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$274+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
VCE — MDW
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Italy to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Italy (IT0) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$621
(Air France)

One-way from

$274
(Kiwi.com)

Popular in

August

Cheapest in

April

Average price

$662
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. 8% potential increase in price ($66 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 January 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 January 30, 2025.

This Air France deal was found by Cheapflights users on 1/30. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/136:40 amFLR - MDW
2 stops16h 41mMultiple Airlines
Wed 2/192:08 pmMDW - FLR
2 stops14h 12mMultiple Airlines
Deal found 1/30$621
This Delta deal was found by Cheapflights users on 1/30. 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.
Fri 2/146:30 amLIN - MDW
2 stops18h 41mDelta
Sun 3/21:26 pmMDW - LIN
2 stops14h 29mDelta
Deal found 1/30$625
This Delta deal was found by Cheapflights users on 1/30. 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.
Fri 3/76:05 amNAP - MDW
2 stops19h 06mDelta
Tue 3/112:55 pmMDW - NAP
2 stops18h 55mDelta
Deal found 1/30$627
This Delta deal was found by Cheapflights users on 1/29. 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 3/256:40 amFLR - MDW
2 stops17h 22mDelta
Sun 3/307:09 pmMDW - FLR
2 stops14h 46mDelta
Deal found 1/29$627
This Delta deal was found by Cheapflights users on 1/30. 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.
Fri 2/146:55 amMXP - MDW
2 stops18h 16mDelta
Sun 3/21:26 pmMDW - MXP
2 stops14h 09mDelta
Deal found 1/30$629
This KLM deal was found by Cheapflights users on 1/30. 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.
Tue 3/1110:05 amMXP - MDW
1 stop18h 18mKLM
Wed 3/199:54 amMDW - MXP
1 stop16h 11mKLM
Deal found 1/30$630
This Delta deal was found by Cheapflights users on 1/30. 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.
Tue 3/116:10 amFCO - MDW
2 stops17h 52mDelta
Mon 3/249:54 amMDW - FCO
1 stop17h 31mDelta
Deal found 1/30$636
This Air France deal was found by Cheapflights users on 1/30. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2611:40 amMXP - MDW
1 stop17h 07mAir France
Mon 9/155:59 pmMDW - MXP
2 stops12h 56mAir France
Deal found 1/30$637
This Air France deal was found by Cheapflights users on 1/30. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:40 amLIN - MDW
2 stops17h 21mMultiple Airlines
Mon 9/155:59 pmMDW - LIN
2 stops12h 56mMultiple Airlines
Deal found 1/30$642
This Delta deal was found by Cheapflights users on 1/30. 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.
Sun 3/26:30 amBLQ - MDW
2 stops18h 41mDelta
Sun 3/96:42 pmMDW - BLQ
2 stops14h 28mDelta
Deal found 1/30$642
This Expedia deal was found by Cheapflights users on 1/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/257:30 pmMXP - MDW
2 stops28h 31mMultiple Airlines
Mon 9/1510:10 amMDW - MXP
1 stop16h 15mMultiple Airlines
Deal found 1/30$645
This Delta deal was found by Cheapflights users on 1/30. 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 3/16:30 amVCE - MDW
2 stops18h 13mDelta
Sun 3/96:42 pmMDW - VCE
2 stops16h 43mDelta
Deal found 1/30$648

Find flights from Italy to Midway within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Thu 2/13

6:40 am-4:21 pm

2 stops16h 41m

Chicago Midway

Wed 2/19

2:08 pm-11:20 am

2 stops14h 12m

$621

MilanChicago

LIN - MDW

LINMDW

Milan Linate

Fri 2/14

6:30 am-6:11 pm

2 stops18h 41m

Chicago Midway

Sun 3/2

1:26 pm-10:55 am

2 stops14h 29m

$625

NaplesChicago

NAP - MDW

NAPMDW

Naples

Fri 3/7

6:05 am-6:11 pm

2 stops19h 06m

Chicago Midway

Mon 3/17

2:55 pm-3:50 pm

2 stops18h 55m

$627

FlorenceChicago

FLR - MDW

FLRMDW

Florence Peretola

Tue 3/25

6:40 am-6:02 pm

2 stops17h 22m

Chicago Midway

Sun 3/30

7:09 pm-4:55 pm

2 stops14h 46m

$627

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Fri 2/14

6:55 am-6:11 pm

2 stops18h 16m

Chicago Midway

Sun 3/2

1:26 pm-10:35 am

2 stops14h 09m

$629

MilanChicago

MXP - MDW

MXPMDW

Milan Malpensa

Tue 3/11

10:05 am-10:23 pm

1 stop18h 18m

Chicago Midway

Wed 3/19

9:54 am-8:05 am

1 stop16h 11m

$630

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Tue 3/11

6:10 am-6:02 pm

2 stops17h 52m

Chicago Midway

Mon 3/24

9:54 am-9:25 am

1 stop17h 31m

$636

BolognaChicago

BLQ - MDW

BLQMDW

Bologna Guglielmo Marconi

Sun 3/2

6:30 am-6:11 pm

2 stops18h 41m

Chicago Midway

Sun 3/9

6:42 pm-3:10 pm

2 stops14h 28m

$642

VeniceChicago

VCE - MDW

VCEMDW

Venice Marco Polo

Sat 3/1

6:30 am-5:43 pm

2 stops18h 13m

Chicago Midway

Sun 3/9

6:42 pm-5:25 pm

2 stops16h 43m

$648

RomeChicago

FCO - MDW

FCOMDW

Rome Fiumicino

Tue 3/11

11:45 am-10:23 pm

1 stop16h 38m

Chicago Midway

Mon 3/24

9:54 am-9:25 am

1 stop17h 31m

$653

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 48 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.

Travel insights for flights from Italy to Midway

Get recent, data-driven insights about flights from Italy to Midway including ideal travel times, pricing trends, and more.

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 January 30, 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
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

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
8,450 reviews
Delta
8.0
Very good
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

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
1,335 reviews
Delta
8.0
Very good
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

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
1,475 reviews
Delta
8.0
Very good
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

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
2,817 reviews
Delta
8.0
Very good
8,450 reviews

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

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?

    $687 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on WestJet and KLM, with prices starting from $697 and $705, respectively.

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

    Most travelers choose Milan Malpensa - Chicago Midway, Rome Fiumicino - Chicago Midway or Milan Linate - 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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