Find Cheap Flights from Chicago Midway to Italy

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago Midway to Italy

(Round-trip)
Depart: Sun Nov 5 2017 Return: Tue Nov 21 2017 Trip spans 17 days
KLM
KLM
MDW
FCO
16h 30m
1 stop
FCO
MDW
16h 20m
1 stop
Depart: Mon Feb 5 2018 Return: Tue Feb 13 2018 Trip spans 9 days
Air France
Air France
MDW
FCO
13h 00m
1 stop
FCO
MDW
16h 43m
1 stop
Depart: Sun Oct 29 2017 Return: Thu Nov 9 2017 Trip spans 12 days
Delta
Delta
MDW
FCO
20h 40m
1 stop
FCO
MDW
19h 57m
2 stops
Depart: Sun Dec 31 2017 Return: Wed Jan 10 2018 Trip spans 11 days
KLM
KLM
MDW
FCO
16h 30m
1 stop
FCO
MDW
16h 43m
1 stop
Depart: Tue Jan 9 2018 Return: Mon Feb 5 2018 Trip spans 28 days
Air France
Air France
MDW
FCO
13h 00m
1 stop
FCO
MDW
16h 43m
1 stop
Depart: Sun Oct 29 2017 Return: Tue Nov 7 2017 Trip spans 10 days
Delta
Delta
MDW
FCO
20h 40m
1 stop
FCO
MDW
18h 03m
2 stops
Depart: Sun Feb 4 2018 Return: Mon Feb 19 2018 Trip spans 16 days
KLM
KLM
MDW
FCO
13h 00m
1 stop
FCO
MDW
18h 28m
1 stop
Depart: Mon Nov 13 2017 Return: Wed Nov 22 2017 Trip spans 10 days
KLM
KLM
MDW
FCO
16h 30m
1 stop
FCO
MDW
18h 00m
2 stops
Depart: Tue Nov 7 2017 Return: Tue Nov 14 2017 Trip spans 8 days
Delta
Delta
MDW
FCO
15h 35m
2 stops
FCO
MDW
16h 49m
2 stops
Depart: Tue Sep 19 2017 Return: Wed Sep 27 2017 Trip spans 9 days
KLM
KLM
MDW
FCO
13h 45m
1 stop
FCO
MDW
13h 50m
1 stop
Depart: Wed Oct 11 2017 Return: Fri Oct 20 2017 Trip spans 10 days
Delta
Delta
MDW
FCO
17h 07m
1 stop
FCO
MDW
15h 36m
2 stops
Depart: Wed Oct 18 2017 Return: Mon Oct 30 2017 Trip spans 13 days
KLM
KLM
MDW
FCO
13h 42m
1 stop
FCO
MDW
15h 59m
2 stops
Depart: Sun Nov 5 2017 Return: Wed Nov 22 2017 Trip spans 18 days
KLM
KLM
MDW
NAP
19h 18m
2 stops
NAP
MDW
17h 45m
2 stops
Depart: Fri Sep 29 2017 Return: Sat Oct 14 2017 Trip spans 16 days
Delta
Delta
MDW
FCO
17h 07m
1 stop
FCO
MDW
16h 50m
2 stops
Depart: Sun Feb 4 2018 Return: Wed Feb 21 2018 Trip spans 18 days
KLM
KLM
MDW
NAP
19h 22m
2 stops
NAP
MDW
18h 55m
2 stops
Depart: Wed Oct 25 2017 Return: Wed Nov 15 2017 Trip spans 22 days
KLM
KLM
MDW
NAP
22h 08m
2 stops
NAP
MDW
19h 52m
2 stops
Depart: Fri Nov 17 2017 Return: Fri Nov 24 2017 Trip spans 8 days
$1081
Select
Delta
Delta
MDW
FCO
13h 50m
2 stops
FCO
MDW
18h 00m
2 stops
Depart: Fri Dec 1 2017 Return: Wed Dec 6 2017 Trip spans 6 days
KLM
KLM
MDW
NAP
20h 45m
2 stops
NAP
MDW
16h 57m
2 stops
Depart: Fri Oct 6 2017 Return: Sun Oct 15 2017 Trip spans 10 days
$1242
Select
Delta
Delta
MDW
NAP
18h 23m
2 stops
NAP
MDW
21h 00m
2 stops
Depart: Mon Sep 18 2017 Return: Tue Sep 26 2017 Trip spans 9 days
KLM
KLM
MDW
NAP
17h 23m
2 stops
NAP
MDW
21h 11m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

Chicago
$660
Destination

Rome
$660
Naples
$752