HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Italy

$290+ Cheap flights from Midway (MDW) to Italy

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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — VCE
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Italy 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 Midway to Italy

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Italy (IT0). 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

$550
(Delta)

One-way from

$290
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$565
Provider with most accurate pricing for Chicago (CHI)-Rome (ROM) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Rome (ROM) flights.
Search Deals
From Chicago Midway to Italy
Search Deals
One-way flight from Chicago Midway to Italy
Search Deals
Highest demand for flights based on searches. 26% potential increase in price ($271 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2025
Search Deals

Find flight deals from Midway to Italy

Cheapest flights from Midway to Italy
Explore the most affordable flight options available from Midway to Italy. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2025.

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.
Thu 3/2712:51 pmMDW - FCO
1 stop12h 04mDelta
Tue 4/111:35 amFCO - MDW
1 stop17h 48mDelta
Deal found 1/29$541
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/109:54 amMDW - VCE
2 stops18h 21mDelta
Mon 3/176:30 amVCE - MDW
2 stops17h 32mDelta
Deal found 1/28$550
This KLM deal was found by Cheapflights users on 1/28. 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.
Tue 4/112:51 pmMDW - FCO
1 stop15h 14mKLM
Wed 4/99:45 amFCO - MDW
1 stop19h 36mKLM
Deal found 1/28$556
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.
Mon 3/1012:51 pmMDW - FCO
1 stop14h 34mAir France
Wed 3/269:20 amFCO - MDW
1 stop19h 03mAir France
Deal found 1/30$562
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 3/2512:51 pmMDW - FCO
1 stop12h 04mMultiple Airlines
Tue 4/19:45 amFCO - MDW
1 stop19h 38mMultiple Airlines
Deal found 1/30$596
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 3/189:54 amMDW - MXP
1 stop16h 11mDelta
Wed 4/211:40 amMXP - MDW
1 stop17h 43mDelta
Deal found 1/29$629
This KLM 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/112:51 pmMDW - MXP
1 stop13h 34mKLM
Wed 4/3011:40 amMXP - MDW
1 stop17h 49mKLM
Deal found 1/29$664
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/510:57 amMDW - NAP
2 stops21h 53mDelta
Wed 3/126:35 amNAP - MDW
2 stops21h 48mDelta
Deal found 1/28$714
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.
Thu 2/279:33 amMDW - LIN
2 stops17h 57mDelta
Fri 3/76:30 amLIN - MDW
2 stops18h 41mDelta
Deal found 1/30$720
This Billigflug 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 Billigflug is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/116:42 pmMDW - FLR
2 stops13h 53mAir France
Tue 3/186:50 amFLR - MDW
2 stops17h 12mAir France
Deal found 1/29$751
This Aeromexico 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/54:00 pmMDW - MXP
1 stop34h 25mAir France
Mon 4/147:20 pmMXP - MDW
2 stops29h 44mAir France
Deal found 1/30$757
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 3/119:54 amMDW - FLR
2 stops17h 11mDelta
Tue 3/186:40 amFLR - MDW
2 stops17h 22mDelta
Deal found 1/30$760

Find flights from Midway to Italy within your budget

Customize your flight search to find flights from Midway to Italy 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

ChicagoVenice

MDW - VCE

MDWVCE

Chicago Midway

Mon 3/10

9:54 am-10:15 am

2 stops18h 21m

Venice Marco Polo

Mon 3/17

6:30 am-6:02 pm

2 stops17h 32m

$550

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Mon 3/10

12:51 pm-9:25 am

1 stop14h 34m

Rome Fiumicino

Wed 3/26

9:20 am-10:23 pm

1 stop19h 03m

$562

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Sun 2/23

12:44 pm-10:30 am

1 stop14h 46m

Rome Fiumicino

Thu 4/3

9:45 am-10:21 pm

1 stop19h 36m

$571

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Tue 3/25

12:51 pm-6:55 am

1 stop12h 04m

Rome Fiumicino

Tue 4/1

9:45 am-10:23 pm

1 stop19h 38m

$596

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 3/18

12:51 pm-8:05 am

1 stop13h 14m

Milan Malpensa

Thu 4/3

11:40 am-10:21 pm

1 stop17h 41m

$629

ChicagoRome

MDW - FCO

MDWFCO

Chicago Midway

Fri 2/21

12:44 pm-10:30 am

1 stop14h 46m

Rome Fiumicino

Wed 3/5

6:10 am-4:20 pm

2 stops17h 10m

$635

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 4/9

12:48 pm-9:25 am

1 stop13h 37m

Milan Malpensa

Wed 4/30

11:40 am-10:29 pm

1 stop17h 49m

$699

ChicagoNaples

MDW - NAP

MDWNAP

Chicago Midway

Wed 3/5

10:57 am-3:50 pm

2 stops21h 53m

Naples

Wed 3/12

6:35 am-10:23 pm

2 stops21h 48m

$714

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Thu 2/27

9:33 am-10:30 am

2 stops17h 57m

Milan Linate

Fri 3/7

6:30 am-6:11 pm

2 stops18h 41m

$720

ChicagoFlorence

MDW - FLR

MDWFLR

Chicago Midway

Tue 3/11

6:42 pm-2:35 pm

2 stops13h 53m

Florence Peretola

Tue 3/18

6:50 am-6:02 pm

2 stops17h 12m

$751

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 58 results
1
2
3
...
6

Best time to book a flight from Midway to Italy

Have a flexible travel schedule? Discover the best time to fly to Italy from Midway 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 Midway to Italy

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

What is the cheapest time of day to fly from MDW to IT?

Find hourly flight availability from Midway to Italy. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 30, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Italy as you normally would.

Rainfall in Italy by month

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

In terms of precipitation, rainfall in Italy ranges from 0.6 - 4.4 inches per month. November is typically the wettest month, when rainfall can reach 4.4 in. June is typically the driest time to visit Italy when rainfall is around 0.6 in.

Temperature in Italy by month

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

If weather is an important factor for your trip to Italy, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 75.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 46.4 F).

Reviews of airlines servicing Italy

Get insights into the airlines that provide service to Italy. 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 Italy. Reviews last updated January 30, 2025.
Peruse reviews from past customers who have flown with Delta, KLM and Air France from Chicago to Italy to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,450 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

KLM
7.8
Good
1,335 reviews
Delta
8.0
Very good
8,450 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Air France
7.4
Good
1,475 reviews
Delta
8.0
Very good
8,450 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Midway to Italy. 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 Chicago Midway Airport to Italy one-way?

    One-way options have recently been found by users for as low as $413 on Delta. Other airlines that offer cheap prices include KLM from $463 and Air France from $624 one-way.

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

    The most popular route from Chicago Midway Airport to Italy is Chicago Midway - Rome Fiumicino. You may also consider Chicago Midway - Milan Malpensa or Chicago Midway - Venice Marco Polo.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Italy 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 Chicago Midway Airport to Italy?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Italy (average of $665). Flying from Chicago Midway Airport to Italy in June is currently the most expensive (average of $1,361). 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

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 Midway to Italy

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

Top airline flying from Midway to Italy

Discover the top airline that operate flights from Midway to Italy. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$575Average$1,178FlexibilityNo cancel feeOn-timeN/A
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.