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$420+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
NAP — MDW
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$608
(Delta)

One-way from

$420
(Kiwi.com)

Popular in

August

Cheapest in

February

Average price

$627
Provider with most accurate pricing for Rome (ROM)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Rome (ROM)-Chicago (CHI) flights.
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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. 6% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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 11/86:30 amBLQ - MDW
2 stops19h 06mDelta
Sat 11/151:00 pmMDW - BLQ
2 stops17h 50mDelta
Deal found 4/29$597
This Delta deal was found by Cheapflights users on 4/29. 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 11/86:30 amLIN - MDW
2 stops19h 06mDelta
Sat 11/155:59 pmMDW - LIN
2 stops13h 01mDelta
Deal found 4/29$607
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 6/176:30 amFCO - MDW
2 stops19h 11mDelta
Wed 7/236:20 pmMDW - FCO
2 stops13h 30mDelta
Deal found 4/29$608
This Delta deal was found by Cheapflights users on 4/29. 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 6/166:30 amFLR - MDW
2 stops18h 10mDelta
Wed 7/91:09 pmMDW - FLR
2 stops12h 56mDelta
Deal found 4/29$609
This Delta deal was found by Cheapflights users on 4/29. 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 11/811:05 amMXP - MDW
1 stop17h 39mDelta
Sat 11/155:59 pmMDW - MXP
2 stops14h 16mDelta
Deal found 4/29$609
This KLM deal was found by Cheapflights users on 4/30. 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.
Thu 5/89:05 amVRN - MDW
2 stops16h 40mKLM
Mon 5/126:25 pmMDW - VRN
2 stops13h 50mKLM
Deal found 4/30$614
This Expedia deal was found by Cheapflights users on 4/29. 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 9/136:20 amBLQ - MDW
2 stops18h 38mAir France
Sat 9/275:59 pmMDW - BLQ
2 stops12h 51mAir France
Deal found 4/29$614
This Air France deal was found by Cheapflights users on 4/29. 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.
Tue 9/911:40 amMXP - MDW
1 stop17h 04mAir France
Tue 9/233:40 pmMDW - MXP
2 stops15h 15mAir France
Deal found 4/29$620
This Delta deal was found by Cheapflights users on 4/29. 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 9/286:50 pmMDW - VCE
2 stops14h 20mDelta
Deal found 4/29$621
This KLM deal was found by Cheapflights users on 4/28. 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.
Sat 5/109:00 amFCO - MDW
1 stop14h 21mKLM
Mon 5/261:08 pmMDW - FCO
1 stop13h 12mKLM
Deal found 4/28$628
This Delta deal was found by Cheapflights users on 4/30. 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 5/176:15 amGOA - MDW
2 stops21h 59mDelta
Sat 5/241:08 pmMDW - GOA
2 stops17h 17mDelta
Deal found 4/30$645
This KLM deal was found by Cheapflights users on 4/29. 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.
Tue 9/911:40 amMXP - MDW
1 stop17h 04mKLM
Tue 9/231:05 pmMDW - MXP
1 stop13h 20mKLM
Deal found 4/29$652

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 May 1, 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

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Tue 6/17

6:30 am-6:41 pm

2 stops19h 11m

Chicago Midway

Wed 7/23

6:20 pm-2:50 pm

2 stops13h 30m

$608

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Mon 6/16

6:30 am-5:40 pm

2 stops18h 10m

Chicago Midway

Wed 7/9

1:09 pm-9:05 am

2 stops12h 56m

$609

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

Wed 10/8

9:15 am-6:36 pm

2 stops16h 21m

Chicago Midway

Wed 10/15

5:59 pm-5:05 pm

2 stops16h 06m

$609

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Wed 5/21

6:40 am-5:45 pm

2 stops18h 05m

Chicago Midway

Tue 5/27

1:08 pm-11:20 am

2 stops15h 12m

$612

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

Sat 9/13

6:20 am-5:58 pm

2 stops18h 38m

Chicago Midway

Sat 9/27

5:59 pm-1:50 pm

2 stops12h 51m

$614

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Sat 5/10

9:00 am-9:14 pm

2 stops19h 14m

Chicago Midway

Mon 5/26

9:16 am-10:25 am

2 stops18h 09m

$614

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 9/9

11:40 am-9:44 pm

1 stop17h 04m

Chicago Midway

Tue 9/23

3:40 pm-1:55 pm

2 stops15h 15m

$620

VeniceChicago

VCE - MDW

VCEMDW

Venice Marco Polo

Sat 9/20

6:00 am-6:36 pm

2 stops19h 36m

Chicago Midway

Sun 9/28

6:50 pm-4:10 pm

2 stops14h 20m

$621

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Sat 5/10

9:00 am-4:21 pm

1 stop14h 21m

Chicago Midway

Mon 5/26

1:08 pm-9:20 am

1 stop13h 12m

$628

GenoaChicago

GOA - MDW

GOAMDW

Genoa Cristoforo Colombo

Sat 5/17

6:15 am-9:14 pm

2 stops21h 59m

Chicago Midway

Sat 5/24

1:08 pm-1:25 pm

2 stops17h 17m

$645

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 41 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 May 1, 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
7,934 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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
1,334 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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
1,446 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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
2,826 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

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?

    $722 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 $845 and $873, 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 Venice Marco Polo - 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
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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