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$381+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — MDW
Apr 9 — Apr 161
Wed 4/9
Wed 4/16
1 adult, Economy
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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 April 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$610
(Delta)

One-way from

$381
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$611
Provider with most accurate pricing for Rome (ROM)-Chicago (CHI) flight deals.
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From Italy to Chicago Midway
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One-way flight from Italy to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 4, 2025.

This Delta deal was found by Cheapflights users on 4/3. 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.
Thu 4/106:00 amBLQ - MDW
2 stops17h 12mDelta
Fri 4/185:59 pmMDW - BLQ
2 stops12h 51mDelta
Deal found 4/3$604
This Delta deal was found by Cheapflights users on 4/3. 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.
Thu 4/106:30 amFLR - MDW
2 stops18h 32mDelta
Mon 4/143:02 pmMDW - FLR
2 stops13h 18mDelta
Deal found 4/3$610
This Delta deal was found by Cheapflights users on 4/3. 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.
Sat 9/206:00 amVCE - MDW
2 stops19h 36mDelta
Sun 9/285:59 pmMDW - VCE
2 stops16h 46mDelta
Deal found 4/3$611
This Delta deal was found by Cheapflights users on 4/3. 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.
Thu 4/106:10 amNAP - MDW
2 stops18h 52mDelta
Fri 4/185:59 pmMDW - NAP
2 stops17h 16mDelta
Deal found 4/3$613
This Delta deal was found by Cheapflights users on 4/3. 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.
Thu 4/106:40 amLIN - MDW
2 stops18h 22mDelta
Wed 4/235:59 pmMDW - LIN
2 stops12h 56mDelta
Deal found 4/3$613
This Delta deal was found by Cheapflights users on 4/3. 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.
Mon 9/1511:40 amMXP - MDW
1 stop17h 04mDelta
Sun 9/285:59 pmMDW - MXP
2 stops12h 56mDelta
Deal found 4/3$613
This KLM deal was found by Cheapflights users on 4/3. 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.
Fri 4/2511:40 amMXP - MDW
1 stop17h 42mKLM
Mon 5/512:48 pmMDW - MXP
1 stop13h 37mKLM
Deal found 4/3$619
This Delta deal was found by Cheapflights users on 4/3. 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.
Thu 4/176:30 amFCO - MDW
2 stops18h 50mDelta
Mon 4/215:59 pmMDW - FCO
2 stops15h 01mDelta
Deal found 4/3$621
This KLM deal was found by Cheapflights users on 4/3. 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.
Mon 4/1411:35 amFCO - MDW
1 stop17h 47mKLM
Mon 4/289:52 amMDW - FCO
1 stop14h 43mKLM
Deal found 4/3$631
This Air France deal was found by Cheapflights users on 4/4. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1411:35 amFCO - MDW
1 stop17h 47mAir France
Mon 4/289:52 amMDW - FCO
1 stop14h 43mAir France
Deal found 4/4$641
This Aeromexico deal was found by Cheapflights users on 4/3. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/811:40 amMXP - MDW
1 stop16h 48mAir France
Mon 5/1212:48 pmMDW - MXP
2 stops18h 07mAir France
Deal found 4/3$736
This Expedia deal was found by Cheapflights users on 4/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/197:40 pmLIN - MDW
2 stops28h 39mMultiple Airlines
Thu 5/15:59 pmMDW - LIN
2 stops18h 46mMultiple Airlines
Deal found 4/3$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 April 4, 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

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

Wed 4/16

6:00 am-5:19 pm

2 stops18h 19m

Chicago Midway

Wed 4/23

9:52 am-8:40 am

2 stops15h 48m

$610

VeniceChicago

VCE - MDW

VCEMDW

Venice Marco Polo

Sat 9/20

6:00 am-6:36 pm

2 stops19h 36m

Chicago Midway

Sun 9/28

5:59 pm-5:45 pm

2 stops16h 46m

$611

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 4/25

6:40 am-5:19 pm

2 stops17h 39m

Chicago Midway

Mon 5/5

5:59 pm-1:55 pm

2 stops12h 56m

$613

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Mon 9/15

11:40 am-9:44 pm

1 stop17h 04m

Chicago Midway

Sun 9/28

5:59 pm-1:55 pm

2 stops12h 56m

$613

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 4/25

11:40 am-10:22 pm

1 stop17h 42m

Chicago Midway

Mon 5/5

12:48 pm-9:25 am

1 stop13h 37m

$619

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Thu 4/17

6:30 am-6:20 pm

2 stops18h 50m

Chicago Midway

Mon 4/21

5:59 pm-4:00 pm

2 stops15h 01m

$621

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Mon 4/14

11:35 am-10:22 pm

1 stop17h 47m

Chicago Midway

Mon 4/28

9:52 am-7:35 am

1 stop14h 43m

$631

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Mon 4/14

11:35 am-10:22 pm

1 stop17h 47m

Chicago Midway

Mon 4/28

9:52 am-7:35 am

1 stop14h 43m

$641

NaplesChicago

NAP - MDW

NAPMDW

Naples

Thu 5/8

6:10 am-5:45 pm

2 stops18h 35m

Chicago Midway

Mon 5/12

1:08 pm-2:20 pm

2 stops18h 12m

$703

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Thu 5/8

11:40 am-9:28 pm

1 stop16h 48m

Chicago Midway

Mon 5/12

12:48 pm-1:55 pm

2 stops18h 07m

$736

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 49 results
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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 April 4, 2025.
Read through reviews of airlines operating flights from Italy to Chicago, such as Delta, KLM and Air France. 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
7,897 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
KLM
7.8
Good
1,323 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air France
7.4
Good
1,427 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,795 reviews
Delta
8.0
Very good
7,897 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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?

    $632 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Delta and KLM, with prices starting from $710 and $820, respectively.

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

    Most travelers choose Milan Malpensa - Chicago Midway, Milan Linate - 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Italy to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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