Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights from Chicago Midway Airport to Italy from $202

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 6/25. 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
Wed 6/5
Wed 6/12

Search hundreds of travel sites at once for deals on flights to Italy

In the last 7 days travelers have searched 42,830,901 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Best Italy Flight Deals

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

Milan
Milan1 stop$720
Florence
Florence2 stops$903
Naples
Naples2 stops$1,040
Palermo
Palermo2 stops$1,090
Bologna
Bologna2 stops$883
Turin
Turin2 stops$1,239

Good to know

Cheapest flight

$202
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 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 45% more expensive 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 10826 reviews
7.9Comfort
7.4Food
8.0Entertainment
8.6Crew
8.2Boarding
Airline reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

8.0 ExcellentCynthia, May 2024ATL - TYS
Read more about Delta reviews

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

Book cheap flights from Chicago to Italy

Recent round-trip flight deals

10/30Wed
2 stopsDelta
16h 35mMDW-FCO
11/12Tue
2 stopsDelta
18h 45mFCO-MDW
$588
10/27Sun
2 stopsDelta
14h 41mMDW-FCO
11/6Wed
2 stopsDelta
18h 45mFCO-MDW
$636
10/31Thu
2 stopsDelta
16h 35mMDW-FCO
11/13Wed
2 stopsDelta
18h 45mFCO-MDW
$638
8/12Mon
1 stopDelta
12h 10mMDW-FCO
8/23Fri
1 stopDelta
14h 29mFCO-MDW
$661
8/12Mon
2 stopsAir France
15h 11mMDW-FCO
8/23Fri
1 stopAir France
14h 29mFCO-MDW
$723
10/17Thu
2 stopsAir France
15h 11mMDW-FCO
11/7Thu
2 stopsAir France
18h 45mFCO-MDW
$732
9/24Tue
1 stopKLM
12h 35mMDW-FCO
10/3Thu
1 stopKLM
13h 33mFCO-MDW
$804
8/4Sun
1 stopKLM
12h 21mMDW-FCO
8/17Sat
1 stopKLM
13h 33mFCO-MDW
$892
6/3Mon
2 stops
19h 25mMDW-FCO
6/11Tue
2 stops
35h 02mFCO-MDW
$947
6/10Mon
2 stops
19h 25mMDW-FCO
6/17Mon
2 stops
16h 22mFCO-MDW
$954

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/25Tue
2 stops
44h 59mMDW-MXP
$202
9/18Wed
2 stops
37h 07mMDW-MXP
$260
9/18Wed
2 stops
33h 17mMDW-LIN
$260
9/16Mon
2 stops
33h 47mMDW-FCO
$267
10/31Thu
2 stopsDelta
15h 40mMDW-FCO
$567
11/1Fri
2 stopsDelta
15h 40mMDW-FCO
$584
10/6Sun
1 stopKLM
12h 35mMDW-FCO
$614
10/18Fri
1 stopKLM
12h 50mMDW-FCO
$664
9/20Fri
2 stopsAir France
18h 16mMDW-FCO
$704
7/14Sun
2 stopsAir France
15h 50mMDW-BRI
$990

Search by stops

Search by airline

Search by price

Last minute flights from Midway to Italy

Last minute flight, train and bus deals

5/7Tue
multi-stopDelta
19h 50mMDW-FCO
5/17Fri
multi-stopDelta
14h 28mFCO-MDW
$773
5/8Wed
multi-stopDelta
15h 48mMDW-FCO
5/15Wed
multi-stopDelta
18h 31mFCO-MDW
$777
5/9Thu
multi-stopKLM
12h 38mMDW-FCO
5/22Wed
multi-stopKLM
16h 36mFCO-MDW
$818
5/9Thu
multi-stopKLM
12h 38mMDW-FCO
5/16Thu
multi-stopKLM
14h 28mFCO-MDW
$823
5/10Fri
multi-stopDelta
15h 14mMDW-FCO
5/17Fri
multi-stopDelta
18h 31mFCO-MDW
$827
5/10Fri
multi-stopKLM
12h 50mMDW-FCO
5/13Mon
multi-stopKLM
14h 28mFCO-MDW
$873
5/7Tue
multi-stopAir France
21h 09mMDW-FCO
5/17Fri
multi-stopAir France
18h 06mFCO-MDW
$1,004
5/11Sat
multi-stop
45h 28mMDW-FCO
5/15Wed
multi-stop
26h 52mFCO-MDW
$1,065
5/11Sat
multi-stopAir France
23h 10mMDW-NAP
5/21Tue
multi-stopAir France
18h 52mNAP-MDW
$2,021
5/8Wed
multi-stop
18h 29mMDW-FCO
5/10Fri
multi-stop
18h 57mFCO-MDW
$2,242

Search by stops

Search by airline

Search by price

Chicago Midway Airport - Italy Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Italy - Chicago Midway Airport

Cabin classes: