 pm - 7:00 amMDW-NAP
29h 30m1 stop
Logo
6:10 am - 10:14 pmNAP-MDW
23h 04m2 stops
$627
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Sun, Sep 28 - Tue, Oct 14
Air France Logo
12:43 pm - 7:00 amMDW-NAP
35h 17m1 stop
Air France Logo
6:10 am - 10:14 pmNAP-MDW
23h 04m2 stops
$628Air France
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Thu, Oct 23 - Fri, Nov 7
Logo
5:56 pm - 2:30 pmMDW-FCO
13h 34m1 stop
Logo
6:45 am - 10:20 pmFCO-MDW
22h 35m2 stops
$637
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Sun, Oct 26 - Wed, Nov 5
KLM Logo
12:48 pm - 9:30 amMDW-FCO
14h 42m1 stop
KLM Logo
12:40 pm - 10:14 pmFCO-MDW
16h 34m1 stop
$654KLM
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.

Which airlines provide the cheapest flights from Chicago Midway Airport to Italy?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Italy were found on Delta ($495) and Air France ($602).

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Good to know

Cheapest flight$233
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.
7.9
DeltaOverall score based on 7954 reviews
7.3Food
7.9Comfort
8.2Boarding
7.9Entertainment
8.5Crew
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

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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