Cheap flights from Midway (MDW) to Italy

MDW — VCE
Sep 27 — Oct 41

How far in advance should I book a flight from Chicago Midway Airport to Italy?

Travelers have found it’s best to book a flight 60 days in advance to save up to 10% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 60 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to Italy 1-2 weeks in advance for as low as $850, or $850 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago Midway Airport to Italy?

Our data shows that November tends to be the cheapest month to fly to Italy from Chicago Midway Airport. Users have commonly found prices around $685 for the month, but tickets can be as low as $418. Due to multiple factors, prepare for potentially higher prices in June.

When is the cheapest time to fly from Chicago Midway Airport to Italy (MDW - IT)?

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.

Cheap flights from Midway to Italy in September, October 2022

The best prices found for MDW to Italy flights for September, October
Oct 12 - Oct 20
MDW

Chicago Midway

MXP

Milan Malpensa

1 stop

20h 30m
MXP

Milan Malpensa

MDW

Chicago Midway

1 stop

18h 29m
$560

KLM

Pick Dates

Deal found 9/19/22

Oct 25 - Nov 30
MDW

Chicago Midway

FCO

Rome Fiumicino

1 stop

17h 00m
FCO

Rome Fiumicino

MDW

Chicago Midway

2 stops

17h 03m
$566

KLM

Pick Dates

Deal found 9/20/22

Oct 23 - Nov 1
MDW

Chicago Midway

FCO

Rome Fiumicino

1 stop

22h 00m
FCO

Rome Fiumicino

MDW

Chicago Midway

2 stops

17h 44m
$568

Delta

Pick Dates

Deal found 9/19/22

Midway to Italy 2022 flight deals

Cheap flights to Italy from Midway found for this year
Nov 14 - Nov 24
MDW

Chicago Midway

FCO

Rome Fiumicino

1 stop

17h 28m
FCO

Rome Fiumicino

MDW

Chicago Midway

1 stop

16h 25m
$553

Delta

Pick Dates

Deal found 9/19/22

Dec 6 - Dec 14
MDW

Chicago Midway

FCO

Rome Fiumicino

1 stop

17h 31m
FCO

Rome Fiumicino

MDW

Chicago Midway

2 stops

19h 23m
$557

Delta

Pick Dates

Deal found 9/21/22

Oct 12 - Oct 20
MDW

Chicago Midway

MXP

Milan Malpensa

1 stop

20h 30m
MXP

Milan Malpensa

MDW

Chicago Midway

1 stop

18h 29m
$560

KLM

Pick Dates

Deal found 9/19/22

Cheap KLM flights from Midway to Italy

Mar 8 - Mar 16
MDW

Chicago Midway

MXP

Milan Malpensa

1 stop

15h 00m
MXP

Milan Malpensa

MDW

Chicago Midway

1 stop

17h 56m
$540

KLM

Pick Dates

Deal found 9/21/22

Oct 12 - Oct 20
MDW

Chicago Midway

MXP

Milan Malpensa

1 stop

20h 30m
MXP

Milan Malpensa

MDW

Chicago Midway

1 stop

18h 29m
$560

KLM

Pick Dates

Deal found 9/19/22

Feb 8 - Feb 15
MDW

Chicago Midway

MXP

Milan Malpensa

2 stops

15h 30m
MXP

Milan Malpensa

MDW

Chicago Midway

2 stops

27h 57m
$564

KLM

Pick Dates

Deal found 9/21/22

Cheap Air France flights from Midway to Italy

Feb 13 - Feb 22
MDW

Chicago Midway

MXP

Milan Malpensa

2 stops

14h 20m
MXP

Milan Malpensa

MDW

Chicago Midway

2 stops

37h 31m
$563

Air France

Pick Dates

Deal found 9/19/22

Jan 11 - May 11
MDW

Chicago Midway

FCO

Rome Fiumicino

2 stops

14h 25m
FCO

Rome Fiumicino

MDW

Chicago Midway

1 stop

13h 09m
$579

Air France

Pick Dates

Deal found 9/20/22

Jan 11 - Jan 25
MDW

Chicago Midway

FCO

Rome Fiumicino

2 stops

14h 25m
FCO

Rome Fiumicino

MDW

Chicago Midway

2 stops

17h 48m
$584

Air France

Pick Dates

Deal found 9/20/22

Last minute flights from Midway to Italy

Late deals on return flights to Italy from Midway, departing today and this week
Sep 27 - Oct 20
MDW

Chicago Midway

FCO

Rome Fiumicino

1 stop

19h 50m
FCO

Rome Fiumicino

MDW

Chicago Midway

1 stop

19h 54m
$748

Delta

Pick Dates

Deal found 9/20/22

Sep 27 - Oct 20
MDW

Chicago Midway

FCO

Rome Fiumicino

2 stops

16h 23m
FCO

Rome Fiumicino

MDW

Chicago Midway

1 stop

19h 54m
$752

Delta

Pick Dates

Deal found 9/21/22

Sep 28 - Oct 12
MDW

Chicago Midway

MXP

Milan Malpensa

1 stop

15h 30m
MXP

Milan Malpensa

MDW

Chicago Midway

1 stop

18h 29m
$762

KLM

Pick Dates

Deal found 9/20/22

One-way flights to Italy from Midway

The cheapest one-way flights from Midway to Italy
Jan 11
MDW

Chicago Midway

NAP

Naples

3 stops

44h 25m
$308

Multiple Airlines

Pick Dates

Deal found 9/20/22

Oct 19
MDW

Chicago Midway

LIN

Milan Linate

3 stops

25h 40m
$314

Multiple Airlines

Pick Dates

Deal found 9/21/22

Oct 18
MDW

Chicago Midway

FCO

Rome Fiumicino

3 stops

40h 00m
$333

Multiple Airlines

Pick Dates

Deal found 9/22/22

Related info for your journey

Useful info, stats and facts about Midway to Italy flights.

Which airlines flying from Chicago Midway to Italy have flexible cancellations due to COVID-19?

Some of our airline partners flying from Chicago Midway to Italy have new flexible policies in place due to COVID-19. Delta and American Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Delta with this kind of flexibility.

Can I find flights from Chicago Midway Airport to Italy for under $600 on Cheapflights?

Yes, there are multiple flights from Chicago Midway Airport to Italy for under $600. The cheapest flight booked recently is on KLM for just $540, but on average you can expect to pay $566.

Are there last-minute flights available from Chicago Midway Airport to Italy for under $800?

There are currently 20+ open flights from Chicago Midway Airport to Italy within the next 7 days for less than $800.

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.

Destination points for flights from Midway to Italy

Select to see more specific information for flights from Midway to all places in Italy

Top airline flying from Midway to Italy

The chart below displays the airlines Cheapflights users traveling from Midway to Italy choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
DeltaCheapest$472Average$710FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
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