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Find cheap flights from Chicago Midway Airport to Italy from $242

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 9/23. 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
Sat 6/29
Sat 7/6

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Best Italy Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Milan
Milan3 stops$1,016
Florence
Florence2 stops$1,042
Naples
Naples2 stops$782
Palermo
Palermo2 stops$1,163
Bologna
Bologna2 stops$949
Turin
Turin2 stops$2,285

Good to know

Cheapest flight

$242
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 to Italy from Chicago Midway Airport 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 to Italy with an airline and back to Chicago Midway Airport 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 to Italy from Chicago Midway Airport 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 cheap flights to Italy

  • Morning departure is around 7% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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 10457 reviews
7.9Comfort
8.0Entertainment
8.2Boarding
7.4Food
8.6Crew
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

They split our family into two trips due to flight overbooking. Horrible experience.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Book cheap flights from Chicago to Italy

Recent round-trip flight deals

11/24Sun
2 stopsDelta
13h 41mMDW-FCO
12/10Tue
1 stopDelta
18h 14mFCO-MDW
$517
11/11Mon
1 stopDelta
15h 30mMDW-FCO
11/22Fri
2 stopsDelta
18h 39mFCO-MDW
$520
10/30Wed
2 stopsKLM
15h 04mMDW-FCO
11/15Fri
2 stopsKLM
18h 55mFCO-MDW
$527
11/5Tue
2 stopsDelta
13h 50mMDW-FCO
11/12Tue
2 stopsDelta
17h 43mFCO-MDW
$536
10/30Wed
2 stopsDelta
16h 35mMDW-FCO
11/6Wed
2 stopsDelta
18h 45mFCO-MDW
$549
11/26Tue
1 stopKLM
12h 50mMDW-FCO
12/2Mon
1 stopKLM
26h 27mFCO-MDW
$556
11/4Mon
2 stopsAir France
16h 50mMDW-FCO
11/13Wed
1 stopAir France
35h 09mFCO-MDW
$568
11/3Sun
2 stopsAir France
21h 55mMDW-FCO
11/14Thu
2 stopsAir France
17h 43mFCO-MDW
$582
6/11Tue
3 stops
25h 50mMDW-MXP
6/25Tue
3 stops
31h 02mMXP-MDW
$1,016
7/23Tue
2 stops
35h 43mMDW-VCE
7/30Tue
1 stop
15h 47mVCE-MDW
$1,017

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Recent one-way flight deals

9/23Mon
2 stops
43h 27mMDW-NAP
$242
7/16Tue
2 stops
44h 43mMDW-VCE
$242
7/14Sun
2 stopsAir France
16h 20mMDW-BLQ
$729
6/16Sun
2 stopsDelta
16h 31mMDW-FLR
$799
7/10Wed
2 stopsDelta
16h 20mMDW-BLQ
$799
9/1Sun
2 stopsWestJet
47h 40mMDW-FCO
$832
6/14Fri
1 stopKLM
12h 35mMDW-FCO
$925
9/22Sun
2 stopsAir France
14h 35mMDW-NAP
$941
6/5Wed
1 stopKLM
12h 38mMDW-FCO
$960
6/12Wed
2 stopsWestJet
44h 11mMDW-FCO
$1,829

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Last minute flights from Midway to Italy

Last minute flight, train and bus deals

6/3Mon
multi-stop
21h 15mMDW-FCO
6/6Thu
multi-stop
32h 26mFCO-MDW
$983
6/3Mon
multi-stop
21h 15mMDW-FCO
6/11Tue
multi-stop
32h 01mFCO-MDW
$1,046
6/3Mon
multi-stop
21h 15mMDW-FCO
6/11Tue
multi-stop
26h 52mFCO-MDW
$1,138
6/4Tue
multi-stopDelta
13h 09mMDW-MXP
8/26Mon
multi-stopDelta
17h 16mMXP-MDW
$1,801
6/4Tue
multi-stopDelta
12h 44mMDW-FLR
6/16Sun
multi-stopDelta
18h 29mFLR-MDW
$2,035
6/4Tue
multi-stopKLM
14h 13mMDW-MXP
8/27Tue
multi-stopKLM
16h 37mMXP-MDW
$2,131
6/2Sun
multi-stopKLM
12h 50mMDW-FCO
7/14Sun
multi-stopKLM
13h 34mFCO-MDW
$2,143
6/3Mon
multi-stopAir France
18h 28mMDW-FCO
6/13Thu
multi-stopAir France
13h 34mFCO-MDW
$2,171
6/2Sun
multi-stopAir France
12h 24mMDW-FCO
7/14Sun
multi-stopAir France
18h 04mFCO-MDW
$2,194
5/30Thu
multi-stopWestJet
44h 55mMDW-FCO
6/5Wed
multi-stopWestJet
28h 12mFCO-MDW
$10,288

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Chicago Midway Airport - Italy Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Italy - Chicago Midway Airport

Cabin classes: