HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$492+ Cheap flights from Italy to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/27. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — MDW
jun. 23 — jun. 301
lun. 6/23
lun. 6/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Italy to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Italy to Midway

Keep the following information in mind while searching for Italy to Midway flight deals. Data was last updated junio 18, 2025.

Round-trip from

$612
(Delta)

One-way from

$492
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$789
From Italy to Chicago Midway
Search Deals
One-way flight from Italy to Chicago Midway
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from Italy to Midway

Cheapest flights from Italy to Midway
Explore the most affordable flight options available from Italy to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 18, 2025.

This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/206:00 amVCE - MDW
2 stops16h 30mDelta
dom. 9/285:59 pmMDW - VCE
2 stops16h 46mDelta
Deal found 6/18$612
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/246:00 amBLQ - MDW
2 stops19h 36mDelta
mié. 10/15:25 pmMDW - BLQ
2 stops16h 10mDelta
Deal found 6/17$612
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/1511:40 amMXP - MDW
1 stop17h 04mDelta
dom. 9/285:59 pmMDW - MXP
2 stops12h 56mDelta
Deal found 6/16$615
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/176:40 amLIN - MDW
2 stops16h 43mDelta
dom. 9/215:59 pmMDW - LIN
2 stops12h 56mDelta
Deal found 6/16$616
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/189:00 amFCO - MDW
1 stop16h 36mDelta
vie. 10/35:59 pmMDW - FCO
2 stops13h 51mDelta
Deal found 6/16$652
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/109:00 amNAP - MDW
1 stop16h 02mDelta
lun. 7/146:20 pmMDW - NAP
2 stops16h 55mDelta
Deal found 6/17$719
This KLM deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/109:00 amNAP - MDW
1 stop16h 02mKLM
lun. 7/1410:30 amMDW - NAP
1 stop13h 35mKLM
Deal found 6/17$723
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/46:30 amFLR - MDW
2 stops19h 11mDelta
lun. 7/76:20 pmMDW - FLR
2 stops16h 00mDelta
Deal found 6/16$727
This KLM deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/311:40 amMXP - MDW
1 stop17h 05mKLM
mié. 7/1612:43 pmMDW - MXP
1 stop13h 42mKLM
Deal found 6/18$733
This KLM deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/19:45 amFCO - MDW
1 stop19h 00mKLM
mié. 7/910:30 amMDW - FCO
1 stop14h 05mKLM
Deal found 6/16$737
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/46:15 amGOA - MDW
2 stops18h 25mDelta
mar. 7/812:43 pmMDW - GOA
2 stops17h 42mDelta
Deal found 6/18$769
This KLM deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/2611:20 amVCE - MDW
1 stop17h 25mKLM
mié. 7/912:43 pmMDW - VCE
1 stop15h 52mKLM
Deal found 6/18$776

Cheapflights Fare Finder

Customize your flight search to find flights from Italy to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated junio 18, 2025.
Use the filters below to find and compare flights from Italy to Chicago Midway Airport that are best for you.

Fly from

Italy

Fly to

Midway

Route

Depart

Return

Price

VeniceChicago

VCE - MDW

VCEMDW

Venice Marco Polo

sáb. 9/20

6:00 am-3:30 pm

2 stops16h 30m

Chicago Midway

dom. 9/28

5:59 pm-5:45 pm

2 stops16h 46m

$612

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

mié. 9/24

6:00 am-6:36 pm

2 stops19h 36m

Chicago Midway

mié. 10/1

5:25 pm-4:35 pm

2 stops16h 10m

$612

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

lun. 9/15

11:40 am-9:44 pm

1 stop17h 04m

Chicago Midway

dom. 9/28

5:59 pm-1:55 pm

2 stops12h 56m

$615

MilanChicago

LIN - MDW

LINMDW

Milan Linate

mié. 9/17

6:40 am-4:23 pm

2 stops16h 43m

Chicago Midway

dom. 9/21

5:59 pm-1:55 pm

2 stops12h 56m

$616

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

jue. 9/18

9:00 am-6:36 pm

1 stop16h 36m

Chicago Midway

vie. 10/3

5:59 pm-2:50 pm

2 stops13h 51m

$652

NaplesChicago

NAP - MDW

NAPMDW

Naples

jue. 7/10

9:00 am-6:02 pm

1 stop16h 02m

Chicago Midway

lun. 7/14

6:20 pm-6:15 pm

2 stops16h 55m

$719

NaplesChicago

NAP - MDW

NAPMDW

Naples

jue. 7/10

9:00 am-6:02 pm

1 stop16h 02m

Chicago Midway

lun. 7/14

10:30 am-7:05 am

1 stop13h 35m

$723

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

vie. 7/4

6:30 am-6:41 pm

2 stops19h 11m

Chicago Midway

lun. 7/7

6:20 pm-5:20 pm

2 stops16h 00m

$727

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

jue. 7/3

11:40 am-9:45 pm

1 stop17h 05m

Chicago Midway

mié. 7/16

12:43 pm-9:25 am

1 stop13h 42m

$733

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

mar. 7/1

9:45 am-9:45 pm

1 stop19h 00m

Chicago Midway

mié. 7/9

10:30 am-7:35 am

1 stop14h 05m

$737

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 50 results
1
2
3
...
5

Best time to book a flight from Italy to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Italy with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Italy to Chicago Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated junio 18, 2025.
Read through reviews of airlines operating flights from Italy to Chicago, such as Delta, KLM and Air Transat. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,364 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air Transat
7.8
Good
398 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Air France
7.5
Good
1,467 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,876 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Italy to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Italy to Chicago Midway Airport one-way?

    $731 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on KLM and WestJet, with prices starting from $747 and $1,078, respectively.

  • What are the most popular routes from Italy to Chicago Midway Airport?

    Most travelers choose Milan Linate - Chicago Midway, Milan Malpensa - Chicago Midway or Rome Fiumicino - Chicago Midway when deciding on the best route from Italy to Chicago Midway Airport.

  • Can I find deals for flights from Italy to Midway that include hotel bookings?

    Yes. In addition to deals on Italy to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Italy to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Italy to Midway.

  • Can I find deals for business class flights from Italy to Midway?

    Yes. Cheapflights offers flight deals from Italy to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Italy to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Italy to Chicago Midway Airport (average of $160). Flying from Italy to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Italy?

Book flights to Italy if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Italy to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Charles de Gaulle to O'Hare Intl flights
Heathrow to O'Hare Intl flights
Frankfurt to O'Hare Intl flights
Frederic Chopin to O'Hare Intl flights
Madrid to O'Hare Intl flights
Frederic Chopin to Midway flights
Orly to O'Hare Intl flights
Dublin to O'Hare Intl flights
Charles de Gaulle to Midway flights
Munich to O'Hare Intl flights
Madrid to Midway flights
Zurich to O'Hare Intl flights
Malpensa to O'Hare Intl flights
Athens to O'Hare Intl flights
Barcelona-El Prat to O'Hare Intl flights
Bruxelles-National to O'Hare Intl flights
Krakow to O'Hare Intl flights
Vienna to O'Hare Intl flights
London City to O'Hare Intl flights
Gatwick to O'Hare Intl flights
Heathrow to Midway flights
Frankfurt-Hahn to O'Hare Intl flights
Istanbul to O'Hare Intl flights
Leonardo da Vinci/Fiumicino to O'Hare Intl flights
Beauvais-Tille to O'Hare Intl flights
Barcelona-El Prat to Midway flights
Amsterdam to O'Hare Intl flights
Linate to O'Hare Intl flights
Bergamo to O'Hare Intl flights
Modlin to O'Hare Intl flights
Berlin to O'Hare Intl flights
Vicenza to O'Hare Intl flights
Edinburgh to O'Hare Intl flights
Oslo Gardermoen to O'Hare Intl flights
Munich to Midway flights
Stansted to O'Hare Intl flights
Bruxelles-National to Midway flights
Luton to O'Hare Intl flights
Copenhagen to O'Hare Intl flights
Lisbon to O'Hare Intl flights
Poznan to O'Hare Intl flights
Belgrade to O'Hare Intl flights
Lyon to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.